diff --git a/internal/channels/telegram/channel.go b/internal/channels/telegram/channel.go
index 24cd98f9..364c8be3 100644
--- a/internal/channels/telegram/channel.go
+++ b/internal/channels/telegram/channel.go
@@ -465,3 +465,36 @@ func resolveThreadIDForSend(threadID int) int {
 	}
 	return threadID
 }
+
+// migrateGroupChat handles a Telegram group→supergroup migration by updating
+// all DB references (paired_devices, sessions, channel_contacts) and invalidating
+// in-memory caches. Safe to call multiple times (idempotent).
+func (c *Channel) migrateGroupChat(ctx context.Context, oldChatID, newChatID int64) {
+	oldStr := fmt.Sprintf("%d", oldChatID)
+	newStr := fmt.Sprintf("%d", newChatID)
+
+	slog.Info("telegram: migrating group chat",
+		"old_chat_id", oldStr, "new_chat_id", newStr, "channel", c.Name())
+
+	// Update DB (paired_devices, sessions, channel_contacts).
+	if c.pairingService != nil {
+		if err := c.pairingService.MigrateGroupChatID(ctx, c.Name(), oldStr, newStr); err != nil {
+			slog.Error("telegram: failed to migrate group chat in DB",
+				"old_chat_id", oldStr, "new_chat_id", newStr, "error", err)
+			return
+		}
+	}
+
+	// Invalidate approvedGroups cache.
+	c.approvedGroups.Delete(oldStr)
+	c.approvedGroups.Store(newStr, true)
+
+	// Clear pairing reply debounce for old group sender.
+	oldGroupSender := fmt.Sprintf("group:%d", oldChatID)
+	c.pairingReplySent.Delete(oldGroupSender)
+
+	// Clear in-memory pending history for old key (will rebuild from DB on next access).
+	if c.groupHistory != nil {
+		c.groupHistory.Clear(oldStr)
+	}
+}
diff --git a/internal/channels/telegram/handlers.go b/internal/channels/telegram/handlers.go
index 76c6fa82..91cc70b0 100644
--- a/internal/channels/telegram/handlers.go
+++ b/internal/channels/telegram/handlers.go
@@ -22,6 +22,15 @@ func (c *Channel) handleMessage(ctx context.Context, update telego.Update) {
 		return
 	}
 
+	// Proactive migration detection: group upgraded to supergroup.
+	// Must run BEFORE isServiceMessage() — migration messages have no text/media.
+	if message.MigrateToChatID != 0 {
+		slog.Info("telegram: group migrated to supergroup (inbound)",
+			"old_chat_id", message.Chat.ID, "new_chat_id", message.MigrateToChatID)
+		c.migrateGroupChat(ctx, message.Chat.ID, message.MigrateToChatID)
+		return
+	}
+
 	// Skip service messages (member added/removed, title changed, etc.).
 	// These have no text/caption and no meaningful media — processing them
 	// pollutes mention gate and history with "[empty message]" entries.
diff --git a/internal/channels/telegram/send.go b/internal/channels/telegram/send.go
index 88e53a38..1d621302 100644
--- a/internal/channels/telegram/send.go
+++ b/internal/channels/telegram/send.go
@@ -28,6 +28,16 @@ var (
 	htmlTagRe            = regexp.MustCompile(`<[^>]*>`)
 )
 
+// extractMigrateChatID checks if a Telegram API error contains a group→supergroup
+// migration indicator and returns the new chat ID, or 0 if not a migration error.
+func extractMigrateChatID(err error) int64 {
+	var apiErr *telegoapi.Error
+	if errors.As(err, &apiErr) && apiErr.Parameters != nil && apiErr.Parameters.MigrateToChatID != 0 {
+		return apiErr.Parameters.MigrateToChatID
+	}
+	return 0
+}
+
 const (
 	sendMaxRetries     = 3
 	sendRetryDelay     = 2 * time.Second
@@ -229,7 +239,17 @@ func (c *Channel) Send(ctx context.Context, msg bus.OutboundMessage) error {
 			c.placeholders.Delete(localKey)
 			_ = c.deleteMessage(ctx, chatID, pID.(int))
 		}
-		return c.sendMediaMessage(ctx, chatID, msg, replyToMsgID, threadID)
+		err := c.sendMediaMessage(ctx, chatID, msg, replyToMsgID, threadID)
+		// Migration fallback: group upgraded to supergroup — retry with new chat ID.
+		if err != nil {
+			if newChatID := extractMigrateChatID(err); newChatID != 0 {
+				slog.Info("telegram: group migrated to supergroup (media send-path)",
+					"old_chat_id", chatID, "new_chat_id", newChatID)
+				c.migrateGroupChat(ctx, chatID, newChatID)
+				return c.sendMediaMessage(ctx, newChatID, msg, replyToMsgID, threadID)
+			}
+		}
+		return err
 	}
 
 	// Text-only message
@@ -407,6 +427,17 @@ func (c *Channel) sendHTMLWithDepth(ctx context.Context, chatID int64, htmlConte
 	})
 
 	if err != nil {
+		// Case 0: Group migrated to supergroup — update DB and retry with new chat ID.
+		if newChatID := extractMigrateChatID(err); newChatID != 0 {
+			slog.Info("telegram: group migrated to supergroup (send-path)",
+				"old_chat_id", chatID, "new_chat_id", newChatID)
+			c.migrateGroupChat(ctx, chatID, newChatID)
+			if depth < maxSplitDepth {
+				return c.sendHTMLWithDepth(ctx, newChatID, htmlContent, replyTo, threadID, depth+1)
+			}
+			return fmt.Errorf("migration retry depth exceeded: %w", err)
+		}
+
 		errStr := err.Error()
 
 		// Case 1: Message too long. Split into smaller chunks and send individually.
diff --git a/internal/http/auth_test.go b/internal/http/auth_test.go
index 34b66cc8..c5c07552 100644
--- a/internal/http/auth_test.go
+++ b/internal/http/auth_test.go
@@ -139,6 +139,9 @@ func (m *mockPairingStore) IsPaired(_ context.Context, senderID, channel string)
 }
 func (m *mockPairingStore) ListPending(context.Context) []store.PairingRequestData { return nil }
 func (m *mockPairingStore) ListPaired(context.Context) []store.PairedDeviceData    { return nil }
+func (m *mockPairingStore) MigrateGroupChatID(context.Context, string, string, string) error {
+	return nil
+}
 
 func TestResolveAuth_GatewayToken(t *testing.T) {
 	setupTestCache(t, nil)
diff --git a/internal/store/pairing_store.go b/internal/store/pairing_store.go
index 2427b4ad..c10a81ce 100644
--- a/internal/store/pairing_store.go
+++ b/internal/store/pairing_store.go
@@ -33,4 +33,8 @@ type PairingStore interface {
 	IsPaired(ctx context.Context, senderID, channel string) (bool, error)
 	ListPending(ctx context.Context) []PairingRequestData
 	ListPaired(ctx context.Context) []PairedDeviceData
+	// MigrateGroupChatID updates all references from oldChatID to newChatID
+	// across paired_devices, sessions, and channel_contacts within a transaction.
+	// Scoped by tenant_id and channel. Idempotent (safe to call multiple times).
+	MigrateGroupChatID(ctx context.Context, channel, oldChatID, newChatID string) error
 }
diff --git a/internal/store/pg/pairing.go b/internal/store/pg/pairing.go
index 1aeca1c3..b14fa31d 100644
--- a/internal/store/pg/pairing.go
+++ b/internal/store/pg/pairing.go
@@ -234,6 +234,67 @@ func (s *PGPairingStore) ListPaired(ctx context.Context) []store.PairedDeviceDat
 	return result
 }
 
+func (s *PGPairingStore) MigrateGroupChatID(ctx context.Context, channel, oldChatID, newChatID string) error {
+	tid := tenantIDForInsert(ctx)
+
+	tx, err := s.db.BeginTx(ctx, nil)
+	if err != nil {
+		return fmt.Errorf("begin migrate tx: %w", err)
+	}
+	defer tx.Rollback()
+
+	// 1. paired_devices: update sender_id and chat_id
+	if _, err := tx.ExecContext(ctx,
+		`UPDATE paired_devices
+		 SET sender_id = REPLACE(sender_id, $1, $2),
+		     chat_id = REPLACE(chat_id, $1, $2)
+		 WHERE sender_id LIKE '%' || $1 || '%'
+		   AND channel = $3
+		   AND tenant_id = $4`,
+		oldChatID, newChatID, channel, tid,
+	); err != nil {
+		return fmt.Errorf("migrate paired_devices: %w", err)
+	}
+
+	// 2. sessions: update session_key and user_id
+	if _, err := tx.ExecContext(ctx,
+		`UPDATE sessions
+		 SET session_key = REPLACE(session_key, ':' || $1, ':' || $2),
+		     user_id = REPLACE(user_id, ':' || $1, ':' || $2)
+		 WHERE session_key LIKE '%:telegram:%:' || $1 || '%'
+		   AND tenant_id = $3`,
+		oldChatID, newChatID, tid,
+	); err != nil {
+		return fmt.Errorf("migrate sessions: %w", err)
+	}
+
+	// 3. channel_contacts: update sender_id
+	if _, err := tx.ExecContext(ctx,
+		`UPDATE channel_contacts
+		 SET sender_id = REPLACE(sender_id, $1, $2)
+		 WHERE sender_id LIKE '%' || $1 || '%'
+		   AND channel_type = 'telegram'
+		   AND tenant_id = $3`,
+		oldChatID, newChatID, tid,
+	); err != nil {
+		return fmt.Errorf("migrate channel_contacts: %w", err)
+	}
+
+	// 4. channel_pending_messages: update history_key
+	if _, err := tx.ExecContext(ctx,
+		`UPDATE channel_pending_messages
+		 SET history_key = REPLACE(history_key, $1, $2)
+		 WHERE history_key LIKE '%' || $1 || '%'
+		   AND channel_name = $3
+		   AND tenant_id = $4`,
+		oldChatID, newChatID, channel, tid,
+	); err != nil {
+		return fmt.Errorf("migrate channel_pending_messages: %w", err)
+	}
+
+	return tx.Commit()
+}
+
 func generatePairingCode() string {
 	b := make([]byte, codeLength)
 	rand.Read(b)
diff --git a/internal/store/sqlitestore/pairing.go b/internal/store/sqlitestore/pairing.go
index 0019f51c..8be7b592 100644
--- a/internal/store/sqlitestore/pairing.go
+++ b/internal/store/sqlitestore/pairing.go
@@ -235,6 +235,67 @@ func (s *SQLitePairingStore) ListPaired(ctx context.Context) []store.PairedDevic
 	return result
 }
 
+func (s *SQLitePairingStore) MigrateGroupChatID(ctx context.Context, channel, oldChatID, newChatID string) error {
+	tid := tenantIDForInsert(ctx)
+
+	tx, err := s.db.BeginTx(ctx, nil)
+	if err != nil {
+		return fmt.Errorf("begin migrate tx: %w", err)
+	}
+	defer tx.Rollback()
+
+	// 1. paired_devices: update sender_id and chat_id
+	if _, err := tx.ExecContext(ctx,
+		`UPDATE paired_devices
+		 SET sender_id = REPLACE(sender_id, ?, ?),
+		     chat_id = REPLACE(chat_id, ?, ?)
+		 WHERE sender_id LIKE '%' || ? || '%'
+		   AND channel = ?
+		   AND tenant_id = ?`,
+		oldChatID, newChatID, oldChatID, newChatID, oldChatID, channel, tid,
+	); err != nil {
+		return fmt.Errorf("migrate paired_devices: %w", err)
+	}
+
+	// 2. sessions: update session_key and user_id
+	if _, err := tx.ExecContext(ctx,
+		`UPDATE sessions
+		 SET session_key = REPLACE(session_key, ':' || ?, ':' || ?),
+		     user_id = REPLACE(user_id, ':' || ?, ':' || ?)
+		 WHERE session_key LIKE '%:telegram:%:' || ? || '%'
+		   AND tenant_id = ?`,
+		oldChatID, newChatID, oldChatID, newChatID, oldChatID, tid,
+	); err != nil {
+		return fmt.Errorf("migrate sessions: %w", err)
+	}
+
+	// 3. channel_contacts: update sender_id
+	if _, err := tx.ExecContext(ctx,
+		`UPDATE channel_contacts
+		 SET sender_id = REPLACE(sender_id, ?, ?)
+		 WHERE sender_id LIKE '%' || ? || '%'
+		   AND channel_type = 'telegram'
+		   AND tenant_id = ?`,
+		oldChatID, newChatID, oldChatID, tid,
+	); err != nil {
+		return fmt.Errorf("migrate channel_contacts: %w", err)
+	}
+
+	// 4. channel_pending_messages: update history_key
+	if _, err := tx.ExecContext(ctx,
+		`UPDATE channel_pending_messages
+		 SET history_key = REPLACE(history_key, ?, ?)
+		 WHERE history_key LIKE '%' || ? || '%'
+		   AND channel_name = ?
+		   AND tenant_id = ?`,
+		oldChatID, newChatID, oldChatID, channel, tid,
+	); err != nil {
+		return fmt.Errorf("migrate channel_pending_messages: %w", err)
+	}
+
+	return tx.Commit()
+}
+
 // parseTimeToMillis parses a Go time.Time string (possibly with monotonic clock suffix)
 // from SQLite and returns Unix milliseconds. Falls back to 0 on parse failure.
 func parseTimeToMillis(s string) int64 {