diff --git a/apps/dashboard/src/app/(app)/[organizationSlug]/[projectId]/settings/organization/organization/billing.tsx b/apps/dashboard/src/app/(app)/[organizationSlug]/[projectId]/settings/organization/organization/billing.tsx
index ad24846c..7ecbe299 100644
--- a/apps/dashboard/src/app/(app)/[organizationSlug]/[projectId]/settings/organization/organization/billing.tsx
+++ b/apps/dashboard/src/app/(app)/[organizationSlug]/[projectId]/settings/organization/organization/billing.tsx
@@ -15,6 +15,7 @@ import { Widget, WidgetBody, WidgetHead } from '@/components/widget';
 import { WidgetTable } from '@/components/widget-table';
 import { useAppParams } from '@/hooks/useAppParams';
 import useWS from '@/hooks/useWS';
+import { showConfirm } from '@/modals';
 import { api } from '@/trpc/client';
 import type { IServiceOrganization } from '@openpanel/db';
 import type { IPolarPrice } from '@openpanel/payments';
@@ -257,12 +258,23 @@ function CheckoutButton({
         disabled={disabled !== null || (isActive && !isCanceled)}
         key={price.id}
         onClick={() => {
-          checkout.mutate({
-            projectId,
-            organizationId: organization.id,
-            productPriceId: price!.id,
-            productId: price.productId,
-          });
+          const createCheckout = () =>
+            checkout.mutate({
+              projectId,
+              organizationId: organization.id,
+              productPriceId: price!.id,
+              productId: price.productId,
+            });
+
+          if (organization.subscriptionStatus === 'active') {
+            showConfirm({
+              title: 'Are you sure?',
+              text: `You're about the change your subscription.`,
+              onConfirm: () => createCheckout(),
+            });
+          } else {
+            createCheckout();
+          }
         }}
         loading={checkout.isLoading}
         className="w-28"
diff --git a/packages/trpc/src/routers/subscription.ts b/packages/trpc/src/routers/subscription.ts
index 8c21aee3..d76725ba 100644
--- a/packages/trpc/src/routers/subscription.ts
+++ b/packages/trpc/src/routers/subscription.ts
@@ -53,16 +53,25 @@ export const subscriptionRouter = createTRPCRouter({
         organization.subscriptionId &&
         organization.subscriptionStatus === 'active'
       ) {
-        if (organization.subscriptionCanceledAt) {
-          await reactivateSubscription(organization.subscriptionId);
+        const existingProduct = organization.subscriptionProductId
+          ? await getProduct(organization.subscriptionProductId)
+          : null;
+
+        // If the existing product is free, cancel the subscription and then jump to the checkout
+        if (existingProduct?.prices.some((p) => p.amountType === 'free')) {
+          await cancelSubscription(organization.subscriptionId);
         } else {
+          if (organization.subscriptionCanceledAt) {
+            await reactivateSubscription(organization.subscriptionId);
+            return null;
+          }
+
           await changeSubscription(
             organization.subscriptionId,
             input.productId,
           );
+          return null;
         }
-
-        return null;
       }
 
       const checkout = await createCheckout({