diff --git a/apps/server/tests/unit/services/claude-usage-service.test.ts b/apps/server/tests/unit/services/claude-usage-service.test.ts
index d16802f6..4b3f3c94 100644
--- a/apps/server/tests/unit/services/claude-usage-service.test.ts
+++ b/apps/server/tests/unit/services/claude-usage-service.test.ts
@@ -551,7 +551,7 @@ Resets in 2h
       expect(result.sessionPercentage).toBe(35);
       expect(pty.spawn).toHaveBeenCalledWith(
         'cmd.exe',
-        ['/c', 'claude', '/usage'],
+        ['/c', 'claude', '--add-dir', 'C:\\Users\\testuser'],
         expect.any(Object)
       );
     });
@@ -582,8 +582,8 @@ Resets in 2h
       // Simulate seeing usage data
       dataCallback!(mockOutput);
 
-      // Advance time to trigger escape key sending
-      vi.advanceTimersByTime(2100);
+      // Advance time to trigger escape key sending (impl uses 3000ms delay)
+      vi.advanceTimersByTime(3100);
 
       expect(mockPty.write).toHaveBeenCalledWith('\x1b');
 
@@ -614,9 +614,10 @@ Resets in 2h
       const promise = windowsService.fetchUsageData();
 
       dataCallback!('authentication_error');
-      exitCallback!({ exitCode: 1 });
 
-      await expect(promise).rejects.toThrow('Authentication required');
+      await expect(promise).rejects.toThrow(
+        "Claude CLI authentication issue. Please run 'claude logout' and then 'claude login' in your terminal to refresh permissions."
+      );
     });
 
     it('should handle timeout with no data on Windows', async () => {
@@ -628,14 +629,18 @@ Resets in 2h
         onExit: vi.fn(),
         write: vi.fn(),
         kill: vi.fn(),
+        killed: false,
       };
       vi.mocked(pty.spawn).mockReturnValue(mockPty as any);
 
       const promise = windowsService.fetchUsageData();
 
-      vi.advanceTimersByTime(31000);
+      // Advance time past timeout (45 seconds)
+      vi.advanceTimersByTime(46000);
 
-      await expect(promise).rejects.toThrow('Command timed out');
+      await expect(promise).rejects.toThrow(
+        'The Claude CLI took too long to respond. This can happen if the CLI is waiting for a trust prompt or is otherwise busy.'
+      );
       expect(mockPty.kill).toHaveBeenCalled();
 
       vi.useRealTimers();
@@ -654,6 +659,7 @@ Resets in 2h
         onExit: vi.fn(),
         write: vi.fn(),
         kill: vi.fn(),
+        killed: false,
       };
       vi.mocked(pty.spawn).mockReturnValue(mockPty as any);
 
@@ -662,8 +668,8 @@ Resets in 2h
       // Simulate receiving usage data
       dataCallback!('Current session\n65% left\nResets in 2h');
 
-      // Advance time past timeout (30 seconds)
-      vi.advanceTimersByTime(31000);
+      // Advance time past timeout (45 seconds)
+      vi.advanceTimersByTime(46000);
 
       // Should resolve with data instead of rejecting
       const result = await promise;
@@ -686,6 +692,7 @@ Resets in 2h
         onExit: vi.fn(),
         write: vi.fn(),
         kill: vi.fn(),
+        killed: false,
       };
       vi.mocked(pty.spawn).mockReturnValue(mockPty as any);
 
@@ -694,8 +701,8 @@ Resets in 2h
       // Simulate seeing usage data
       dataCallback!('Current session\n65% left');
 
-      // Advance 2s to trigger ESC
-      vi.advanceTimersByTime(2100);
+      // Advance 3s to trigger ESC (impl uses 3000ms delay)
+      vi.advanceTimersByTime(3100);
       expect(mockPty.write).toHaveBeenCalledWith('\x1b');
 
       // Advance another 2s to trigger SIGTERM fallback