diff --git a/packages/cli/src/lib/init/types.ts b/packages/cli/src/lib/init/types.ts
index 7ea6a8721..e2a9f6c96 100644
--- a/packages/cli/src/lib/init/types.ts
+++ b/packages/cli/src/lib/init/types.ts
@@ -226,6 +226,9 @@ export type ToolResult = {
 
 // Wizard output
 export type WizardOutput = {
+  bailCategory?: "expected" | "unexpected";
+  bailReason?: string;
+  bailStep?: string;
   platform?: string;
   projectDir?: string;
   features?: string[];
diff --git a/packages/cli/src/lib/init/wizard-runner.ts b/packages/cli/src/lib/init/wizard-runner.ts
index 5ef492164..00e035e9b 100644
--- a/packages/cli/src/lib/init/wizard-runner.ts
+++ b/packages/cli/src/lib/init/wizard-runner.ts
@@ -68,6 +68,7 @@ import type {
   ToolPayload,
   ToolResult,
   WizardOptions,
+  WizardOutput,
   WorkflowRunResult,
 } from "./types.js";
 import { getUIAsync } from "./ui/factory.js";
@@ -1191,6 +1192,23 @@ function syncWorkflowStepStatuses(
   }
 }
 
+function tagWorkflowFailure(output: WizardOutput | undefined): void {
+  const bailCategory = output?.bailCategory;
+  setTag("wizard.outcome", bailCategory === "expected" ? "bailed" : "errored");
+  if (bailCategory !== undefined) {
+    setTag("wizard.bail_category", bailCategory);
+  }
+  if (output?.bailReason !== undefined) {
+    setTag("wizard.bail_reason", output.bailReason);
+  }
+  if (output?.bailStep !== undefined) {
+    setTag("wizard.step", output.bailStep);
+  }
+  if (output?.exitCode !== undefined) {
+    setTag("wizard.exit_code", output.exitCode);
+  }
+}
+
 // biome-ignore lint/nursery/useMaxParams: existing 4-param shape; cwd is a defaulted extension
 export async function handleFinalResult(
   result: WorkflowRunResult,
@@ -1211,10 +1229,7 @@ export async function handleFinalResult(
     // Map workflow-internal exit codes to semantic EXIT.* constants
     const workflowCode = result.result?.exitCode;
     const exitCode = mapWorkflowExitCode(workflowCode);
-    setTag("wizard.outcome", "errored");
-    if (workflowCode !== undefined) {
-      setTag("wizard.exit_code", workflowCode);
-    }
+    tagWorkflowFailure(result.result);
     throw new WizardError(
       result.error ?? result.result?.message ?? "Workflow returned an error",
       { exitCode }
diff --git a/packages/cli/test/lib/wizard-runner-handle-final-result.mocked.test.ts b/packages/cli/test/lib/wizard-runner-handle-final-result.mocked.test.ts
index d433f5e5e..105fb329d 100644
--- a/packages/cli/test/lib/wizard-runner-handle-final-result.mocked.test.ts
+++ b/packages/cli/test/lib/wizard-runner-handle-final-result.mocked.test.ts
@@ -148,6 +148,67 @@ describe("handleFinalResult", () => {
     });
   });
 
+  describe("workflow bail telemetry", () => {
+    test("marks explicitly expected workflow exits as bailed", async () => {
+      const result = makeBailResult({
+        bailCategory: "expected",
+        bailReason: "unknown_platform",
+        bailStep: "detect-platform",
+        exitCode: 20,
+      });
+
+      await expect(
+        handleFinalResult(
+          result,
+          makeSpinnerHandle(),
+          makeSpinState(),
+          makeUI()
+        )
+      ).rejects.toThrow(WizardError);
+
+      expect(tags["wizard.outcome"]).toBe("bailed");
+      expect(tags["wizard.bail_category"]).toBe("expected");
+      expect(tags["wizard.bail_reason"]).toBe("unknown_platform");
+      expect(tags["wizard.step"]).toBe("detect-platform");
+    });
+
+    test("keeps unexpected and unclassified workflow exits as errors", async () => {
+      const unexpected = makeBailResult({
+        bailCategory: "unexpected",
+        bailReason: "agent_failure",
+        bailStep: "plan-codemods",
+      });
+
+      await expect(
+        handleFinalResult(
+          unexpected,
+          makeSpinnerHandle(),
+          makeSpinState(),
+          makeUI()
+        )
+      ).rejects.toThrow(WizardError);
+
+      expect(tags["wizard.outcome"]).toBe("errored");
+      expect(tags["wizard.bail_category"]).toBe("unexpected");
+
+      for (const key of Object.keys(tags)) {
+        delete tags[key];
+      }
+
+      await expect(
+        handleFinalResult(
+          makeBailResult(),
+          makeSpinnerHandle(),
+          makeSpinState(),
+          makeUI()
+        )
+      ).rejects.toThrow(WizardError);
+
+      expect(tags["wizard.outcome"]).toBe("errored");
+      expect(tags["wizard.bail_category"]).toBeUndefined();
+    });
+  });
+
   describe("WizardError message — result.error fallback", () => {
     test("uses result.error when result.result is absent (plain workflow failure)", async () => {
       const result: WorkflowRunResult = {