diff --git a/apps/web/src/auth/edge/with-auth.ts b/apps/web/src/auth/edge/with-auth.ts
index 226c7f5d1..2ca2a771f 100644
--- a/apps/web/src/auth/edge/with-auth.ts
+++ b/apps/web/src/auth/edge/with-auth.ts
@@ -15,19 +15,22 @@ export const withAuth = (
   middleware: (request: NextAuthRequest) => Promise<NextResponse>,
 ) => {
   return async (request: NextAuthRequest) => {
-    let legacySession: Session | null = null;
+    let session: Session | null = null;
 
     try {
-      legacySession = await getLegacySession();
+      session = await auth();
     } catch (e) {
       console.error(e);
     }
 
-    let session = legacySession;
+    let isLegacySession = false;
 
     if (!session) {
       try {
-        session = await auth();
+        session = await getLegacySession();
+        if (session) {
+          isLegacySession = true;
+        }
       } catch (e) {
         console.error(e);
       }
@@ -50,7 +53,7 @@ export const withAuth = (
 
     const middlewareRes = await middleware(request);
 
-    if (legacySession) {
+    if (isLegacySession) {
       try {
         await migrateLegacyJWT(middlewareRes);
       } catch (e) {
diff --git a/apps/web/src/auth/legacy/next-auth-cookie-migration.ts b/apps/web/src/auth/legacy/next-auth-cookie-migration.ts
index 0faac5613..8995c2357 100644
--- a/apps/web/src/auth/legacy/next-auth-cookie-migration.ts
+++ b/apps/web/src/auth/legacy/next-auth-cookie-migration.ts
@@ -58,6 +58,7 @@ export async function migrateLegacyJWT(res: NextResponse) {
       salt: newCookieName,
     });
 
+    // Set new session cookie
     res.cookies.set(newCookieName, newJWT, {
       httpOnly: true,
       secure: isSecureCookie,
@@ -65,6 +66,14 @@ export async function migrateLegacyJWT(res: NextResponse) {
       sameSite: "lax",
       path: "/",
     });
-    res.cookies.delete(oldCookieName);
+
+    // Delete the old cookie
+    res.cookies.set(oldCookieName, "", {
+      httpOnly: true,
+      secure: isSecureCookie,
+      expires: new Date(0),
+      sameSite: "lax",
+      path: "/",
+    });
   }
 }
diff --git a/apps/web/src/next-auth.ts b/apps/web/src/next-auth.ts
index 9f34fa13b..60b17daf4 100644
--- a/apps/web/src/next-auth.ts
+++ b/apps/web/src/next-auth.ts
@@ -177,12 +177,12 @@ const {
 });
 
 const auth = async () => {
-  const session = await getLegacySession();
+  const session = await originalAuth();
   if (session) {
     return session;
   }
 
-  return originalAuth();
+  return getLegacySession();
 };
 
 export { auth, handlers, signIn, signOut };