diff --git a/components/Shell.tsx b/components/Shell.tsx
index 3b86d37c96..707d688373 100644
--- a/components/Shell.tsx
+++ b/components/Shell.tsx
@@ -16,6 +16,7 @@ import React, { ReactNode, useEffect, useState } from "react";
 import { Toaster } from "react-hot-toast";
 
 import LicenseBanner from "@ee/components/LicenseBanner";
+import TrialBanner from "@ee/components/TrialBanner";
 import HelpMenuItemDynamic from "@ee/lib/intercom/HelpMenuItemDynamic";
 
 import classNames from "@lib/classNames";
@@ -242,6 +243,7 @@ export default function Shell(props: {
                   ))}
                 </nav>
               </div>
+              <TrialBanner />
               <div className="p-2 pt-2 pr-2 m-2 rounded-sm hover:bg-gray-100">
                 <span className="hidden lg:inline">
                   <UserDropdown />
diff --git a/ee/components/TrialBanner.tsx b/ee/components/TrialBanner.tsx
new file mode 100644
index 0000000000..fc63226c24
--- /dev/null
+++ b/ee/components/TrialBanner.tsx
@@ -0,0 +1,35 @@
+import dayjs from "dayjs";
+
+import { TRIAL_LIMIT_DAYS } from "@lib/config/constants";
+import { useLocale } from "@lib/hooks/useLocale";
+
+import { useMeQuery } from "@components/Shell";
+import Button from "@components/ui/Button";
+
+const TrialBanner = () => {
+  const { t } = useLocale();
+  const query = useMeQuery();
+  const user = query.data;
+
+  if (!user || user.plan !== "TRIAL") return null;
+
+  const trialDaysLeft = dayjs(user.createdDate)
+    .add(TRIAL_LIMIT_DAYS + 1, "day")
+    .diff(dayjs(), "day");
+
+  return (
+    <div
+      className="p-4 m-4 text-sm font-medium text-center text-gray-600 bg-yellow-200 rounded-md"
+      data-testid="trial-banner">
+      <div className="mb-2 text-left">{t("trial_days_left", { days: trialDaysLeft })}</div>
+      <Button
+        href="/api/upgrade"
+        color="minimal"
+        className="justify-center w-full border-2 border-gray-600 hover:bg-yellow-100">
+        {t("upgrade_now")}
+      </Button>
+    </div>
+  );
+};
+
+export default TrialBanner;
diff --git a/ee/lib/stripe/client.ts b/ee/lib/stripe/client.ts
index f326e54fb2..a89840f0f8 100644
--- a/ee/lib/stripe/client.ts
+++ b/ee/lib/stripe/client.ts
@@ -1,4 +1,5 @@
-import { loadStripe, Stripe } from "@stripe/stripe-js";
+import { Stripe } from "@stripe/stripe-js";
+import { loadStripe } from "@stripe/stripe-js/pure";
 import { stringify } from "querystring";
 
 import { Maybe } from "@trpc/server";
diff --git a/lib/config/constants.ts b/lib/config/constants.ts
index b686c6f7da..e69f03ed85 100644
--- a/lib/config/constants.ts
+++ b/lib/config/constants.ts
@@ -1,2 +1,4 @@
 export const BASE_URL = process.env.BASE_URL || `https://${process.env.VERCEL_URL}`;
+export const WEBSITE_URL = process.env.NEXT_PUBLIC_APP_URL || "https://cal.com";
 export const IS_PRODUCTION = process.env.NODE_ENV === "production";
+export const TRIAL_LIMIT_DAYS = 14;
diff --git a/next-i18next.config.js b/next-i18next.config.js
index 6ab76d68aa..4d723d9bc8 100644
--- a/next-i18next.config.js
+++ b/next-i18next.config.js
@@ -7,4 +7,5 @@ module.exports = {
     locales: ["en", "fr", "it", "ru", "es", "de", "pt", "ro", "nl", "pt-BR", "es-419", "ko", "ja"],
   },
   localePath: path.resolve("./public/static/locales"),
+  reloadOnPrerender: process.env.NODE_ENV !== "production",
 };
diff --git a/pages/api/cron/downgradeUsers.ts b/pages/api/cron/downgradeUsers.ts
index 0e1a1aa88f..fd60c8d236 100644
--- a/pages/api/cron/downgradeUsers.ts
+++ b/pages/api/cron/downgradeUsers.ts
@@ -1,10 +1,9 @@
 import dayjs from "dayjs";
 import type { NextApiRequest, NextApiResponse } from "next";
 
+import { TRIAL_LIMIT_DAYS } from "@lib/config/constants";
 import prisma from "@lib/prisma";
 
-const TRIAL_LIMIT_DAYS = 14;
-
 export default async function handler(req: NextApiRequest, res: NextApiResponse) {
   const apiKey = req.headers.authorization || req.query.apiKey;
   if (process.env.CRON_API_KEY !== apiKey) {
diff --git a/pages/api/upgrade.ts b/pages/api/upgrade.ts
new file mode 100644
index 0000000000..e415ce62b6
--- /dev/null
+++ b/pages/api/upgrade.ts
@@ -0,0 +1,50 @@
+import { Prisma } from "@prisma/client";
+import type { NextApiRequest, NextApiResponse } from "next";
+
+import { getSession } from "@lib/auth";
+import { WEBSITE_URL } from "@lib/config/constants";
+import { HttpError as HttpCode } from "@lib/core/http/error";
+import prisma from "@lib/prisma";
+
+export default async function handler(req: NextApiRequest, res: NextApiResponse) {
+  const session = await getSession({ req });
+  if (!session?.user?.id) {
+    return res.status(401).json({ message: "Not authenticated" });
+  }
+
+  if (req.method !== "GET") {
+    throw new HttpCode({ statusCode: 405, message: "Method Not Allowed" });
+  }
+
+  const user = await prisma.user.findUnique({
+    rejectOnNotFound: true,
+    where: {
+      id: session.user.id,
+    },
+    select: {
+      email: true,
+      metadata: true,
+    },
+  });
+
+  try {
+    const response = await fetch(`${WEBSITE_URL}/api/upgrade`, {
+      method: "POST",
+      credentials: "include",
+      headers: {
+        "Content-Type": "application/json",
+      },
+      body: JSON.stringify({
+        stripeCustomerId: (user.metadata as Prisma.JsonObject)?.stripeCustomerId,
+        email: user.email,
+        fromApp: true,
+      }),
+    });
+    const data = await response.json();
+
+    res.redirect(303, data.url);
+  } catch (error) {
+    console.error(`error`, error);
+    res.redirect(303, req.headers.origin || "/");
+  }
+}
diff --git a/pages/auth/login.tsx b/pages/auth/login.tsx
index e77375eff8..69358ee769 100644
--- a/pages/auth/login.tsx
+++ b/pages/auth/login.tsx
@@ -5,6 +5,7 @@ import { useRouter } from "next/router";
 import { useState } from "react";
 
 import { ErrorCode, getSession } from "@lib/auth";
+import { WEBSITE_URL } from "@lib/config/constants";
 import { useLocale } from "@lib/hooks/useLocale";
 import { inferSSRProps } from "@lib/types/inferSSRProps";
 
@@ -176,7 +177,7 @@ export default function Login({ csrfToken }: inferSSRProps<typeof getServerSideP
         </div>
         <div className="mt-4 text-sm text-center text-neutral-600">
           {t("dont_have_an_account")} {/* replace this with your account creation flow */}
-          <a href="https://cal.com/signup" className="font-medium text-neutral-900">
+          <a href={`${WEBSITE_URL}/signup`} className="font-medium text-neutral-900">
             {t("create_an_account")}
           </a>
         </div>
diff --git a/playwright/lib/globalSetup.ts b/playwright/lib/globalSetup.ts
index 273c6b0345..c5cbcfdd70 100644
--- a/playwright/lib/globalSetup.ts
+++ b/playwright/lib/globalSetup.ts
@@ -26,7 +26,7 @@ async function globalSetup(/* config: FullConfig */) {
   await loginAsUser("onboarding", browser);
   //   await loginAsUser("free-first-hidden", browser);
   await loginAsUser("pro", browser);
-  //   await loginAsUser("trial", browser);
+  await loginAsUser("trial", browser);
   await loginAsUser("free", browser);
   //   await loginAsUser("usa", browser);
   //   await loginAsUser("teamfree", browser);
diff --git a/playwright/trial.test.ts b/playwright/trial.test.ts
new file mode 100644
index 0000000000..debb80eae5
--- /dev/null
+++ b/playwright/trial.test.ts
@@ -0,0 +1,13 @@
+import { expect, test } from "@playwright/test";
+
+// Using logged in state from globalSteup
+test.use({ storageState: "playwright/artifacts/trialStorageState.json" });
+
+test("Trial banner should be visible to TRIAL users", async ({ page }) => {
+  // Try to go homepage
+  await page.goto("/");
+  // It should redirect you to the event-types page
+  await page.waitForSelector("[data-testid=event-types]");
+
+  await expect(page.locator(`[data-testid=trial-banner]`)).toBeVisible();
+});
diff --git a/public/static/locales/en/common.json b/public/static/locales/en/common.json
index 473fc7942e..f51147fb22 100644
--- a/public/static/locales/en/common.json
+++ b/public/static/locales/en/common.json
@@ -1,4 +1,8 @@
 {
+  "trial_days_left": "You have $t(day, {\"count\": {{days}} }) left on your PRO trial",
+  "day": "{{count}} day", 
+  "day_plural": "{{count}} days",
+  "upgrade_now": "Upgrade now",
   "accept_invitation": "Accept Invitation",
   "calcom_explained": "Cal.com is the open source Calendly alternative putting you in control of your own data, workflow and appearance.",
   "have_any_questions": "Have questions? We're here to help.",