diff --git a/src/chat/chat_attachment.c b/src/chat/chat_attachment.c
index 07f3528a2..b5193482c 100644
--- a/src/chat/chat_attachment.c
+++ b/src/chat/chat_attachment.c
@@ -110,9 +110,20 @@ static int ak_parent(const char* path) {
     char parent[1040]; snprintf(parent, sizeof(parent), "%s", path);
     for (char* p = parent + 1; *p; p++) {
         if (*p != '/') continue;
-        *p = 0; int rc = utun_mkdir(parent, 0700); *p = '/';
-        if (rc && errno != EEXIST) { DEBUG_ERROR(DEBUG_CATEGORY_MEDIA, "attachment keys: mkdir failed path=%s: %s", parent, strerror(errno)); return -1; }
+#ifdef _WIN32
+        if (p == parent + 2 && parent[1] == ':') continue; /* Корень C:/ уже существует; mkdir("C:") может вернуть EACCES. */
+#endif
+        *p = 0;
+        int rc = utun_mkdir(parent, 0700);
+        int error = errno;
+        if (rc && error != EEXIST) {
+            DEBUG_ERROR(DEBUG_CATEGORY_MEDIA, "attachment keys: mkdir failed directory=%s output=%s errno=%d error=%s",
+                        parent, path, error, strerror(error));
+            return -1;
+        }
+        *p = '/';
     }
+    DEBUG_DEBUG(DEBUG_CATEGORY_MEDIA, "attachment keys: parent directories ready output=%s", path);
     return 0;
 }
 
diff --git a/src/media_async/attachment_send.c b/src/media_async/attachment_send.c
index 8fa0d22d1..30bb7ece9 100644
--- a/src/media_async/attachment_send.c
+++ b/src/media_async/attachment_send.c
@@ -45,6 +45,9 @@ static void attachment_prepare_work(void* arg) {
     char parent[1024]; snprintf(parent, sizeof(parent), "%s", req->output);
     for (char* p = parent + 1; *p; p++) {
         if (*p != '/') continue;
+#ifdef _WIN32
+        if (p == parent + 2 && parent[1] == ':') continue; /* Корень C:/ уже существует; mkdir("C:") может вернуть EACCES. */
+#endif
         *p = 0;
         int rc = utun_mkdir(parent, 0700);
         int error = errno;