diff --git a/starsky/starsky/clientapp/src/components/molecules/menu-option-rotate-image-90/internal/trigger-file-hash-request.spec.tsx b/starsky/starsky/clientapp/src/components/molecules/menu-option-rotate-image-90/internal/trigger-file-hash-request.spec.tsx
index e29dffa0c..476240686 100644
--- a/starsky/starsky/clientapp/src/components/molecules/menu-option-rotate-image-90/internal/trigger-file-hash-request.spec.tsx
+++ b/starsky/starsky/clientapp/src/components/molecules/menu-option-rotate-image-90/internal/trigger-file-hash-request.spec.tsx
@@ -14,9 +14,15 @@ describe("TriggerFileHashRequest", () => {
     }
   } as IDetailView;
 
-  it("returns immediately when the file hash changes on the first attempt", () => {
+  beforeEach(() => {
     jest.useFakeTimers();
+  });
+
+  afterEach(() => {
+    jest.useRealTimers();
+  });
 
+  it("returns immediately when the file hash changes on the first attempt", () => {
     const requestSpy = jest
       .spyOn(RequestNewFileHash, "RequestNewFileHash")
       .mockResolvedValueOnce(true);
@@ -31,6 +37,42 @@ describe("TriggerFileHashRequest", () => {
     jest.advanceTimersByTime(1);
     jest.runAllTimers();
     expect(requestSpy).toHaveBeenCalledTimes(1);
-    jest.useRealTimers();
+  });
+
+  it("retry when failed", () => {
+    const requestSpy = jest
+      .spyOn(RequestNewFileHash, "RequestNewFileHash")
+      .mockResolvedValueOnce(false);
+
+    const setIsLoading = jest.fn();
+    TriggerFileHashRequest(state, setIsLoading, jest.fn(), 1, 1);
+
+    act(() => {
+      jest.advanceTimersByTime(100);
+    });
+
+    jest.advanceTimersByTime(1);
+    jest.runAllTimers();
+    expect(requestSpy).toHaveBeenCalledTimes(2);
+  });
+
+  it("retry when failed (max 3 times)", () => {
+    const requestSpy = jest
+      .spyOn(RequestNewFileHash, "RequestNewFileHash")
+      .mockResolvedValueOnce(false)
+      .mockResolvedValueOnce(false)
+      .mockResolvedValueOnce(false)
+      .mockResolvedValueOnce(false);
+
+    const setIsLoading = jest.fn();
+    TriggerFileHashRequest(state, setIsLoading, jest.fn(), 1, 1);
+
+    act(() => {
+      jest.advanceTimersByTime(100);
+    });
+
+    jest.advanceTimersByTime(1);
+    jest.runAllTimers();
+    expect(requestSpy).toHaveBeenCalledTimes(3);
   });
 });