diff --git a/src/media_async/attachment_send.c b/src/media_async/attachment_send.c
index c8347dd3..fa69789a 100644
--- a/src/media_async/attachment_send.c
+++ b/src/media_async/attachment_send.c
@@ -9,6 +9,7 @@
 #include "../../lib/audio_compressor.h"
 #include "../utun_instance.h"
 #include "../chat/chat_core.h"
+#include "../chat/chat_event.h"
 #include "../dm/dm_media.h"
 #include "../video/video.h"
 #include "media_async.h"
@@ -45,11 +46,11 @@ static void attachment_prepare_work(void* arg) {
     } else if (req->transcode) req->error = 0; /* FFmpeg worker стартует после создания каталога. */
     else {
         req->error = ma_copy_file(req->source, req->output);
-        if (!req->error && req->temporary_source && remove(req->source)) {
-            DEBUG_ERROR(DEBUG_CATEGORY_MEDIA, "attachment: source cleanup failed path=%s", req->source); req->error = -1;
-        }
     }
 done:
+    if (req->temporary_source && 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);
     if (req->error && remove(req->output) && errno != ENOENT)
         DEBUG_WARN(DEBUG_CATEGORY_MEDIA, "attachment: partial output cleanup failed path=%s", req->output);
@@ -59,10 +60,12 @@ done:
 static void attachment_publish(struct attachment_send_req* req, int error) {
     attachment_release_pcm(req); /* Submit мог завершиться ошибкой до запуска work. */
     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);
         u_free(req); return;
     }
+    chat_event_attachment(req->inst, req->is_dm, req->target, req->id, 1);
     DEBUG_INFO(DEBUG_CATEGORY_MEDIA, "attachment: prepared target=%s pm=%d kind=%d duration=%u dimensions=%ux%u",
                req->target, req->is_dm, req->info.kind, req->info.duration_ms, req->info.width, req->info.height);
     if (req->is_dm) {
@@ -72,7 +75,11 @@ static void attachment_publish(struct attachment_send_req* req, int error) {
             snprintf(file->conv, sizeof(file->conv), "%s", req->target);
             snprintf(file->path, sizeof(file->path), "%s", req->output);
             dm_send_file_trampoline(file);
-        } else DEBUG_ERROR(DEBUG_CATEGORY_MEDIA, "attachment: PM dispatch allocation failed");
+        } else {
+            DEBUG_ERROR(DEBUG_CATEGORY_MEDIA, "attachment: PM dispatch allocation failed");
+            chat_event_attachment(req->inst, req->is_dm, req->target, req->id, 2);
+            if (remove(req->output)) DEBUG_WARN(DEBUG_CATEGORY_MEDIA, "attachment: rejected output cleanup failed");
+        }
     } else {
         char text[384];
         if (req->info.kind == ATTACHMENT_VOICE) snprintf(text, sizeof(text), "wf=%s;dur=%u;", req->info.waveform, req->info.duration_ms);
@@ -88,7 +95,11 @@ static void attachment_publish(struct attachment_send_req* req, int error) {
             message->duration_ms = req->info.duration_ms; message->width = req->info.width; message->height = req->info.height;
             message->data = (uint8_t*)(message + 1); message->data_len = (uint32_t)length; memcpy(message->data, text, length);
             chat_core_submit_trampoline(message);
-        } else DEBUG_ERROR(DEBUG_CATEGORY_MEDIA, "attachment: channel dispatch allocation failed");
+        } else {
+            DEBUG_ERROR(DEBUG_CATEGORY_MEDIA, "attachment: channel dispatch allocation failed");
+            chat_event_attachment(req->inst, req->is_dm, req->target, req->id, 2);
+            if (remove(req->output)) DEBUG_WARN(DEBUG_CATEGORY_MEDIA, "attachment: rejected output cleanup failed");
+        }
     }
     u_free(req);
 }
@@ -126,6 +137,7 @@ void attachment_send_trampoline(void* arg) {
         DEBUG_ERROR(DEBUG_CATEGORY_MEDIA, "attachment: UUID generation failed"); attachment_release_pcm(req); u_free(req); return;
     }
     for (unsigned i = 0; i < 16; i++) snprintf(hex + 2 * i, 3, "%02x", uuid[i]);
+    memcpy(req->id, uuid, sizeof(req->id));
     const char* base = req->inst->config->global.db_path;
     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");
@@ -134,5 +146,6 @@ void attachment_send_trampoline(void* arg) {
     }
     if (!req->info.name[0]) snprintf(req->info.name, sizeof(req->info.name), "%s.%s", hex,
                                    req->info.kind == ATTACHMENT_VOICE ? "opus" : "mp4");
+    chat_event_attachment(req->inst, req->is_dm, req->target, req->id, 0);
     media_async_submit(req->inst->media_async, req->inst->ua, attachment_prepare_work, req, attachment_prepare_done, req);
 }
diff --git a/src/media_async/attachment_send.h b/src/media_async/attachment_send.h
index ad596d47..c7cc6e1b 100644
--- a/src/media_async/attachment_send.h
+++ b/src/media_async/attachment_send.h
@@ -15,6 +15,7 @@ struct attachment_send_req {
     char target[64];
     int is_dm;
     struct attachment_info info;
+    uint8_t id[16];
     char source[1024], output[1024];
     int transcode, temporary_source;
     const int16_t* pcm;