diff --git a/packages/twenty-front/src/effect-components/PageChangeEffect.tsx b/packages/twenty-front/src/effect-components/PageChangeEffect.tsx
index b86a15c6d..54c052c7a 100644
--- a/packages/twenty-front/src/effect-components/PageChangeEffect.tsx
+++ b/packages/twenty-front/src/effect-components/PageChangeEffect.tsx
@@ -64,7 +64,8 @@ export const PageChangeEffect = () => {
       isMatchingOngoingUserCreationRoute ||
       isMatchingLocation(AppPath.CreateWorkspace) ||
       isMatchingLocation(AppPath.CreateProfile) ||
-      isMatchingLocation(AppPath.PlanRequired);
+      isMatchingLocation(AppPath.PlanRequired) ||
+      isMatchingLocation(AppPath.PlanRequiredSuccess);
 
     const navigateToSignUp = () => {
       enqueueSnackBar('workspace does not exist', {
@@ -81,12 +82,20 @@ export const PageChangeEffect = () => {
       navigate(AppPath.SignIn);
     } else if (
       onboardingStatus &&
-      [OnboardingStatus.Canceled, OnboardingStatus.Incomplete].includes(
-        onboardingStatus,
-      ) &&
+      onboardingStatus === OnboardingStatus.Incomplete &&
       !isMatchingLocation(AppPath.PlanRequired)
     ) {
       navigate(AppPath.PlanRequired);
+    } else if (
+      onboardingStatus &&
+      [OnboardingStatus.Unpaid, OnboardingStatus.Canceled].includes(
+        onboardingStatus,
+      ) &&
+      !isMatchingLocation(SettingsPath.Billing)
+    ) {
+      navigate(
+        `${AppPath.SettingsCatchAll.replace('/*', '')}/${SettingsPath.Billing}`,
+      );
     } else if (
       onboardingStatus === OnboardingStatus.OngoingWorkspaceActivation &&
       !isMatchingLocation(AppPath.CreateWorkspace) &&
diff --git a/packages/twenty-front/src/modules/auth/hooks/__test__/useOnboardingStatus.test.ts b/packages/twenty-front/src/modules/auth/hooks/__test__/useOnboardingStatus.test.ts
index ab47fa3af..0758ed0d7 100644
--- a/packages/twenty-front/src/modules/auth/hooks/__test__/useOnboardingStatus.test.ts
+++ b/packages/twenty-front/src/modules/auth/hooks/__test__/useOnboardingStatus.test.ts
@@ -104,7 +104,13 @@ describe('useOnboardingStatus', () => {
         ...currentWorkspace,
         subscriptionStatus: 'canceled',
       });
-      setCurrentWorkspaceMember(currentWorkspaceMember);
+      setCurrentWorkspaceMember({
+        ...currentWorkspaceMember,
+        name: {
+          firstName: 'John',
+          lastName: 'Doe',
+        },
+      });
     });
 
     expect(result.current.onboardingStatus).toBe('canceled');
@@ -178,4 +184,60 @@ describe('useOnboardingStatus', () => {
 
     expect(result.current.onboardingStatus).toBe('completed');
   });
+
+  it('should return "past_due"', async () => {
+    const { result } = renderHooks();
+    const {
+      setTokenPair,
+      setBilling,
+      setCurrentWorkspace,
+      setCurrentWorkspaceMember,
+    } = result.current;
+
+    act(() => {
+      setTokenPair(tokenPair);
+      setBilling(billing);
+      setCurrentWorkspace({
+        ...currentWorkspace,
+        subscriptionStatus: 'past_due',
+      });
+      setCurrentWorkspaceMember({
+        ...currentWorkspaceMember,
+        name: {
+          firstName: 'John',
+          lastName: 'Doe',
+        },
+      });
+    });
+
+    expect(result.current.onboardingStatus).toBe('past_due');
+  });
+
+  it('should return "unpaid"', async () => {
+    const { result } = renderHooks();
+    const {
+      setTokenPair,
+      setBilling,
+      setCurrentWorkspace,
+      setCurrentWorkspaceMember,
+    } = result.current;
+
+    act(() => {
+      setTokenPair(tokenPair);
+      setBilling(billing);
+      setCurrentWorkspace({
+        ...currentWorkspace,
+        subscriptionStatus: 'unpaid',
+      });
+      setCurrentWorkspaceMember({
+        ...currentWorkspaceMember,
+        name: {
+          firstName: 'John',
+          lastName: 'Doe',
+        },
+      });
+    });
+
+    expect(result.current.onboardingStatus).toBe('unpaid');
+  });
 });
diff --git a/packages/twenty-front/src/modules/auth/utils/getOnboardingStatus.ts b/packages/twenty-front/src/modules/auth/utils/getOnboardingStatus.ts
index 4479e730e..0ed331041 100644
--- a/packages/twenty-front/src/modules/auth/utils/getOnboardingStatus.ts
+++ b/packages/twenty-front/src/modules/auth/utils/getOnboardingStatus.ts
@@ -4,6 +4,8 @@ import { WorkspaceMember } from '@/workspace-member/types/WorkspaceMember';
 export enum OnboardingStatus {
   Incomplete = 'incomplete',
   Canceled = 'canceled',
+  Unpaid = 'unpaid',
+  PastDue = 'past_due',
   OngoingUserCreation = 'ongoing_user_creation',
   OngoingWorkspaceActivation = 'ongoing_workspace_activation',
   OngoingProfileCreation = 'ongoing_profile_creation',
@@ -41,10 +43,6 @@ export const getOnboardingStatus = ({
     return OnboardingStatus.Incomplete;
   }
 
-  if (isBillingEnabled && currentWorkspace.subscriptionStatus === 'canceled') {
-    return OnboardingStatus.Canceled;
-  }
-
   if (currentWorkspace.activationStatus !== 'active') {
     return OnboardingStatus.OngoingWorkspaceActivation;
   }
@@ -56,5 +54,17 @@ export const getOnboardingStatus = ({
     return OnboardingStatus.OngoingProfileCreation;
   }
 
+  if (isBillingEnabled && currentWorkspace.subscriptionStatus === 'canceled') {
+    return OnboardingStatus.Canceled;
+  }
+
+  if (isBillingEnabled && currentWorkspace.subscriptionStatus === 'past_due') {
+    return OnboardingStatus.PastDue;
+  }
+
+  if (isBillingEnabled && currentWorkspace.subscriptionStatus === 'unpaid') {
+    return OnboardingStatus.Unpaid;
+  }
+
   return OnboardingStatus.Completed;
 };
diff --git a/packages/twenty-front/src/modules/billing/components/ManageYourSubscription.tsx b/packages/twenty-front/src/modules/billing/components/ManageYourSubscription.tsx
deleted file mode 100644
index e95067d18..000000000
--- a/packages/twenty-front/src/modules/billing/components/ManageYourSubscription.tsx
+++ /dev/null
@@ -1,24 +0,0 @@
-import { IconCreditCard } from '@/ui/display/icon';
-import { Button } from '@/ui/input/button/components/Button';
-import { useBillingPortalSessionQuery } from '~/generated/graphql.tsx';
-export const ManageYourSubscription = () => {
-  const { data, loading } = useBillingPortalSessionQuery({
-    variables: {
-      returnUrlPath: '/settings/billing',
-    },
-  });
-  const handleButtonClick = () => {
-    if (data) {
-      window.location.replace(data.billingPortalSession.url);
-    }
-  };
-  return (
-    <Button
-      Icon={IconCreditCard}
-      title="View billing details"
-      variant="secondary"
-      onClick={handleButtonClick}
-      disabled={loading}
-    />
-  );
-};
diff --git a/packages/twenty-front/src/modules/ui/display/info/components/Info.tsx b/packages/twenty-front/src/modules/ui/display/info/components/Info.tsx
new file mode 100644
index 000000000..bb674eabd
--- /dev/null
+++ b/packages/twenty-front/src/modules/ui/display/info/components/Info.tsx
@@ -0,0 +1,65 @@
+import React from 'react';
+import { css, useTheme } from '@emotion/react';
+import styled from '@emotion/styled';
+
+import { IconInfoCircle } from '@/ui/display/icon';
+import { Button } from '@/ui/input/button/components/Button.tsx';
+
+export type InfoAccent = 'blue' | 'danger';
+export type InfoProps = {
+  accent?: InfoAccent;
+  text: string;
+  buttonTitle: string;
+  onClick: (event: React.MouseEvent<HTMLButtonElement>) => void;
+};
+
+const StyledTextContainer = styled.div`
+  display: flex;
+  gap: ${({ theme }) => theme.spacing(2)};
+`;
+
+const StyledInfo = styled.div<Pick<InfoProps, 'accent'>>`
+  align-items: center;
+  border-radius: ${({ theme }) => theme.border.radius.md};
+  display: flex;
+  font-weight: ${({ theme }) => theme.font.weight.medium};
+  justify-content: space-between;
+  max-width: 512px;
+  padding: ${({ theme }) => theme.spacing(2)};
+  ${({ theme, accent }) => {
+    switch (accent) {
+      case 'blue':
+        return css`
+          background: ${theme.color.blueAccent20};
+          color: ${theme.color.blue50};
+        `;
+      case 'danger':
+        return css`
+          background: ${theme.color.red10};
+          color: ${theme.color.red};
+        `;
+    }
+  }}
+`;
+export const Info = ({
+  accent = 'blue',
+  text,
+  buttonTitle,
+  onClick,
+}: InfoProps) => {
+  const theme = useTheme();
+  return (
+    <StyledInfo accent={accent}>
+      <StyledTextContainer>
+        <IconInfoCircle size={theme.icon.size.md} />
+        {text}
+      </StyledTextContainer>
+      <Button
+        title={buttonTitle}
+        onClick={onClick}
+        size={'small'}
+        variant={'secondary'}
+      />
+    </StyledInfo>
+  );
+};
diff --git a/packages/twenty-front/src/modules/ui/display/info/components/__stories__/Info.stories.tsx b/packages/twenty-front/src/modules/ui/display/info/components/__stories__/Info.stories.tsx
new file mode 100644
index 000000000..98ac1e317
--- /dev/null
+++ b/packages/twenty-front/src/modules/ui/display/info/components/__stories__/Info.stories.tsx
@@ -0,0 +1,45 @@
+import { Meta, StoryObj } from '@storybook/react';
+
+import { Info, InfoAccent } from '@/ui/display/info/components/Info.tsx';
+import { CatalogDecorator } from '~/testing/decorators/CatalogDecorator.tsx';
+import { ComponentDecorator } from '~/testing/decorators/ComponentDecorator.tsx';
+import { CatalogStory } from '~/testing/types.ts';
+
+const meta: Meta<typeof Info> = {
+  title: 'UI/Display/Info/Info',
+  component: Info,
+};
+
+export default meta;
+type Story = StoryObj<typeof Info>;
+
+export const Default: Story = {
+  args: {
+    accent: 'blue',
+    text: 'An info component',
+    buttonTitle: 'Update',
+  },
+  decorators: [ComponentDecorator],
+};
+
+export const Catalog: CatalogStory<Story, typeof Info> = {
+  args: {
+    text: 'An info component',
+    buttonTitle: 'Update',
+  },
+  argTypes: {
+    accent: { control: false },
+  },
+  parameters: {
+    catalog: {
+      dimensions: [
+        {
+          name: 'accents',
+          values: ['blue', 'danger'] satisfies InfoAccent[],
+          props: (accent: InfoAccent) => ({ accent }),
+        },
+      ],
+    },
+  },
+  decorators: [CatalogDecorator],
+};
diff --git a/packages/twenty-front/src/modules/ui/layout/page/DefaultLayout.tsx b/packages/twenty-front/src/modules/ui/layout/page/DefaultLayout.tsx
index 3c872dd17..18efeb419 100644
--- a/packages/twenty-front/src/modules/ui/layout/page/DefaultLayout.tsx
+++ b/packages/twenty-front/src/modules/ui/layout/page/DefaultLayout.tsx
@@ -76,7 +76,13 @@ export const DefaultLayout = ({ children }: DefaultLayoutProps) => {
   const isMatchingLocation = useIsMatchingLocation();
   const showAuthModal = useMemo(() => {
     return (
-      (onboardingStatus && onboardingStatus !== OnboardingStatus.Completed) ||
+      (onboardingStatus &&
+        [
+          OnboardingStatus.Incomplete,
+          OnboardingStatus.OngoingUserCreation,
+          OnboardingStatus.OngoingProfileCreation,
+          OnboardingStatus.OngoingWorkspaceActivation,
+        ].includes(onboardingStatus)) ||
       isMatchingLocation(AppPath.ResetPassword)
     );
   }, [isMatchingLocation, onboardingStatus]);
diff --git a/packages/twenty-front/src/pages/settings/SettingsBilling.tsx b/packages/twenty-front/src/pages/settings/SettingsBilling.tsx
index 29989ccfb..650788fb9 100644
--- a/packages/twenty-front/src/pages/settings/SettingsBilling.tsx
+++ b/packages/twenty-front/src/pages/settings/SettingsBilling.tsx
@@ -1,30 +1,104 @@
+import React from 'react';
 import styled from '@emotion/styled';
+import { useRecoilValue } from 'recoil';
 
-import { ManageYourSubscription } from '@/billing/components/ManageYourSubscription.tsx';
+import { useOnboardingStatus } from '@/auth/hooks/useOnboardingStatus.ts';
+import { currentWorkspaceState } from '@/auth/states/currentWorkspaceState.ts';
+import { OnboardingStatus } from '@/auth/utils/getOnboardingStatus.ts';
 import { SettingsBillingCoverImage } from '@/billing/components/SettingsBillingCoverImage.tsx';
+import { supportChatState } from '@/client-config/states/supportChatState.ts';
 import { SettingsPageContainer } from '@/settings/components/SettingsPageContainer';
-import { IconCurrencyDollar } from '@/ui/display/icon';
+import { SupportChat } from '@/support/components/SupportChat.tsx';
+import { IconCreditCard, IconCurrencyDollar } from '@/ui/display/icon';
+import { Info } from '@/ui/display/info/components/Info.tsx';
 import { H1Title } from '@/ui/display/typography/components/H1Title.tsx';
 import { H2Title } from '@/ui/display/typography/components/H2Title.tsx';
+import { Button } from '@/ui/input/button/components/Button.tsx';
 import { SubMenuTopBarContainer } from '@/ui/layout/page/SubMenuTopBarContainer';
 import { Section } from '@/ui/layout/section/components/Section.tsx';
+import { useBillingPortalSessionQuery } from '~/generated/graphql.tsx';
 
 const StyledH1Title = styled(H1Title)`
   margin-bottom: 0;
 `;
 
-export const SettingsBilling = () => (
-  <SubMenuTopBarContainer Icon={IconCurrencyDollar} title="Billing">
-    <SettingsPageContainer>
-      <StyledH1Title title="Billing" />
-      <SettingsBillingCoverImage />
-      <Section>
-        <H2Title
-          title="Manage your subscription"
-          description="Edit payment method, see your invoices and more"
-        />
-        <ManageYourSubscription />
-      </Section>
-    </SettingsPageContainer>
-  </SubMenuTopBarContainer>
-);
+const StyledInvisibleChat = styled.div`
+  display: none;
+`;
+
+export const SettingsBilling = () => {
+  const onboardingStatus = useOnboardingStatus();
+  const supportChat = useRecoilValue(supportChatState);
+  const currentWorkspace = useRecoilValue(currentWorkspaceState);
+  const { data, loading } = useBillingPortalSessionQuery({
+    variables: {
+      returnUrlPath: '/settings/billing',
+    },
+  });
+
+  const displayPaymentFailInfo =
+    onboardingStatus === OnboardingStatus.PastDue ||
+    onboardingStatus === OnboardingStatus.Unpaid;
+
+  const displaySubscriptionCanceledInfo =
+    onboardingStatus === OnboardingStatus.Canceled;
+
+  const openBillingPortal = () => {
+    if (data) {
+      window.location.replace(data.billingPortalSession.url);
+    }
+  };
+
+  const openChat = () => {
+    if (supportChat.supportDriver) {
+      window.FrontChat?.('show');
+    } else {
+      window.location.href =
+        'mailto:felix@twenty.com?' +
+        `subject=Subscription Recovery for workspace ${currentWorkspace?.id}&` +
+        'body=Hey,%0D%0A%0D%0AMy subscription is canceled and I would like to subscribe a new one.' +
+        'Can you help me?%0D%0A%0D%0ACheers';
+    }
+  };
+
+  return (
+    <SubMenuTopBarContainer Icon={IconCurrencyDollar} title="Billing">
+      <SettingsPageContainer>
+        <StyledH1Title title="Billing" />
+        <SettingsBillingCoverImage />
+        {displaySubscriptionCanceledInfo && (
+          <Info
+            text={'Subscription canceled. Please contact us to start a new one'}
+            buttonTitle={'Contact Us'}
+            accent={'danger'}
+            onClick={openChat}
+          />
+        )}
+        {displayPaymentFailInfo && (
+          <Info
+            text={'Last payment failed. Please update your billing details.'}
+            buttonTitle={'Update'}
+            accent={'danger'}
+            onClick={openBillingPortal}
+          />
+        )}
+        <Section>
+          <H2Title
+            title="Manage your subscription"
+            description="Edit payment method, see your invoices and more"
+          />
+          <Button
+            Icon={IconCreditCard}
+            title="View billing details"
+            variant="secondary"
+            onClick={openBillingPortal}
+            disabled={loading}
+          />
+        </Section>
+      </SettingsPageContainer>
+      <StyledInvisibleChat>
+        <SupportChat />
+      </StyledInvisibleChat>
+    </SubMenuTopBarContainer>
+  );
+};
diff --git a/packages/twenty-server/src/core/billing/billing.controller.ts b/packages/twenty-server/src/core/billing/billing.controller.ts
index e49533b84..c0cb2dd97 100644
--- a/packages/twenty-server/src/core/billing/billing.controller.ts
+++ b/packages/twenty-server/src/core/billing/billing.controller.ts
@@ -38,9 +38,14 @@ export class BillingController {
       req.rawBody,
     );
 
+    if (event.type === WebhookEvent.SETUP_INTENT_SUCCEEDED) {
+      await this.billingService.handleUnpaidInvoices(event.data);
+    }
+
     if (
       event.type === WebhookEvent.CUSTOMER_SUBSCRIPTION_CREATED ||
-      event.type === WebhookEvent.CUSTOMER_SUBSCRIPTION_UPDATED
+      event.type === WebhookEvent.CUSTOMER_SUBSCRIPTION_UPDATED ||
+      event.type === WebhookEvent.CUSTOMER_SUBSCRIPTION_DELETED
     ) {
       const workspaceId = event.data.object.metadata?.workspaceId;
 
diff --git a/packages/twenty-server/src/core/billing/billing.service.ts b/packages/twenty-server/src/core/billing/billing.service.ts
index ee8406d08..f17256c2f 100644
--- a/packages/twenty-server/src/core/billing/billing.service.ts
+++ b/packages/twenty-server/src/core/billing/billing.service.ts
@@ -20,6 +20,8 @@ export enum AvailableProduct {
 export enum WebhookEvent {
   CUSTOMER_SUBSCRIPTION_CREATED = 'customer.subscription.created',
   CUSTOMER_SUBSCRIPTION_UPDATED = 'customer.subscription.updated',
+  CUSTOMER_SUBSCRIPTION_DELETED = 'customer.subscription.deleted',
+  SETUP_INTENT_SUCCEEDED = 'setup_intent.succeeded',
 }
 
 @Injectable()
@@ -74,9 +76,12 @@ export class BillingService {
     return Object.values(result).sort((a, b) => a.unitAmount - b.unitAmount);
   }
 
-  async getBillingSubscription(workspaceId: string) {
+  async getBillingSubscription(criteria: {
+    workspaceId?: string;
+    stripeCustomerId?: string;
+  }) {
     return await this.billingSubscriptionRepository.findOneOrFail({
-      where: { workspaceId },
+      where: criteria,
       relations: ['billingSubscriptionItems'],
     });
   }
@@ -85,7 +90,9 @@ export class BillingService {
     workspaceId: string,
     stripeProductId = this.environmentService.getBillingStripeBasePlanProductId(),
   ) {
-    const billingSubscription = await this.getBillingSubscription(workspaceId);
+    const billingSubscription = await this.getBillingSubscription({
+      workspaceId,
+    });
 
     const billingSubscriptionItem =
       billingSubscription.billingSubscriptionItems.filter(
@@ -162,6 +169,22 @@ export class BillingService {
     }
   }
 
+  async handleUnpaidInvoices(data: Stripe.SetupIntentSucceededEvent.Data) {
+    try {
+      const billingSubscription = await this.getBillingSubscription({
+        stripeCustomerId: data.object.customer as string,
+      });
+
+      if (billingSubscription.status === 'unpaid') {
+        await this.stripeService.collectLastInvoice(
+          billingSubscription.stripeSubscriptionId,
+        );
+      }
+    } catch (err) {
+      return;
+    }
+  }
+
   async upsertBillingSubscription(
     workspaceId: string,
     data:
@@ -176,7 +199,7 @@ export class BillingService {
         status: data.object.status,
       },
       {
-        conflictPaths: ['stripeSubscriptionId'],
+        conflictPaths: ['workspaceId'],
         skipUpdateIfNoValuesChanged: true,
       },
     );
@@ -185,7 +208,9 @@ export class BillingService {
       subscriptionStatus: data.object.status,
     });
 
-    const billingSubscription = await this.getBillingSubscription(workspaceId);
+    const billingSubscription = await this.getBillingSubscription({
+      workspaceId,
+    });
 
     await this.billingSubscriptionItemRepository.upsert(
       data.object.items.data.map((item) => {
@@ -198,7 +223,7 @@ export class BillingService {
         };
       }),
       {
-        conflictPaths: ['stripeSubscriptionItemId', 'billingSubscriptionId'],
+        conflictPaths: ['billingSubscriptionId', 'stripeProductId'],
         skipUpdateIfNoValuesChanged: true,
       },
     );
diff --git a/packages/twenty-server/src/core/billing/stripe/stripe.service.ts b/packages/twenty-server/src/core/billing/stripe/stripe.service.ts
index 2c68c7a6c..f57515797 100644
--- a/packages/twenty-server/src/core/billing/stripe/stripe.service.ts
+++ b/packages/twenty-server/src/core/billing/stripe/stripe.service.ts
@@ -80,4 +80,23 @@ export class StripeService {
       cancel_url: cancelUrl,
     });
   }
+
+  async collectLastInvoice(stripeSubscriptionId: string) {
+    const subscription = await this.stripe.subscriptions.retrieve(
+      stripeSubscriptionId,
+      { expand: ['latest_invoice'] },
+    );
+    const latestInvoice = subscription.latest_invoice;
+
+    if (
+      !(
+        latestInvoice &&
+        typeof latestInvoice !== 'string' &&
+        latestInvoice.status === 'draft'
+      )
+    ) {
+      return;
+    }
+    await this.stripe.invoices.pay(latestInvoice.id);
+  }
 }