diff --git a/weed/operation/upload_content.go b/weed/operation/upload_content.go
index f469b2273..0775ca4d8 100644
--- a/weed/operation/upload_content.go
+++ b/weed/operation/upload_content.go
@@ -371,7 +371,16 @@ func (uploader *Uploader) upload_content(ctx context.Context, fillBufferFunction
 	} else {
 		reqReader = bytes.NewReader(option.BytesBuffer.Bytes())
 	}
-	req, postErr := http.NewRequest(http.MethodPost, option.UploadUrl, reqReader)
+	// Ensure the request will not hang indefinitely: if no deadline is set on ctx,
+	// apply a conservative default timeout.
+	ctxWithTimeout := ctx
+	if _, hasDeadline := ctx.Deadline(); !hasDeadline {
+		var cancel context.CancelFunc
+		// Default timeout chosen to be generous for large uploads but finite to avoid hangs.
+		ctxWithTimeout, cancel = context.WithTimeout(ctx, 10*time.Minute)
+		defer cancel()
+	}
+	req, postErr := http.NewRequestWithContext(ctxWithTimeout, http.MethodPost, option.UploadUrl, reqReader)
 	if postErr != nil {
 		glog.V(1).InfofCtx(ctx, "create upload request %s: %v", option.UploadUrl, postErr)
 		return nil, fmt.Errorf("create upload request %s: %v", option.UploadUrl, postErr)
diff --git a/weed/operation/upload_content_test.go b/weed/operation/upload_content_test.go
new file mode 100644
index 000000000..326aff619
--- /dev/null
+++ b/weed/operation/upload_content_test.go
@@ -0,0 +1,61 @@
+package operation
+
+import (
+	"bytes"
+	"context"
+	"io"
+	"net/http"
+	"net/http/httptest"
+	"testing"
+	"time"
+)
+
+// Test that Upload respects request context timeout and does not hang indefinitely
+func TestUploadTimesOutOnStalledConnectionViaContext(t *testing.T) {
+	// Create a test server that stalls and never writes a response
+	ts := httptest.NewUnstartedServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		// Do not read the body and do not write a response; just stall
+		select {
+		case <-time.After(10 * time.Second):
+		case <-r.Context().Done():
+			// Proactively close the underlying connection to avoid server Close delay
+			if hj, ok := w.(http.Hijacker); ok {
+				if conn, _, err := hj.Hijack(); err == nil {
+					_ = conn.Close()
+				}
+			}
+		}
+	}))
+	// Make the server's own timeouts aggressive so Close does not block long
+	ts.Config.ReadTimeout = 200 * time.Millisecond
+	ts.Config.WriteTimeout = 200 * time.Millisecond
+	ts.Config.IdleTimeout = 200 * time.Millisecond
+	ts.Start()
+	defer ts.Close()
+
+	u, err := NewUploader()
+	if err != nil {
+		t.Fatalf("failed to create uploader: %v", err)
+	}
+
+	// Short timeout to make the test fast
+	ctx, cancel := context.WithTimeout(context.Background(), 200*time.Millisecond)
+	defer cancel()
+
+	data := bytes.Repeat([]byte("a"), 1024)
+	// Call the lower-level upload to avoid internal retries and keep test fast
+	_, err = u.upload_content(ctx, func(w io.Writer) error {
+		_, writeErr := w.Write(data)
+		return writeErr
+	}, len(data), &UploadOption{
+		UploadUrl: ts.URL + "/upload",
+		Filename:  "test.bin",
+		MimeType:  "application/octet-stream",
+	})
+
+	if err == nil {
+		t.Fatalf("expected timeout error, got nil")
+	}
+}
+
+