diff --git a/src/core/checkpoints/__tests__/checkpoint.test.ts b/src/core/checkpoints/__tests__/checkpoint.test.ts
index 299ff823b8..1b13706d47 100644
--- a/src/core/checkpoints/__tests__/checkpoint.test.ts
+++ b/src/core/checkpoints/__tests__/checkpoint.test.ts
@@ -475,7 +475,9 @@ describe("Checkpoint functionality", () => {
 					const provider = mockTask.providerRef.deref()
 					provider?.postMessageToWebview({
 						type: "checkpointInitWarning",
-						checkpointWarning: i18nModule.t("common:errors.wait_checkpoint_long_time", { timeout: 5 }),
+						checkpointWarning: i18nModule.t("common:errors.wait_checkpoint_long_time", {
+							timeout: mockTask.checkpointTimeout,
+						}),
 					})
 				}
 
@@ -486,11 +488,11 @@ describe("Checkpoint functionality", () => {
 			expect(simulateConditionCheck(4000)).toBe(false)
 			expect(mockProvider.postMessageToWebview).not.toHaveBeenCalled()
 
-			// Test: At 5 seconds, warning should be sent
+			// Test: At 5 seconds, warning should be sent with configured timeout (15 seconds)
 			expect(simulateConditionCheck(5000)).toBe(false)
 			expect(mockProvider.postMessageToWebview).toHaveBeenCalledWith({
 				type: "checkpointInitWarning",
-				checkpointWarning: "Checkpoint initialization is taking longer than 5 seconds...",
+				checkpointWarning: "Checkpoint initialization is taking longer than 15 seconds...",
 			})
 
 			// Test: At 6 seconds, warning should not be sent again (warningShown is true)
@@ -558,10 +560,11 @@ describe("Checkpoint functionality", () => {
 		})
 
 		it("should use WARNING_THRESHOLD_MS constant of 5000ms", () => {
-			// Verify the warning threshold is 5 seconds by checking the implementation
+			// Verify the warning threshold is 5 seconds - this determines WHEN to show the warning
+			// but the timeout value shown to user should be the configured checkpointTimeout
 			const WARNING_THRESHOLD_MS = 5000
 			expect(WARNING_THRESHOLD_MS).toBe(5000)
-			expect(WARNING_THRESHOLD_MS / 1000).toBe(5) // Used in the i18n call
+			expect(WARNING_THRESHOLD_MS / 1000).toBe(5) // Used to check elapsed time
 		})
 
 		it("should convert checkpointTimeout to milliseconds", () => {
@@ -581,11 +584,11 @@ describe("Checkpoint functionality", () => {
 			const i18nModule = await import("../../../i18n")
 			vi.clearAllMocks()
 
-			// Test warning message i18n key
-			const warningMessage = i18nModule.t("common:errors.wait_checkpoint_long_time", { timeout: 5 })
-			expect(warningMessage).toBe("Checkpoint initialization is taking longer than 5 seconds...")
+			// Test warning message i18n key - should use configured timeout
+			const warningMessage = i18nModule.t("common:errors.wait_checkpoint_long_time", { timeout: 15 })
+			expect(warningMessage).toBe("Checkpoint initialization is taking longer than 15 seconds...")
 
-			// Test timeout error message i18n key
+			// Test timeout error message i18n key - should use configured timeout
 			const errorMessage = i18nModule.t("common:errors.init_checkpoint_fail_long_time", { timeout: 30 })
 			expect(errorMessage).toBe("Checkpoint initialization failed after 30 seconds")
 		})
diff --git a/src/core/checkpoints/index.ts b/src/core/checkpoints/index.ts
index 64a8ad1cfe..0b03be15dd 100644
--- a/src/core/checkpoints/index.ts
+++ b/src/core/checkpoints/index.ts
@@ -86,7 +86,7 @@ export async function getCheckpointService(task: Task, { interval = 250 }: { int
 					// Show warning if we're past the threshold and haven't shown it yet
 					if (!warningShown && elapsed >= WARNING_THRESHOLD_MS) {
 						warningShown = true
-						sendCheckpointInitWarn(task, "WAIT_TIMEOUT", WARNING_THRESHOLD_MS / 1000)
+						sendCheckpointInitWarn(task, "WAIT_TIMEOUT", task.checkpointTimeout)
 					}
 
 					console.log(