diff --git a/src/dm/dm_media.c b/src/dm/dm_media.c
index 917ea0ec..b6496e7c 100644
--- a/src/dm/dm_media.c
+++ b/src/dm/dm_media.c
@@ -620,16 +620,24 @@ static void dm_source_cleanup(void* arg) {
 }
 
 static void dm_source_cleaned(void* arg, int error) {
-    if (error) DEBUG_WARN(DEBUG_CATEGORY_DM, "dm_media: source cleanup cancelled error=%d", error);
+    if (error) {
+        DEBUG_WARN(DEBUG_CATEGORY_DM, "dm_media: source cleanup cancelled error=%d", error);
+        dm_source_cleanup(arg);
+    }
     u_free(arg);
 }
 
 void dm_send_file_trampoline(void* arg) {
     struct dm_file_req* req = arg;
     if (!req) return;
-    if (dm_send_file(req->inst, req->conv, req->path, &req->info, req->remove_source) && req->remove_source) {
-        media_async_submit(req->inst->media_async, req->inst->ua, dm_source_cleanup, req, dm_source_cleaned, req);
-        return;
+    if (dm_send_file(req->inst, req->conv, req->path, &req->info, req->remove_source)) {
+        const uint8_t rejected[16] = {0};
+        chat_event_attachment(req->inst, 1, req->conv, rejected, 2);
+        if (req->remove_source) {
+            media_async_submit(req->inst ? req->inst->media_async : NULL, req->inst ? req->inst->ua : NULL,
+                               dm_source_cleanup, req, dm_source_cleaned, req);
+            return;
+        }
     }
     u_free(req);
 }
diff --git a/src/media_async/attachment_send.c b/src/media_async/attachment_send.c
index 0776dae7..109f7c5f 100644
--- a/src/media_async/attachment_send.c
+++ b/src/media_async/attachment_send.c
@@ -48,7 +48,7 @@ static void attachment_prepare_work(void* arg) {
         req->error = ma_copy_file(req->source, req->output);
     }
 done:
-    if (req->temporary_source && remove(req->source) && errno != ENOENT) {
+    if (req->temporary_source && !req->transcode && remove(req->source) && errno != ENOENT) {
         DEBUG_ERROR(DEBUG_CATEGORY_MEDIA, "attachment: source cleanup failed path=%s", req->source); req->error = -1;
     }
     attachment_release_pcm(req);
@@ -59,12 +59,14 @@ done:
 /* Один выбор транспорта после общей подготовки; групповой индекс и PM crypto не смешиваются. */
 static void attachment_publish(struct attachment_send_req* req, int error) {
     attachment_release_pcm(req); /* Submit мог завершиться ошибкой до запуска work. */
+    if (req->temporary_source && remove(req->source) && errno != ENOENT) {
+        DEBUG_ERROR(DEBUG_CATEGORY_MEDIA, "attachment: abandoned source cleanup failed path=%s", req->source);
+        error = -1;
+    }
     if (error || req->error || attachment_validate(&req->info)) {
         chat_event_attachment(req->inst, req->is_dm, req->target, req->id, 2);
         DEBUG_ERROR(DEBUG_CATEGORY_MEDIA, "attachment: preparation failed target=%s error=%d worker=%d", req->target, error, req->error);
         if (remove(req->output) && errno != ENOENT) DEBUG_WARN(DEBUG_CATEGORY_MEDIA, "attachment: output cleanup failed path=%s", req->output);
-        if (req->temporary_source && remove(req->source) && errno != ENOENT)
-            DEBUG_WARN(DEBUG_CATEGORY_MEDIA, "attachment: abandoned source cleanup failed path=%s", req->source);
         u_free(req); return;
     }
     chat_event_attachment(req->inst, req->is_dm, req->target, req->id, 1);
@@ -132,11 +134,11 @@ void attachment_send_trampoline(void* arg) {
     if (!req->inst || !req->inst->chat_core || !req->inst->media_async || !req->target[0] ||
         strspn(req->target, "0123456789") != strlen(req->target)) {
         DEBUG_ERROR(DEBUG_CATEGORY_MEDIA, "attachment: invalid target/stopped service");
-        attachment_release_pcm(req); u_free(req); return;
+        attachment_publish(req, -1); return;
     }
     uint8_t uuid[16]; char hex[33];
     if (RAND_bytes(uuid, sizeof(uuid)) != 1) {
-        DEBUG_ERROR(DEBUG_CATEGORY_MEDIA, "attachment: UUID generation failed"); attachment_release_pcm(req); u_free(req); return;
+        DEBUG_ERROR(DEBUG_CATEGORY_MEDIA, "attachment: UUID generation failed"); attachment_publish(req, -1); return;
     }
     for (unsigned i = 0; i < 16; i++) snprintf(hex + 2 * i, 3, "%02x", uuid[i]);
     memcpy(req->id, uuid, sizeof(req->id));
@@ -144,7 +146,7 @@ void attachment_send_trampoline(void* arg) {
     int n = snprintf(req->output, sizeof(req->output), "%s/media/%s/%s.%s", base[0] ? base : ".",
                      req->is_dm ? "pm-prepared" : req->target, hex, req->info.kind == ATTACHMENT_VOICE ? "opus" : "mp4");
     if (n < 0 || (size_t)n >= sizeof(req->output)) {
-        DEBUG_ERROR(DEBUG_CATEGORY_MEDIA, "attachment: output path too long"); attachment_release_pcm(req); u_free(req); return;
+        DEBUG_ERROR(DEBUG_CATEGORY_MEDIA, "attachment: output path too long"); req->output[0] = 0; attachment_publish(req, -1); return;
     }
     if (!req->info.name[0]) snprintf(req->info.name, sizeof(req->info.name), "%s.%s", hex,
                                    req->info.kind == ATTACHMENT_VOICE ? "opus" : "mp4");