diff --git a/app/services/grok/services/image_edit.py b/app/services/grok/services/image_edit.py
index 5d94abd..8d1df16 100644
--- a/app/services/grok/services/image_edit.py
+++ b/app/services/grok/services/image_edit.py
@@ -64,6 +64,31 @@ def _is_upload_rejected_error(exc: Exception) -> bool:
     return False
 
 
+def _is_upload_network_error(exc: Exception) -> bool:
+    """判断是否为网络连通/网关挑战类上传失败。"""
+    msg = str(exc or "").lower()
+    if (
+        "tls connect error" in msg
+        or "timed out" in msg
+        or "timeout" in msg
+        or "connection" in msg
+        or "proxy" in msg
+        or "curl: (35)" in msg
+    ):
+        return True
+
+    details = getattr(exc, "details", None)
+    if isinstance(details, dict):
+        status = details.get("status")
+        body = str(details.get("body") or "").lower()
+        if status == 403 and ("just a moment" in body or "cloudflare" in body):
+            return True
+        if "tls connect error" in body or "timed out" in body:
+            return True
+
+    return False
+
+
 class ImageEditService:
     """Image edit orchestration service."""
 
@@ -470,6 +495,13 @@ class ImageEditService:
                     code="upload_rejected",
                     status_code=400,
                 )
+            if _is_upload_network_error(e):
+                raise AppException(
+                    message="图片上传失败：网络连接异常，请稍后重试",
+                    error_type=ErrorType.SERVER.value,
+                    code="upload_network_error",
+                    status_code=502,
+                )
             raise AppException(
                 message="图片上传失败，请稍后重试",
                 error_type=ErrorType.SERVER.value,
diff --git a/app/services/reverse/assets_upload.py b/app/services/reverse/assets_upload.py
index 6c1f24b..cb8f3c9 100644
--- a/app/services/reverse/assets_upload.py
+++ b/app/services/reverse/assets_upload.py
@@ -203,6 +203,7 @@ class AssetsUploadReverse:
                             "AssetsUpload transient exception, mark as retryable: "
                             f"{err_msg}"
                         )
+                        last_fallback_error: UpstreamException | None = None
                         # 部分 '"code"' 异常不会走到上面的降级分支，这里再强制兜底一次。
                         try:
                             response = await session.post(
@@ -228,6 +229,8 @@ class AssetsUploadReverse:
                                 details={"status": response.status_code, "body": body_preview},
                             )
                         except Exception as forced_direct_err:
+                            if isinstance(forced_direct_err, UpstreamException):
+                                last_fallback_error = forced_direct_err
                             logger.warning(
                                 "AssetsUpload forced direct fallback failed, "
                                 f"error={forced_direct_err}"
@@ -254,11 +257,15 @@ class AssetsUploadReverse:
                                 details={"status": response.status_code, "body": body_preview},
                             )
                         except Exception as forced_urllib_err:
+                            if isinstance(forced_urllib_err, UpstreamException):
+                                last_fallback_error = forced_urllib_err
                             logger.warning(
                                 "AssetsUpload forced urllib fallback failed, "
                                 f"error={forced_urllib_err}"
                             )
 
+                        if last_fallback_error is not None:
+                            raise last_fallback_error
                         raise UpstreamException(
                             message=f"AssetsUpload transient failure: {err_msg}",
                             details={"status": 403, "error": err_msg},