From 5cd10b594af34184295cf67d03ca544967774ac3 Mon Sep 17 00:00:00 2001
From: lc6464 <64722907+lc6464@users.noreply.github.com>
Date: Sat, 25 Apr 2026 23:43:10 +0800
Subject: [PATCH 1/8] feat(pico): add support for tool_calls in chat messages

---
 pkg/agent/agent.go                            |   2 +
 pkg/agent/agent_outbound.go                   |  90 ++++++++
 pkg/agent/agent_test.go                       |  49 +++--
 pkg/agent/pipeline_execute.go                 |   4 +-
 pkg/agent/pipeline_llm.go                     |  40 ++--
 pkg/channels/pico/pico.go                     |  32 ++-
 pkg/channels/pico/protocol.go                 |   9 +-
 pkg/utils/visible_tool_calls.go               | 109 ++++++++++
 web/backend/api/session.go                    | 184 ++++------------
 web/backend/api/session_test.go               | 205 +++++++-----------
 web/frontend/src/api/sessions.ts              |  13 +-
 .../src/components/chat/assistant-message.tsx | 124 +++++++++--
 .../src/components/chat/chat-page.tsx         |   5 +-
 .../features/chat/assistant-message-state.ts  | 105 +++++++++
 web/frontend/src/features/chat/history.ts     |  15 +-
 web/frontend/src/features/chat/protocol.ts    |  91 ++------
 web/frontend/src/features/chat/tool-calls.ts  | 122 +++++++++++
 web/frontend/src/i18n/locales/en.json         |   3 +
 web/frontend/src/i18n/locales/zh.json         |   3 +
 web/frontend/src/store/chat.ts                |  19 +-
 20 files changed, 815 insertions(+), 409 deletions(-)
 create mode 100644 pkg/utils/visible_tool_calls.go
 create mode 100644 web/frontend/src/features/chat/assistant-message-state.ts
 create mode 100644 web/frontend/src/features/chat/tool-calls.ts

diff --git a/pkg/agent/agent.go b/pkg/agent/agent.go
index 3e9bd845e..2c456dca7 100644
--- a/pkg/agent/agent.go
+++ b/pkg/agent/agent.go
@@ -111,8 +111,10 @@ const (
 	sessionKeyAgentPrefix      = "agent:"
 	pendingTurnPrefix          = "pending-"
 	metadataKeyMessageKind     = "message_kind"
+	metadataKeyToolCalls       = "tool_calls"
 	messageKindThought         = "thought"
 	messageKindToolFeedback    = "tool_feedback"
+	messageKindToolCalls       = "tool_calls"
 	metadataKeyAccountID       = "account_id"
 	metadataKeyGuildID         = "guild_id"
 	metadataKeyTeamID          = "team_id"
diff --git a/pkg/agent/agent_outbound.go b/pkg/agent/agent_outbound.go
index 7e36e4ad8..fcf8cf1a1 100644
--- a/pkg/agent/agent_outbound.go
+++ b/pkg/agent/agent_outbound.go
@@ -4,13 +4,17 @@ package agent
 
 import (
 	"context"
+	"encoding/json"
 	"errors"
 	"fmt"
+	"strings"
 	"time"
 
 	"github.com/sipeed/picoclaw/pkg/bus"
 	"github.com/sipeed/picoclaw/pkg/logger"
+	"github.com/sipeed/picoclaw/pkg/providers"
 	"github.com/sipeed/picoclaw/pkg/tools"
+	"github.com/sipeed/picoclaw/pkg/utils"
 )
 
 func (al *AgentLoop) maybePublishError(ctx context.Context, channel, chatID, sessionKey string, err error) bool {
@@ -123,6 +127,92 @@ func (al *AgentLoop) publishPicoReasoning(ctx context.Context, reasoningContent,
 	}
 }
 
+func (al *AgentLoop) publishPicoToolCallInterim(
+	ctx context.Context,
+	ts *turnState,
+	reasoningContent string,
+	content string,
+	toolCalls []providers.ToolCall,
+) {
+	if ts == nil || ts.chatID == "" || al == nil || al.bus == nil {
+		return
+	}
+
+	if strings.TrimSpace(reasoningContent) != "" {
+		pubCtx, pubCancel := context.WithTimeout(ctx, 3*time.Second)
+		err := al.bus.PublishOutbound(
+			pubCtx,
+			outboundMessageForTurnWithKind(ts, reasoningContent, messageKindThought),
+		)
+		pubCancel()
+		if err != nil && !errors.Is(err, context.DeadlineExceeded) &&
+			!errors.Is(err, context.Canceled) &&
+			!errors.Is(err, bus.ErrBusClosed) {
+			logger.WarnCF("agent", "Failed to publish pico reasoning", map[string]any{
+				"channel": ts.channel,
+				"chat_id": ts.chatID,
+				"error":   err.Error(),
+			})
+		}
+	}
+
+	if !ts.opts.AllowInterimPicoPublish {
+		return
+	}
+
+	if strings.TrimSpace(content) != "" {
+		pubCtx, pubCancel := context.WithTimeout(ctx, 3*time.Second)
+		err := al.bus.PublishOutbound(pubCtx, outboundMessageForTurn(ts, content))
+		pubCancel()
+		if err != nil && !errors.Is(err, context.DeadlineExceeded) &&
+			!errors.Is(err, context.Canceled) &&
+			!errors.Is(err, bus.ErrBusClosed) {
+			logger.WarnCF("agent", "Failed to publish pico interim assistant content", map[string]any{
+				"channel": ts.channel,
+				"chat_id": ts.chatID,
+				"error":   err.Error(),
+			})
+		}
+	}
+
+	visibleToolCalls := utils.BuildVisibleToolCalls(
+		toolCalls,
+		al.cfg.Agents.Defaults.GetToolFeedbackMaxArgsLength(),
+	)
+	if len(visibleToolCalls) == 0 {
+		return
+	}
+
+	rawToolCalls, err := json.Marshal(visibleToolCalls)
+	if err != nil {
+		logger.WarnCF("agent", "Failed to serialize pico tool calls", map[string]any{
+			"channel": ts.channel,
+			"chat_id": ts.chatID,
+			"error":   err.Error(),
+		})
+		return
+	}
+
+	msg := outboundMessageForTurnWithKind(ts, "", messageKindToolCalls)
+	if msg.Context.Raw == nil {
+		msg.Context.Raw = map[string]string{}
+	}
+	msg.Context.Raw[metadataKeyToolCalls] = string(rawToolCalls)
+
+	pubCtx, pubCancel := context.WithTimeout(ctx, 3*time.Second)
+	err = al.bus.PublishOutbound(pubCtx, msg)
+	pubCancel()
+	if err != nil && !errors.Is(err, context.DeadlineExceeded) &&
+		!errors.Is(err, context.Canceled) &&
+		!errors.Is(err, bus.ErrBusClosed) {
+		logger.WarnCF("agent", "Failed to publish pico tool calls", map[string]any{
+			"channel": ts.channel,
+			"chat_id": ts.chatID,
+			"error":   err.Error(),
+		})
+	}
+}
+
 func (al *AgentLoop) handleReasoning(
 	ctx context.Context,
 	reasoningContent, channelName, channelID string,
diff --git a/pkg/agent/agent_test.go b/pkg/agent/agent_test.go
index 01657d43a..17d169ca6 100644
--- a/pkg/agent/agent_test.go
+++ b/pkg/agent/agent_test.go
@@ -3987,6 +3987,7 @@ func TestProcessMessage_PublishesToolFeedbackWhenEnabled(t *testing.T) {
 
 	select {
 	case outbound := <-msgBus.OutboundChan():
+		escapedHeartbeatFile := strings.ReplaceAll(heartbeatFile, `\`, `\\`)
 		if outbound.Channel != "telegram" {
 			t.Fatalf("tool feedback channel = %q, want %q", outbound.Channel, "telegram")
 		}
@@ -4008,7 +4009,7 @@ func TestProcessMessage_PublishesToolFeedbackWhenEnabled(t *testing.T) {
 		if !strings.Contains(outbound.Content, "\"path\":") {
 			t.Fatalf("tool feedback content = %q, want serialized tool arguments", outbound.Content)
 		}
-		if !strings.Contains(outbound.Content, heartbeatFile) {
+		if !strings.Contains(outbound.Content, escapedHeartbeatFile) {
 			t.Fatalf("tool feedback content = %q, want tool argument value", outbound.Content)
 		}
 		if strings.Contains(outbound.Content, "Previous turn explanation") {
@@ -4250,6 +4251,7 @@ func TestProcessMessage_DoesNotLeakReasoningContentInToolFeedback(t *testing.T)
 
 	select {
 	case outbound := <-msgBus.OutboundChan():
+		escapedHeartbeatFile := strings.ReplaceAll(heartbeatFile, `\`, `\\`)
 		if !strings.Contains(outbound.Content, "`read_file`") {
 			t.Fatalf("tool feedback content = %q, want read_file summary", outbound.Content)
 		}
@@ -4262,7 +4264,7 @@ func TestProcessMessage_DoesNotLeakReasoningContentInToolFeedback(t *testing.T)
 		if !strings.Contains(outbound.Content, "\"path\":") {
 			t.Fatalf("tool feedback content = %q, want serialized tool arguments", outbound.Content)
 		}
-		if !strings.Contains(outbound.Content, heartbeatFile) {
+		if !strings.Contains(outbound.Content, escapedHeartbeatFile) {
 			t.Fatalf("tool feedback content = %q, want tool argument value", outbound.Content)
 		}
 		if strings.Contains(outbound.Content, "Read README.md first") {
@@ -4422,22 +4424,28 @@ func TestRun_PicoPublishesAssistantContentDuringToolCallsWithoutFinalDuplicate(t
 		t.Fatalf("PublishInbound() error = %v", err)
 	}
 
-	outputs := make([]string, 0, 2)
+	outputs := make([]bus.OutboundMessage, 0, 3)
 	deadline := time.After(2 * time.Second)
-	for len(outputs) < 2 {
+	for len(outputs) < 3 {
 		select {
 		case outbound := <-msgBus.OutboundChan():
-			outputs = append(outputs, outbound.Content)
+			outputs = append(outputs, outbound)
 		case <-deadline:
 			t.Fatalf("timed out waiting for pico outputs, got %v", outputs)
 		}
 	}
 
-	if outputs[0] != "intermediate model text" {
-		t.Fatalf("first outbound content = %q, want %q", outputs[0], "intermediate model text")
+	if outputs[0].Content != "intermediate model text" {
+		t.Fatalf("first outbound content = %q, want %q", outputs[0].Content, "intermediate model text")
 	}
-	if outputs[1] != "final model text" {
-		t.Fatalf("second outbound content = %q, want %q", outputs[1], "final model text")
+	if outputs[1].Context.Raw[metadataKeyMessageKind] != messageKindToolCalls {
+		t.Fatalf("second outbound = %+v, want tool_calls message", outputs[1])
+	}
+	if !strings.Contains(outputs[1].Context.Raw[metadataKeyToolCalls], "tool_limit_test_tool") {
+		t.Fatalf("second outbound tool_calls = %q, want tool name", outputs[1].Context.Raw[metadataKeyToolCalls])
+	}
+	if outputs[2].Content != "final model text" {
+		t.Fatalf("third outbound content = %q, want %q", outputs[2].Content, "final model text")
 	}
 
 	runCancel()
@@ -4552,22 +4560,31 @@ func TestRun_PicoToolFeedbackSuppressesDuplicateInterimAssistantContent(t *testi
 		t.Fatalf("PublishInbound() error = %v", err)
 	}
 
-	outputs := make([]string, 0, 2)
+	outputs := make([]bus.OutboundMessage, 0, 3)
 	deadline := time.After(2 * time.Second)
-	for len(outputs) < 2 {
+	for len(outputs) < 3 {
 		select {
 		case outbound := <-msgBus.OutboundChan():
-			outputs = append(outputs, outbound.Content)
+			outputs = append(outputs, outbound)
 		case <-deadline:
 			t.Fatalf("timed out waiting for pico outputs, got %v", outputs)
 		}
 	}
 
-	if outputs[0] != "🔧 `tool_limit_test_tool`\nintermediate model text\n```json\n{\n  \"value\": \"x\"\n}\n```" {
-		t.Fatalf("first outbound content = %q, want tool feedback summary", outputs[0])
+	if outputs[0].Content != "intermediate model text" {
+		t.Fatalf("first outbound content = %q, want %q", outputs[0].Content, "intermediate model text")
 	}
-	if outputs[1] != "final model text" {
-		t.Fatalf("second outbound content = %q, want %q", outputs[1], "final model text")
+	if outputs[1].Context.Raw[metadataKeyMessageKind] != messageKindToolCalls {
+		t.Fatalf("second outbound = %+v, want tool_calls message", outputs[1])
+	}
+	if outputs[1].Content != "" {
+		t.Fatalf("second outbound content = %q, want empty tool_calls content", outputs[1].Content)
+	}
+	if !strings.Contains(outputs[1].Context.Raw[metadataKeyToolCalls], "tool_limit_test_tool") {
+		t.Fatalf("second outbound tool_calls = %q, want tool name", outputs[1].Context.Raw[metadataKeyToolCalls])
+	}
+	if outputs[2].Content != "final model text" {
+		t.Fatalf("third outbound content = %q, want %q", outputs[2].Content, "final model text")
 	}
 
 	runCancel()
diff --git a/pkg/agent/pipeline_execute.go b/pkg/agent/pipeline_execute.go
index 0cf3eaa9a..c8ad93943 100644
--- a/pkg/agent/pipeline_execute.go
+++ b/pkg/agent/pipeline_execute.go
@@ -80,7 +80,7 @@ toolLoop:
 						},
 					)
 
-					if shouldPublishToolFeedback(al.cfg, ts) {
+					if shouldPublishToolFeedback(al.cfg, ts) && ts.channel != "pico" {
 						toolFeedbackMaxLen := al.cfg.Agents.Defaults.GetToolFeedbackMaxArgsLength()
 						toolFeedbackExplanation := toolFeedbackExplanationForToolCall(
 							exec.response,
@@ -362,7 +362,7 @@ toolLoop:
 			},
 		)
 
-		if shouldPublishToolFeedback(al.cfg, ts) {
+		if shouldPublishToolFeedback(al.cfg, ts) && ts.channel != "pico" {
 			toolFeedbackMaxLen := al.cfg.Agents.Defaults.GetToolFeedbackMaxArgsLength()
 			toolFeedbackExplanation := toolFeedbackExplanationForToolCall(
 				exec.response,
diff --git a/pkg/agent/pipeline_llm.go b/pkg/agent/pipeline_llm.go
index a954c0ca6..895f00489 100644
--- a/pkg/agent/pipeline_llm.go
+++ b/pkg/agent/pipeline_llm.go
@@ -10,7 +10,6 @@ import (
 	"strings"
 	"time"
 
-	"github.com/sipeed/picoclaw/pkg/bus"
 	"github.com/sipeed/picoclaw/pkg/constants"
 	"github.com/sipeed/picoclaw/pkg/logger"
 	"github.com/sipeed/picoclaw/pkg/providers"
@@ -383,7 +382,11 @@ func (p *Pipeline) CallLLM(
 	}
 
 	reasoningContent := responseReasoningContent(exec.response)
-	if ts.channel == "pico" {
+	shouldPublishPicoToolCallInterim := ts.channel == "pico" && len(exec.response.ToolCalls) > 0
+	if shouldPublishPicoToolCallInterim {
+		// Pico tool-call turns publish their reasoning/content/tool summary as a
+		// structured sequence after the tool-call payload is normalized below.
+	} else if ts.channel == "pico" {
 		go al.publishPicoReasoning(turnCtx, reasoningContent, ts.chatID)
 	} else {
 		go al.handleReasoning(
@@ -419,30 +422,6 @@ func (p *Pipeline) CallLLM(
 	}
 	logger.DebugCF("agent", "LLM response", llmResponseFields)
 
-	if al.bus != nil &&
-		ts.channel == "pico" &&
-		len(exec.response.ToolCalls) > 0 &&
-		ts.opts.AllowInterimPicoPublish &&
-		!shouldPublishToolFeedback(al.cfg, ts) {
-		if strings.TrimSpace(exec.response.Content) != "" {
-			outCtx, outCancel := context.WithTimeout(turnCtx, 3*time.Second)
-			publishErr := al.bus.PublishOutbound(outCtx, bus.OutboundMessage{
-				Channel: ts.channel,
-				ChatID:  ts.chatID,
-				Content: exec.response.Content,
-			})
-			outCancel()
-			if publishErr != nil {
-				logger.WarnCF("agent", "Failed to publish pico interim tool-call content", map[string]any{
-					"error":     publishErr.Error(),
-					"channel":   ts.channel,
-					"chat_id":   ts.chatID,
-					"iteration": iteration,
-				})
-			}
-		}
-	}
-
 	// No-tool-call path: steering check and direct response
 	if len(exec.response.ToolCalls) == 0 || exec.gracefulTerminal {
 		responseContent := exec.response.Content
@@ -531,6 +510,15 @@ func (p *Pipeline) CallLLM(
 		ts.recordPersistedMessage(assistantMsg)
 		ts.ingestMessage(turnCtx, al, assistantMsg)
 	}
+	if shouldPublishPicoToolCallInterim {
+		al.publishPicoToolCallInterim(
+			turnCtx,
+			ts,
+			reasoningContent,
+			exec.response.Content,
+			assistantMsg.ToolCalls,
+		)
+	}
 
 	return ControlToolLoop, nil
 }
diff --git a/pkg/channels/pico/pico.go b/pkg/channels/pico/pico.go
index 31360b3de..9bd8a5b5d 100644
--- a/pkg/channels/pico/pico.go
+++ b/pkg/channels/pico/pico.go
@@ -23,6 +23,7 @@ import (
 	"github.com/sipeed/picoclaw/pkg/config"
 	"github.com/sipeed/picoclaw/pkg/identity"
 	"github.com/sipeed/picoclaw/pkg/logger"
+	"github.com/sipeed/picoclaw/pkg/utils"
 )
 
 // picoConn represents a single WebSocket connection.
@@ -57,8 +58,17 @@ func outboundMessageIsToolFeedback(msg bus.OutboundMessage) bool {
 	return strings.EqualFold(strings.TrimSpace(msg.Context.Raw["message_kind"]), "tool_feedback")
 }
 
+func outboundMessageIsToolCalls(msg bus.OutboundMessage) bool {
+	if len(msg.Context.Raw) == 0 {
+		return false
+	}
+	return strings.EqualFold(strings.TrimSpace(msg.Context.Raw["message_kind"]), MessageKindToolCalls)
+}
+
 func outboundMessageFinalizesTrackedToolFeedback(msg bus.OutboundMessage) bool {
-	return !outboundMessageIsToolFeedback(msg) && !outboundMessageIsThought(msg)
+	return !outboundMessageIsToolFeedback(msg) &&
+		!outboundMessageIsThought(msg) &&
+		!outboundMessageIsToolCalls(msg)
 }
 
 // writeJSON sends a JSON message to the connection with write locking.
@@ -289,6 +299,7 @@ func (c *PicoChannel) Send(ctx context.Context, msg bus.OutboundMessage) ([]stri
 	}
 	isThought := outboundMessageIsThought(msg)
 	isToolFeedback := outboundMessageIsToolFeedback(msg)
+	isToolCalls := outboundMessageIsToolCalls(msg)
 	if isToolFeedback {
 		if msgID, handled, err := c.progress.Update(ctx, msg.ChatID, msg.Content); handled {
 			if err != nil {
@@ -315,6 +326,12 @@ func (c *PicoChannel) Send(ctx context.Context, msg bus.OutboundMessage) ([]stri
 		PayloadKeyThought: isThought,
 		"message_id":      msgID,
 	}
+	if isToolCalls {
+		payload[PayloadKeyKind] = MessageKindToolCalls
+		if toolCalls, ok := picoToolCallsPayload(msg); ok {
+			payload[PayloadKeyToolCalls] = toolCalls
+		}
+	}
 	setContextUsagePayload(payload, msg.ContextUsage)
 	outMsg := newMessage(TypeMessageCreate, payload)
 
@@ -1070,6 +1087,19 @@ func setContextUsagePayload(payload map[string]any, u *bus.ContextUsage) {
 	}
 }
 
+func picoToolCallsPayload(msg bus.OutboundMessage) ([]utils.VisibleToolCall, bool) {
+	raw := strings.TrimSpace(msg.Context.Raw[PayloadKeyToolCalls])
+	if raw == "" {
+		return nil, false
+	}
+
+	var toolCalls []utils.VisibleToolCall
+	if err := json.Unmarshal([]byte(raw), &toolCalls); err != nil || len(toolCalls) == 0 {
+		return nil, false
+	}
+	return toolCalls, true
+}
+
 func (c *PicoChannel) editMessage(
 	ctx context.Context,
 	chatID string,
diff --git a/pkg/channels/pico/protocol.go b/pkg/channels/pico/protocol.go
index 8a27b8c93..46e8fa3ee 100644
--- a/pkg/channels/pico/protocol.go
+++ b/pkg/channels/pico/protocol.go
@@ -19,10 +19,13 @@ const (
 	TypeError         = "error"
 	TypePong          = "pong"
 
-	PayloadKeyContent = "content"
-	PayloadKeyThought = "thought"
+	PayloadKeyContent   = "content"
+	PayloadKeyThought   = "thought"
+	PayloadKeyKind      = "kind"
+	PayloadKeyToolCalls = "tool_calls"
 
-	MessageKindThought = "thought"
+	MessageKindThought   = "thought"
+	MessageKindToolCalls = "tool_calls"
 )
 
 // PicoMessage is the wire format for all Pico Protocol messages.
diff --git a/pkg/utils/visible_tool_calls.go b/pkg/utils/visible_tool_calls.go
new file mode 100644
index 000000000..37a5f60da
--- /dev/null
+++ b/pkg/utils/visible_tool_calls.go
@@ -0,0 +1,109 @@
+package utils
+
+import (
+	"bytes"
+	"encoding/json"
+	"strings"
+
+	"github.com/sipeed/picoclaw/pkg/providers"
+)
+
+type VisibleToolCall struct {
+	ID           string                       `json:"id,omitempty"`
+	Type         string                       `json:"type,omitempty"`
+	Function     *VisibleToolCallFunction     `json:"function,omitempty"`
+	ExtraContent *VisibleToolCallExtraContent `json:"extra_content,omitempty"`
+}
+
+type VisibleToolCallFunction struct {
+	Name      string `json:"name,omitempty"`
+	Arguments string `json:"arguments,omitempty"`
+}
+
+type VisibleToolCallExtraContent struct {
+	ToolFeedbackExplanation string `json:"tool_feedback_explanation,omitempty"`
+}
+
+func BuildVisibleToolCalls(
+	toolCalls []providers.ToolCall,
+	maxArgsLen int,
+) []VisibleToolCall {
+	if len(toolCalls) == 0 {
+		return nil
+	}
+
+	visible := make([]VisibleToolCall, 0, len(toolCalls))
+	for _, tc := range toolCalls {
+		name, _ := VisibleToolCallNameAndArguments(tc)
+		argsPreview := VisibleToolCallArgumentsPreview(tc, maxArgsLen)
+		explanation := ""
+		if tc.ExtraContent != nil {
+			explanation = strings.TrimSpace(tc.ExtraContent.ToolFeedbackExplanation)
+			if maxArgsLen > 0 {
+				explanation = Truncate(explanation, maxArgsLen)
+			}
+		}
+		if name == "" && explanation == "" && argsPreview == "" {
+			continue
+		}
+
+		visibleCall := VisibleToolCall{
+			ID:   strings.TrimSpace(tc.ID),
+			Type: strings.TrimSpace(tc.Type),
+		}
+		if visibleCall.Type == "" {
+			visibleCall.Type = "function"
+		}
+		if name != "" || argsPreview != "" {
+			visibleCall.Function = &VisibleToolCallFunction{
+				Name:      name,
+				Arguments: argsPreview,
+			}
+		}
+		if explanation != "" {
+			visibleCall.ExtraContent = &VisibleToolCallExtraContent{
+				ToolFeedbackExplanation: explanation,
+			}
+		}
+
+		visible = append(visible, visibleCall)
+	}
+
+	if len(visible) == 0 {
+		return nil
+	}
+	return visible
+}
+
+func VisibleToolCallNameAndArguments(tc providers.ToolCall) (string, string) {
+	name := strings.TrimSpace(tc.Name)
+	argsJSON := ""
+	if tc.Function != nil {
+		if name == "" {
+			name = strings.TrimSpace(tc.Function.Name)
+		}
+		argsJSON = strings.TrimSpace(tc.Function.Arguments)
+	}
+	if argsJSON == "" && len(tc.Arguments) > 0 {
+		if encodedArgs, err := json.Marshal(tc.Arguments); err == nil {
+			argsJSON = string(encodedArgs)
+		}
+	}
+	return name, strings.TrimSpace(argsJSON)
+}
+
+func VisibleToolCallArgumentsPreview(tc providers.ToolCall, maxLen int) string {
+	_, argsJSON := VisibleToolCallNameAndArguments(tc)
+	if argsJSON == "" {
+		return ""
+	}
+
+	var pretty bytes.Buffer
+	if err := json.Indent(&pretty, []byte(argsJSON), "", "  "); err == nil {
+		argsJSON = pretty.String()
+	}
+	if maxLen > 0 {
+		return Truncate(argsJSON, maxLen)
+	}
+	return argsJSON
+}
diff --git a/web/backend/api/session.go b/web/backend/api/session.go
index 83819f319..7d0c11fb0 100644
--- a/web/backend/api/session.go
+++ b/web/backend/api/session.go
@@ -2,7 +2,6 @@ package api
 
 import (
 	"bufio"
-	"bytes"
 	"encoding/json"
 	"errors"
 	"net/http"
@@ -53,6 +52,7 @@ type sessionChatMessage struct {
 	Kind        string                  `json:"kind,omitempty"`
 	Media       []string                `json:"media,omitempty"`
 	Attachments []sessionChatAttachment `json:"attachments,omitempty"`
+	ToolCalls   []utils.VisibleToolCall `json:"tool_calls,omitempty"`
 }
 
 type sessionChatAttachment struct {
@@ -456,7 +456,10 @@ func truncateRunes(s string, maxLen int) string {
 }
 
 func sessionChatMessageVisible(msg sessionChatMessage) bool {
-	return strings.TrimSpace(msg.Content) != "" || len(msg.Media) > 0 || len(msg.Attachments) > 0
+	return strings.TrimSpace(msg.Content) != "" ||
+		len(msg.Media) > 0 ||
+		len(msg.Attachments) > 0 ||
+		len(msg.ToolCalls) > 0
 }
 
 func sessionChatMessagePreview(msg sessionChatMessage) string {
@@ -475,6 +478,9 @@ func sessionChatMessagePreview(msg sessionChatMessage) string {
 		}
 		return "[attachment]"
 	}
+	if len(msg.ToolCalls) > 0 {
+		return "[tool call]"
+	}
 	return ""
 }
 
@@ -521,25 +527,11 @@ func sessionTranscriptMessages(
 				}
 			}
 
-			toolSummaryMessages := visibleAssistantToolSummaryMessages(msg.ToolCalls, toolFeedbackMaxArgsLength)
-			if len(toolSummaryMessages) > 0 {
-				transcript = append(transcript, toolSummaryMessages...)
-			}
-
+			toolCallsMsg, hasToolCallsMsg := assistantToolCallsMessage(
+				msg.ToolCalls,
+				toolFeedbackMaxArgsLength,
+			)
 			visibleToolMessages := visibleAssistantToolMessages(msg.ToolCalls)
-			if len(visibleToolMessages) > 0 {
-				transcript = append(transcript, visibleToolMessages...)
-			}
-
-			// When assistant content exactly matches the rendered tool summary or
-			// tool-delivered message, skip it to avoid duplicates. Distinct content
-			// must remain visible in restored session history.
-			if len(msg.ToolCalls) > 0 &&
-				len(msg.Media) == 0 &&
-				len(attachments) == 0 &&
-				assistantToolCallContentDuplicated(msg.Content, toolSummaryMessages, visibleToolMessages) {
-				continue
-			}
 
 			// Pico web chat can persist both visible `message` tool output and a
 			// later plain assistant reply in the same turn. Hide only the fixed
@@ -547,6 +539,12 @@ func sessionTranscriptMessages(
 			content := msg.Content
 			if assistantMessageInternalOnly(msg) {
 				if len(attachments) == 0 {
+					if hasToolCallsMsg {
+						transcript = append(transcript, toolCallsMsg)
+					}
+					if len(visibleToolMessages) > 0 {
+						transcript = append(transcript, visibleToolMessages...)
+					}
 					continue
 				}
 				content = ""
@@ -559,10 +557,22 @@ func sessionTranscriptMessages(
 				Attachments: attachments,
 			}
 			if !sessionChatMessageVisible(chatMsg) {
+				if hasToolCallsMsg {
+					transcript = append(transcript, toolCallsMsg)
+				}
+				if len(visibleToolMessages) > 0 {
+					transcript = append(transcript, visibleToolMessages...)
+				}
 				continue
 			}
 
 			transcript = append(transcript, chatMsg)
+			if hasToolCallsMsg {
+				transcript = append(transcript, toolCallsMsg)
+			}
+			if len(visibleToolMessages) > 0 {
+				transcript = append(transcript, visibleToolMessages...)
+			}
 		}
 	}
 
@@ -580,51 +590,6 @@ func filterSessionChatMessages(messages []sessionChatMessage) []sessionChatMessa
 	return filtered
 }
 
-func assistantToolCallContentDuplicated(
-	content string,
-	toolSummaryMessages []sessionChatMessage,
-	visibleToolMessages []sessionChatMessage,
-) bool {
-	content = strings.TrimSpace(content)
-	if content == "" {
-		return false
-	}
-
-	for _, msg := range toolSummaryMessages {
-		if toolSummaryContainsContent(msg.Content, content) {
-			return true
-		}
-	}
-	for _, msg := range visibleToolMessages {
-		if strings.TrimSpace(msg.Content) == content {
-			return true
-		}
-	}
-	return false
-}
-
-func toolSummaryContainsContent(summary, content string) bool {
-	summary = strings.TrimSpace(summary)
-	content = strings.TrimSpace(content)
-	if summary == "" || content == "" {
-		return false
-	}
-	if summary == content {
-		return true
-	}
-
-	_, body, hasBody := strings.Cut(summary, "\n")
-	if !hasBody {
-		return false
-	}
-	body = strings.TrimSpace(body)
-	if body == content {
-		return true
-	}
-	firstSection, _, _ := strings.Cut(body, "\n```")
-	return strings.TrimSpace(firstSection) == content
-}
-
 func sessionAttachments(msg providers.Message) []sessionChatAttachment {
 	if len(msg.Attachments) == 0 {
 		return nil
@@ -720,80 +685,34 @@ func assistantThoughtMessage(msg providers.Message) (sessionChatMessage, bool) {
 	}, true
 }
 
-func visibleAssistantToolSummaryMessages(
+func assistantToolCallsMessage(
 	toolCalls []providers.ToolCall,
 	toolFeedbackMaxArgsLength int,
-) []sessionChatMessage {
+) (sessionChatMessage, bool) {
 	if len(toolCalls) == 0 {
-		return nil
+		return sessionChatMessage{}, false
 	}
 	if toolFeedbackMaxArgsLength <= 0 {
 		toolFeedbackMaxArgsLength = defaultToolFeedbackMaxArgsLength()
 	}
 
-	messages := make([]sessionChatMessage, 0, len(toolCalls))
-	for _, tc := range toolCalls {
-		name, argsJSON := toolCallNameAndArguments(tc)
-		if strings.TrimSpace(name) == "" {
-			continue
-		}
-		if name == "web_search" || name == "web_fetch" {
-			continue
-		}
-		if name == "message" {
-			if _, ok := parseMessageToolContent(argsJSON); ok {
-				continue
-			}
-		}
-
-		messages = append(messages, sessionChatMessage{
-			Role: "assistant",
-			Content: utils.FormatToolFeedbackMessage(
-				name,
-				visibleAssistantToolFeedbackExplanation(tc, toolFeedbackMaxArgsLength),
-				visibleAssistantToolArgsPreview(tc, toolFeedbackMaxArgsLength),
-			),
-		})
+	visibleToolCalls := utils.BuildVisibleToolCalls(toolCalls, toolFeedbackMaxArgsLength)
+	if len(visibleToolCalls) == 0 {
+		return sessionChatMessage{}, false
 	}
 
-	return messages
-}
-
-func visibleAssistantToolFeedbackExplanation(
-	tc providers.ToolCall,
-	toolFeedbackMaxArgsLength int,
-) string {
-	if tc.ExtraContent != nil {
-		if explanation := strings.TrimSpace(tc.ExtraContent.ToolFeedbackExplanation); explanation != "" {
-			return utils.Truncate(explanation, toolFeedbackMaxArgsLength)
-		}
-	}
-	return ""
+	return sessionChatMessage{
+		Role:      "assistant",
+		Kind:      "tool_calls",
+		ToolCalls: visibleToolCalls,
+	}, true
 }
 
 func visibleAssistantToolArgsPreview(
 	tc providers.ToolCall,
 	toolFeedbackMaxArgsLength int,
 ) string {
-	argsJSON := ""
-	if tc.Function != nil {
-		argsJSON = tc.Function.Arguments
-	}
-	if strings.TrimSpace(argsJSON) == "" && len(tc.Arguments) > 0 {
-		if encodedArgs, err := json.MarshalIndent(tc.Arguments, "", "  "); err == nil {
-			argsJSON = string(encodedArgs)
-		}
-	}
-	argsJSON = strings.TrimSpace(argsJSON)
-	if argsJSON == "" {
-		return ""
-	}
-	var pretty bytes.Buffer
-	if err := json.Indent(&pretty, []byte(argsJSON), "", "  "); err == nil {
-		argsJSON = pretty.String()
-	}
-
-	return utils.Truncate(argsJSON, toolFeedbackMaxArgsLength)
+	return utils.VisibleToolCallArgumentsPreview(tc, toolFeedbackMaxArgsLength)
 }
 
 func visibleAssistantToolMessages(toolCalls []providers.ToolCall) []sessionChatMessage {
@@ -803,7 +722,7 @@ func visibleAssistantToolMessages(toolCalls []providers.ToolCall) []sessionChatM
 
 	messages := make([]sessionChatMessage, 0, len(toolCalls))
 	for _, tc := range toolCalls {
-		name, argsJSON := toolCallNameAndArguments(tc)
+		name, argsJSON := utils.VisibleToolCallNameAndArguments(tc)
 		if name != "message" {
 			continue
 		}
@@ -820,23 +739,6 @@ func visibleAssistantToolMessages(toolCalls []providers.ToolCall) []sessionChatM
 	return messages
 }
 
-func toolCallNameAndArguments(tc providers.ToolCall) (string, string) {
-	name := tc.Name
-	argsJSON := ""
-	if tc.Function != nil {
-		if name == "" {
-			name = tc.Function.Name
-		}
-		argsJSON = tc.Function.Arguments
-	}
-	if strings.TrimSpace(argsJSON) == "" && len(tc.Arguments) > 0 {
-		if encodedArgs, err := json.Marshal(tc.Arguments); err == nil {
-			argsJSON = string(encodedArgs)
-		}
-	}
-	return name, argsJSON
-}
-
 func parseMessageToolContent(argsJSON string) (string, bool) {
 	var args struct {
 		Content string `json:"content"`
diff --git a/web/backend/api/session_test.go b/web/backend/api/session_test.go
index ec91b9792..8ef26df5f 100644
--- a/web/backend/api/session_test.go
+++ b/web/backend/api/session_test.go
@@ -32,6 +32,25 @@ func sessionsTestDir(t *testing.T, configPath string) string {
 	return dir
 }
 
+func assertVisibleToolCallMessage(
+	t *testing.T,
+	msg sessionChatMessage,
+	toolName string,
+) utils.VisibleToolCall {
+	t.Helper()
+
+	if msg.Role != "assistant" || msg.Kind != "tool_calls" {
+		t.Fatalf("message = %#v, want assistant/tool_calls", msg)
+	}
+	if len(msg.ToolCalls) != 1 {
+		t.Fatalf("len(message.ToolCalls) = %d, want 1", len(msg.ToolCalls))
+	}
+	if got := msg.ToolCalls[0].Function; got == nil || got.Name != toolName {
+		t.Fatalf("tool call = %#v, want function %q", msg.ToolCalls[0], toolName)
+	}
+	return msg.ToolCalls[0]
+}
+
 func TestHandleListSessions_JSONLStorage(t *testing.T) {
 	configPath, cleanup := setupOAuthTestEnv(t)
 	defer cleanup()
@@ -516,11 +535,7 @@ func TestHandleGetSession_SkipsTransientThoughtMessages(t *testing.T) {
 	}
 
 	var resp struct {
-		Messages []struct {
-			Role    string `json:"role"`
-			Content string `json:"content"`
-			Kind    string `json:"kind"`
-		} `json:"messages"`
+		Messages []sessionChatMessage `json:"messages"`
 	}
 	if err := json.Unmarshal(rec.Body.Bytes(), &resp); err != nil {
 		t.Fatalf("Unmarshal() error = %v", err)
@@ -569,11 +584,7 @@ func TestHandleGetSession_ReconstructsThoughtFromAssistantReasoningContent(t *te
 	}
 
 	var resp struct {
-		Messages []struct {
-			Role    string `json:"role"`
-			Content string `json:"content"`
-			Kind    string `json:"kind"`
-		} `json:"messages"`
+		Messages []sessionChatMessage `json:"messages"`
 	}
 	if err := json.Unmarshal(rec.Body.Bytes(), &resp); err != nil {
 		t.Fatalf("Unmarshal() error = %v", err)
@@ -667,11 +678,7 @@ func TestHandleGetSession_ReconstructsRefreshMatrixForThoughtAndToolSummary(t *t
 	}
 
 	var resp struct {
-		Messages []struct {
-			Role    string `json:"role"`
-			Content string `json:"content"`
-			Kind    string `json:"kind"`
-		} `json:"messages"`
+		Messages []sessionChatMessage `json:"messages"`
 	}
 	if err := json.Unmarshal(rec.Body.Bytes(), &resp); err != nil {
 		t.Fatalf("Unmarshal() error = %v", err)
@@ -694,20 +701,14 @@ func TestHandleGetSession_ReconstructsRefreshMatrixForThoughtAndToolSummary(t *t
 	assertMessage(2, "assistant", "", "plain visible")
 	assertMessage(3, "user", "", "turn2")
 	assertMessage(4, "assistant", "thought", "tool thought")
-	if !strings.Contains(resp.Messages[5].Content, "`read_file`") {
-		t.Fatalf("messages[5] = %#v, want read_file tool summary", resp.Messages[5])
-	}
+	assertVisibleToolCallMessage(t, resp.Messages[5], "read_file")
 	assertMessage(6, "user", "", "turn3")
-	if !strings.Contains(resp.Messages[7].Content, "`list_dir`") {
-		t.Fatalf("messages[7] = %#v, want list_dir tool summary", resp.Messages[7])
-	}
-	assertMessage(8, "assistant", "", "tool visible only")
+	assertMessage(7, "assistant", "", "tool visible only")
+	assertVisibleToolCallMessage(t, resp.Messages[8], "list_dir")
 	assertMessage(9, "user", "", "turn4")
 	assertMessage(10, "assistant", "thought", "tool mixed thought")
-	if !strings.Contains(resp.Messages[11].Content, "`exec`") {
-		t.Fatalf("messages[11] = %#v, want exec tool summary", resp.Messages[11])
-	}
-	assertMessage(12, "assistant", "", "tool visible and thought")
+	assertMessage(11, "assistant", "", "tool visible and thought")
+	assertVisibleToolCallMessage(t, resp.Messages[12], "exec")
 }
 
 func TestHandleGetSession_ReconstructsVisibleMessageToolOutputWithoutDuplicateSummary(t *testing.T) {
@@ -758,27 +759,20 @@ func TestHandleGetSession_ReconstructsVisibleMessageToolOutputWithoutDuplicateSu
 	}
 
 	var resp struct {
-		Messages []struct {
-			Role    string `json:"role"`
-			Content string `json:"content"`
-		} `json:"messages"`
+		Messages []sessionChatMessage `json:"messages"`
 	}
 	if err := json.Unmarshal(rec.Body.Bytes(), &resp); err != nil {
 		t.Fatalf("Unmarshal() error = %v", err)
 	}
-	if len(resp.Messages) != 2 {
-		t.Fatalf("len(resp.Messages) = %d, want 2", len(resp.Messages))
+	if len(resp.Messages) != 3 {
+		t.Fatalf("len(resp.Messages) = %d, want 3", len(resp.Messages))
 	}
 	if resp.Messages[0].Role != "user" || resp.Messages[0].Content != "test" {
 		t.Fatalf("first message = %#v, want user/test", resp.Messages[0])
 	}
-	if resp.Messages[1].Role != "assistant" || resp.Messages[1].Content != "visible tool output" {
-		t.Fatalf("assistant message = %#v, want visible tool output", resp.Messages[1])
-	}
-	for _, msg := range resp.Messages {
-		if msg.Role == "tool" || strings.Contains(msg.Content, "`message`") {
-			t.Fatalf("unexpected raw tool or duplicate message-tool summary: %#v", msg)
-		}
+	assertVisibleToolCallMessage(t, resp.Messages[1], "message")
+	if resp.Messages[2].Role != "assistant" || resp.Messages[2].Content != "visible tool output" {
+		t.Fatalf("assistant message = %#v, want visible tool output", resp.Messages[2])
 	}
 }
 
@@ -829,25 +823,23 @@ func TestHandleGetSession_PreservesFinalAssistantReplyAfterMessageToolOutput(t *
 	}
 
 	var resp struct {
-		Messages []struct {
-			Role    string `json:"role"`
-			Content string `json:"content"`
-		} `json:"messages"`
+		Messages []sessionChatMessage `json:"messages"`
 	}
 	if err := json.Unmarshal(rec.Body.Bytes(), &resp); err != nil {
 		t.Fatalf("Unmarshal() error = %v", err)
 	}
-	if len(resp.Messages) != 3 {
-		t.Fatalf("len(resp.Messages) = %d, want 3", len(resp.Messages))
+	if len(resp.Messages) != 4 {
+		t.Fatalf("len(resp.Messages) = %d, want 4", len(resp.Messages))
 	}
 	if resp.Messages[0].Role != "user" || resp.Messages[0].Content != "test" {
 		t.Fatalf("first message = %#v, want user/test", resp.Messages[0])
 	}
-	if resp.Messages[1].Role != "assistant" || resp.Messages[1].Content != "visible tool output" {
-		t.Fatalf("interim assistant message = %#v, want visible tool output", resp.Messages[1])
+	assertVisibleToolCallMessage(t, resp.Messages[1], "message")
+	if resp.Messages[2].Role != "assistant" || resp.Messages[2].Content != "visible tool output" {
+		t.Fatalf("interim assistant message = %#v, want visible tool output", resp.Messages[2])
 	}
-	if resp.Messages[2].Role != "assistant" || resp.Messages[2].Content != "final assistant reply" {
-		t.Fatalf("final assistant message = %#v, want final assistant reply", resp.Messages[2])
+	if resp.Messages[3].Role != "assistant" || resp.Messages[3].Content != "final assistant reply" {
+		t.Fatalf("final assistant message = %#v, want final assistant reply", resp.Messages[3])
 	}
 }
 
@@ -904,8 +896,8 @@ func TestHandleListSessions_MessageCountUsesVisibleTranscript(t *testing.T) {
 	if len(items) != 1 {
 		t.Fatalf("len(items) = %d, want 1", len(items))
 	}
-	if items[0].MessageCount != 2 {
-		t.Fatalf("items[0].MessageCount = %d, want 2", items[0].MessageCount)
+	if items[0].MessageCount != 3 {
+		t.Fatalf("items[0].MessageCount = %d, want 3", items[0].MessageCount)
 	}
 }
 
@@ -959,25 +951,24 @@ func TestHandleGetSession_DoesNotDuplicateAssistantToolCallContent(t *testing.T)
 	}
 
 	var resp struct {
-		Messages []struct {
-			Role    string `json:"role"`
-			Content string `json:"content"`
-		} `json:"messages"`
+		Messages []sessionChatMessage `json:"messages"`
 	}
 	if err := json.Unmarshal(rec.Body.Bytes(), &resp); err != nil {
 		t.Fatalf("Unmarshal() error = %v", err)
 	}
-	if len(resp.Messages) != 2 {
-		t.Fatalf("len(resp.Messages) = %d, want 2", len(resp.Messages))
+	if len(resp.Messages) != 3 {
+		t.Fatalf("len(resp.Messages) = %d, want 3", len(resp.Messages))
 	}
 	if resp.Messages[0].Role != "user" || resp.Messages[0].Content != "check file" {
 		t.Fatalf("first message = %#v, want user/check file", resp.Messages[0])
 	}
-	if !strings.Contains(resp.Messages[1].Content, "`read_file`") {
-		t.Fatalf("tool summary message = %#v, want read_file summary", resp.Messages[1])
+	if resp.Messages[1].Content != "Read the file before replying." {
+		t.Fatalf("assistant content = %#v, want preserved assistant content", resp.Messages[1])
 	}
-	if !strings.Contains(resp.Messages[1].Content, "Read the file before replying.") {
-		t.Fatalf("tool summary message = %#v, want tool explanation", resp.Messages[1])
+	toolCall := assertVisibleToolCallMessage(t, resp.Messages[2], "read_file")
+	if toolCall.ExtraContent == nil ||
+		toolCall.ExtraContent.ToolFeedbackExplanation != "Read the file before replying." {
+		t.Fatalf("tool call = %#v, want explanation", toolCall)
 	}
 }
 
@@ -1030,10 +1021,7 @@ func TestHandleGetSession_PreservesDistinctAssistantToolCallContent(t *testing.T
 	}
 
 	var resp struct {
-		Messages []struct {
-			Role    string `json:"role"`
-			Content string `json:"content"`
-		} `json:"messages"`
+		Messages []sessionChatMessage `json:"messages"`
 	}
 	if err := json.Unmarshal(rec.Body.Bytes(), &resp); err != nil {
 		t.Fatalf("Unmarshal() error = %v", err)
@@ -1041,13 +1029,11 @@ func TestHandleGetSession_PreservesDistinctAssistantToolCallContent(t *testing.T
 	if len(resp.Messages) != 3 {
 		t.Fatalf("len(resp.Messages) = %d, want 3", len(resp.Messages))
 	}
-	if !strings.Contains(resp.Messages[1].Content, "`read_file`") {
-		t.Fatalf("tool summary message = %#v, want read_file summary", resp.Messages[1])
-	}
-	if resp.Messages[2].Role != "assistant" ||
-		resp.Messages[2].Content != "I will summarize the findings after reading the file." {
-		t.Fatalf("assistant content = %#v, want preserved distinct content", resp.Messages[2])
+	if resp.Messages[1].Role != "assistant" ||
+		resp.Messages[1].Content != "I will summarize the findings after reading the file." {
+		t.Fatalf("assistant content = %#v, want preserved distinct content", resp.Messages[1])
 	}
+	assertVisibleToolCallMessage(t, resp.Messages[2], "read_file")
 }
 
 func TestHandleGetSession_PreservesMediaWhenAssistantToolCallContentDuplicatesSummary(t *testing.T) {
@@ -1100,11 +1086,7 @@ func TestHandleGetSession_PreservesMediaWhenAssistantToolCallContentDuplicatesSu
 	}
 
 	var resp struct {
-		Messages []struct {
-			Role    string   `json:"role"`
-			Content string   `json:"content"`
-			Media   []string `json:"media"`
-		} `json:"messages"`
+		Messages []sessionChatMessage `json:"messages"`
 	}
 	if err := json.Unmarshal(rec.Body.Bytes(), &resp); err != nil {
 		t.Fatalf("Unmarshal() error = %v", err)
@@ -1112,23 +1094,16 @@ func TestHandleGetSession_PreservesMediaWhenAssistantToolCallContentDuplicatesSu
 	if len(resp.Messages) != 3 {
 		t.Fatalf("len(resp.Messages) = %d, want 3", len(resp.Messages))
 	}
-	if !strings.Contains(resp.Messages[1].Content, "`view_image`") {
-		t.Fatalf("tool summary message = %#v, want view_image summary", resp.Messages[1])
+	if resp.Messages[1].Role != "assistant" {
+		t.Fatalf("assistant message role = %q, want assistant", resp.Messages[1].Role)
 	}
-	if resp.Messages[2].Role != "assistant" {
-		t.Fatalf("assistant message role = %q, want assistant", resp.Messages[2].Role)
+	if resp.Messages[1].Content != "Reviewing the generated screenshot." {
+		t.Fatalf("assistant content = %q, want preserved duplicated content with media", resp.Messages[1].Content)
 	}
-	if resp.Messages[2].Content != "Reviewing the generated screenshot." {
-		t.Fatalf("assistant content = %q, want preserved duplicated content with media", resp.Messages[2].Content)
-	}
-	if len(resp.Messages[2].Media) != 1 || resp.Messages[2].Media[0] != "data:image/png;base64,abc123" {
-		t.Fatalf("assistant media = %#v, want preserved media", resp.Messages[2].Media)
-	}
-	for _, msg := range resp.Messages {
-		if msg.Role == "tool" || strings.Contains(msg.Content, "raw read_file result") {
-			t.Fatalf("unexpected raw tool result in history: %#v", msg)
-		}
+	if len(resp.Messages[1].Media) != 1 || resp.Messages[1].Media[0] != "data:image/png;base64,abc123" {
+		t.Fatalf("assistant media = %#v, want preserved media", resp.Messages[1].Media)
 	}
+	assertVisibleToolCallMessage(t, resp.Messages[2], "view_image")
 }
 
 func TestHandleGetSession_PreservesAttachmentsWhenAssistantToolCallContentDuplicatesSummary(t *testing.T) {
@@ -1198,21 +1173,19 @@ func TestHandleGetSession_PreservesAttachmentsWhenAssistantToolCallContentDuplic
 	if len(resp.Messages) != 3 {
 		t.Fatalf("len(resp.Messages) = %d, want 3", len(resp.Messages))
 	}
-	if !strings.Contains(resp.Messages[1].Content, "`read_file`") {
-		t.Fatalf("tool summary message = %#v, want read_file summary", resp.Messages[1])
+	if resp.Messages[1].Role != "assistant" {
+		t.Fatalf("assistant message role = %q, want assistant", resp.Messages[1].Role)
 	}
-	if resp.Messages[2].Role != "assistant" {
-		t.Fatalf("assistant message role = %q, want assistant", resp.Messages[2].Role)
+	if resp.Messages[1].Content != "Reviewing the generated report." {
+		t.Fatalf("assistant content = %q, want preserved duplicated content", resp.Messages[1].Content)
 	}
-	if resp.Messages[2].Content != "Reviewing the generated report." {
-		t.Fatalf("assistant content = %q, want preserved duplicated content", resp.Messages[2].Content)
+	if len(resp.Messages[1].Attachments) != 1 {
+		t.Fatalf("len(assistant.Attachments) = %d, want 1", len(resp.Messages[1].Attachments))
 	}
-	if len(resp.Messages[2].Attachments) != 1 {
-		t.Fatalf("len(assistant.Attachments) = %d, want 1", len(resp.Messages[2].Attachments))
-	}
-	if resp.Messages[2].Attachments[0].URL != "https://example.com/report.txt" {
-		t.Fatalf("attachment url = %q, want report URL", resp.Messages[2].Attachments[0].URL)
+	if resp.Messages[1].Attachments[0].URL != "https://example.com/report.txt" {
+		t.Fatalf("attachment url = %q, want report URL", resp.Messages[1].Attachments[0].URL)
 	}
+	assertVisibleToolCallMessage(t, resp.Messages[2], "read_file")
 }
 
 func TestHandleGetSession_UsesConfiguredToolFeedbackMaxArgsLength(t *testing.T) {
@@ -1273,10 +1246,7 @@ func TestHandleGetSession_UsesConfiguredToolFeedbackMaxArgsLength(t *testing.T)
 	}
 
 	var resp struct {
-		Messages []struct {
-			Role    string `json:"role"`
-			Content string `json:"content"`
-		} `json:"messages"`
+		Messages []sessionChatMessage `json:"messages"`
 	}
 	err = json.Unmarshal(rec.Body.Bytes(), &resp)
 	if err != nil {
@@ -1287,17 +1257,15 @@ func TestHandleGetSession_UsesConfiguredToolFeedbackMaxArgsLength(t *testing.T)
 	}
 
 	wantPreview := utils.Truncate(explanation, 20)
-	if !strings.Contains(resp.Messages[1].Content, wantPreview) {
-		t.Fatalf("tool summary = %q, want preview %q", resp.Messages[1].Content, wantPreview)
-	}
 	wantArgsPreview := visibleAssistantToolArgsPreview(providers.ToolCall{
 		Function: &providers.FunctionCall{Arguments: argsJSON},
 	}, 20)
-	if !strings.Contains(resp.Messages[1].Content, wantArgsPreview) {
-		t.Fatalf("tool summary = %q, want args preview %q", resp.Messages[1].Content, wantArgsPreview)
+	toolCall := assertVisibleToolCallMessage(t, resp.Messages[1], "read_file")
+	if toolCall.ExtraContent == nil || toolCall.ExtraContent.ToolFeedbackExplanation != wantPreview {
+		t.Fatalf("tool call = %#v, want preview %q", toolCall, wantPreview)
 	}
-	if !strings.Contains(resp.Messages[1].Content, "`read_file`") {
-		t.Fatalf("tool summary = %q, want read_file summary", resp.Messages[1].Content)
+	if toolCall.Function == nil || toolCall.Function.Arguments != wantArgsPreview {
+		t.Fatalf("tool call = %#v, want args preview %q", toolCall, wantArgsPreview)
 	}
 }
 
@@ -1357,10 +1325,7 @@ func TestHandleGetSession_FallsBackToLegacyToolArgumentsWhenExplanationMissing(t
 	}
 
 	var resp struct {
-		Messages []struct {
-			Role    string `json:"role"`
-			Content string `json:"content"`
-		} `json:"messages"`
+		Messages []sessionChatMessage `json:"messages"`
 	}
 	if err := json.Unmarshal(rec.Body.Bytes(), &resp); err != nil {
 		t.Fatalf("Unmarshal() error = %v", err)
@@ -1372,11 +1337,9 @@ func TestHandleGetSession_FallsBackToLegacyToolArgumentsWhenExplanationMissing(t
 	wantPreview := visibleAssistantToolArgsPreview(providers.ToolCall{
 		Function: &providers.FunctionCall{Arguments: argsJSON},
 	}, 20)
-	if !strings.Contains(resp.Messages[1].Content, "`read_file`") {
-		t.Fatalf("tool summary = %q, want read_file summary", resp.Messages[1].Content)
-	}
-	if !strings.Contains(resp.Messages[1].Content, wantPreview) {
-		t.Fatalf("tool summary = %q, want legacy args preview %q", resp.Messages[1].Content, wantPreview)
+	toolCall := assertVisibleToolCallMessage(t, resp.Messages[1], "read_file")
+	if toolCall.Function == nil || toolCall.Function.Arguments != wantPreview {
+		t.Fatalf("tool call = %#v, want legacy args preview %q", toolCall, wantPreview)
 	}
 }
 
diff --git a/web/frontend/src/api/sessions.ts b/web/frontend/src/api/sessions.ts
index d98914a59..edd7d7c27 100644
--- a/web/frontend/src/api/sessions.ts
+++ b/web/frontend/src/api/sessions.ts
@@ -14,7 +14,7 @@ export interface SessionDetail {
   messages: {
     role: "user" | "assistant"
     content: string
-    kind?: "normal" | "thought"
+    kind?: "normal" | "thought" | "tool_calls"
     media?: string[]
     attachments?: {
       type?: "image" | "audio" | "video" | "file"
@@ -22,6 +22,17 @@ export interface SessionDetail {
       filename?: string
       content_type?: string
     }[]
+    tool_calls?: {
+      id?: string
+      type?: string
+      function?: {
+        name?: string
+        arguments?: string
+      }
+      extra_content?: {
+        tool_feedback_explanation?: string
+      }
+    }[]
   }[]
   summary: string
   created: string
diff --git a/web/frontend/src/components/chat/assistant-message.tsx b/web/frontend/src/components/chat/assistant-message.tsx
index 814ddc2f9..07a3c0abc 100644
--- a/web/frontend/src/components/chat/assistant-message.tsx
+++ b/web/frontend/src/components/chat/assistant-message.tsx
@@ -5,6 +5,7 @@ import {
   IconCopy,
   IconDownload,
   IconFileText,
+  IconTool,
 } from "@tabler/icons-react"
 import { useState } from "react"
 import { useTranslation } from "react-i18next"
@@ -17,24 +18,34 @@ import remarkGfm from "remark-gfm"
 import { Button } from "@/components/ui/button"
 import { formatMessageTime } from "@/hooks/use-pico-chat"
 import { cn } from "@/lib/utils"
-import { type ChatAttachment } from "@/store/chat"
+import {
+  type AssistantMessageKind,
+  type ChatAttachment,
+  type ChatToolCall,
+} from "@/store/chat"
 
 interface AssistantMessageProps {
   content: string
   attachments?: ChatAttachment[]
-  isThought?: boolean
+  kind?: AssistantMessageKind
+  toolCalls?: ChatToolCall[]
   timestamp?: string | number
 }
 
 export function AssistantMessage({
   content,
   attachments = [],
-  isThought = false,
+  kind = "normal",
+  toolCalls = [],
   timestamp = "",
 }: AssistantMessageProps) {
   const { t } = useTranslation()
   const [isCopied, setIsCopied] = useState(false)
+  const isThought = kind === "thought"
+  const isToolCalls = kind === "tool_calls"
+  const isCollapsedBlock = isThought || isToolCalls
   const hasText = content.trim().length > 0
+  const hasToolCalls = toolCalls.length > 0
   const imageAttachments = attachments.filter(
     (attachment) => attachment.type === "image",
   )
@@ -52,9 +63,13 @@ export function AssistantMessage({
     })
   }
 
+  const collapsedLabel = isThought
+    ? t("chat.reasoningLabel")
+    : t("chat.toolCallsLabel")
+
   return (
     <div className="group flex w-full flex-col gap-1.5">
-      {!isThought && (
+      {!isCollapsedBlock && (
         <div className="text-muted-foreground/60 flex items-center justify-between gap-2 px-1 text-xs opacity-70">
           <div className="flex items-center gap-2">
             <span>PicoClaw</span>
@@ -68,23 +83,27 @@ export function AssistantMessage({
         </div>
       )}
 
-      {(hasText || isThought) && (
+      {(hasText || isCollapsedBlock || hasToolCalls) && (
         <div
           className={cn(
             "relative overflow-hidden rounded-xl border",
-            isThought
+            isCollapsedBlock
               ? "border-border/30 bg-muted/20 text-muted-foreground dark:border-border/20 dark:bg-muted/10"
               : "bg-card text-card-foreground border-border/60",
           )}
         >
-          {isThought && (
+          {isCollapsedBlock && (
             <div
               className="text-muted-foreground/60 hover:text-muted-foreground/80 flex cursor-pointer items-center justify-between px-3 py-2 text-[12px] font-medium transition-colors select-none"
               onClick={() => setIsExpanded(!isExpanded)}
             >
               <div className="flex items-center gap-1.5">
-                <IconBrain className="size-3.5" />
-                <span>{t("chat.reasoningLabel")}</span>
+                {isThought ? (
+                  <IconBrain className="size-3.5" />
+                ) : (
+                  <IconTool className="size-3.5" />
+                )}
+                <span>{collapsedLabel}</span>
               </div>
               <IconChevronDown
                 className={cn(
@@ -94,7 +113,77 @@ export function AssistantMessage({
               />
             </div>
           )}
-          {(!isThought || isExpanded) && hasText && (
+          {(!isCollapsedBlock || isExpanded) && isToolCalls && hasToolCalls && (
+            <div className="space-y-3 px-3 pt-0 pb-3">
+              {toolCalls.map((toolCall, index) => {
+                const explanation =
+                  toolCall.extraContent?.toolFeedbackExplanation?.trim() ?? ""
+                const toolName = toolCall.function?.name?.trim() ?? ""
+                const toolArguments = toolCall.function?.arguments?.trim() ?? ""
+                const hasFunctionSummary = toolName || toolArguments
+
+                if (!explanation && !hasFunctionSummary) {
+                  return null
+                }
+
+                return (
+                  <div
+                    key={toolCall.id ?? `${toolName}-${index}`}
+                    className={cn(
+                      "space-y-3",
+                      index > 0 && "border-border/20 border-t pt-3",
+                    )}
+                  >
+                    {explanation && (
+                      <div className="space-y-1.5">
+                        <div className="text-muted-foreground/55 text-[11px] font-medium tracking-wide uppercase">
+                          {t("chat.toolCallExplanationLabel")}
+                        </div>
+                        <div className="prose dark:prose-invert prose-p:my-1.5 prose-p:whitespace-pre-wrap max-w-none text-[13px] leading-relaxed [overflow-wrap:anywhere] break-words opacity-75">
+                          <ReactMarkdown
+                            remarkPlugins={[remarkGfm]}
+                            rehypePlugins={[
+                              rehypeRaw,
+                              rehypeSanitize,
+                              rehypeHighlight,
+                            ]}
+                          >
+                            {explanation}
+                          </ReactMarkdown>
+                        </div>
+                      </div>
+                    )}
+
+                    {hasFunctionSummary && (
+                      <div
+                        className={cn(
+                          "space-y-1.5",
+                          explanation && "border-border/20 border-t pt-3",
+                        )}
+                      >
+                        <div className="text-muted-foreground/55 text-[11px] font-medium tracking-wide uppercase">
+                          {t("chat.toolCallFunctionLabel")}
+                        </div>
+                        <div className="bg-background/55 border-border/25 space-y-2 rounded-lg border px-3 py-2.5">
+                          {toolName && (
+                            <div className="text-foreground/75 font-mono text-[12px] font-semibold">
+                              {toolName}
+                            </div>
+                          )}
+                          {toolArguments && (
+                            <pre className="text-muted-foreground/75 overflow-x-auto font-mono text-[12px] leading-relaxed break-words whitespace-pre-wrap">
+                              {toolArguments}
+                            </pre>
+                          )}
+                        </div>
+                      </div>
+                    )}
+                  </div>
+                )
+              })}
+            </div>
+          )}
+          {(!isCollapsedBlock || isExpanded) && !isToolCalls && hasText && (
             <div
               className={cn(
                 "prose dark:prose-invert prose-pre:my-2 prose-pre:overflow-x-auto prose-pre:rounded-lg prose-pre:border prose-pre:bg-zinc-100 prose-pre:p-0 prose-pre:text-zinc-900 dark:prose-pre:bg-zinc-950 dark:prose-pre:text-zinc-100 max-w-none [overflow-wrap:anywhere] break-words",
@@ -112,7 +201,7 @@ export function AssistantMessage({
             </div>
           )}
 
-          {!isThought && hasText && (
+          {!isCollapsedBlock && hasText && (
             <Button
               variant="ghost"
               size="icon"
@@ -139,7 +228,7 @@ export function AssistantMessage({
               href={attachment.url}
               target="_blank"
               rel="noreferrer"
-              className="group/img relative overflow-hidden rounded-xl border border-border/50 bg-muted/30 shadow-sm transition-colors hover:border-border/80"
+              className="group/img border-border/50 bg-muted/30 hover:border-border/80 relative overflow-hidden rounded-xl border shadow-sm transition-colors"
             >
               <img
                 src={attachment.url}
@@ -159,20 +248,21 @@ export function AssistantMessage({
               key={`${attachment.url}-${index}`}
               href={attachment.url}
               download={attachment.filename}
-              className="group/file flex w-fit min-w-[220px] max-w-sm items-center gap-3.5 rounded-xl border border-border/60 bg-card px-4 py-3 transition-all duration-300 hover:-translate-y-0.5 hover:border-violet-500/30 hover:shadow-sm dark:hover:border-violet-500/40"
+              className="group/file border-border/60 bg-card flex w-fit max-w-sm min-w-[220px] items-center gap-3.5 rounded-xl border px-4 py-3 transition-all duration-300 hover:-translate-y-0.5 hover:border-violet-500/30 hover:shadow-sm dark:hover:border-violet-500/40"
             >
               <div className="flex h-10 w-10 shrink-0 items-center justify-center rounded-lg text-violet-400 ring-1 ring-violet-500/10 dark:bg-violet-500/10 dark:text-violet-400 dark:ring-violet-500/30">
                 <IconFileText className="h-5 w-5" />
               </div>
               <div className="flex min-w-0 flex-1 flex-col pr-1">
-                <span className="truncate text-[14px] font-medium leading-tight text-foreground/90 transition-colors group-hover/file:text-violet-600 dark:group-hover/file:text-violet-400">
+                <span className="text-foreground/90 truncate text-[14px] leading-tight font-medium transition-colors group-hover/file:text-violet-600 dark:group-hover/file:text-violet-400">
                   {attachment.filename || "Download file"}
                 </span>
-                <span className="mt-1 text-[12px] font-medium text-muted-foreground/70">
-                  {attachment.filename?.split(".").pop()?.toUpperCase() || "FILE"}
+                <span className="text-muted-foreground/70 mt-1 text-[12px] font-medium">
+                  {attachment.filename?.split(".").pop()?.toUpperCase() ||
+                    "FILE"}
                 </span>
               </div>
-              <div className="flex h-8 w-8 shrink-0 items-center justify-center rounded-full bg-muted/60 text-muted-foreground/50 transition-all duration-300 group-hover/file:bg-violet-400 group-hover/file:text-white group-hover/file:shadow-sm dark:bg-muted/20 dark:group-hover/file:bg-violet-400">
+              <div className="bg-muted/60 text-muted-foreground/50 dark:bg-muted/20 flex h-8 w-8 shrink-0 items-center justify-center rounded-full transition-all duration-300 group-hover/file:bg-violet-400 group-hover/file:text-white group-hover/file:shadow-sm dark:group-hover/file:bg-violet-400">
                 <IconDownload className="h-4 w-4 transition-transform duration-300 group-hover/file:-translate-y-[1px]" />
               </div>
             </a>
diff --git a/web/frontend/src/components/chat/chat-page.tsx b/web/frontend/src/components/chat/chat-page.tsx
index b0244c0b5..03d1a8a36 100644
--- a/web/frontend/src/components/chat/chat-page.tsx
+++ b/web/frontend/src/components/chat/chat-page.tsx
@@ -269,7 +269,7 @@ export function ChatPage() {
           )
         }
       >
-        <div className="hidden items-center gap-2 rounded-lg border border-border/60 px-3 py-1.5 sm:flex">
+        <div className="border-border/60 hidden items-center gap-2 rounded-lg border px-3 py-1.5 sm:flex">
           <span className="text-muted-foreground text-sm">
             {t("chat.showThoughts")}
           </span>
@@ -333,7 +333,8 @@ export function ChatPage() {
                   <AssistantMessage
                     content={msg.content}
                     attachments={msg.attachments}
-                    isThought={msg.kind === "thought"}
+                    kind={msg.kind}
+                    toolCalls={msg.toolCalls}
                     timestamp={msg.timestamp}
                   />
                 ) : (
diff --git a/web/frontend/src/features/chat/assistant-message-state.ts b/web/frontend/src/features/chat/assistant-message-state.ts
new file mode 100644
index 000000000..9c9bf0428
--- /dev/null
+++ b/web/frontend/src/features/chat/assistant-message-state.ts
@@ -0,0 +1,105 @@
+import type { AssistantMessageKind, ChatMessage } from "../../store/chat.ts"
+import { parseToolCallsFromContent, parseToolCallsValue } from "./tool-calls.ts"
+
+type AssistantToolCalls = ChatMessage["toolCalls"]
+type ExistingAssistantMessageState = Pick<ChatMessage, "kind" | "toolCalls">
+
+export interface AssistantMessageCreateState {
+  content: string
+  kind: AssistantMessageKind
+  toolCalls?: AssistantToolCalls
+}
+
+export interface AssistantMessageUpdateState {
+  content: string
+  kind?: AssistantMessageKind
+  toolCalls?: AssistantToolCalls
+}
+
+function parseAssistantMessageKind(
+  payload: Record<string, unknown>,
+  toolCalls?: AssistantToolCalls,
+): AssistantMessageKind {
+  if (payload.thought === true) {
+    return "thought"
+  }
+  if (payload.kind === "tool_calls" || toolCalls) {
+    return "tool_calls"
+  }
+  return "normal"
+}
+
+function hasExplicitAssistantKindPayload(
+  payload: Record<string, unknown>,
+): boolean {
+  return (
+    typeof payload.thought === "boolean" ||
+    payload.kind === "tool_calls" ||
+    payload.tool_calls !== undefined
+  )
+}
+
+function parseAssistantToolCalls(
+  payload: Record<string, unknown>,
+  content: string,
+): AssistantToolCalls {
+  return (
+    parseToolCallsValue(payload.tool_calls) ??
+    parseToolCallsFromContent(content)
+  )
+}
+
+export function parseAssistantMessageCreateState(
+  payload: Record<string, unknown>,
+): AssistantMessageCreateState {
+  const content = typeof payload.content === "string" ? payload.content : ""
+  const toolCalls = parseAssistantToolCalls(payload, content)
+
+  return {
+    content,
+    kind: parseAssistantMessageKind(payload, toolCalls),
+    toolCalls,
+  }
+}
+
+export function parseAssistantMessageUpdateState(
+  payload: Record<string, unknown>,
+  existing?: ExistingAssistantMessageState,
+): AssistantMessageUpdateState {
+  const content = typeof payload.content === "string" ? payload.content : ""
+  const toolCalls = parseAssistantToolCalls(payload, content)
+
+  if (hasExplicitAssistantKindPayload(payload)) {
+    const kind = parseAssistantMessageKind(payload, toolCalls)
+    return {
+      content,
+      kind,
+      toolCalls: kind === "tool_calls" ? toolCalls : undefined,
+    }
+  }
+
+  if (toolCalls) {
+    return {
+      content,
+      kind: "tool_calls",
+      toolCalls,
+    }
+  }
+
+  if (existing?.kind === "thought" || existing?.kind === "tool_calls") {
+    return {
+      content,
+      kind: "normal",
+      toolCalls: undefined,
+    }
+  }
+
+  if (existing?.toolCalls) {
+    return {
+      content,
+      toolCalls: undefined,
+    }
+  }
+
+  return { content }
+}
diff --git a/web/frontend/src/features/chat/history.ts b/web/frontend/src/features/chat/history.ts
index 6c8691fba..9fc35bc1e 100644
--- a/web/frontend/src/features/chat/history.ts
+++ b/web/frontend/src/features/chat/history.ts
@@ -1,5 +1,9 @@
 import { getSessionHistory } from "@/api/sessions"
 import { normalizeUnixTimestamp } from "@/features/chat/state"
+import {
+  parseToolCallsValue,
+  toolCallsSignature,
+} from "@/features/chat/tool-calls"
 import type { ChatAttachment, ChatMessage } from "@/store/chat"
 
 function toChatAttachments({
@@ -45,8 +49,11 @@ export async function loadSessionMessages(
     id: `hist-${index}-${Date.now()}`,
     role: message.role,
     content: message.content,
-    kind:
-      message.role === "assistant" ? (message.kind ?? "normal") : undefined,
+    kind: message.role === "assistant" ? (message.kind ?? "normal") : undefined,
+    toolCalls:
+      message.role === "assistant"
+        ? parseToolCallsValue(message.tool_calls)
+        : undefined,
     attachments: toChatAttachments({
       media: message.media,
       attachments: message.attachments,
@@ -79,7 +86,9 @@ function messageSignature(message: ChatMessage): string {
 
   return `${message.role}\u0000${message.content}\u0000${normalizeMessageTimestamp(
     message.timestamp,
-  )}\u0000${message.kind ?? ""}\u0000${attachmentSignature}`
+  )}\u0000${message.kind ?? ""}\u0000${attachmentSignature}\u0000${toolCallsSignature(
+    message.toolCalls,
+  )}`
 }
 
 function comparableTimestamp(timestamp: number | string): number {
diff --git a/web/frontend/src/features/chat/protocol.ts b/web/frontend/src/features/chat/protocol.ts
index 3c4259014..7b5c5e17b 100644
--- a/web/frontend/src/features/chat/protocol.ts
+++ b/web/frontend/src/features/chat/protocol.ts
@@ -1,10 +1,12 @@
 import { toast } from "sonner"
 
+import {
+  parseAssistantMessageCreateState,
+  parseAssistantMessageUpdateState,
+} from "@/features/chat/assistant-message-state"
 import { normalizeUnixTimestamp } from "@/features/chat/state"
 import {
-  type AssistantMessageKind,
   type ChatAttachment,
-  type ChatMessage,
   type ContextUsage,
   updateChatStore,
 } from "@/store/chat"
@@ -17,16 +19,6 @@ export interface PicoMessage {
   payload?: Record<string, unknown>
 }
 
-function parseAssistantMessageKind(
-  payload: Record<string, unknown>,
-): AssistantMessageKind {
-  return payload.thought === true ? "thought" : "normal"
-}
-
-function hasAssistantKindPayload(payload: Record<string, unknown>): boolean {
-  return typeof payload.thought === "boolean"
-}
-
 function parseAttachments(
   payload: Record<string, unknown>,
 ): ChatAttachment[] | undefined {
@@ -91,35 +83,6 @@ function parseContextUsage(
   }
 }
 
-function isToolFeedbackMessage(message: ChatMessage): boolean {
-  if (message.role !== "assistant") {
-    return false
-  }
-
-  const firstLine = message.content.split("\n", 1)[0]?.trim() ?? ""
-  return /^🔧\s+`[^`]+`/.test(firstLine)
-}
-
-function findToolFeedbackMessageIndex(messages: ChatMessage[]): number {
-  let lastUserIndex = -1
-  for (let i = messages.length - 1; i >= 0; i -= 1) {
-    if (messages[i].role === "user") {
-      lastUserIndex = i
-      break
-    }
-  }
-
-  for (let i = messages.length - 1; i >= 0; i -= 1) {
-    if (i <= lastUserIndex) {
-      break
-    }
-    if (isToolFeedbackMessage(messages[i])) {
-      return i
-    }
-  }
-  return -1
-}
-
 export function handlePicoMessage(
   message: PicoMessage,
   expectedSessionId: string,
@@ -133,9 +96,9 @@ export function handlePicoMessage(
   switch (message.type) {
     case "message.create":
     case "media.create": {
-      const content = (payload.content as string) || ""
       const messageId = (payload.message_id as string) || `pico-${Date.now()}`
-      const kind = parseAssistantMessageKind(payload)
+      const { content, kind, toolCalls } =
+        parseAssistantMessageCreateState(payload)
       const attachments = parseAttachments(payload)
       const contextUsage = parseContextUsage(payload)
       const timestamp =
@@ -152,6 +115,7 @@ export function handlePicoMessage(
             role: "assistant",
             content,
             kind,
+            ...(toolCalls ? { toolCalls } : {}),
             attachments,
             timestamp,
           },
@@ -163,10 +127,7 @@ export function handlePicoMessage(
     }
 
     case "message.update": {
-      const content = (payload.content as string) || ""
       const messageId = payload.message_id as string
-      const hasKind = hasAssistantKindPayload(payload)
-      const kind = parseAssistantMessageKind(payload)
       const attachments = parseAttachments(payload)
       const contextUsage = parseContextUsage(payload)
       const timestamp =
@@ -186,11 +147,14 @@ export function handlePicoMessage(
               return msg
             }
             found = true
+            const { content, kind, toolCalls } =
+              parseAssistantMessageUpdateState(payload, msg)
             return {
               ...msg,
               id: messageId,
               content,
-              ...(hasKind ? { kind } : {}),
+              kind,
+              toolCalls,
               ...(attachments ? { attachments } : {}),
             }
           })
@@ -198,20 +162,8 @@ export function handlePicoMessage(
             return messages
           }
 
-          const fallbackIndex = findToolFeedbackMessageIndex(messages)
-          if (fallbackIndex >= 0) {
-            return messages.map((msg, index) =>
-              index === fallbackIndex
-                ? {
-                    ...msg,
-                    id: messageId,
-                    content,
-                    ...(hasKind ? { kind } : {}),
-                    ...(attachments ? { attachments } : {}),
-                  }
-                : msg,
-            )
-          }
+          const { content, kind, toolCalls } =
+            parseAssistantMessageUpdateState(payload)
 
           return [
             ...messages,
@@ -219,7 +171,8 @@ export function handlePicoMessage(
               id: messageId,
               role: "assistant" as const,
               content,
-              ...(hasKind ? { kind } : {}),
+              kind,
+              toolCalls,
               ...(attachments ? { attachments } : {}),
               timestamp,
             },
@@ -237,19 +190,7 @@ export function handlePicoMessage(
       }
 
       updateChatStore((prev) => ({
-        messages: (() => {
-          const exactMessages = prev.messages.filter((msg) => msg.id !== messageId)
-          if (exactMessages.length !== prev.messages.length) {
-            return exactMessages
-          }
-
-          const fallbackIndex = findToolFeedbackMessageIndex(prev.messages)
-          if (fallbackIndex < 0) {
-            return prev.messages
-          }
-
-          return prev.messages.filter((_, index) => index !== fallbackIndex)
-        })(),
+        messages: prev.messages.filter((msg) => msg.id !== messageId),
       }))
       break
     }
diff --git a/web/frontend/src/features/chat/tool-calls.ts b/web/frontend/src/features/chat/tool-calls.ts
new file mode 100644
index 000000000..e92dca1bb
--- /dev/null
+++ b/web/frontend/src/features/chat/tool-calls.ts
@@ -0,0 +1,122 @@
+import type { ChatToolCall } from "@/store/chat"
+
+function parseLegacyToolFeedbackContent(
+  content: string,
+): ChatToolCall[] | undefined {
+  const trimmed = content.trim()
+  const match = /^🔧\s+`([^`]+)`(?:\n([\s\S]*))?$/.exec(trimmed)
+  if (!match) {
+    return undefined
+  }
+
+  const toolName = match[1]?.trim() ?? ""
+  const body = match[2]?.trim() ?? ""
+  const codeFence = /```(?:json)?\n([\s\S]*?)\n```/m.exec(body)
+  const argumentsText = codeFence?.[1]?.trim() ?? ""
+  const explanation = body.replace(/```(?:json)?\n[\s\S]*?\n```/gm, "").trim()
+
+  return [
+    {
+      type: "function",
+      function: {
+        name: toolName,
+        ...(argumentsText ? { arguments: argumentsText } : {}),
+      },
+      ...(explanation
+        ? {
+            extraContent: {
+              toolFeedbackExplanation: explanation,
+            },
+          }
+        : {}),
+    },
+  ]
+}
+
+export function parseToolCallsValue(raw: unknown): ChatToolCall[] | undefined {
+  if (!Array.isArray(raw)) {
+    return undefined
+  }
+
+  const toolCalls: ChatToolCall[] = []
+  for (const item of raw) {
+    if (!item || typeof item !== "object") {
+      continue
+    }
+
+    const toolCall = item as Record<string, unknown>
+    const rawFunction =
+      toolCall.function && typeof toolCall.function === "object"
+        ? (toolCall.function as Record<string, unknown>)
+        : null
+    const rawExtraContent =
+      toolCall.extra_content && typeof toolCall.extra_content === "object"
+        ? (toolCall.extra_content as Record<string, unknown>)
+        : null
+
+    const nextToolCall: ChatToolCall = {
+      ...(typeof toolCall.id === "string" ? { id: toolCall.id } : {}),
+      ...(typeof toolCall.type === "string" ? { type: toolCall.type } : {}),
+    }
+
+    if (rawFunction) {
+      const name =
+        typeof rawFunction.name === "string" ? rawFunction.name : undefined
+      const argumentsText =
+        typeof rawFunction.arguments === "string"
+          ? rawFunction.arguments
+          : undefined
+
+      if (name || argumentsText) {
+        nextToolCall.function = {
+          ...(name ? { name } : {}),
+          ...(argumentsText ? { arguments: argumentsText } : {}),
+        }
+      }
+    }
+
+    if (rawExtraContent) {
+      const toolFeedbackExplanation =
+        typeof rawExtraContent.tool_feedback_explanation === "string"
+          ? rawExtraContent.tool_feedback_explanation
+          : undefined
+
+      if (toolFeedbackExplanation) {
+        nextToolCall.extraContent = {
+          toolFeedbackExplanation,
+        }
+      }
+    }
+
+    if (
+      nextToolCall.id ||
+      nextToolCall.type ||
+      nextToolCall.function ||
+      nextToolCall.extraContent
+    ) {
+      toolCalls.push(nextToolCall)
+    }
+  }
+
+  return toolCalls.length > 0 ? toolCalls : undefined
+}
+
+export function parseToolCallsFromContent(
+  content: string,
+): ChatToolCall[] | undefined {
+  return parseLegacyToolFeedbackContent(content)
+}
+
+export function toolCallsSignature(toolCalls?: ChatToolCall[]): string {
+  return (toolCalls ?? [])
+    .map((toolCall) =>
+      [
+        toolCall.id ?? "",
+        toolCall.type ?? "",
+        toolCall.function?.name ?? "",
+        toolCall.function?.arguments ?? "",
+        toolCall.extraContent?.toolFeedbackExplanation ?? "",
+      ].join("\u0001"),
+    )
+    .join("\u0002")
+}
diff --git a/web/frontend/src/i18n/locales/en.json b/web/frontend/src/i18n/locales/en.json
index 9ab28c894..6833fb481 100644
--- a/web/frontend/src/i18n/locales/en.json
+++ b/web/frontend/src/i18n/locales/en.json
@@ -60,6 +60,9 @@
       "step4": "Almost there..."
     },
     "reasoningLabel": "Reasoning",
+    "toolCallsLabel": "Tool calls",
+    "toolCallExplanationLabel": "Call note",
+    "toolCallFunctionLabel": "Call summary",
     "showThoughts": "Show reasoning",
     "toolLabel": "Tool",
     "history": "History",
diff --git a/web/frontend/src/i18n/locales/zh.json b/web/frontend/src/i18n/locales/zh.json
index 2dde62818..542fff751 100644
--- a/web/frontend/src/i18n/locales/zh.json
+++ b/web/frontend/src/i18n/locales/zh.json
@@ -60,6 +60,9 @@
       "step4": "马上就好..."
     },
     "reasoningLabel": "思考",
+    "toolCallsLabel": "工具调用",
+    "toolCallExplanationLabel": "调用提示",
+    "toolCallFunctionLabel": "调用摘要",
     "showThoughts": "展示思考过程",
     "toolLabel": "工具",
     "history": "历史记录",
diff --git a/web/frontend/src/store/chat.ts b/web/frontend/src/store/chat.ts
index 1749a7d2f..43e39d938 100644
--- a/web/frontend/src/store/chat.ts
+++ b/web/frontend/src/store/chat.ts
@@ -13,7 +13,23 @@ export interface ChatAttachment {
   contentType?: string
 }
 
-export type AssistantMessageKind = "normal" | "thought"
+export interface ChatToolCallFunction {
+  name?: string
+  arguments?: string
+}
+
+export interface ChatToolCallExtraContent {
+  toolFeedbackExplanation?: string
+}
+
+export interface ChatToolCall {
+  id?: string
+  type?: string
+  function?: ChatToolCallFunction
+  extraContent?: ChatToolCallExtraContent
+}
+
+export type AssistantMessageKind = "normal" | "thought" | "tool_calls"
 
 export interface ChatMessage {
   id: string
@@ -22,6 +38,7 @@ export interface ChatMessage {
   timestamp: number | string
   kind?: AssistantMessageKind
   attachments?: ChatAttachment[]
+  toolCalls?: ChatToolCall[]
 }
 
 export interface ContextUsage {

From 6d04d15ce064c8f05f20f898983fb73154b6e44f Mon Sep 17 00:00:00 2001
From: lc6464 <64722907+lc6464@users.noreply.github.com>
Date: Sun, 26 Apr 2026 00:40:55 +0800
Subject: [PATCH 2/8] fix(tool-feedback): dedupe duplicate content and keep
 full explanations

---
 pkg/agent/agent_outbound.go            | 13 ++--
 pkg/agent/agent_test.go                | 90 ++++++++++++++++++++------
 pkg/agent/agent_utils.go               | 10 ++-
 pkg/agent/pipeline_execute.go          |  2 -
 pkg/agent/pipeline_llm.go              |  1 -
 pkg/config/config.go                   |  2 +-
 pkg/utils/tool_feedback_dedupe.go      | 39 +++++++++++
 pkg/utils/tool_feedback_dedupe_test.go | 55 ++++++++++++++++
 pkg/utils/visible_tool_calls.go        |  3 -
 pkg/utils/visible_tool_calls_test.go   | 33 ++++++++++
 web/backend/api/session.go             |  3 +
 web/backend/api/session_test.go        | 83 ++++++++++++++++++++----
 web/frontend/src/i18n/locales/en.json  |  4 +-
 web/frontend/src/i18n/locales/zh.json  |  4 +-
 14 files changed, 288 insertions(+), 54 deletions(-)
 create mode 100644 pkg/utils/tool_feedback_dedupe.go
 create mode 100644 pkg/utils/tool_feedback_dedupe_test.go
 create mode 100644 pkg/utils/visible_tool_calls_test.go

diff --git a/pkg/agent/agent_outbound.go b/pkg/agent/agent_outbound.go
index fcf8cf1a1..1728f6f79 100644
--- a/pkg/agent/agent_outbound.go
+++ b/pkg/agent/agent_outbound.go
@@ -160,7 +160,14 @@ func (al *AgentLoop) publishPicoToolCallInterim(
 		return
 	}
 
-	if strings.TrimSpace(content) != "" {
+	visibleToolCalls := utils.BuildVisibleToolCalls(
+		toolCalls,
+		al.cfg.Agents.Defaults.GetToolFeedbackMaxArgsLength(),
+	)
+	duplicateToolCallContent := len(visibleToolCalls) > 0 &&
+		utils.ToolCallExplanationDuplicatesContent(content, toolCalls)
+
+	if strings.TrimSpace(content) != "" && !duplicateToolCallContent {
 		pubCtx, pubCancel := context.WithTimeout(ctx, 3*time.Second)
 		err := al.bus.PublishOutbound(pubCtx, outboundMessageForTurn(ts, content))
 		pubCancel()
@@ -175,10 +182,6 @@ func (al *AgentLoop) publishPicoToolCallInterim(
 		}
 	}
 
-	visibleToolCalls := utils.BuildVisibleToolCalls(
-		toolCalls,
-		al.cfg.Agents.Defaults.GetToolFeedbackMaxArgsLength(),
-	)
 	if len(visibleToolCalls) == 0 {
 		return
 	}
diff --git a/pkg/agent/agent_test.go b/pkg/agent/agent_test.go
index 17d169ca6..4047ab74d 100644
--- a/pkg/agent/agent_test.go
+++ b/pkg/agent/agent_test.go
@@ -1892,7 +1892,7 @@ func TestToolFeedbackExplanationFromResponse_UsesCurrentContentFirst(t *testing.
 		{Role: "tool", Content: "tool output", ToolCallID: "call_1"},
 	}
 
-	got := toolFeedbackExplanationFromResponse(response, messages, 300)
+	got := toolFeedbackExplanationFromResponse(response, messages)
 	if got != "Read README.md first" {
 		t.Fatalf("toolFeedbackExplanationFromResponse() = %q, want current content", got)
 	}
@@ -1936,7 +1936,7 @@ func TestToolFeedbackExplanationFromResponse_UsesExplicitToolCallExtraContent(t
 		{Role: "tool", Content: "tool output", ToolCallID: "call_1"},
 	}
 
-	got := toolFeedbackExplanationFromResponse(response, messages, 300)
+	got := toolFeedbackExplanationFromResponse(response, messages)
 	if got != "Read README.md first to confirm the current project structure." {
 		t.Fatalf("toolFeedbackExplanationFromResponse() = %q, want explicit tool feedback explanation", got)
 	}
@@ -1963,8 +1963,8 @@ func TestToolFeedbackExplanationForToolCall_PrefersToolSpecificExtraContent(t *t
 		},
 	}
 
-	got1 := toolFeedbackExplanationForToolCall(response, response.ToolCalls[0], nil, 300)
-	got2 := toolFeedbackExplanationForToolCall(response, response.ToolCalls[1], nil, 300)
+	got1 := toolFeedbackExplanationForToolCall(response, response.ToolCalls[0], nil)
+	got2 := toolFeedbackExplanationForToolCall(response, response.ToolCalls[1], nil)
 	if got1 != "Read README.md first." {
 		t.Fatalf("toolFeedbackExplanationForToolCall() first = %q, want tool-specific explanation", got1)
 	}
@@ -1993,7 +1993,7 @@ func TestToolFeedbackExplanationForToolCall_DoesNotReuseAnotherToolCallExplanati
 		{Role: "user", Content: "inspect the config and update the example"},
 	}
 
-	got := toolFeedbackExplanationForToolCall(response, response.ToolCalls[0], messages, 300)
+	got := toolFeedbackExplanationForToolCall(response, response.ToolCalls[0], messages)
 	want := utils.ToolFeedbackContinuationHint + ": inspect the config and update the example"
 	if got != want {
 		t.Fatalf("toolFeedbackExplanationForToolCall() = %q, want %q", got, want)
@@ -2012,13 +2012,31 @@ func TestToolFeedbackExplanationFromResponse_DoesNotUseReasoningContent(t *testi
 		{Role: "tool", Content: "tool output", ToolCallID: "call_1"},
 	}
 
-	got := toolFeedbackExplanationFromResponse(response, messages, 300)
+	got := toolFeedbackExplanationFromResponse(response, messages)
 	want := utils.ToolFeedbackContinuationHint + ": Inspect README.md and update the config example."
 	if got != want {
 		t.Fatalf("toolFeedbackExplanationFromResponse() = %q, want latest user content fallback", got)
 	}
 }
 
+func TestToolFeedbackExplanationForToolCall_DoesNotTruncateLongExplanation(t *testing.T) {
+	explanation := "Read README.md first to confirm the current project structure before editing the config example."
+	response := &providers.LLMResponse{
+		ToolCalls: []providers.ToolCall{{
+			ID:   "call_1",
+			Name: "read_file",
+			ExtraContent: &providers.ExtraContent{
+				ToolFeedbackExplanation: explanation,
+			},
+		}},
+	}
+
+	got := toolFeedbackExplanationForToolCall(response, response.ToolCalls[0], nil)
+	if got != explanation {
+		t.Fatalf("toolFeedbackExplanationForToolCall() = %q, want full explanation", got)
+	}
+}
+
 func TestToolFeedbackArgsPreview_UsesJSONAndTruncates(t *testing.T) {
 	got := toolFeedbackArgsPreview(map[string]any{
 		"path":  "README.md",
@@ -2064,6 +2082,43 @@ func (m *picoInterleavedContentProvider) GetDefaultModel() string {
 	return "pico-interleaved-content-model"
 }
 
+type picoDistinctToolCallContentProvider struct {
+	calls int
+}
+
+func (m *picoDistinctToolCallContentProvider) Chat(
+	ctx context.Context,
+	messages []providers.Message,
+	tools []providers.ToolDefinition,
+	model string,
+	opts map[string]any,
+) (*providers.LLMResponse, error) {
+	m.calls++
+	if m.calls == 1 {
+		return &providers.LLMResponse{
+			Content: "intermediate model text",
+			ToolCalls: []providers.ToolCall{{
+				ID:        "call_tool_limit_test",
+				Type:      "function",
+				Name:      "tool_limit_test_tool",
+				Arguments: map[string]any{"value": "x"},
+				ExtraContent: &providers.ExtraContent{
+					ToolFeedbackExplanation: "Read the file before replying.",
+				},
+			}},
+		}, nil
+	}
+
+	return &providers.LLMResponse{
+		Content:   "final model text",
+		ToolCalls: []providers.ToolCall{},
+	}, nil
+}
+
+func (m *picoDistinctToolCallContentProvider) GetDefaultModel() string {
+	return "pico-distinct-tool-call-content-model"
+}
+
 type toolLimitOnlyProvider struct{}
 
 func (m *toolLimitOnlyProvider) Chat(
@@ -4398,7 +4453,7 @@ func TestRun_PicoPublishesAssistantContentDuringToolCallsWithoutFinalDuplicate(t
 	}
 
 	msgBus := bus.NewMessageBus()
-	provider := &picoInterleavedContentProvider{}
+	provider := &picoDistinctToolCallContentProvider{}
 	al := NewAgentLoop(cfg, msgBus, provider)
 
 	agent := al.GetRegistry().GetDefaultAgent()
@@ -4562,7 +4617,7 @@ func TestRun_PicoToolFeedbackSuppressesDuplicateInterimAssistantContent(t *testi
 
 	outputs := make([]bus.OutboundMessage, 0, 3)
 	deadline := time.After(2 * time.Second)
-	for len(outputs) < 3 {
+	for len(outputs) < 2 {
 		select {
 		case outbound := <-msgBus.OutboundChan():
 			outputs = append(outputs, outbound)
@@ -4571,20 +4626,17 @@ func TestRun_PicoToolFeedbackSuppressesDuplicateInterimAssistantContent(t *testi
 		}
 	}
 
-	if outputs[0].Content != "intermediate model text" {
-		t.Fatalf("first outbound content = %q, want %q", outputs[0].Content, "intermediate model text")
+	if outputs[0].Context.Raw[metadataKeyMessageKind] != messageKindToolCalls {
+		t.Fatalf("first outbound = %+v, want tool_calls message", outputs[0])
 	}
-	if outputs[1].Context.Raw[metadataKeyMessageKind] != messageKindToolCalls {
-		t.Fatalf("second outbound = %+v, want tool_calls message", outputs[1])
+	if outputs[0].Content != "" {
+		t.Fatalf("first outbound content = %q, want empty tool_calls content", outputs[0].Content)
 	}
-	if outputs[1].Content != "" {
-		t.Fatalf("second outbound content = %q, want empty tool_calls content", outputs[1].Content)
+	if !strings.Contains(outputs[0].Context.Raw[metadataKeyToolCalls], "tool_limit_test_tool") {
+		t.Fatalf("first outbound tool_calls = %q, want tool name", outputs[0].Context.Raw[metadataKeyToolCalls])
 	}
-	if !strings.Contains(outputs[1].Context.Raw[metadataKeyToolCalls], "tool_limit_test_tool") {
-		t.Fatalf("second outbound tool_calls = %q, want tool name", outputs[1].Context.Raw[metadataKeyToolCalls])
-	}
-	if outputs[2].Content != "final model text" {
-		t.Fatalf("third outbound content = %q, want %q", outputs[2].Content, "final model text")
+	if outputs[1].Content != "final model text" {
+		t.Fatalf("second outbound content = %q, want %q", outputs[1].Content, "final model text")
 	}
 
 	runCancel()
diff --git a/pkg/agent/agent_utils.go b/pkg/agent/agent_utils.go
index 4ba75cde4..bbfb3f2ae 100644
--- a/pkg/agent/agent_utils.go
+++ b/pkg/agent/agent_utils.go
@@ -115,7 +115,6 @@ func latestUserContent(messages []providers.Message) string {
 func toolFeedbackExplanationFromResponse(
 	response *providers.LLMResponse,
 	messages []providers.Message,
-	maxLen int,
 ) string {
 	if response == nil {
 		return ""
@@ -127,7 +126,7 @@ func toolFeedbackExplanationFromResponse(
 	if explanation == "" {
 		explanation = toolFeedbackExplanationFromMessages(messages)
 	}
-	return utils.Truncate(explanation, maxLen)
+	return explanation
 }
 
 func toolFeedbackExplanationFromToolCalls(toolCalls []providers.ToolCall) string {
@@ -146,22 +145,21 @@ func toolFeedbackExplanationForToolCall(
 	response *providers.LLMResponse,
 	toolCall providers.ToolCall,
 	messages []providers.Message,
-	maxLen int,
 ) string {
 	if toolCall.ExtraContent != nil {
 		if explanation := strings.TrimSpace(toolCall.ExtraContent.ToolFeedbackExplanation); explanation != "" {
-			return utils.Truncate(explanation, maxLen)
+			return explanation
 		}
 	}
 	if response == nil {
-		return utils.Truncate(toolFeedbackExplanationFromMessages(messages), maxLen)
+		return toolFeedbackExplanationFromMessages(messages)
 	}
 
 	explanation := strings.TrimSpace(response.Content)
 	if explanation == "" {
 		explanation = toolFeedbackExplanationFromMessages(messages)
 	}
-	return utils.Truncate(explanation, maxLen)
+	return explanation
 }
 
 func toolFeedbackExplanationFromMessages(messages []providers.Message) string {
diff --git a/pkg/agent/pipeline_execute.go b/pkg/agent/pipeline_execute.go
index c8ad93943..9935f2c9e 100644
--- a/pkg/agent/pipeline_execute.go
+++ b/pkg/agent/pipeline_execute.go
@@ -86,7 +86,6 @@ toolLoop:
 							exec.response,
 							tc,
 							messages,
-							toolFeedbackMaxLen,
 						)
 						feedbackMsg := utils.FormatToolFeedbackMessage(
 							toolName,
@@ -368,7 +367,6 @@ toolLoop:
 				exec.response,
 				tc,
 				messages,
-				toolFeedbackMaxLen,
 			)
 			feedbackMsg := utils.FormatToolFeedbackMessage(
 				toolName,
diff --git a/pkg/agent/pipeline_llm.go b/pkg/agent/pipeline_llm.go
index 895f00489..6bf55fa39 100644
--- a/pkg/agent/pipeline_llm.go
+++ b/pkg/agent/pipeline_llm.go
@@ -478,7 +478,6 @@ func (p *Pipeline) CallLLM(
 			exec.response,
 			tc,
 			exec.messages,
-			al.cfg.Agents.Defaults.GetToolFeedbackMaxArgsLength(),
 		)
 		extraContent := tc.ExtraContent
 		if strings.TrimSpace(toolFeedbackExplanation) != "" {
diff --git a/pkg/config/config.go b/pkg/config/config.go
index 6bb8d3ce6..305c3a5c0 100644
--- a/pkg/config/config.go
+++ b/pkg/config/config.go
@@ -287,7 +287,7 @@ func (d *AgentDefaults) GetMaxMediaSize() int {
 	return DefaultMaxMediaSize
 }
 
-// GetToolFeedbackMaxArgsLength returns the max visible text length for tool feedback messages.
+// GetToolFeedbackMaxArgsLength returns the max visible text length for tool argument previews.
 func (d *AgentDefaults) GetToolFeedbackMaxArgsLength() int {
 	if d.ToolFeedback.MaxArgsLength > 0 {
 		return d.ToolFeedback.MaxArgsLength
diff --git a/pkg/utils/tool_feedback_dedupe.go b/pkg/utils/tool_feedback_dedupe.go
new file mode 100644
index 000000000..b1adb60eb
--- /dev/null
+++ b/pkg/utils/tool_feedback_dedupe.go
@@ -0,0 +1,39 @@
+package utils
+
+import (
+	"strings"
+
+	"github.com/sipeed/picoclaw/pkg/providers"
+)
+
+func normalizeToolFeedbackComparisonText(text string) string {
+	text = strings.ReplaceAll(text, "\r\n", "\n")
+	text = strings.ReplaceAll(text, "\r", "\n")
+	text = strings.TrimSpace(text)
+	if text == "" {
+		return ""
+	}
+	return strings.Join(strings.Fields(text), " ")
+}
+
+func ToolCallExplanationDuplicatesContent(content string, toolCalls []providers.ToolCall) bool {
+	normalizedContent := normalizeToolFeedbackComparisonText(content)
+	if normalizedContent == "" || len(toolCalls) == 0 {
+		return false
+	}
+
+	for _, tc := range toolCalls {
+		if tc.ExtraContent == nil {
+			continue
+		}
+		explanation := normalizeToolFeedbackComparisonText(tc.ExtraContent.ToolFeedbackExplanation)
+		if explanation == "" {
+			continue
+		}
+		if explanation == normalizedContent {
+			return true
+		}
+	}
+
+	return false
+}
diff --git a/pkg/utils/tool_feedback_dedupe_test.go b/pkg/utils/tool_feedback_dedupe_test.go
new file mode 100644
index 000000000..cc587080f
--- /dev/null
+++ b/pkg/utils/tool_feedback_dedupe_test.go
@@ -0,0 +1,55 @@
+package utils
+
+import (
+	"testing"
+
+	"github.com/sipeed/picoclaw/pkg/providers"
+)
+
+func TestToolCallExplanationDuplicatesContent(t *testing.T) {
+	t.Run("exact duplicate", func(t *testing.T) {
+		toolCalls := []providers.ToolCall{{
+			ExtraContent: &providers.ExtraContent{
+				ToolFeedbackExplanation: "Read the file before replying.",
+			},
+		}}
+
+		if !ToolCallExplanationDuplicatesContent("Read the file before replying.", toolCalls) {
+			t.Fatal("expected duplicated content to be detected")
+		}
+	})
+
+	t.Run("whitespace normalized duplicate", func(t *testing.T) {
+		toolCalls := []providers.ToolCall{{
+			ExtraContent: &providers.ExtraContent{
+				ToolFeedbackExplanation: "Read   the file\nbefore replying.",
+			},
+		}}
+
+		if !ToolCallExplanationDuplicatesContent("  Read the file before replying.  ", toolCalls) {
+			t.Fatal("expected whitespace-only differences to be ignored")
+		}
+	})
+
+	t.Run("distinct content", func(t *testing.T) {
+		toolCalls := []providers.ToolCall{{
+			ExtraContent: &providers.ExtraContent{
+				ToolFeedbackExplanation: "Read the file before replying.",
+			},
+		}}
+
+		if ToolCallExplanationDuplicatesContent(
+			"I will summarize the findings after reading the file.",
+			toolCalls,
+		) {
+			t.Fatal("expected distinct content to remain visible")
+		}
+	})
+
+	t.Run("missing explanation", func(t *testing.T) {
+		toolCalls := []providers.ToolCall{{}}
+		if ToolCallExplanationDuplicatesContent("Read the file before replying.", toolCalls) {
+			t.Fatal("expected empty tool explanations to skip dedupe")
+		}
+	})
+}
diff --git a/pkg/utils/visible_tool_calls.go b/pkg/utils/visible_tool_calls.go
index 37a5f60da..8c4d89a51 100644
--- a/pkg/utils/visible_tool_calls.go
+++ b/pkg/utils/visible_tool_calls.go
@@ -39,9 +39,6 @@ func BuildVisibleToolCalls(
 		explanation := ""
 		if tc.ExtraContent != nil {
 			explanation = strings.TrimSpace(tc.ExtraContent.ToolFeedbackExplanation)
-			if maxArgsLen > 0 {
-				explanation = Truncate(explanation, maxArgsLen)
-			}
 		}
 		if name == "" && explanation == "" && argsPreview == "" {
 			continue
diff --git a/pkg/utils/visible_tool_calls_test.go b/pkg/utils/visible_tool_calls_test.go
new file mode 100644
index 000000000..fe9467c57
--- /dev/null
+++ b/pkg/utils/visible_tool_calls_test.go
@@ -0,0 +1,33 @@
+package utils
+
+import (
+	"testing"
+
+	"github.com/sipeed/picoclaw/pkg/providers"
+)
+
+func TestBuildVisibleToolCalls_DoesNotTruncateExplanation(t *testing.T) {
+	explanation := "Read README.md first to confirm the current project structure before editing the config example."
+	toolCalls := []providers.ToolCall{{
+		ID:   "call_1",
+		Type: "function",
+		Function: &providers.FunctionCall{
+			Name:      "read_file",
+			Arguments: `{"path":"README.md","start_line":1,"end_line":10,"extra":"abcdefghijklmnopqrstuvwxyz"}`,
+		},
+		ExtraContent: &providers.ExtraContent{
+			ToolFeedbackExplanation: explanation,
+		},
+	}}
+
+	visible := BuildVisibleToolCalls(toolCalls, 20)
+	if len(visible) != 1 {
+		t.Fatalf("len(visible) = %d, want 1", len(visible))
+	}
+	if visible[0].ExtraContent == nil || visible[0].ExtraContent.ToolFeedbackExplanation != explanation {
+		t.Fatalf("visible explanation = %#v, want %q", visible[0].ExtraContent, explanation)
+	}
+	if visible[0].Function == nil || visible[0].Function.Arguments == "" {
+		t.Fatalf("visible function = %#v, want truncated args preview", visible[0].Function)
+	}
+}
diff --git a/web/backend/api/session.go b/web/backend/api/session.go
index 7d0c11fb0..cc18ee6e1 100644
--- a/web/backend/api/session.go
+++ b/web/backend/api/session.go
@@ -549,6 +549,9 @@ func sessionTranscriptMessages(
 				}
 				content = ""
 			}
+			if hasToolCallsMsg && utils.ToolCallExplanationDuplicatesContent(content, msg.ToolCalls) {
+				content = ""
+			}
 
 			chatMsg := sessionChatMessage{
 				Role:        "assistant",
diff --git a/web/backend/api/session_test.go b/web/backend/api/session_test.go
index 8ef26df5f..760935db7 100644
--- a/web/backend/api/session_test.go
+++ b/web/backend/api/session_test.go
@@ -901,6 +901,67 @@ func TestHandleListSessions_MessageCountUsesVisibleTranscript(t *testing.T) {
 	}
 }
 
+func TestHandleListSessions_DeduplicatesAssistantToolCallContentFromVisibleTranscript(t *testing.T) {
+	configPath, cleanup := setupOAuthTestEnv(t)
+	defer cleanup()
+
+	dir := sessionsTestDir(t, configPath)
+	store, err := memory.NewJSONLStore(dir)
+	if err != nil {
+		t.Fatalf("NewJSONLStore() error = %v", err)
+	}
+
+	sessionKey := picoSessionPrefix + "list-deduped-tool-content"
+	for _, msg := range []providers.Message{
+		{Role: "user", Content: "check file"},
+		{
+			Role:    "assistant",
+			Content: "Read the file before replying.",
+			ToolCalls: []providers.ToolCall{
+				{
+					ID:   "call_1",
+					Type: "function",
+					Function: &providers.FunctionCall{
+						Name:      "read_file",
+						Arguments: `{"path":"README.md"}`,
+					},
+					ExtraContent: &providers.ExtraContent{
+						ToolFeedbackExplanation: "Read the file before replying.",
+					},
+				},
+			},
+		},
+		{Role: "tool", Content: "raw read_file result", ToolCallID: "call_1"},
+	} {
+		if err := store.AddFullMessage(nil, sessionKey, msg); err != nil {
+			t.Fatalf("AddFullMessage() error = %v", err)
+		}
+	}
+
+	h := NewHandler(configPath)
+	mux := http.NewServeMux()
+	h.RegisterRoutes(mux)
+
+	rec := httptest.NewRecorder()
+	req := httptest.NewRequest(http.MethodGet, "/api/sessions", nil)
+	mux.ServeHTTP(rec, req)
+
+	if rec.Code != http.StatusOK {
+		t.Fatalf("status = %d, want %d, body=%s", rec.Code, http.StatusOK, rec.Body.String())
+	}
+
+	var items []sessionListItem
+	if err := json.Unmarshal(rec.Body.Bytes(), &items); err != nil {
+		t.Fatalf("Unmarshal() error = %v", err)
+	}
+	if len(items) != 1 {
+		t.Fatalf("len(items) = %d, want 1", len(items))
+	}
+	if items[0].MessageCount != 2 {
+		t.Fatalf("items[0].MessageCount = %d, want 2", items[0].MessageCount)
+	}
+}
+
 func TestHandleGetSession_DoesNotDuplicateAssistantToolCallContent(t *testing.T) {
 	configPath, cleanup := setupOAuthTestEnv(t)
 	defer cleanup()
@@ -956,16 +1017,13 @@ func TestHandleGetSession_DoesNotDuplicateAssistantToolCallContent(t *testing.T)
 	if err := json.Unmarshal(rec.Body.Bytes(), &resp); err != nil {
 		t.Fatalf("Unmarshal() error = %v", err)
 	}
-	if len(resp.Messages) != 3 {
-		t.Fatalf("len(resp.Messages) = %d, want 3", len(resp.Messages))
+	if len(resp.Messages) != 2 {
+		t.Fatalf("len(resp.Messages) = %d, want 2", len(resp.Messages))
 	}
 	if resp.Messages[0].Role != "user" || resp.Messages[0].Content != "check file" {
 		t.Fatalf("first message = %#v, want user/check file", resp.Messages[0])
 	}
-	if resp.Messages[1].Content != "Read the file before replying." {
-		t.Fatalf("assistant content = %#v, want preserved assistant content", resp.Messages[1])
-	}
-	toolCall := assertVisibleToolCallMessage(t, resp.Messages[2], "read_file")
+	toolCall := assertVisibleToolCallMessage(t, resp.Messages[1], "read_file")
 	if toolCall.ExtraContent == nil ||
 		toolCall.ExtraContent.ToolFeedbackExplanation != "Read the file before replying." {
 		t.Fatalf("tool call = %#v, want explanation", toolCall)
@@ -1097,8 +1155,8 @@ func TestHandleGetSession_PreservesMediaWhenAssistantToolCallContentDuplicatesSu
 	if resp.Messages[1].Role != "assistant" {
 		t.Fatalf("assistant message role = %q, want assistant", resp.Messages[1].Role)
 	}
-	if resp.Messages[1].Content != "Reviewing the generated screenshot." {
-		t.Fatalf("assistant content = %q, want preserved duplicated content with media", resp.Messages[1].Content)
+	if resp.Messages[1].Content != "" {
+		t.Fatalf("assistant content = %q, want duplicate content suppressed", resp.Messages[1].Content)
 	}
 	if len(resp.Messages[1].Media) != 1 || resp.Messages[1].Media[0] != "data:image/png;base64,abc123" {
 		t.Fatalf("assistant media = %#v, want preserved media", resp.Messages[1].Media)
@@ -1176,8 +1234,8 @@ func TestHandleGetSession_PreservesAttachmentsWhenAssistantToolCallContentDuplic
 	if resp.Messages[1].Role != "assistant" {
 		t.Fatalf("assistant message role = %q, want assistant", resp.Messages[1].Role)
 	}
-	if resp.Messages[1].Content != "Reviewing the generated report." {
-		t.Fatalf("assistant content = %q, want preserved duplicated content", resp.Messages[1].Content)
+	if resp.Messages[1].Content != "" {
+		t.Fatalf("assistant content = %q, want duplicate content suppressed", resp.Messages[1].Content)
 	}
 	if len(resp.Messages[1].Attachments) != 1 {
 		t.Fatalf("len(assistant.Attachments) = %d, want 1", len(resp.Messages[1].Attachments))
@@ -1256,13 +1314,12 @@ func TestHandleGetSession_UsesConfiguredToolFeedbackMaxArgsLength(t *testing.T)
 		t.Fatalf("len(resp.Messages) = %d, want at least 2", len(resp.Messages))
 	}
 
-	wantPreview := utils.Truncate(explanation, 20)
 	wantArgsPreview := visibleAssistantToolArgsPreview(providers.ToolCall{
 		Function: &providers.FunctionCall{Arguments: argsJSON},
 	}, 20)
 	toolCall := assertVisibleToolCallMessage(t, resp.Messages[1], "read_file")
-	if toolCall.ExtraContent == nil || toolCall.ExtraContent.ToolFeedbackExplanation != wantPreview {
-		t.Fatalf("tool call = %#v, want preview %q", toolCall, wantPreview)
+	if toolCall.ExtraContent == nil || toolCall.ExtraContent.ToolFeedbackExplanation != explanation {
+		t.Fatalf("tool call = %#v, want full explanation %q", toolCall, explanation)
 	}
 	if toolCall.Function == nil || toolCall.Function.Arguments != wantArgsPreview {
 		t.Fatalf("tool call = %#v, want args preview %q", toolCall, wantArgsPreview)
diff --git a/web/frontend/src/i18n/locales/en.json b/web/frontend/src/i18n/locales/en.json
index 6833fb481..e29a4ccdf 100644
--- a/web/frontend/src/i18n/locales/en.json
+++ b/web/frontend/src/i18n/locales/en.json
@@ -612,8 +612,8 @@
       "tool_feedback_enabled_hint": "Send a short execution note into the current chat before each tool runs.",
       "tool_feedback_separate_messages": "Separate Feedback Messages",
       "tool_feedback_separate_messages_hint": "Keep each tool feedback update as its own chat message instead of reusing a single placeholder/progress message.",
-      "tool_feedback_max_args_length": "Tool Feedback Length",
-      "tool_feedback_max_args_length_hint": "Maximum number of characters shown in each tool feedback message. Set to 0 to use the default.",
+      "tool_feedback_max_args_length": "Tool Args Preview Length",
+      "tool_feedback_max_args_length_hint": "Maximum number of characters shown in each tool argument preview. Set to 0 to use the default.",
       "exec_enabled": "Allow Commands",
       "exec_enabled_hint": "Enable or disable command execution for the app. When disabled, no command requests will run.",
       "allow_remote": "Allow Remote Commands",
diff --git a/web/frontend/src/i18n/locales/zh.json b/web/frontend/src/i18n/locales/zh.json
index 542fff751..d9698c65e 100644
--- a/web/frontend/src/i18n/locales/zh.json
+++ b/web/frontend/src/i18n/locales/zh.json
@@ -612,8 +612,8 @@
       "tool_feedback_enabled_hint": "在每次执行工具前，先向当前会话发送一条简短的执行说明",
       "tool_feedback_separate_messages": "分开发送反馈消息",
       "tool_feedback_separate_messages_hint": "让每次工具反馈都保留为独立消息，而不是反复复用同一条占位/进度消息",
-      "tool_feedback_max_args_length": "工具反馈长度",
-      "tool_feedback_max_args_length_hint": "每条工具反馈消息中展示的字符上限。设为 0 时使用默认值",
+      "tool_feedback_max_args_length": "工具参数预览长度",
+      "tool_feedback_max_args_length_hint": "每条工具参数预览中展示的字符上限。设为 0 时使用默认值",
       "exec_enabled": "允许命令执行",
       "exec_enabled_hint": "控制应用是否允许执行命令。关闭后，所有命令请求都不会执行",
       "allow_remote": "允许远程命令执行",

From 303ff8137de6ef680af1d7ab1746a0efc97df28d Mon Sep 17 00:00:00 2001
From: lc6464 <64722907+lc6464@users.noreply.github.com>
Date: Sun, 26 Apr 2026 00:50:18 +0800
Subject: [PATCH 3/8] feat(chat): unify reasoning and tool call visibility

---
 .../src/components/chat/chat-page.tsx         | 19 ++++++++++++-------
 web/frontend/src/i18n/locales/en.json         |  2 +-
 web/frontend/src/i18n/locales/zh.json         |  2 +-
 web/frontend/src/store/chat.ts                |  7 ++++---
 4 files changed, 18 insertions(+), 12 deletions(-)

diff --git a/web/frontend/src/components/chat/chat-page.tsx b/web/frontend/src/components/chat/chat-page.tsx
index 03d1a8a36..3ad811dae 100644
--- a/web/frontend/src/components/chat/chat-page.tsx
+++ b/web/frontend/src/components/chat/chat-page.tsx
@@ -23,7 +23,7 @@ import { usePicoChat } from "@/hooks/use-pico-chat"
 import { useSessionHistory } from "@/hooks/use-session-history"
 import type { ConnectionState } from "@/store/chat"
 import type { ChatAttachment } from "@/store/chat"
-import { showThoughtsAtom } from "@/store/chat"
+import { showAssistantDetailsAtom } from "@/store/chat"
 import type { GatewayState } from "@/store/gateway"
 
 const MAX_IMAGE_SIZE_BYTES = 7 * 1024 * 1024
@@ -112,7 +112,9 @@ export function ChatPage() {
   const [hasScrolled, setHasScrolled] = useState(false)
   const [input, setInput] = useState("")
   const [attachments, setAttachments] = useState<ChatAttachment[]>([])
-  const [showThoughts, setShowThoughts] = useAtom(showThoughtsAtom)
+  const [showAssistantDetails, setShowAssistantDetails] = useAtom(
+    showAssistantDetailsAtom,
+  )
 
   const {
     messages,
@@ -271,12 +273,12 @@ export function ChatPage() {
       >
         <div className="border-border/60 hidden items-center gap-2 rounded-lg border px-3 py-1.5 sm:flex">
           <span className="text-muted-foreground text-sm">
-            {t("chat.showThoughts")}
+            {t("chat.showAssistantDetails")}
           </span>
           <Switch
-            checked={showThoughts}
-            onCheckedChange={setShowThoughts}
-            aria-label={t("chat.showThoughts")}
+            checked={showAssistantDetails}
+            onCheckedChange={setShowAssistantDetails}
+            aria-label={t("chat.showAssistantDetails")}
             size="sm"
           />
         </div>
@@ -323,7 +325,10 @@ export function ChatPage() {
           )}
 
           {messages.map((msg) => {
-            if (msg.kind === "thought" && !showThoughts) {
+            if (
+              !showAssistantDetails &&
+              (msg.kind === "thought" || msg.kind === "tool_calls")
+            ) {
               return null
             }
 
diff --git a/web/frontend/src/i18n/locales/en.json b/web/frontend/src/i18n/locales/en.json
index e29a4ccdf..a30dc0471 100644
--- a/web/frontend/src/i18n/locales/en.json
+++ b/web/frontend/src/i18n/locales/en.json
@@ -63,7 +63,7 @@
     "toolCallsLabel": "Tool calls",
     "toolCallExplanationLabel": "Call note",
     "toolCallFunctionLabel": "Call summary",
-    "showThoughts": "Show reasoning",
+    "showAssistantDetails": "Show reasoning and tool calls",
     "toolLabel": "Tool",
     "history": "History",
     "noHistory": "No chat history yet",
diff --git a/web/frontend/src/i18n/locales/zh.json b/web/frontend/src/i18n/locales/zh.json
index d9698c65e..efe3dc32a 100644
--- a/web/frontend/src/i18n/locales/zh.json
+++ b/web/frontend/src/i18n/locales/zh.json
@@ -63,7 +63,7 @@
     "toolCallsLabel": "工具调用",
     "toolCallExplanationLabel": "调用提示",
     "toolCallFunctionLabel": "调用摘要",
-    "showThoughts": "展示思考过程",
+    "showAssistantDetails": "展示思考过程与工具调用",
     "toolLabel": "工具",
     "history": "历史记录",
     "noHistory": "暂无对话历史",
diff --git a/web/frontend/src/store/chat.ts b/web/frontend/src/store/chat.ts
index 43e39d938..7a078d097 100644
--- a/web/frontend/src/store/chat.ts
+++ b/web/frontend/src/store/chat.ts
@@ -65,7 +65,8 @@ export interface ChatStoreState {
 
 type ChatStorePatch = Partial<ChatStoreState>
 
-const SHOW_THOUGHTS_STORAGE_KEY = "picoclaw:chat-show-thoughts"
+// Keep the legacy storage value so existing user preferences survive the rename.
+const SHOW_ASSISTANT_DETAILS_STORAGE_KEY = "picoclaw:chat-show-thoughts"
 
 const DEFAULT_CHAT_STATE: ChatStoreState = {
   messages: [],
@@ -76,8 +77,8 @@ const DEFAULT_CHAT_STATE: ChatStoreState = {
 }
 
 export const chatAtom = atom<ChatStoreState>(DEFAULT_CHAT_STATE)
-export const showThoughtsAtom = atomWithStorage<boolean>(
-  SHOW_THOUGHTS_STORAGE_KEY,
+export const showAssistantDetailsAtom = atomWithStorage<boolean>(
+  SHOW_ASSISTANT_DETAILS_STORAGE_KEY,
   true,
 )
 

From 9d42282672ec85c7777fba28af27d34a8acc832b Mon Sep 17 00:00:00 2001
From: lc6464 <64722907+lc6464@users.noreply.github.com>
Date: Sun, 26 Apr 2026 01:19:19 +0800
Subject: [PATCH 4/8] fix(chat): tolerate animated legacy tool feedback parsing

---
 web/frontend/src/features/chat/assistant-message-state.ts | 7 +++++--
 web/frontend/src/features/chat/tool-calls.ts              | 3 ++-
 2 files changed, 7 insertions(+), 3 deletions(-)

diff --git a/web/frontend/src/features/chat/assistant-message-state.ts b/web/frontend/src/features/chat/assistant-message-state.ts
index 9c9bf0428..b38b9c3a4 100644
--- a/web/frontend/src/features/chat/assistant-message-state.ts
+++ b/web/frontend/src/features/chat/assistant-message-state.ts
@@ -1,5 +1,8 @@
-import type { AssistantMessageKind, ChatMessage } from "../../store/chat.ts"
-import { parseToolCallsFromContent, parseToolCallsValue } from "./tool-calls.ts"
+import {
+  parseToolCallsFromContent,
+  parseToolCallsValue,
+} from "@/features/chat/tool-calls.ts"
+import type { AssistantMessageKind, ChatMessage } from "@/store/chat.ts"
 
 type AssistantToolCalls = ChatMessage["toolCalls"]
 type ExistingAssistantMessageState = Pick<ChatMessage, "kind" | "toolCalls">
diff --git a/web/frontend/src/features/chat/tool-calls.ts b/web/frontend/src/features/chat/tool-calls.ts
index e92dca1bb..c3b9b4777 100644
--- a/web/frontend/src/features/chat/tool-calls.ts
+++ b/web/frontend/src/features/chat/tool-calls.ts
@@ -4,7 +4,8 @@ function parseLegacyToolFeedbackContent(
   content: string,
 ): ChatToolCall[] | undefined {
   const trimmed = content.trim()
-  const match = /^🔧\s+`([^`]+)`(?:\n([\s\S]*))?$/.exec(trimmed)
+  const match =
+    /^🔧\s+`([^`\n\r]*?)(?:\.{1,2})?`[^\n\r]*(?:\r?\n([\s\S]*))?$/.exec(trimmed)
   if (!match) {
     return undefined
   }

From bfc37b784e31d531483163444a3bb1da9b9949dd Mon Sep 17 00:00:00 2001
From: lc6464 <64722907+lc6464@users.noreply.github.com>
Date: Sun, 26 Apr 2026 19:43:25 +0800
Subject: [PATCH 5/8] fix(channels): bypass placeholder edits for thought and
 tool calls

---
 pkg/channels/manager.go      | 14 ++++++
 pkg/channels/manager_test.go | 98 ++++++++++++++++++++++++++++++++++++
 2 files changed, 112 insertions(+)

diff --git a/pkg/channels/manager.go b/pkg/channels/manager.go
index 7974a39e4..d56c4fd9b 100644
--- a/pkg/channels/manager.go
+++ b/pkg/channels/manager.go
@@ -134,6 +134,14 @@ func outboundMessageIsToolFeedback(msg bus.OutboundMessage) bool {
 	return strings.EqualFold(strings.TrimSpace(msg.Context.Raw["message_kind"]), "tool_feedback")
 }
 
+func outboundMessageBypassesPlaceholderEdit(msg bus.OutboundMessage) bool {
+	if len(msg.Context.Raw) == 0 {
+		return false
+	}
+	kind := strings.TrimSpace(msg.Context.Raw["message_kind"])
+	return strings.EqualFold(kind, "thought") || strings.EqualFold(kind, "tool_calls")
+}
+
 func outboundMediaChannel(msg bus.OutboundMediaMessage) string {
 	return msg.Context.Channel
 }
@@ -332,6 +340,12 @@ func (m *Manager) preSend(ctx context.Context, name string, msg bus.OutboundMess
 				}
 				return nil, false
 			}
+			if outboundMessageBypassesPlaceholderEdit(msg) {
+				if deleter, ok := ch.(MessageDeleter); ok {
+					deleter.DeleteMessage(ctx, chatID, entry.id) // best effort
+				}
+				return nil, false
+			}
 			if editor, ok := ch.(MessageEditor); ok {
 				content := msg.Content
 				trackedContent := msg.Content
diff --git a/pkg/channels/manager_test.go b/pkg/channels/manager_test.go
index a5d7c2838..8803134db 100644
--- a/pkg/channels/manager_test.go
+++ b/pkg/channels/manager_test.go
@@ -1131,6 +1131,104 @@ func TestPreSend_ToolFeedbackSeparateMessagesDeletesPlaceholderAndSkipsEdit(t *t
 	}
 }
 
+func TestPreSend_ThoughtPlaceholderDeleteAndSkipsEdit(t *testing.T) {
+	m := newTestManager()
+
+	ch := &mockDeletingMessageEditor{
+		mockMessageEditor: mockMessageEditor{
+			editFn: func(_ context.Context, _, _, _ string) error {
+				t.Fatal("expected thought message to bypass placeholder edit")
+				return nil
+			},
+		},
+	}
+
+	m.RecordPlaceholder("test", "123", "456")
+
+	msg := testOutboundMessage(bus.OutboundMessage{
+		Channel: "test",
+		ChatID:  "123",
+		Content: "thinking trace",
+		Context: bus.InboundContext{
+			Channel: "test",
+			ChatID:  "123",
+			Raw: map[string]string{
+				"message_kind": "thought",
+			},
+		},
+	})
+
+	msgIDs, handled := m.preSend(context.Background(), "test", msg, ch)
+	if handled {
+		t.Fatalf("expected thought message to fall through so the channel can send a structured message, got %v", msgIDs)
+	}
+	if ch.deleteCalls != 1 {
+		t.Fatalf("expected placeholder deletion, got %d delete calls", ch.deleteCalls)
+	}
+	if ch.deletedChatID != "123" || ch.deletedMessageID != "456" {
+		t.Fatalf("unexpected placeholder deletion target: %s/%s", ch.deletedChatID, ch.deletedMessageID)
+	}
+	if _, ok := m.placeholders.Load("test:123"); ok {
+		t.Fatal("expected placeholder to be consumed before structured thought send")
+	}
+}
+
+func TestSendWithRetry_ToolCallsPlaceholderDeleteAndFallsThroughToSend(t *testing.T) {
+	m := newTestManager()
+
+	ch := &mockDeletingMessageEditor{
+		mockMessageEditor: mockMessageEditor{
+			mockChannel: mockChannel{
+				sendFn: func(_ context.Context, msg bus.OutboundMessage) error {
+					if got := msg.Context.Raw["message_kind"]; got != "tool_calls" {
+						t.Fatalf("expected tool_calls message kind, got %q", got)
+					}
+					if msg.Content != "" {
+						t.Fatalf("expected empty tool_calls content, got %q", msg.Content)
+					}
+					return nil
+				},
+			},
+			editFn: func(_ context.Context, _, _, _ string) error {
+				t.Fatal("expected tool_calls message to bypass placeholder edit")
+				return nil
+			},
+		},
+	}
+
+	m.RecordPlaceholder("test", "123", "456")
+
+	w := &channelWorker{
+		ch:      ch,
+		limiter: rate.NewLimiter(rate.Inf, 1),
+	}
+
+	msg := testOutboundMessage(bus.OutboundMessage{
+		Channel: "test",
+		ChatID:  "123",
+		Context: bus.InboundContext{
+			Channel: "test",
+			ChatID:  "123",
+			Raw: map[string]string{
+				"message_kind": "tool_calls",
+				"tool_calls":   `[{"tool_feedback_explanation":"Looking up config","function":{"name":"read_file","arguments":"{}"}}]`,
+			},
+		},
+	})
+
+	m.sendWithRetry(context.Background(), "test", w, msg)
+
+	if ch.deleteCalls != 1 {
+		t.Fatalf("expected placeholder deletion, got %d delete calls", ch.deleteCalls)
+	}
+	if ch.deletedChatID != "123" || ch.deletedMessageID != "456" {
+		t.Fatalf("unexpected placeholder deletion target: %s/%s", ch.deletedChatID, ch.deletedMessageID)
+	}
+	if len(ch.sentMessages) != 1 {
+		t.Fatalf("expected structured tool_calls message to be sent once, got %d", len(ch.sentMessages))
+	}
+}
+
 func TestPreSend_NonToolFeedbackSeparateMessagesClearsTrackedMessageWithoutDismiss(t *testing.T) {
 	m := newTestManager()
 	m.config = &config.Config{

From 1acab59fc7136fea9d7f7edd7ca37117996bd341 Mon Sep 17 00:00:00 2001
From: lc6464 <64722907+lc6464@users.noreply.github.com>
Date: Sun, 26 Apr 2026 19:48:22 +0800
Subject: [PATCH 6/8] fix(tests): format error message

---
 pkg/channels/manager_test.go | 5 ++++-
 1 file changed, 4 insertions(+), 1 deletion(-)

diff --git a/pkg/channels/manager_test.go b/pkg/channels/manager_test.go
index 8803134db..1a783cc3e 100644
--- a/pkg/channels/manager_test.go
+++ b/pkg/channels/manager_test.go
@@ -1160,7 +1160,10 @@ func TestPreSend_ThoughtPlaceholderDeleteAndSkipsEdit(t *testing.T) {
 
 	msgIDs, handled := m.preSend(context.Background(), "test", msg, ch)
 	if handled {
-		t.Fatalf("expected thought message to fall through so the channel can send a structured message, got %v", msgIDs)
+		t.Fatalf(
+			"expected thought message to fall through so the channel can send a structured message, got %v",
+			msgIDs,
+		)
 	}
 	if ch.deleteCalls != 1 {
 		t.Fatalf("expected placeholder deletion, got %d delete calls", ch.deleteCalls)

From 1b9e7e32bdd7ad1e2c8559a3f7552df880095755 Mon Sep 17 00:00:00 2001
From: LC <64722907+lc6464@users.noreply.github.com>
Date: Sun, 26 Apr 2026 19:59:55 +0800
Subject: [PATCH 7/8] fix(chat): add `\r?` for regular expressions

Co-authored-by: Copilot <175728472+Copilot@users.noreply.github.com>
---
 web/frontend/src/features/chat/tool-calls.ts | 4 ++--
 1 file changed, 2 insertions(+), 2 deletions(-)

diff --git a/web/frontend/src/features/chat/tool-calls.ts b/web/frontend/src/features/chat/tool-calls.ts
index c3b9b4777..bf306c5e5 100644
--- a/web/frontend/src/features/chat/tool-calls.ts
+++ b/web/frontend/src/features/chat/tool-calls.ts
@@ -12,9 +12,9 @@ function parseLegacyToolFeedbackContent(
 
   const toolName = match[1]?.trim() ?? ""
   const body = match[2]?.trim() ?? ""
-  const codeFence = /```(?:json)?\n([\s\S]*?)\n```/m.exec(body)
+  const codeFence = /```(?:json)?\r?\n([\s\S]*?)\r?\n```/m.exec(body)
   const argumentsText = codeFence?.[1]?.trim() ?? ""
-  const explanation = body.replace(/```(?:json)?\n[\s\S]*?\n```/gm, "").trim()
+  const explanation = body.replace(/```(?:json)?\r?\n[\s\S]*?\r?\n```/gm, "").trim()
 
   return [
     {

From d6b38c42361bd423fd895909e647ed8503bba6b7 Mon Sep 17 00:00:00 2001
From: lc6464 <64722907+lc6464@users.noreply.github.com>
Date: Sun, 26 Apr 2026 20:13:13 +0800
Subject: [PATCH 8/8] fix(chat): update tool_calls structure and ensure kind is
 always set

---
 pkg/channels/manager_test.go                         |  2 +-
 .../src/features/chat/assistant-message-state.ts     | 12 ++++++++----
 web/frontend/src/features/chat/tool-calls.ts         |  4 +++-
 3 files changed, 12 insertions(+), 6 deletions(-)

diff --git a/pkg/channels/manager_test.go b/pkg/channels/manager_test.go
index 1a783cc3e..6c518780d 100644
--- a/pkg/channels/manager_test.go
+++ b/pkg/channels/manager_test.go
@@ -1214,7 +1214,7 @@ func TestSendWithRetry_ToolCallsPlaceholderDeleteAndFallsThroughToSend(t *testin
 			ChatID:  "123",
 			Raw: map[string]string{
 				"message_kind": "tool_calls",
-				"tool_calls":   `[{"tool_feedback_explanation":"Looking up config","function":{"name":"read_file","arguments":"{}"}}]`,
+				"tool_calls":   `[{"id":"call_1","type":"function","function":{"name":"read_file","arguments":"{}"},"extra_content":{"tool_feedback_explanation":"Looking up config"}}]`,
 			},
 		},
 	})
diff --git a/web/frontend/src/features/chat/assistant-message-state.ts b/web/frontend/src/features/chat/assistant-message-state.ts
index b38b9c3a4..54eb6163f 100644
--- a/web/frontend/src/features/chat/assistant-message-state.ts
+++ b/web/frontend/src/features/chat/assistant-message-state.ts
@@ -1,8 +1,8 @@
 import {
   parseToolCallsFromContent,
   parseToolCallsValue,
-} from "@/features/chat/tool-calls.ts"
-import type { AssistantMessageKind, ChatMessage } from "@/store/chat.ts"
+} from "@/features/chat/tool-calls"
+import type { AssistantMessageKind, ChatMessage } from "@/store/chat"
 
 type AssistantToolCalls = ChatMessage["toolCalls"]
 type ExistingAssistantMessageState = Pick<ChatMessage, "kind" | "toolCalls">
@@ -15,7 +15,7 @@ export interface AssistantMessageCreateState {
 
 export interface AssistantMessageUpdateState {
   content: string
-  kind?: AssistantMessageKind
+  kind: AssistantMessageKind
   toolCalls?: AssistantToolCalls
 }
 
@@ -100,9 +100,13 @@ export function parseAssistantMessageUpdateState(
   if (existing?.toolCalls) {
     return {
       content,
+      kind: existing.kind ?? "normal",
       toolCalls: undefined,
     }
   }
 
-  return { content }
+  return {
+    content,
+    kind: existing?.kind ?? "normal",
+  }
 }
diff --git a/web/frontend/src/features/chat/tool-calls.ts b/web/frontend/src/features/chat/tool-calls.ts
index bf306c5e5..31d685863 100644
--- a/web/frontend/src/features/chat/tool-calls.ts
+++ b/web/frontend/src/features/chat/tool-calls.ts
@@ -14,7 +14,9 @@ function parseLegacyToolFeedbackContent(
   const body = match[2]?.trim() ?? ""
   const codeFence = /```(?:json)?\r?\n([\s\S]*?)\r?\n```/m.exec(body)
   const argumentsText = codeFence?.[1]?.trim() ?? ""
-  const explanation = body.replace(/```(?:json)?\r?\n[\s\S]*?\r?\n```/gm, "").trim()
+  const explanation = body
+    .replace(/```(?:json)?\r?\n[\s\S]*?\r?\n```/gm, "")
+    .trim()
 
   return [
     {