diff --git a/frontend/__snapshots__/scenes-other-billing-v2--billing-v-2-with-discount.png b/frontend/__snapshots__/scenes-other-billing-v2--billing-v-2-with-discount.png
index 737014b62b7f5..8eeeafbc340a1 100644
Binary files a/frontend/__snapshots__/scenes-other-billing-v2--billing-v-2-with-discount.png and b/frontend/__snapshots__/scenes-other-billing-v2--billing-v-2-with-discount.png differ
diff --git a/frontend/__snapshots__/scenes-other-billing-v2--billing-v-2.png b/frontend/__snapshots__/scenes-other-billing-v2--billing-v-2.png
index 4922e2d6ca640..3df423c0ff684 100644
Binary files a/frontend/__snapshots__/scenes-other-billing-v2--billing-v-2.png and b/frontend/__snapshots__/scenes-other-billing-v2--billing-v-2.png differ
diff --git a/frontend/src/lib/components/BillingAlertsV2.tsx b/frontend/src/lib/components/BillingAlertsV2.tsx
index 1748f0c91d4c2..21a4023a6262a 100644
--- a/frontend/src/lib/components/BillingAlertsV2.tsx
+++ b/frontend/src/lib/components/BillingAlertsV2.tsx
@@ -7,7 +7,7 @@ import { LemonBanner } from 'lib/lemon-ui/LemonBanner'
 
 export function BillingAlertsV2(): JSX.Element | null {
     const { billingAlert } = useValues(billingLogic)
-    const { reportBillingAlertShown } = useActions(billingLogic)
+    const { reportBillingAlertShown, reportBillingAlertActionClicked } = useActions(billingLogic)
     const { currentLocation } = useValues(router)
     const [alertHidden, setAlertHidden] = useState(false)
 
@@ -21,14 +21,19 @@ export function BillingAlertsV2(): JSX.Element | null {
         return null
     }
 
-    const showButton = currentLocation.pathname !== urls.organizationBilling()
+    const showButton = billingAlert.contactSupport || currentLocation.pathname !== urls.organizationBilling()
 
     const buttonProps = billingAlert.contactSupport
         ? {
               to: 'mailto:sales@posthog.com',
-              children: 'Contact support',
+              children: billingAlert.buttonCTA || 'Contact support',
+              onClick: () => reportBillingAlertActionClicked(billingAlert),
+          }
+        : {
+              to: urls.organizationBilling(),
+              children: 'Manage billing',
+              onClick: () => reportBillingAlertActionClicked(billingAlert),
           }
-        : { to: urls.organizationBilling(), children: 'Manage billing' }
 
     return (
         <div className="my-4">
@@ -36,6 +41,7 @@ export function BillingAlertsV2(): JSX.Element | null {
                 type={billingAlert.status}
                 action={showButton ? buttonProps : undefined}
                 onClose={billingAlert.status !== 'error' ? () => setAlertHidden(true) : undefined}
+                dismissKey={billingAlert.dismissKey}
             >
                 <b>{billingAlert.title}</b>
                 <br />
diff --git a/frontend/src/scenes/billing/Billing.tsx b/frontend/src/scenes/billing/Billing.tsx
index 87f2ab775409b..481b89aa9defd 100644
--- a/frontend/src/scenes/billing/Billing.tsx
+++ b/frontend/src/scenes/billing/Billing.tsx
@@ -264,7 +264,7 @@ export function Billing(): JSX.Element {
                 </div>
             </div>
 
-            <div className="flex justify-between">
+            <div className="flex justify-between mt-4">
                 <h2>Products</h2>
                 {isOnboarding && upgradeAllProductsLink && (
                     <LemonButton
diff --git a/frontend/src/scenes/billing/billingLogic.ts b/frontend/src/scenes/billing/billingLogic.ts
index b279a9f9bf62e..920e524ced18e 100644
--- a/frontend/src/scenes/billing/billingLogic.ts
+++ b/frontend/src/scenes/billing/billingLogic.ts
@@ -21,8 +21,10 @@ export const ALLOCATION_THRESHOLD_BLOCK = 1.2 // Threshold to block usage
 export interface BillingAlertConfig {
     status: 'info' | 'warning' | 'error'
     title: string
-    message: string
+    message?: string
     contactSupport?: boolean
+    buttonCTA?: string
+    dismissKey?: string
 }
 
 const parseBillingResponse = (data: Partial<BillingV2Type>): BillingV2Type => {
@@ -54,6 +56,7 @@ export const billingLogic = kea<billingLogicType>([
     actions({
         setShowLicenseDirectInput: (show: boolean) => ({ show }),
         reportBillingAlertShown: (alertConfig: BillingAlertConfig) => ({ alertConfig }),
+        reportBillingAlertActionClicked: (alertConfig: BillingAlertConfig) => ({ alertConfig }),
         reportBillingV2Shown: true,
         registerInstrumentationProps: true,
         setRedirectPath: true,
@@ -130,9 +133,22 @@ export const billingLogic = kea<billingLogicType>([
             (s) => [s.preflight, s.billing],
             (preflight, billing): boolean => !!preflight?.is_debug && !billing?.billing_period,
         ],
+        projectedTotalAmountUsd: [
+            (s) => [s.billing],
+            (billing: BillingV2Type): number => {
+                if (!billing) {
+                    return 0
+                }
+                let projectedTotal = 0
+                for (const product of billing.products || []) {
+                    projectedTotal += parseFloat(product.projected_amount_usd || '0')
+                }
+                return projectedTotal
+            },
+        ],
         billingAlert: [
-            (s) => [s.billing, s.preflight],
-            (billing, preflight): BillingAlertConfig | undefined => {
+            (s) => [s.billing, s.preflight, s.projectedTotalAmountUsd],
+            (billing, preflight, projectedTotalAmountUsd): BillingAlertConfig | undefined => {
                 if (!billing || !preflight?.cloud) {
                     return
                 }
@@ -163,7 +179,7 @@ export const billingLogic = kea<billingLogicType>([
                     }
                 }
 
-                const productOverLimit = billing.products?.find((x) => {
+                const productOverLimit = billing.products?.find((x: BillingProductV2Type) => {
                     return x.percentage_usage > 1
                 })
 
@@ -190,6 +206,21 @@ export const billingLogic = kea<billingLogicType>([
                         )}% of your ${productApproachingLimit.usage_key.toLowerCase()} allocation.`,
                     }
                 }
+
+                if (
+                    billing.current_total_amount_usd_after_discount &&
+                    (parseFloat(billing.current_total_amount_usd_after_discount) > 1000 ||
+                        projectedTotalAmountUsd > 1000) &&
+                    billing.billing_period?.interval === 'month'
+                ) {
+                    return {
+                        status: 'info',
+                        title: `Switch to annual up-front billing to save up to 20% on your bill.`,
+                        contactSupport: true,
+                        buttonCTA: 'Contact sales',
+                        dismissKey: 'annual-billing-cta',
+                    }
+                }
             },
         ],
     }),
@@ -231,6 +262,11 @@ export const billingLogic = kea<billingLogicType>([
                 ...alertConfig,
             })
         },
+        reportBillingAlertActionClicked: ({ alertConfig }) => {
+            posthog.capture('billing alert action clicked', {
+                ...alertConfig,
+            })
+        },
         loadBillingSuccess: () => {
             if (
                 router.values.location.pathname.includes('/organization/billing') &&
@@ -276,7 +312,6 @@ export const billingLogic = kea<billingLogicType>([
             }
         },
     })),
-
     afterMount(({ actions }) => {
         actions.loadBilling()
     }),