diff --git a/web/backend/api/pico.go b/web/backend/api/pico.go
index 66b0bb92d..439a41a1c 100644
--- a/web/backend/api/pico.go
+++ b/web/backend/api/pico.go
@@ -181,17 +181,16 @@ func (h *Handler) handlePicoMediaProxy() http.HandlerFunc {
 		}
 
 		gateway.mu.Lock()
-		uiToken := gateway.picoToken
+		picoToken := gateway.picoToken
 		gateway.mu.Unlock()
 
-		token := tokenPrefix + uiToken
-		if token == "" {
+		if picoToken == "" {
 			logger.Warnf("Missing Pico token for media proxy")
 			http.Error(w, "Invalid Pico token", http.StatusForbidden)
 			return
 		}
 
-		h.createPicoHTTPProxy(token).ServeHTTP(w, r)
+		h.createPicoHTTPProxy(picoToken).ServeHTTP(w, r)
 	}
 }
 
diff --git a/web/backend/api/pico_test.go b/web/backend/api/pico_test.go
index 6bdf0c6ca..77fe1039b 100644
--- a/web/backend/api/pico_test.go
+++ b/web/backend/api/pico_test.go
@@ -668,7 +668,7 @@ func TestCreatePicoHTTPProxyInjectsGatewayAuth(t *testing.T) {
 		t.Fatalf("SaveConfig() error = %v", err)
 	}
 
-	proxy := h.createPicoHTTPProxy(tokenPrefix + "test-token" + "ui-token")
+	proxy := h.createPicoHTTPProxy("ui-token")
 	var capturedPath string
 	var capturedAuth string
 	proxy.Transport = roundTripFunc(func(req *http.Request) (*http.Response, error) {
@@ -692,12 +692,83 @@ func TestCreatePicoHTTPProxyInjectsGatewayAuth(t *testing.T) {
 	if capturedPath != "/pico/media/attachment-1" {
 		t.Fatalf("capturedPath = %q, want %q", capturedPath, "/pico/media/attachment-1")
 	}
-	expected := "Bearer " + tokenPrefix + "test-token" + "ui-token"
+	expected := "Bearer ui-token"
 	if capturedAuth != expected {
 		t.Fatalf("Authorization = %q, want %q", capturedAuth, expected)
 	}
 }
 
+func TestHandlePicoMediaProxyUsesRawBearerToken(t *testing.T) {
+	home := t.TempDir()
+	t.Setenv("PICOCLAW_HOME", home)
+
+	configPath := filepath.Join(t.TempDir(), "config.json")
+	h := NewHandler(configPath)
+	handler := h.handlePicoMediaProxy()
+
+	server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		if r.URL.Path != "/pico/media/attachment-1" {
+			t.Fatalf("path = %q, want %q", r.URL.Path, "/pico/media/attachment-1")
+		}
+		if got := r.Header.Get("Authorization"); got != "Bearer ui-token" {
+			t.Fatalf("Authorization = %q, want %q", got, "Bearer ui-token")
+		}
+		w.WriteHeader(http.StatusOK)
+		_, _ = io.WriteString(w, "proxied-media")
+	}))
+	defer server.Close()
+
+	cfg := config.DefaultConfig()
+	cfg.Gateway.Host = "127.0.0.1"
+	cfg.Gateway.Port = mustGatewayTestPort(t, server.URL)
+	bc := cfg.Channels["pico"]
+	bc.Enabled = true
+	decoded, err := bc.GetDecoded()
+	if err != nil {
+		t.Fatalf("GetDecoded() error = %v", err)
+	}
+	decoded.(*config.PicoSettings).SetToken("ui-token")
+	if err := config.SaveConfig(configPath, cfg); err != nil {
+		t.Fatalf("SaveConfig() error = %v", err)
+	}
+
+	cmd := startGatewayLikeProcess(t)
+	t.Cleanup(func() {
+		if cmd.Process != nil {
+			_ = cmd.Process.Kill()
+		}
+		_ = cmd.Wait()
+	})
+
+	origPidData := gateway.pidData
+	origPicoToken := gateway.picoToken
+	origCmd := gateway.cmd
+	t.Cleanup(func() {
+		gateway.mu.Lock()
+		gateway.pidData = origPidData
+		gateway.picoToken = origPicoToken
+		gateway.cmd = origCmd
+		gateway.mu.Unlock()
+	})
+
+	gateway.mu.Lock()
+	gateway.pidData = &ppid.PidFileData{PID: cmd.Process.Pid}
+	gateway.picoToken = "ui-token"
+	gateway.cmd = cmd
+	gateway.mu.Unlock()
+
+	req := newPicoProxyRequest(http.MethodGet, "/pico/media/attachment-1")
+	rec := httptest.NewRecorder()
+	handler(rec, req)
+
+	if rec.Code != http.StatusOK {
+		t.Fatalf("status = %d, want %d", rec.Code, http.StatusOK)
+	}
+	if body := rec.Body.String(); body != "proxied-media" {
+		t.Fatalf("body = %q, want %q", body, "proxied-media")
+	}
+}
+
 func TestHandleWebSocketProxyRejectsStalePidDataAfterProcessExit(t *testing.T) {
 	tmpDir := t.TempDir()
 	t.Setenv("HOME", tmpDir)
diff --git a/web/frontend/src/components/chat/assistant-message.tsx b/web/frontend/src/components/chat/assistant-message.tsx
index 2901b574a..4dfc261c2 100644
--- a/web/frontend/src/components/chat/assistant-message.tsx
+++ b/web/frontend/src/components/chat/assistant-message.tsx
@@ -69,113 +69,117 @@ export function AssistantMessage({
         </div>
       )}
 
-      <div
-        className={cn(
-          "relative overflow-hidden rounded-xl border",
-          isThought
-            ? "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 && (
-          <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>
-            </div>
-            <IconChevronDown
-              className={cn(
-                "size-3.5 opacity-0 transition-all duration-200 group-hover:opacity-100",
-                isExpanded ? "rotate-180" : "",
-              )}
-            />
-          </div>
-        )}
-        {(!isThought || isExpanded) && 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",
-              isThought
-                ? "prose-p:my-1.5 px-3 pt-0 pb-3 text-[13px] leading-relaxed opacity-70"
-                : "prose-p:my-2 p-4 text-[15px] leading-relaxed",
-            )}
-          >
-            <ReactMarkdown
-              remarkPlugins={[remarkGfm]}
-              rehypePlugins={[rehypeRaw, rehypeSanitize, rehypeHighlight]}
+      {(hasText || isThought) && (
+        <div
+          className={cn(
+            "relative overflow-hidden rounded-xl border",
+            isThought
+              ? "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 && (
+            <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)}
             >
-              {content}
-            </ReactMarkdown>
-          </div>
-        )}
-
-        {(imageAttachments.length > 0 || fileAttachments.length > 0) && (
-          <div
-            className={cn("flex flex-col gap-3", hasText ? "px-4 pb-4" : "p-4")}
-          >
-            {imageAttachments.length > 0 && (
-              <div className="flex flex-wrap gap-3">
-                {imageAttachments.map((attachment, index) => (
-                  <a
-                    key={`${attachment.url}-${index}`}
-                    href={attachment.url}
-                    target="_blank"
-                    rel="noreferrer"
-                    className="overflow-hidden rounded-xl border"
-                  >
-                    <img
-                      src={attachment.url}
-                      alt={attachment.filename || "Attachment"}
-                      className="max-h-72 max-w-full object-cover"
-                    />
-                  </a>
-                ))}
+              <div className="flex items-center gap-1.5">
+                <IconBrain className="size-3.5" />
+                <span>{t("chat.reasoningLabel")}</span>
               </div>
-            )}
+              <IconChevronDown
+                className={cn(
+                  "size-3.5 opacity-0 transition-all duration-200 group-hover:opacity-100",
+                  isExpanded ? "rotate-180" : "",
+                )}
+              />
+            </div>
+          )}
+          {(!isThought || isExpanded) && 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",
+                isThought
+                  ? "prose-p:my-1.5 px-3 pt-0 pb-3 text-[13px] leading-relaxed opacity-70"
+                  : "prose-p:my-2 p-4 text-[15px] leading-relaxed",
+              )}
+            >
+              <ReactMarkdown
+                remarkPlugins={[remarkGfm]}
+                rehypePlugins={[rehypeRaw, rehypeSanitize, rehypeHighlight]}
+              >
+                {content}
+              </ReactMarkdown>
+            </div>
+          )}
 
-            {fileAttachments.length > 0 && (
-              <div className="flex flex-col gap-2">
-                {fileAttachments.map((attachment, index) => (
-                  <a
-                    key={`${attachment.url}-${index}`}
-                    href={attachment.url}
-                    download={attachment.filename}
-                    className="bg-background/70 hover:bg-background/90 flex items-center justify-between gap-3 rounded-xl border px-3 py-2 transition-colors"
-                  >
-                    <span className="flex min-w-0 items-center gap-2">
-                      <IconFileText className="text-muted-foreground size-4 shrink-0" />
-                      <span className="truncate text-sm">
-                        {attachment.filename || "Download attachment"}
-                      </span>
-                    </span>
-                    <IconDownload className="text-muted-foreground size-4 shrink-0" />
-                  </a>
-                ))}
+          {!isThought && hasText && (
+            <Button
+              variant="ghost"
+              size="icon"
+              className={cn(
+                "bg-background/50 hover:bg-background/80 absolute top-2 right-2 h-7 w-7 opacity-0 transition-opacity group-hover:opacity-100",
+              )}
+              onClick={handleCopy}
+            >
+              {isCopied ? (
+                <IconCheck className="h-4 w-4 text-green-500" />
+              ) : (
+                <IconCopy className="text-muted-foreground h-4 w-4" />
+              )}
+            </Button>
+          )}
+        </div>
+      )}
+
+      {imageAttachments.length > 0 && (
+        <div className="mt-1 flex flex-wrap gap-2">
+          {imageAttachments.map((attachment, index) => (
+            <a
+              key={`${attachment.url}-${index}`}
+              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"
+            >
+              <img
+                src={attachment.url}
+                alt={attachment.filename || "Attached image"}
+                className="max-h-80 max-w-[280px] object-contain transition-transform duration-300 group-hover/img:scale-[1.02]"
+              />
+              <div className="absolute inset-0 bg-black/0 transition-colors group-hover/img:bg-black/10 dark:group-hover/img:bg-black/20" />
+            </a>
+          ))}
+        </div>
+      )}
+
+      {fileAttachments.length > 0 && (
+        <div className="mt-1 flex flex-wrap gap-3">
+          {fileAttachments.map((attachment, index) => (
+            <a
+              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"
+            >
+              <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>
-        )}
-
-        {!isThought && hasText && (
-          <Button
-            variant="ghost"
-            size="icon"
-            className={cn(
-              "bg-background/50 hover:bg-background/80 absolute top-2 right-2 h-7 w-7 opacity-0 transition-opacity group-hover:opacity-100",
-            )}
-            onClick={handleCopy}
-          >
-            {isCopied ? (
-              <IconCheck className="h-4 w-4 text-green-500" />
-            ) : (
-              <IconCopy className="text-muted-foreground h-4 w-4" />
-            )}
-          </Button>
-        )}
-      </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">
+                  {attachment.filename || "Download file"}
+                </span>
+                <span className="mt-1 text-[12px] font-medium text-muted-foreground/70">
+                  {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">
+                <IconDownload className="h-4 w-4 transition-transform duration-300 group-hover/file:-translate-y-[1px]" />
+              </div>
+            </a>
+          ))}
+        </div>
+      )}
     </div>
   )
 }