diff --git a/pkg/channels/telegram/telegram.go b/pkg/channels/telegram/telegram.go
index a28ae1bb9..c74eb20d5 100644
--- a/pkg/channels/telegram/telegram.go
+++ b/pkg/channels/telegram/telegram.go
@@ -184,23 +184,49 @@ func (c *TelegramChannel) Send(ctx context.Context, msg bus.OutboundMessage) err
 
 	for _, chunk := range mdChunks {
 		htmlContent := markdownToTelegramHTML(chunk)
-		tgMsg := tu.Message(tu.ID(chatID), htmlContent)
-		tgMsg.ParseMode = telego.ModeHTML
 
-		if _, err = c.bot.SendMessage(ctx, tgMsg); err != nil {
-			logger.ErrorCF("telegram", "HTML parse failed, falling back to plain text", map[string]any{
-				"error": err.Error(),
-			})
-			tgMsg.ParseMode = ""
-			if _, err = c.bot.SendMessage(ctx, tgMsg); err != nil {
-				return fmt.Errorf("telegram send: %w", channels.ErrTemporary)
+		// If HTML expansion pushes the chunk over Telegram's 4096-char limit,
+		// re-split the markdown chunk with a proportionally smaller maxLen.
+		if len([]rune(htmlContent)) > 4096 {
+			ratio := float64(len([]rune(chunk))) / float64(len([]rune(htmlContent)))
+			smallerLen := int(float64(4096) * ratio * 0.95) // 5% safety margin
+			if smallerLen < 100 {
+				smallerLen = 100
 			}
+			subChunks := channels.SplitMessage(chunk, smallerLen)
+			for _, sub := range subChunks {
+				if err := c.sendHTMLChunk(ctx, chatID, markdownToTelegramHTML(sub)); err != nil {
+					return err
+				}
+			}
+			continue
+		}
+
+		if err := c.sendHTMLChunk(ctx, chatID, htmlContent); err != nil {
+			return err
 		}
 	}
 
 	return nil
 }
 
+// sendHTMLChunk sends a single HTML message, falling back to plain text on parse failure.
+func (c *TelegramChannel) sendHTMLChunk(ctx context.Context, chatID int64, htmlContent string) error {
+	tgMsg := tu.Message(tu.ID(chatID), htmlContent)
+	tgMsg.ParseMode = telego.ModeHTML
+
+	if _, err := c.bot.SendMessage(ctx, tgMsg); err != nil {
+		logger.ErrorCF("telegram", "HTML parse failed, falling back to plain text", map[string]any{
+			"error": err.Error(),
+		})
+		tgMsg.ParseMode = ""
+		if _, err = c.bot.SendMessage(ctx, tgMsg); err != nil {
+			return fmt.Errorf("telegram send: %w", channels.ErrTemporary)
+		}
+	}
+	return nil
+}
+
 // StartTyping implements channels.TypingCapable.
 // It sends ChatAction(typing) immediately and then repeats every 4 seconds
 // (Telegram's typing indicator expires after ~5s) in a background goroutine.
diff --git a/pkg/channels/telegram/telegram_test.go b/pkg/channels/telegram/telegram_test.go
index b93ea37ac..9d26bdd1a 100644
--- a/pkg/channels/telegram/telegram_test.go
+++ b/pkg/channels/telegram/telegram_test.go
@@ -196,6 +196,32 @@ func TestSend_LongMessage_HTMLFallback_StopsOnError(t *testing.T) {
 	assert.Equal(t, 2, len(caller.calls), "should stop after first chunk fails both HTML and plain text")
 }
 
+func TestSend_MarkdownShortButHTMLLong_MultipleCalls(t *testing.T) {
+	caller := &stubCaller{
+		callFn: func(ctx context.Context, url string, data *ta.RequestData) (*ta.Response, error) {
+			return successResponse(t), nil
+		},
+	}
+	ch := newTestChannel(t, caller)
+
+	// Create markdown whose length is <= 4096 but whose HTML expansion is much longer.
+	// "**a**" (5 chars) becomes "<b>a</b>" (8 chars) in HTML, so repeating it many times
+	// yields HTML that exceeds Telegram's limit while markdown stays within it.
+	markdownContent := strings.Repeat("**a** ", 700) // ~4200 chars markdown, but HTML ~5600+ chars
+	assert.LessOrEqual(t, len([]rune(markdownContent)), 4200, "markdown content should be near Telegram limit")
+
+	htmlExpanded := markdownToTelegramHTML(markdownContent)
+	assert.Greater(t, len([]rune(htmlExpanded)), 4096, "HTML expansion must exceed Telegram limit for this test to be meaningful")
+
+	err := ch.Send(context.Background(), bus.OutboundMessage{
+		ChatID:  "12345",
+		Content: markdownContent,
+	})
+
+	assert.NoError(t, err)
+	assert.Greater(t, len(caller.calls), 1, "markdown-short but HTML-long message should be split into multiple SendMessage calls")
+}
+
 func TestSend_NotRunning(t *testing.T) {
 	caller := &stubCaller{
 		callFn: func(ctx context.Context, url string, data *ta.RequestData) (*ta.Response, error) {