diff --git a/apps/web/pages/api/link.ts b/apps/web/pages/api/link.ts
index 9a0ebdba51..a2f51f2e1e 100644
--- a/apps/web/pages/api/link.ts
+++ b/apps/web/pages/api/link.ts
@@ -4,6 +4,7 @@ import { z } from "zod";
 import { symmetricDecrypt } from "@calcom/lib/crypto";
 import { defaultResponder } from "@calcom/lib/server";
 import prisma from "@calcom/prisma";
+import { UserPermissionRole } from "@calcom/prisma/enums";
 import { TRPCError } from "@calcom/trpc/server";
 import { createContext } from "@calcom/trpc/server/createContext";
 import { viewerRouter } from "@calcom/trpc/server/routers/viewer/_router";
@@ -38,9 +39,22 @@ async function handler(req: NextApiRequest, res: NextApiResponse<Response>) {
     where: { id: userId },
   });
 
+  /** We shape the session as required by tRPC router */
+  async function sessionGetter() {
+    return {
+      user: {
+        id: userId,
+        username: "" /* Not used in this context */,
+        role: UserPermissionRole.USER,
+      },
+      hasValidLicense: true,
+      expires: "" /* Not used in this context */,
+    };
+  }
+
   try {
     /** @see https://trpc.io/docs/server-side-calls */
-    const ctx = await createContext({ req, res });
+    const ctx = await createContext({ req, res }, sessionGetter);
     const caller = viewerRouter.createCaller({
       ...ctx,
       req,
@@ -55,7 +69,7 @@ async function handler(req: NextApiRequest, res: NextApiResponse<Response>) {
     });
   } catch (e) {
     let message = "Error confirming booking";
-    if (e instanceof TRPCError) message = e.message;
+    if (e instanceof TRPCError) message = (e as TRPCError).message;
     res.redirect(`/booking/${bookingUid}?error=${encodeURIComponent(message)}`);
     return;
   }
diff --git a/packages/trpc/server/createContext.ts b/packages/trpc/server/createContext.ts
index eee4d65acc..f7a0c565fd 100644
--- a/packages/trpc/server/createContext.ts
+++ b/packages/trpc/server/createContext.ts
@@ -61,10 +61,10 @@ export async function createContextInner(opts: CreateInnerContextOptions) {
  * Creates context for an incoming request
  * @link https://trpc.io/docs/context
  */
-export const createContext = async ({ req, res }: CreateContextOptions) => {
+export const createContext = async ({ req, res }: CreateContextOptions, sessionGetter?: GetSessionFn) => {
   const locale = getLocaleFromHeaders(req);
-
-  const contextInner = await createContextInner({ locale });
+  const session = !!sessionGetter ? await sessionGetter({ req, res }) : null;
+  const contextInner = await createContextInner({ locale, session });
   return {
     ...contextInner,
     req,
diff --git a/packages/trpc/server/middlewares/sessionMiddleware.ts b/packages/trpc/server/middlewares/sessionMiddleware.ts
index 922ff29bde..77d2f86efc 100644
--- a/packages/trpc/server/middlewares/sessionMiddleware.ts
+++ b/packages/trpc/server/middlewares/sessionMiddleware.ts
@@ -101,11 +101,18 @@ export async function getUserFromSession(ctx: TRPCContextInner, session: Maybe<S
 
 export type UserFromSession = Awaited<ReturnType<typeof getUserFromSession>>;
 
-const getUserSession = async (ctx: TRPCContextInner) => {
-  const { getServerSession } = await import("@calcom/features/auth/lib/getServerSession");
+const getSession = async (ctx: TRPCContextInner) => {
   const { req, res } = ctx;
+  const { getServerSession } = await import("@calcom/features/auth/lib/getServerSession");
+  return req ? await getServerSession({ req, res }) : null;
+};
 
-  const session = req ? await getServerSession({ req, res }) : null;
+const getUserSession = async (ctx: TRPCContextInner) => {
+  /**
+   * It is possible that the session and user have already been added to the context by a previous middleware
+   * or when creating the context
+   */
+  const session = ctx.session || (await getSession(ctx));
   const user = session ? await getUserFromSession(ctx, session) : null;
 
   return { user, session };