diff --git a/packages/twenty-front/src/modules/onboarding/components/OnboardingStepLayout.tsx b/packages/twenty-front/src/modules/onboarding/components/OnboardingStepLayout.tsx
index 1e18008ef6..91c52396f1 100644
--- a/packages/twenty-front/src/modules/onboarding/components/OnboardingStepLayout.tsx
+++ b/packages/twenty-front/src/modules/onboarding/components/OnboardingStepLayout.tsx
@@ -1,10 +1,13 @@
 import { OnboardingLayout } from '@/onboarding/components/OnboardingLayout';
 import { OnboardingTransitionOutlet } from '@/onboarding/components/OnboardingTransitionOutlet';
 import { useOnboardingFreeCreditsTotal } from '@/onboarding/hooks/useOnboardingFreeCreditsTotal';
+import { usePreloadStripeForPlanRequiredStep } from '@/onboarding/hooks/usePreloadStripeForPlanRequiredStep';
 
 export const OnboardingStepLayout = () => {
   const freeCredits = useOnboardingFreeCreditsTotal();
 
+  usePreloadStripeForPlanRequiredStep();
+
   return (
     <OnboardingLayout freeCredits={freeCredits}>
       <OnboardingTransitionOutlet />
diff --git a/packages/twenty-front/src/modules/onboarding/hooks/__tests__/usePreloadStripeForPlanRequiredStep.test.ts b/packages/twenty-front/src/modules/onboarding/hooks/__tests__/usePreloadStripeForPlanRequiredStep.test.ts
new file mode 100644
index 0000000000..9d2364ad69
--- /dev/null
+++ b/packages/twenty-front/src/modules/onboarding/hooks/__tests__/usePreloadStripeForPlanRequiredStep.test.ts
@@ -0,0 +1,101 @@
+import { act, renderHook } from '@testing-library/react';
+import { Provider as JotaiProvider } from 'jotai';
+import { createElement } from 'react';
+
+import { currentWorkspaceState } from '@/auth/states/currentWorkspaceState';
+import { billingState } from '@/client-config/states/billingState';
+import { usePreloadStripeForPlanRequiredStep } from '@/onboarding/hooks/usePreloadStripeForPlanRequiredStep';
+import { useSetAtomState } from '@/ui/utilities/state/jotai/hooks/useSetAtomState';
+import {
+  jotaiStore,
+  resetJotaiStore,
+} from '@/ui/utilities/state/jotai/jotaiStore';
+
+import { loadStripe } from '@stripe/stripe-js/pure';
+import { mockCurrentWorkspace } from '~/testing/mock-data/users';
+
+jest.mock('@stripe/stripe-js/pure', () => ({
+  loadStripe: jest.fn().mockResolvedValue(null),
+}));
+
+const loadStripeMock = jest.mocked(loadStripe);
+
+const Wrapper = ({ children }: { children: React.ReactNode }) =>
+  createElement(JotaiProvider, { store: jotaiStore }, children);
+
+type RenderHooksOptions = {
+  isBillingEnabled?: boolean;
+  withSubscription?: boolean;
+  stripePublishableKey?: string;
+};
+
+const renderHooks = ({
+  isBillingEnabled = true,
+  withSubscription = false,
+  stripePublishableKey,
+}: RenderHooksOptions = {}) => {
+  const { result } = renderHook(
+    () => {
+      const setCurrentWorkspace = useSetAtomState(currentWorkspaceState);
+      const setBilling = useSetAtomState(billingState);
+      usePreloadStripeForPlanRequiredStep();
+      return { setCurrentWorkspace, setBilling };
+    },
+    {
+      wrapper: Wrapper,
+    },
+  );
+
+  act(() => {
+    result.current.setCurrentWorkspace({
+      ...mockCurrentWorkspace,
+      billingSubscriptions: withSubscription
+        ? mockCurrentWorkspace.billingSubscriptions
+        : [],
+    });
+    result.current.setBilling({
+      __typename: 'Billing',
+      isBillingEnabled,
+      trialPeriods: [],
+      stripePublishableKey,
+    });
+  });
+};
+
+describe('usePreloadStripeForPlanRequiredStep', () => {
+  beforeEach(() => {
+    resetJotaiStore();
+    jest.clearAllMocks();
+  });
+
+  it('should preload Stripe when billing is enabled and the workspace has no subscription', () => {
+    renderHooks({ stripePublishableKey: 'pk_test_preload' });
+
+    expect(loadStripeMock).toHaveBeenCalledTimes(1);
+    expect(loadStripeMock).toHaveBeenCalledWith('pk_test_preload');
+  });
+
+  it('should not preload Stripe when billing is disabled', () => {
+    renderHooks({
+      isBillingEnabled: false,
+      stripePublishableKey: 'pk_test_billing_disabled',
+    });
+
+    expect(loadStripeMock).not.toHaveBeenCalled();
+  });
+
+  it('should not preload Stripe when the workspace already has a subscription', () => {
+    renderHooks({
+      withSubscription: true,
+      stripePublishableKey: 'pk_test_with_subscription',
+    });
+
+    expect(loadStripeMock).not.toHaveBeenCalled();
+  });
+
+  it('should not preload Stripe when the publishable key is missing', () => {
+    renderHooks();
+
+    expect(loadStripeMock).not.toHaveBeenCalled();
+  });
+});
diff --git a/packages/twenty-front/src/modules/onboarding/hooks/usePreloadStripeForPlanRequiredStep.ts b/packages/twenty-front/src/modules/onboarding/hooks/usePreloadStripeForPlanRequiredStep.ts
new file mode 100644
index 0000000000..a73dec27ff
--- /dev/null
+++ b/packages/twenty-front/src/modules/onboarding/hooks/usePreloadStripeForPlanRequiredStep.ts
@@ -0,0 +1,26 @@
+import { isNonEmptyString } from '@sniptt/guards';
+import { useEffect } from 'react';
+
+import { currentWorkspaceState } from '@/auth/states/currentWorkspaceState';
+import { billingState } from '@/client-config/states/billingState';
+import { getIsPlanRequired } from '@/onboarding/utils/getIsPlanRequired';
+import { getStripePromise } from '@/settings/billing/utils/getStripePromise';
+import { useAtomStateValue } from '@/ui/utilities/state/jotai/hooks/useAtomStateValue';
+
+export const usePreloadStripeForPlanRequiredStep = () => {
+  const billing = useAtomStateValue(billingState);
+  const currentWorkspace = useAtomStateValue(currentWorkspaceState);
+
+  const isPlanRequired = getIsPlanRequired({
+    isBillingEnabled: billing?.isBillingEnabled ?? false,
+    currentWorkspace,
+  });
+
+  const publishableKey = billing?.stripePublishableKey;
+
+  useEffect(() => {
+    if (isPlanRequired && isNonEmptyString(publishableKey)) {
+      void getStripePromise(publishableKey);
+    }
+  }, [isPlanRequired, publishableKey]);
+};
diff --git a/packages/twenty-front/src/modules/onboarding/hooks/useSetNextOnboardingStatus.ts b/packages/twenty-front/src/modules/onboarding/hooks/useSetNextOnboardingStatus.ts
index 385534b65e..0f96a39383 100644
--- a/packages/twenty-front/src/modules/onboarding/hooks/useSetNextOnboardingStatus.ts
+++ b/packages/twenty-front/src/modules/onboarding/hooks/useSetNextOnboardingStatus.ts
@@ -9,6 +9,7 @@ import {
   currentWorkspaceState,
 } from '@/auth/states/currentWorkspaceState';
 import { billingState } from '@/client-config/states/billingState';
+import { getIsPlanRequired } from '@/onboarding/utils/getIsPlanRequired';
 import { useAtomStateValue } from '@/ui/utilities/state/jotai/hooks/useAtomStateValue';
 
 import { useCallback } from 'react';
@@ -26,9 +27,10 @@ const getNextOnboardingStatus = ({
   currentWorkspace,
   isBillingEnabled,
 }: GetNextOnboardingStatusArgs) => {
-  const isPlanRequired =
-    isBillingEnabled &&
-    (currentWorkspace?.billingSubscriptions?.length ?? 0) === 0;
+  const isPlanRequired = getIsPlanRequired({
+    isBillingEnabled,
+    currentWorkspace,
+  });
 
   if (currentUser?.onboardingStatus === OnboardingStatus.WORKSPACE_ACTIVATION) {
     return OnboardingStatus.SYNC_EMAIL;
diff --git a/packages/twenty-front/src/modules/onboarding/utils/getIsPlanRequired.ts b/packages/twenty-front/src/modules/onboarding/utils/getIsPlanRequired.ts
new file mode 100644
index 0000000000..0e7e653117
--- /dev/null
+++ b/packages/twenty-front/src/modules/onboarding/utils/getIsPlanRequired.ts
@@ -0,0 +1,11 @@
+import { type CurrentWorkspace } from '@/auth/states/currentWorkspaceState';
+
+export const getIsPlanRequired = ({
+  isBillingEnabled,
+  currentWorkspace,
+}: {
+  isBillingEnabled: boolean;
+  currentWorkspace: Pick<CurrentWorkspace, 'billingSubscriptions'> | null;
+}) =>
+  isBillingEnabled &&
+  (currentWorkspace?.billingSubscriptions?.length ?? 0) === 0;
diff --git a/packages/twenty-front/src/modules/settings/billing/hooks/useStripePromise.ts b/packages/twenty-front/src/modules/settings/billing/hooks/useStripePromise.ts
index e38be9a163..2af348948e 100644
--- a/packages/twenty-front/src/modules/settings/billing/hooks/useStripePromise.ts
+++ b/packages/twenty-front/src/modules/settings/billing/hooks/useStripePromise.ts
@@ -1,30 +1,14 @@
 import { billingState } from '@/client-config/states/billingState';
+import { getStripePromise } from '@/settings/billing/utils/getStripePromise';
 import { useAtomStateValue } from '@/ui/utilities/state/jotai/hooks/useAtomStateValue';
+import { isNonEmptyString } from '@sniptt/guards';
 import { type Stripe } from '@stripe/stripe-js';
-import { loadStripe } from '@stripe/stripe-js/pure';
-import { isDefined } from 'twenty-shared/utils';
-
-const stripePromiseByKey = new Map<string, Promise<Stripe | null>>();
-
-const getStripePromise = (publishableKey: string): Promise<Stripe | null> => {
-  const existingPromise = stripePromiseByKey.get(publishableKey);
-
-  if (isDefined(existingPromise)) {
-    return existingPromise;
-  }
-
-  const stripePromise = loadStripe(publishableKey);
-
-  stripePromiseByKey.set(publishableKey, stripePromise);
-
-  return stripePromise;
-};
 
 export const useStripePromise = (): Promise<Stripe | null> | null => {
   const billing = useAtomStateValue(billingState);
   const publishableKey = billing?.stripePublishableKey;
 
-  return isDefined(publishableKey) && publishableKey !== ''
+  return isNonEmptyString(publishableKey)
     ? getStripePromise(publishableKey)
     : null;
 };
diff --git a/packages/twenty-front/src/modules/settings/billing/utils/__tests__/getStripePromise.test.ts b/packages/twenty-front/src/modules/settings/billing/utils/__tests__/getStripePromise.test.ts
new file mode 100644
index 0000000000..083bd8aefc
--- /dev/null
+++ b/packages/twenty-front/src/modules/settings/billing/utils/__tests__/getStripePromise.test.ts
@@ -0,0 +1,42 @@
+import { loadStripe } from '@stripe/stripe-js/pure';
+
+import { getStripePromise } from '@/settings/billing/utils/getStripePromise';
+
+jest.mock('@stripe/stripe-js/pure', () => ({
+  loadStripe: jest.fn(),
+}));
+
+const loadStripeMock = jest.mocked(loadStripe);
+
+describe('getStripePromise', () => {
+  beforeEach(() => {
+    jest.clearAllMocks();
+  });
+
+  it('should load Stripe once per publishable key', async () => {
+    loadStripeMock.mockResolvedValue(null);
+
+    const firstPromise = getStripePromise('pk_test_dedup');
+    const secondPromise = getStripePromise('pk_test_dedup');
+
+    expect(secondPromise).toBe(firstPromise);
+    expect(loadStripeMock).toHaveBeenCalledTimes(1);
+
+    await expect(firstPromise).resolves.toBeNull();
+  });
+
+  it('should retry loading Stripe after a failed load', async () => {
+    loadStripeMock
+      .mockRejectedValueOnce(new Error('Failed to load Stripe.js'))
+      .mockResolvedValueOnce(null);
+
+    await expect(getStripePromise('pk_test_retry')).rejects.toThrow(
+      'Failed to load Stripe.js',
+    );
+
+    const retriedPromise = getStripePromise('pk_test_retry');
+
+    expect(loadStripeMock).toHaveBeenCalledTimes(2);
+    await expect(retriedPromise).resolves.toBeNull();
+  });
+});
diff --git a/packages/twenty-front/src/modules/settings/billing/utils/getStripePromise.ts b/packages/twenty-front/src/modules/settings/billing/utils/getStripePromise.ts
new file mode 100644
index 0000000000..b47e612bea
--- /dev/null
+++ b/packages/twenty-front/src/modules/settings/billing/utils/getStripePromise.ts
@@ -0,0 +1,26 @@
+import { type Stripe } from '@stripe/stripe-js';
+import { loadStripe } from '@stripe/stripe-js/pure';
+import { isDefined } from 'twenty-shared/utils';
+
+const stripePromiseByKey = new Map<string, Promise<Stripe | null>>();
+
+export const getStripePromise = (
+  publishableKey: string,
+): Promise<Stripe | null> => {
+  const existingPromise = stripePromiseByKey.get(publishableKey);
+
+  if (isDefined(existingPromise)) {
+    return existingPromise;
+  }
+
+  const stripePromise = loadStripe(publishableKey);
+
+  stripePromiseByKey.set(publishableKey, stripePromise);
+
+  // Drop failed loads so a later call can retry
+  stripePromise.catch(() => {
+    stripePromiseByKey.delete(publishableKey);
+  });
+
+  return stripePromise;
+};