diff --git a/apps/web/src/dialogs/settings/subscription-settings.ts b/apps/web/src/dialogs/settings/subscription-settings.ts
index d50f8fac1..ad112a91e 100644
--- a/apps/web/src/dialogs/settings/subscription-settings.ts
+++ b/apps/web/src/dialogs/settings/subscription-settings.ts
@@ -163,25 +163,56 @@ export const SubscriptionSettings: SettingsGroup[] = [
             title: "Cancel",
             variant: "error",
             async action() {
-              const cancelTrial = await ConfirmDialog.show({
-                title: "Cancel trial?",
-                message:
-                  "Cancel your trial to stop all future charges permanently. You will be immediately downgraded to the Free plan.",
-                negativeButtonText: "No",
-                positiveButtonText: "Yes"
-              });
-              if (cancelTrial) {
-                await TaskManager.startTask({
-                  type: "modal",
-                  title: "Cancelling your trial",
-                  subtitle: "Please wait...",
-                  action: () => db.subscriptions.cancel()
-                })
-                  .catch((e) => showToast("error", e.message))
-                  .then(() =>
-                    showToast("success", "Your trial has been canceled.")
-                  );
+              const canExtend =
+                !useUserStore.getState().user?.subscription?.extensionsAvailed
+                  ?.length;
+
+              if (canExtend) {
+                const isExtending = await ConfirmDialog.show({
+                  title: "We're sorry to see you go!",
+                  message:
+                    "Before you cancel, did you just need more time to test? We'd love to give you an extra 14 days, completely free.",
+                  negativeButtonText: "No, cancel my trial",
+                  positiveButtonText: "Yes, extend my trial"
+                });
+                if (isExtending) {
+                  const error = await TaskManager.startTask({
+                    type: "modal",
+                    title: "Extending your trial",
+                    subtitle: "Please wait...",
+                    action: async () => {
+                      await db.subscriptions.extend();
+                      await useUserStore.getState().refreshUser();
+                      showToast(
+                        "success",
+                        "Your trial has been extended by 14 days. Enjoy!"
+                      );
+                    }
+                  });
+                  if (error instanceof Error) showToast("error", error.message);
+                  return;
+                }
+              } else {
+                const cancelTrial = await ConfirmDialog.show({
+                  title: "Cancel trial?",
+                  message:
+                    "Cancel your trial to stop all future charges permanently. You will be immediately downgraded to the Free plan.",
+                  negativeButtonText: "No",
+                  positiveButtonText: "Yes"
+                });
+                if (!cancelTrial) return;
               }
+
+              await TaskManager.startTask({
+                type: "modal",
+                title: "Cancelling your trial",
+                subtitle: "Please wait...",
+                action: () => db.subscriptions.cancel()
+              })
+                .catch((e) => showToast("error", e.message))
+                .then(() =>
+                  showToast("success", "Your trial has been canceled.")
+                );
             }
           }
         ]
diff --git a/packages/core/src/api/subscriptions.ts b/packages/core/src/api/subscriptions.ts
index fa88b44c8..dc390dbca 100644
--- a/packages/core/src/api/subscriptions.ts
+++ b/packages/core/src/api/subscriptions.ts
@@ -102,6 +102,14 @@ export default class Subscriptions {
     await http.post(`${hosts.SUBSCRIPTIONS_HOST}/${endpoint}`, null, token);
   }
 
+  async extend() {
+    const token = await this.db.tokenManager.getAccessToken();
+    const user = await this.db.user.getUser();
+    if (!token || !user || isLegacySubscription(user)) return;
+    const endpoint = `subscriptions/v2/extend`;
+    await http.post(`${hosts.SUBSCRIPTIONS_HOST}/${endpoint}`, null, token);
+  }
+
   async pause() {
     const token = await this.db.tokenManager.getAccessToken();
     const user = await this.db.user.getUser();
diff --git a/packages/core/src/types.ts b/packages/core/src/types.ts
index 4cf8f2903..553badbf4 100644
--- a/packages/core/src/types.ts
+++ b/packages/core/src/types.ts
@@ -630,6 +630,12 @@ export enum SubscriptionProvider {
   GIFT_CARD = 4
 }
 
+type SubscriptionExtension = {
+  expiry: number;
+  timestamp: number;
+  type: "trial_extension";
+};
+
 export type User = {
   id: string;
   email: string;
@@ -661,6 +667,7 @@ export type User = {
     plan: SubscriptionPlan;
     status: SubscriptionStatus;
     trialsAvailed?: SubscriptionPlan[];
+    extensionsAvailed?: SubscriptionExtension[];
     updateURL: string | null;
     googlePurchaseToken: string | null;
   };
diff --git a/packages/core/src/utils/constants.ts b/packages/core/src/utils/constants.ts
index 5092da87b..1a41db5b2 100644
--- a/packages/core/src/utils/constants.ts
+++ b/packages/core/src/utils/constants.ts
@@ -52,7 +52,7 @@ export const hosts = {
     : "http://localhost:6264",
   NOTESNOOK_HOST: isProduction()
     ? "https://notesnook.com"
-    : "http://localhost:8787"
+    : "http://localhost:3001"
 };
 
 export default hosts;