diff --git a/frontend/src/components/AccountMenu.tsx b/frontend/src/components/AccountMenu.tsx
index 5f8c0e75..03ffb22e 100644
--- a/frontend/src/components/AccountMenu.tsx
+++ b/frontend/src/components/AccountMenu.tsx
@@ -49,6 +49,7 @@ import { Link } from "@tanstack/react-router";
 import { getBillingService } from "@/billing/billingService";
 import { useState } from "react";
 import type { TeamStatus } from "@/types/team";
+import { Alert, AlertDescription } from "@/components/ui/alert";
 import { TeamManagementDialog } from "@/components/team/TeamManagementDialog";
 import { ApiKeyManagementDialog } from "@/components/apikeys/ApiKeyManagementDialog";
 import packageJson from "../../package.json";
@@ -110,6 +111,7 @@ export function AccountMenu() {
   const [isTeamDialogOpen, setIsTeamDialogOpen] = useState(false);
   const [isApiKeyDialogOpen, setIsApiKeyDialogOpen] = useState(false);
   const [showAboutMenu, setShowAboutMenu] = useState(false);
+  const [portalError, setPortalError] = useState<string | null>(null);
 
   const hasStripeAccount = billingStatus?.stripe_customer_id !== null;
   const productName = billingStatus?.product_name || "";
@@ -176,6 +178,7 @@ export function AccountMenu() {
 
     try {
       setIsPortalLoading(true);
+      setPortalError(null);
       const billingService = getBillingService();
       const url = await billingService.getPortalUrl();
 
@@ -211,6 +214,9 @@ export function AccountMenu() {
       window.open(url, "_blank");
     } catch (error) {
       console.error("Error fetching portal URL:", error);
+      setPortalError(
+        "Unable to open subscription management. Please try again or contact support@opensecret.cloud."
+      );
     } finally {
       setIsPortalLoading(false);
     }
@@ -448,6 +454,12 @@ export function AccountMenu() {
           </DropdownMenuContent>
           <AccountDialog />
           <ConfirmDeleteDialog />
+          {portalError && (
+            <Alert variant="destructive" className="mt-2">
+              <AlertCircle className="h-4 w-4" />
+              <AlertDescription>{portalError}</AlertDescription>
+            </Alert>
+          )}
           <TeamManagementDialog
             open={isTeamDialogOpen}
             onOpenChange={setIsTeamDialogOpen}
diff --git a/frontend/src/components/team/TeamInviteDialog.tsx b/frontend/src/components/team/TeamInviteDialog.tsx
index e655f7ad..659e73c2 100644
--- a/frontend/src/components/team/TeamInviteDialog.tsx
+++ b/frontend/src/components/team/TeamInviteDialog.tsx
@@ -32,7 +32,6 @@ export function TeamInviteDialog({ open, onOpenChange, teamStatus }: TeamInviteD
   const [isPortalLoading, setIsPortalLoading] = useState(false);
   const queryClient = useQueryClient();
   const { billingStatus } = useLocalState();
-
   const seatsAvailable = teamStatus?.seats_available || 0;
   const hasStripeAccount = billingStatus?.stripe_customer_id !== null;
 
@@ -40,6 +39,7 @@ export function TeamInviteDialog({ open, onOpenChange, teamStatus }: TeamInviteD
     if (!hasStripeAccount) return;
 
     try {
+      setError(null);
       setIsPortalLoading(true);
       const billingService = getBillingService();
       const url = await billingService.getPortalUrl();
@@ -71,6 +71,9 @@ export function TeamInviteDialog({ open, onOpenChange, teamStatus }: TeamInviteD
       window.open(url, "_blank", "noopener,noreferrer");
     } catch (error) {
       console.error("Failed to open billing portal:", error);
+      setError(
+        "Unable to open subscription management. Please try again or contact support@opensecret.cloud."
+      );
     } finally {
       setIsPortalLoading(false);
     }
diff --git a/frontend/src/routes/pricing.tsx b/frontend/src/routes/pricing.tsx
index 3c12de9f..19427f58 100644
--- a/frontend/src/routes/pricing.tsx
+++ b/frontend/src/routes/pricing.tsx
@@ -6,7 +6,8 @@ import { FullPageMain } from "@/components/FullPageMain";
 import { getBillingService } from "@/billing/billingService";
 import { useQuery } from "@tanstack/react-query";
 import { MarketingHeader } from "@/components/MarketingHeader";
-import { Loader2, Check, AlertTriangle, Bitcoin, Tag } from "lucide-react";
+import { Loader2, Check, AlertTriangle, AlertCircle, Bitcoin, Tag } from "lucide-react";
+import { Alert, AlertDescription } from "@/components/ui/alert";
 import type { DiscountResponse } from "@/billing/billingApi";
 import { Badge } from "@/components/ui/badge";
 import { useLocalState } from "@/state/useLocalState";
@@ -198,6 +199,7 @@ function PricingFAQ() {
 
 function PricingPage() {
   const [checkoutError, setCheckoutError] = useState<string>("");
+  const [portalError, setPortalError] = useState<string | null>(null);
   const [loadingProductId, setLoadingProductId] = useState<string | null>(null);
   const [useBitcoin, setUseBitcoin] = useState(false);
   const [showTeamSeatDialog, setShowTeamSeatDialog] = useState(false);
@@ -476,6 +478,7 @@ function PricingPage() {
 
   const handleButtonClick = useCallback(
     (product: Product) => {
+      setPortalError(null);
       const targetPlanName = product.name.toLowerCase();
       const isFreeplan = targetPlanName.includes("free");
       const isTeamPlan = targetPlanName.includes("team");
@@ -612,6 +615,15 @@ function PricingPage() {
         return;
       }
 
+      // If the user is already on a paid plan (including team) and portal URL failed to load,
+      // show an error instead of silently falling through to checkout
+      if (isCurrentPlan) {
+        setPortalError(
+          "Unable to open subscription management. Please try again or contact support@opensecret.cloud."
+        );
+        return;
+      }
+
       // If no portal URL exists and it's not a free plan user upgrading,
       // create checkout session
       // For team plans, show seat selection dialog first
@@ -785,6 +797,16 @@ function PricingPage() {
           </div>
         )}
 
+        {/* Portal Error Message */}
+        {portalError && (
+          <div className="w-full max-w-7xl mx-auto mt-4 px-4 sm:px-6 lg:px-8">
+            <Alert variant="destructive">
+              <AlertCircle className="h-4 w-4" />
+              <AlertDescription>{portalError}</AlertDescription>
+            </Alert>
+          </div>
+        )}
+
         {/* Promotion Banner */}
         {discount?.active && (
           <div className="w-full max-w-7xl mx-auto mt-4 px-4 sm:px-6 lg:px-8">