diff --git a/internal/channels/telegram/format.go b/internal/channels/telegram/format.go
index 2be7df09..65ad4803 100644
--- a/internal/channels/telegram/format.go
+++ b/internal/channels/telegram/format.go
@@ -365,17 +365,44 @@ func chunkHTML(text string, maxLen int) []string {
 			break
 		}
 
-		// Find best split point within maxLen
+		// Strategy: search backwards for best natural breakpoint within maxLen.
 		cutAt := maxLen
-		// Prefer paragraph boundary
+
+		// 1. Look for preferred boundaries: paragraph, then newline, then space.
 		if idx := strings.LastIndex(remaining[:cutAt], "\n\n"); idx > 0 {
-			cutAt = idx + 1 // include first newline
+			cutAt = idx + 2
 		} else if idx := strings.LastIndex(remaining[:cutAt], "\n"); idx > 0 {
 			cutAt = idx + 1
 		} else if idx := strings.LastIndex(remaining[:cutAt], " "); idx > 0 {
 			cutAt = idx + 1
 		}
 
+		// 2. Safety: ensure we don't cut in the middle of an HTML tag or entity.
+		// Tag check: find last '<' and see if it was closed before cutAt.
+		if lastOpen := strings.LastIndex(remaining[:cutAt], "<"); lastOpen != -1 {
+			lastClose := strings.LastIndex(remaining[:cutAt], ">")
+			if lastOpen > lastClose {
+				// We're inside a tag (e.g. "<a hre"). Move cutAt back to start of tag.
+				// This ensures the tag remains whole in the next chunk.
+				cutAt = lastOpen
+			}
+		}
+
+		// Entity check: find last '&' and see if it was closed before cutAt.
+		if lastOpen := strings.LastIndex(remaining[:cutAt], "&"); lastOpen != -1 {
+			lastClose := strings.LastIndex(remaining[:cutAt], ";")
+			if lastOpen > lastClose {
+				// Inside an entity (e.g. "&am"). Move cutAt back to start of entity.
+				cutAt = lastOpen
+			}
+		}
+
+		// 3. Fallback for monolithic blocks: if boundaries or safety moved cutAt to 0,
+		// force progress by using maxLen anyway. This avoids infinite loops.
+		if cutAt <= 0 {
+			cutAt = maxLen
+		}
+
 		chunks = append(chunks, strings.TrimRight(remaining[:cutAt], " \n"))
 		remaining = strings.TrimLeft(remaining[cutAt:], " \n")
 	}
diff --git a/internal/channels/telegram/format_test.go b/internal/channels/telegram/format_test.go
index 4952358d..72014a72 100644
--- a/internal/channels/telegram/format_test.go
+++ b/internal/channels/telegram/format_test.go
@@ -61,3 +61,72 @@ func TestRenderTableAsCode_Vietnamese(t *testing.T) {
 		}
 	}
 }
+
+func TestChunkHTML(t *testing.T) {
+	tests := []struct {
+		name   string
+		input  string
+		maxLen int
+		want   []string
+	}{
+		{
+			name:   "natural boundary",
+			input:  "hello world",
+			maxLen: 6,
+			want:   []string{"hello", "world"},
+		},
+		{
+			name:   "tag exceeds maxLen uses fallback",
+			input:  "hello <a href='url'>link</a> world",
+			maxLen: 12,
+			want:   []string{"hello", "<a href='url", "'>link</a>", "world"},
+		},
+		{
+			name:   "avoid mid-tag split safe",
+			input:  "hello <a href='url'>link</a> world",
+			maxLen: 25,
+			// "hello " (6) -> remaining "<a href='url'>link</a> world" (28)
+			// maxLen 25. remaining[:25] is "<a href='url'>link</a> wo"
+			// lastOpen is at "</a" (18). lastClose at "</a>" (21).
+			// lastOpen < lastClose (18 < 21). No cut change from safety.
+			// lastSpace is at index 22 (" world"). cutAt=23.
+			want: []string{"hello", "<a href='url'>link</a>", "world"},
+		},
+		{
+			name:   "avoid mid-entity split",
+			input:  "hello &amp; world",
+			maxLen: 9,
+			// "hello " (6) -> then "&amp; world"
+			// At second chunk: remaining="&amp; world", maxLen=9
+			// remaining[:9] is "&amp; wor"
+			// lastSpace is at index 5. cutAt=6.
+			want: []string{"hello", "&amp;", "world"},
+		},
+		{
+			name:   "monolithic fallback",
+			input:  "monolithicblock",
+			maxLen: 5,
+			want:   []string{"monol", "ithic", "block"},
+		},
+		{
+			name:   "paragraph preferred",
+			input:  "para1\n\npara2\nline3",
+			maxLen: 10,
+			want:   []string{"para1", "para2", "line3"},
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			got := chunkHTML(tt.input, tt.maxLen)
+			if len(got) != len(tt.want) {
+				t.Fatalf("chunkHTML() returned %d chunks, want %d\ngot:  %q\nwant: %q", len(got), len(tt.want), got, tt.want)
+			}
+			for i := range got {
+				if got[i] != tt.want[i] {
+					t.Errorf("chunk[%d] = %q, want %q", i, got[i], tt.want[i])
+				}
+			}
+		})
+	}
+}
diff --git a/internal/channels/telegram/send.go b/internal/channels/telegram/send.go
index e1d19e63..0e4a1503 100644
--- a/internal/channels/telegram/send.go
+++ b/internal/channels/telegram/send.go
@@ -22,12 +22,14 @@ var (
 	parseErrRe           = regexp.MustCompile(`(?i)can't parse entities|parse entities|find end of the entity`)
 	messageNotModifiedRe = regexp.MustCompile(`(?i)message is not modified`)
 	threadNotFoundRe     = regexp.MustCompile(`(?i)message thread not found`)
+	messageTooLongRe     = regexp.MustCompile(`(?i)message is too long|entities too long`)
 	htmlTagRe            = regexp.MustCompile(`<[^>]*>`)
 )
 
 const (
 	sendMaxRetries     = 3
 	sendRetryDelay     = 2 * time.Second
+	maxSplitDepth      = 5               // max recursion depth for "message too long" splitting
 	photoSizeThreshold = 5 * 1024 * 1024 // 5 MB — images larger than this are sent as documents to avoid Telegram compression
 )
 
@@ -269,8 +271,12 @@ func (c *Channel) sendMediaMessage(ctx context.Context, chatID int64, msg bus.Ou
 
 // sendHTML sends a single HTML message, falling back to plain text if Telegram rejects the HTML.
 // replyTo and threadID are optional (0 = omit). General topic (1) is handled by resolveThreadIDForSend.
-func (c *Channel) sendHTML(ctx context.Context, chatID int64, html string, replyTo, threadID int) error {
-	tgMsg := tu.Message(tu.ID(chatID), html)
+func (c *Channel) sendHTML(ctx context.Context, chatID int64, htmlContent string, replyTo, threadID int) error {
+	return c.sendHTMLWithDepth(ctx, chatID, htmlContent, replyTo, threadID, 0)
+}
+
+func (c *Channel) sendHTMLWithDepth(ctx context.Context, chatID int64, htmlContent string, replyTo, threadID, depth int) error {
+	tgMsg := tu.Message(tu.ID(chatID), htmlContent)
 	tgMsg.ParseMode = telego.ModeHTML
 
 	// TS ref: buildTelegramThreadParams() — General topic (1) must be omitted.
@@ -288,17 +294,67 @@ func (c *Channel) sendHTML(ctx context.Context, chatID int64, html string, reply
 		_, e := c.bot.SendMessage(ctx, tgMsg)
 		return e
 	})
-	if err != nil && parseErrRe.MatchString(err.Error()) {
-		slog.Warn("HTML parse failed, falling back to plain text", "error", err)
-		tgMsg.ParseMode = ""
-		tgMsg.Text = stripHTML(tgMsg.Text)
-		_, err = c.bot.SendMessage(ctx, tgMsg)
-	}
-	// TS ref: withTelegramThreadFallback — retry without thread ID when topic is deleted.
-	if err != nil && tgMsg.MessageThreadID != 0 && threadNotFoundRe.MatchString(err.Error()) {
-		slog.Warn("thread not found, retrying without message_thread_id", "thread_id", tgMsg.MessageThreadID)
-		tgMsg.MessageThreadID = 0
-		_, err = c.bot.SendMessage(ctx, tgMsg)
+
+	if err != nil {
+		errStr := err.Error()
+
+		// Case 1: Message too long. Split into smaller chunks and send individually.
+		if messageTooLongRe.MatchString(errStr) {
+			if depth >= maxSplitDepth {
+				return fmt.Errorf("max split depth (%d) exceeded: %w", maxSplitDepth, err)
+			}
+			slog.Warn("Telegram rejected message as too long, splitting further", "len", len(htmlContent), "depth", depth)
+			newMaxLen := len(htmlContent) / 2
+			if newMaxLen < 100 {
+				return err // too small to split meaningfully
+			}
+
+			innerChunks := chunkHTML(htmlContent, newMaxLen)
+			for i, chunk := range innerChunks {
+				r := 0
+				if i == 0 {
+					r = replyTo
+				}
+				if sendErr := c.sendHTMLWithDepth(ctx, chatID, chunk, r, threadID, depth+1); sendErr != nil {
+					return sendErr
+				}
+			}
+			return nil
+		}
+
+		// Case 2: Parse error. Fallback to plain text.
+		if parseErrRe.MatchString(errStr) {
+			slog.Warn("HTML parse failed, falling back to plain text", "error", err)
+			tgMsg.ParseMode = ""
+			tgMsg.Text = stripHTML(htmlContent)
+			_, err = c.bot.SendMessage(ctx, tgMsg)
+
+			// If plain text is STILL too long, split it.
+			if err != nil && messageTooLongRe.MatchString(err.Error()) {
+				slog.Warn("Plain text fallback too long, splitting further", "len", len(tgMsg.Text))
+				innerChunks := chunkPlainText(tgMsg.Text, 4000) // use default safe limit
+				for i, chunk := range innerChunks {
+					msg := tu.Message(tu.ID(chatID), chunk)
+					msg.ReplyParameters = tgMsg.ReplyParameters
+					if i > 0 {
+						msg.ReplyParameters = nil
+					}
+					msg.MessageThreadID = tgMsg.MessageThreadID
+					_, err = c.bot.SendMessage(ctx, msg)
+					if err != nil {
+						return err
+					}
+				}
+				return nil
+			}
+		}
+
+		// Case 3: Thread not found. Re-check err (may have changed after Case 2 fallback).
+		if err != nil && tgMsg.MessageThreadID != 0 && threadNotFoundRe.MatchString(err.Error()) {
+			slog.Warn("thread not found, retrying without message_thread_id", "thread_id", tgMsg.MessageThreadID)
+			tgMsg.MessageThreadID = 0
+			_, err = c.bot.SendMessage(ctx, tgMsg)
+		}
 	}
 	return err
 }