diff --git a/ui/src/components/OnboardingWizard.step.test.tsx b/ui/src/components/OnboardingWizard.step.test.tsx
index 2cd21b29f6..ceb0d8a400 100644
--- a/ui/src/components/OnboardingWizard.step.test.tsx
+++ b/ui/src/components/OnboardingWizard.step.test.tsx
@@ -229,6 +229,53 @@ describe("OnboardingWizard — which step it lands on", () => {
     vi.clearAllMocks();
   });
 
+  /**
+   * The progress strip counts the walk the customer is actually on, and the two
+   * runs that enter on the agent step are on different walks.
+   *
+   * Both have a company already, so `entryStep` cannot tell them apart. What
+   * does is `enableManagedSandboxOnly` — the cloud-tenant shape. A cloud tenant
+   * was asked for its organization's name by Cloud, one screen earlier, so its
+   * walk is four and this is the second. A self-hosted company that simply has
+   * no agents yet was asked nothing before this, so its walk is three.
+   */
+  describe("progress strip length", () => {
+    function announcedCount(): string | null {
+      return (
+        [...document.querySelectorAll(".sr-only")]
+          .map((element) => element.textContent?.trim() ?? "")
+          .find((text) => /^Step \d+ of \d+$/.test(text)) ?? null
+      );
+    }
+
+    it("counts four on a cloud tenant, continuing the count Cloud started", async () => {
+      mockInstanceSettingsApi.getExperimental.mockResolvedValue({
+        enableManagedSandboxOnly: true,
+      });
+      routerState.pathname = "/PC1/onboarding";
+      await render();
+      await settle();
+
+      expect(currentStep()).toBe("agent");
+      expect(announcedCount()).toBe("Step 2 of 4");
+    });
+
+    it("counts three on a self-hosted company that has no agents yet", async () => {
+      // Nothing was asked before this step here, so a fourth segment would be
+      // one the run can never fill — and it would credit the customer with a
+      // step they never walked.
+      mockInstanceSettingsApi.getExperimental.mockResolvedValue({
+        enableManagedSandboxOnly: false,
+      });
+      routerState.pathname = "/PC1/onboarding";
+      await render();
+      await settle();
+
+      expect(currentStep()).toBe("agent");
+      expect(announcedCount()).toBe("Step 1 of 3");
+    });
+  });
+
   it("opens a company that already has its mission on the agent step", async () => {
     // The point of the change: Cloud collected the mission at signup and the
     // seed wrote it as a company-level goal, so asking for it again asks a
diff --git a/ui/src/components/OnboardingWizard.tsx b/ui/src/components/OnboardingWizard.tsx
index ea13f62506..e71b581ad7 100644
--- a/ui/src/components/OnboardingWizard.tsx
+++ b/ui/src/components/OnboardingWizard.tsx
@@ -890,10 +890,13 @@ function OnboardingWizardInner({
     queryFn: () => instanceSettingsApi.get(),
     enabled: effectiveOnboardingOpen && step === 4,
   });
+  // Wanted across the whole arc, not just the connect step. The progress strip
+  // reads it too — see `enteredFromCloud` — and a value fetched only on step 4
+  // would let the strip change length as the customer walked through it.
   const { data: experimentalSettingsForLogin } = useQuery({
     queryKey: queryKeys.instance.experimentalSettings,
     queryFn: () => instanceSettingsApi.getExperimental(),
-    enabled: effectiveOnboardingOpen && step === 4,
+    enabled: effectiveOnboardingOpen && step >= 3 && step <= 5,
   });
   const resolvedLoginEnvironmentId = useMemo(() => {
     try {
@@ -2004,7 +2007,21 @@ function OnboardingWizardInner({
   }
 
   const isAgentArcStep = agentArcStepFor(step) !== null;
-  const showsAgentArcStepper = isAgentArcStep && entryStep >= 3;
+  /**
+   * True when the organization was named in Cloud rather than here.
+   *
+   * `enableManagedSandboxOnly` is the cloud-tenant shape — the connect step
+   * already resolves its login environment through it. A tenant wearing it did
+   * not ask for the organization's name, because Cloud did, so the walk the
+   * customer is on is four steps and this is the second.
+   *
+   * A self-hosted run that enters at the agent step is a different case with
+   * the same `entryStep`: an existing company that has no agents yet. There was
+   * no naming screen before it, so its walk really is three, and it keeps the
+   * shorter strip.
+   */
+  const enteredFromCloud = experimentalSettingsForLogin?.enableManagedSandboxOnly === true;
+  const showsAgentArcStepper = isAgentArcStep && entryStep >= 3 && !enteredFromCloud;
 
   const launchStateIncomplete = step === 5 && (!createdCompanyId || !createdAgentId);
   const visibleError = error ?? (launchStateIncomplete ? INCOMPLETE_ONBOARDING_STATE_MESSAGE : null);