fix err and placeholder

pkg/channels/manager.go

@@ -206,6 +206,40 @@ func (m *Manager) preSend(ctx context.Context, name string, msg bus.OutboundMess
 	return false
 }
 
+// preSendMedia handles typing stop, reaction undo, and placeholder cleanup
+// before sending media attachments. Unlike preSend for text messages, media
+// delivery never edits the placeholder because there is no text payload to
+// replace it with; it only attempts to delete the placeholder when possible.
+func (m *Manager) preSendMedia(ctx context.Context, name string, msg bus.OutboundMediaMessage, ch Channel) {
+	key := name + ":" + msg.ChatID
+
+	// 1. Stop typing
+	if v, loaded := m.typingStops.LoadAndDelete(key); loaded {
+		if entry, ok := v.(typingEntry); ok {
+			entry.stop() // idempotent, safe
+		}
+	}
+
+	// 2. Undo reaction
+	if v, loaded := m.reactionUndos.LoadAndDelete(key); loaded {
+		if entry, ok := v.(reactionEntry); ok {
+			entry.undo() // idempotent, safe
+		}
+	}
+
+	// 3. Clear any finalized stream marker for this chat before media delivery.
+	m.streamActive.LoadAndDelete(key)
+
+	// 4. Delete placeholder if present.
+	if v, loaded := m.placeholders.LoadAndDelete(key); loaded {
+		if entry, ok := v.(placeholderEntry); ok && entry.id != "" {
+			if deleter, ok := ch.(MessageDeleter); ok {
+				deleter.DeleteMessage(ctx, msg.ChatID, entry.id) // best effort
+			}
+		}
+	}
+}
+
 func NewManager(cfg *config.Config, messageBus *bus.MessageBus, store media.MediaStore) (*Manager, error) {
 	m := &Manager{
 		channels:      make(map[string]Channel),
@@ -779,7 +813,8 @@ func (m *Manager) runMediaWorker(ctx context.Context, name string, w *channelWor
 }
 
 // sendMediaWithRetry sends a media message through the channel with rate limiting and
-// retry logic. It returns nil on success, or the last error after retries.
+// retry logic. It returns nil on success, or the last error after retries,
+// including when the channel does not support MediaSender.
 func (m *Manager) sendMediaWithRetry(
 	ctx context.Context,
 	name string,
@@ -788,10 +823,12 @@ func (m *Manager) sendMediaWithRetry(
 ) error {
 	ms, ok := w.ch.(MediaSender)
 	if !ok {
-		logger.DebugCF("channels", "Channel does not support MediaSender, skipping media", map[string]any{
+		err := fmt.Errorf("channel %q does not support media sending", name)
+		logger.WarnCF("channels", "Channel does not support MediaSender", map[string]any{
 			"channel": name,
+			"error":   err.Error(),
 		})
-		return nil
+		return err
 	}
 
 	// Rate limit: wait for token
@@ -799,6 +836,9 @@ func (m *Manager) sendMediaWithRetry(
 		return err
 	}
 
+	// Pre-send: stop typing and clean up any placeholder before sending media.
+	m.preSendMedia(ctx, name, msg, w.ch)
+
 	var lastErr error
 	for attempt := 0; attempt <= maxRetries; attempt++ {
 		lastErr = ms.SendMedia(ctx, msg)

pkg/channels/manager_test.go

@@ -4,6 +4,7 @@ import (
 	"context"
 	"errors"
 	"fmt"
+	"strings"
 	"sync"
 	"sync/atomic"
 	"testing"
@@ -57,6 +58,26 @@ func (m *mockMediaChannel) SendMedia(ctx context.Context, msg bus.OutboundMediaM
 	return nil
 }
 
+type mockDeletingMediaChannel struct {
+	mockMediaChannel
+	deleteCalls int
+	lastDeleted struct {
+		chatID    string
+		messageID string
+	}
+}
+
+func (m *mockDeletingMediaChannel) DeleteMessage(
+	_ context.Context,
+	chatID string,
+	messageID string,
+) error {
+	m.deleteCalls++
+	m.lastDeleted.chatID = chatID
+	m.lastDeleted.messageID = messageID
+	return nil
+}
+
 // newTestManager creates a minimal Manager suitable for unit tests.
 func newTestManager() *Manager {
 	return &Manager{
@@ -278,6 +299,69 @@ func TestSendMedia_PropagatesFailure(t *testing.T) {
 	}
 }
 
+func TestSendMedia_UnsupportedChannelReturnsError(t *testing.T) {
+	m := newTestManager()
+	ch := &mockChannel{
+		sendFn: func(_ context.Context, _ bus.OutboundMessage) error {
+			return nil
+		},
+	}
+	w := &channelWorker{
+		ch:      ch,
+		limiter: rate.NewLimiter(rate.Inf, 1),
+	}
+	m.channels["test"] = ch
+	m.workers["test"] = w
+
+	err := m.SendMedia(context.Background(), bus.OutboundMediaMessage{
+		Channel: "test",
+		ChatID:  "chat1",
+		Parts:   []bus.MediaPart{{Ref: "media://abc"}},
+	})
+	if err == nil {
+		t.Fatal("expected SendMedia to return error for unsupported channel")
+	}
+	if !strings.Contains(err.Error(), "does not support media sending") {
+		t.Fatalf("unexpected error: %v", err)
+	}
+}
+
+func TestSendMedia_DeletesPlaceholderBeforeSending(t *testing.T) {
+	m := newTestManager()
+	ch := &mockDeletingMediaChannel{
+		mockMediaChannel: mockMediaChannel{
+			sendMediaFn: func(_ context.Context, _ bus.OutboundMediaMessage) error {
+				return nil
+			},
+		},
+	}
+	w := &channelWorker{
+		ch:      ch,
+		limiter: rate.NewLimiter(rate.Inf, 1),
+	}
+	m.channels["test"] = ch
+	m.workers["test"] = w
+	m.RecordPlaceholder("test", "chat1", "placeholder-1")
+
+	err := m.SendMedia(context.Background(), bus.OutboundMediaMessage{
+		Channel: "test",
+		ChatID:  "chat1",
+		Parts:   []bus.MediaPart{{Ref: "media://abc"}},
+	})
+	if err != nil {
+		t.Fatalf("SendMedia() error = %v", err)
+	}
+	if ch.deleteCalls != 1 {
+		t.Fatalf("expected placeholder delete to be called once, got %d", ch.deleteCalls)
+	}
+	if ch.lastDeleted.chatID != "chat1" || ch.lastDeleted.messageID != "placeholder-1" {
+		t.Fatalf("unexpected placeholder deletion target: %+v", ch.lastDeleted)
+	}
+	if len(ch.sentMediaMessages) != 1 {
+		t.Fatalf("expected media to be sent once, got %d", len(ch.sentMediaMessages))
+	}
+}
+
 func TestSendWithRetry_UnknownError(t *testing.T) {
 	m := newTestManager()
 	var callCount int