diff --git a/codex-rs/codex-api/src/files.rs b/codex-rs/codex-api/src/files.rs
index 9e308e01a4..bf84997e62 100644
--- a/codex-rs/codex-api/src/files.rs
+++ b/codex-rs/codex-api/src/files.rs
@@ -401,7 +401,10 @@ fn non_empty_string(value: Option<String>) -> Option<String> {
 
 fn is_process_upload_stream_error_event(event: &str) -> bool {
     let event_tail = event.rsplit(['.', '_']).next().unwrap_or(event);
-    matches!(event_tail, "error" | "cancelled" | "unknown")
+    matches!(
+        event_tail,
+        "error" | "failed" | "cancelled" | "canceled" | "unknown"
+    )
 }
 
 fn authorized_request(
@@ -489,10 +492,14 @@ fn should_attach_auth_to_openai_file_url(download_url: &Url, base_url: &str) ->
     let Ok(base_url) = Url::parse(base_url) else {
         return false;
     };
-    match (download_url.host_str(), base_url.host_str()) {
-        (Some(download_host), Some(base_host)) => download_host.eq_ignore_ascii_case(base_host),
-        _ => false,
-    }
+    download_url
+        .scheme()
+        .eq_ignore_ascii_case(base_url.scheme())
+        && download_url.port_or_known_default() == base_url.port_or_known_default()
+        && match (download_url.host_str(), base_url.host_str()) {
+            (Some(download_host), Some(base_host)) => download_host.eq_ignore_ascii_case(base_host),
+            _ => false,
+        }
 }
 
 fn build_reqwest_client() -> reqwest::Client {
@@ -686,4 +693,84 @@ mod tests {
         assert_eq!(uploaded.mime_type, Some("text/plain".to_string()));
         assert_eq!(uploaded.library_file_id, Some("library_123".to_string()));
     }
+
+    #[test]
+    fn should_attach_auth_only_for_same_origin() {
+        let base_url = "https://chatgpt.com/backend-api";
+
+        assert!(should_attach_auth_to_openai_file_url(
+            &Url::parse("https://chatgpt.com/files/file_123/content").expect("valid url"),
+            base_url,
+        ));
+        assert!(!should_attach_auth_to_openai_file_url(
+            &Url::parse("http://chatgpt.com/files/file_123/content").expect("valid url"),
+            base_url,
+        ));
+        assert!(!should_attach_auth_to_openai_file_url(
+            &Url::parse("https://chatgpt.com:8443/files/file_123/content").expect("valid url"),
+            base_url,
+        ));
+    }
+
+    #[tokio::test]
+    async fn upload_local_file_fails_when_process_upload_stream_reports_failed_event() {
+        let server = MockServer::start().await;
+        Mock::given(method("POST"))
+            .and(path("/backend-api/files"))
+            .and(header("chatgpt-account-id", "account_id"))
+            .and(body_json(serde_json::json!({
+                "file_name": "hello.txt",
+                "file_size": 5,
+                "use_case": "codex",
+                "store_in_library": true,
+            })))
+            .respond_with(
+                ResponseTemplate::new(200)
+                    .set_body_json(serde_json::json!({"file_id": "file_123", "upload_url": format!("{}/upload/file_123", server.uri())})),
+            )
+            .mount(&server)
+            .await;
+        Mock::given(method("PUT"))
+            .and(path("/upload/file_123"))
+            .and(header("content-length", "5"))
+            .respond_with(ResponseTemplate::new(200))
+            .mount(&server)
+            .await;
+        Mock::given(method("POST"))
+            .and(path("/backend-api/files/process_upload_stream"))
+            .respond_with(ResponseTemplate::new(200).set_body_bytes(
+                concat!(
+                    "{\"file_id\":\"file_123\",\"event\":\"indexing.completed\",\"message\":\"\",",
+                    "\"extra\":{\"metadata_object_id\":\"library_123\"}}\n",
+                    "{\"file_id\":\"file_123\",\"event\":\"indexing.failed\",",
+                    "\"message\":\"indexing failed\",\"extra\":null}\n",
+                )
+                .as_bytes()
+                .to_vec(),
+            ))
+            .mount(&server)
+            .await;
+
+        let base_url = base_url_for(&server);
+        let dir = TempDir::new().expect("temp dir");
+        let path = dir.path().join("hello.txt");
+        tokio::fs::write(&path, b"hello").await.expect("write file");
+
+        let error = upload_local_file(
+            &base_url,
+            &chatgpt_auth(),
+            &path,
+            &OpenAiFileUploadOptions {
+                store_in_library: true,
+            },
+        )
+        .await
+        .expect_err("upload should fail");
+
+        assert!(matches!(
+            error,
+            OpenAiFileError::UploadFailed { ref file_id, ref message }
+                if file_id == "file_123" && message == "indexing failed"
+        ));
+    }
 }
diff --git a/codex-rs/core/src/mcp_openai_file.rs b/codex-rs/core/src/mcp_openai_file.rs
index 891d5493b4..f34265685c 100644
--- a/codex-rs/core/src/mcp_openai_file.rs
+++ b/codex-rs/core/src/mcp_openai_file.rs
@@ -148,10 +148,10 @@ async fn build_uploaded_local_argument_value(
         "uri": uploaded.uri,
         "file_size_bytes": uploaded.file_size_bytes,
     });
-    if uploaded.library_file_id.is_none() {
-        if let Some(uploaded_object) = uploaded_value.as_object_mut() {
-            uploaded_object.remove("library_file_id");
-        }
+    if uploaded.library_file_id.is_none()
+        && let Some(uploaded_object) = uploaded_value.as_object_mut()
+    {
+        uploaded_object.remove("library_file_id");
     }
     Ok(uploaded_value)
 }