diff --git a/tests/Makefile.am b/tests/Makefile.am
index e1f4ba5f..56b2646c 100644
--- a/tests/Makefile.am
+++ b/tests/Makefile.am
@@ -84,6 +84,7 @@ check_PROGRAMS = \
 	test_dm_media \
 	test_dm_worker \
 	test_attachment \
+	test_attachment_send \
 	test_call \
 	test_call_headless \
 	test_radio \
@@ -194,6 +195,8 @@ test_reality_config_LDADD = $(LIBUTUN) $(CRYPTO_LIBS) $(COMMON_LIBS)
 test_dm_SOURCES = test_dm.c
 test_attachment_SOURCES = test_attachment.c
 test_attachment_LDADD = $(LIBUTUN) $(CRYPTO_LIBS) $(COMMON_LIBS)
+test_attachment_send_SOURCES = test_attachment_send.c
+test_attachment_send_LDADD = $(LIBUTUN) $(CRYPTO_LIBS) $(COMMON_LIBS)
 test_dm_CFLAGS = -I$(top_srcdir)/src -I$(top_srcdir)/src/transport_layer -I$(top_srcdir)/lib
 test_dm_LDADD = $(LIBUTUN) $(CRYPTO_LIBS) $(COMMON_LIBS)
 
diff --git a/tests/test_attachment_send.c b/tests/test_attachment_send.c
new file mode 100644
index 00000000..ef68be6d
--- /dev/null
+++ b/tests/test_attachment_send.c
@@ -0,0 +1,99 @@
+/* Общая подготовка: закреплённый target, реальный Opus, отмена и собственный cache. */
+#include <stdio.h>
+#include <string.h>
+#include <pthread.h>
+#include "../lib/mem.h"
+#include "../lib/debug_config.h"
+#include "../src/utun_instance.h"
+#include "../src/chat/chat_core.h"
+#include "../src/chat/chat_event.h"
+#include "../src/dm/dm_core.h"
+#include "../src/dm/dm_crypto.h"
+#include "../src/media_async/attachment_send.h"
+#include "test_utils.h"
+
+#define REQUIRE(value) do { if (!(value)) { DEBUG_ERROR(DEBUG_CATEGORY_MEDIA, "attachment send check line=%d", __LINE__); return 1; } } while (0)
+struct test_state {
+    pthread_t event_thread;
+    char target[68];
+    int released, release_in_worker, starts, ready, failed;
+    int16_t pcm[48000];
+};
+static struct test_state test;
+
+static void release_pcm(void* owner) {
+    struct test_state* state = owner;
+    state->released++; state->release_in_worker = !pthread_equal(pthread_self(), state->event_thread);
+}
+
+static void event(struct UTUN_INSTANCE* inst, int type, const uint8_t* data, int length) {
+    (void)inst;
+    if (type != CHAT_EVT_ATTACHMENT_PREPARATION) return;
+    if (length < 18 || length != 18 + data[0] || data[0] >= sizeof(test.target)) { test.failed++; return; }
+    memcpy(test.target, data + 1, data[0]); test.target[data[0]] = 0;
+    int state = data[length - 1];
+    if (state == 0) test.starts++;
+    else if (state == 1) test.ready++;
+    else test.failed++;
+}
+
+static int count(struct UTUN_INSTANCE* inst) {
+    sqlite3_stmt* statement = NULL;
+    if (sqlite3_prepare_v2(inst->topo_sqlite_db, "SELECT count(*) FROM dm_messages", -1, &statement, NULL)) return -1;
+    int result = sqlite3_step(statement) == SQLITE_ROW ? sqlite3_column_int(statement, 0) : -1;
+    sqlite3_finalize(statement); return result;
+}
+
+int main(void) {
+    debug_config_init(); debug_set_level(DEBUG_LEVEL_ERROR);
+    test.event_thread = pthread_self();
+    char dir[512] = "/tmp/utun_attachment_XXXXXX", config[1024], conv[64];
+    REQUIRE(!test_mkdtemp(dir));
+    snprintf(config, sizeof(config), "[global]\ndb_path=%s\n[chatserver]\ngroup_autoconnect=0\nstorage_autoload=0\n", dir);
+    struct UASYNC* ua = uasync_create(); REQUIRE(ua);
+    struct UTUN_INSTANCE* inst = utun_instance_create_from_str(ua, config); REQUIRE(inst);
+    REQUIRE(!utun_core_start(inst) && !chat_service_start(inst));
+    chat_event_set_handler(inst, event);
+    struct SC_MYKEYS peer; uint8_t ed[32];
+    REQUIRE(!sc_generate_keypair(&peer) && !sc_derive_ed25519_pubkey(peer.private_key, ed));
+    uint64_t peer_id = sc_derive_node_id_from_pubkey(peer.public_key);
+    REQUIRE(!dm_start(inst, peer_id, peer.public_key, ed, "test", NULL));
+    snprintf(conv, sizeof(conv), "%llu", (unsigned long long)dm_derive_conv_id(inst->node_id, peer_id));
+    struct attachment_send_req* req = u_calloc(1, sizeof(*req)); REQUIRE(req);
+    req->inst = inst; req->is_dm = 1; req->info.kind = ATTACHMENT_VOICE; req->preset = 1;
+    snprintf(req->target, sizeof(req->target), "%s", conv);
+    req->pcm = test.pcm; req->pcm_count = 48000; req->pcm_owner = &test; req->pcm_release = release_pcm;
+    char active_target[64]; snprintf(active_target, sizeof(active_target), "%s", conv);
+    attachment_send_trampoline(req);
+    snprintf(active_target, sizeof(active_target), "999"); /* Выбор GUI изменился до completion. */
+    for (unsigned i = 0; i < 500 && count(inst) == 0; i++) uasync_poll(ua, 20);
+    REQUIRE(count(inst) == 1 && test.released == 1 && test.release_in_worker && test.starts == 2 && test.ready == 2 && !test.failed);
+    char expected[68], json[8192]; size_t length;
+    snprintf(expected, sizeof(expected), "dm:%s", conv);
+    REQUIRE(!strcmp(test.target, expected) && strcmp(active_target, conv));
+    REQUIRE(!dm_list_messages_json(inst, conv, 20, 0, json, sizeof(json), &length));
+    REQUIRE(strstr(json, "\"content_type\":\"audio/opus\"") && strstr(json, "\"duration_ms\":1000"));
+    REQUIRE(!dm_list_messages_json(inst, active_target, 20, 0, json, sizeof(json), &length) && !strcmp(json, "[]"));
+
+    /* Остановка до poll завершает preparation с CANCELLED, без регистрации сообщения. */
+    req = u_calloc(1, sizeof(*req)); REQUIRE(req);
+    req->inst = inst; req->is_dm = 1; req->info.kind = ATTACHMENT_VOICE; req->preset = 1;
+    snprintf(req->target, sizeof(req->target), "%s", conv);
+    req->pcm = test.pcm; req->pcm_count = 48000; req->pcm_owner = &test; req->pcm_release = release_pcm;
+    attachment_send_trampoline(req);
+    chat_service_stop(inst);
+    REQUIRE(test.released == 2 && test.failed == 1 && count(inst) == 1);
+    uasync_poll(ua, 0); REQUIRE(test.failed == 1);
+
+    /* Отклонение после stop удаляет только переданный собственный cache. */
+    req = u_calloc(1, sizeof(*req)); REQUIRE(req);
+    req->inst = inst; req->is_dm = 1; req->temporary_source = 1; snprintf(req->target, sizeof(req->target), "%s", conv);
+    snprintf(req->source, sizeof(req->source), "%s/cache.mp4", dir);
+    char cache[1024]; snprintf(cache, sizeof(cache), "%s", req->source);
+    FILE* file = fopen(cache, "wb"); REQUIRE(file); REQUIRE(fputc(42, file) != EOF && !fclose(file));
+    attachment_send_trampoline(req);
+    REQUIRE(test.failed == 2 && access(cache, F_OK) != 0);
+    utun_instance_destroy(inst); uasync_destroy(ua, 0);
+    printf("test_attachment_send: pinned PM target, worker PCM ownership, cancel and cache cleanup PASS\n");
+    return 0;
+}
diff --git a/tests/test_dm_media.c b/tests/test_dm_media.c
index ab11ca5e..d76a78eb 100644
--- a/tests/test_dm_media.c
+++ b/tests/test_dm_media.c
@@ -275,6 +275,12 @@ static void tick(void* arg) {
     case 5:
         if (file_correct(t) && value(m, "SELECT count(*) FROM dm_custody") == 0 &&
             value(s, "SELECT count(*) FROM dm_media_jobs WHERE receipt IS NOT NULL AND body IS NULL") == 1) {
+            char json[8192]; size_t length;
+            if (dm_list_messages_json(b, t->conv, 20, 0, json, sizeof(json), &length) ||
+                !strstr(json, "\"content_type\":\"video/mp4\"") || !strstr(json, "\"duration_ms\":3000") ||
+                !strstr(json, "\"width\":640") || !strstr(json, "\"height\":480")) {
+                failure(t, "encrypted video metadata lost after offline custody restart"); return;
+            }
             uint8_t stored[24]; memcpy(stored, t->id, 16);
             uint64_t expiry = ntp_time_get_seconds(s) + 100; memcpy(stored + 16, &expiry, 8);
             control(t, S, t->ids[M], DM_MEDIA_STORED, stored, sizeof(stored));