diff --git a/apps/web/pages/api/auth/signup.ts b/apps/web/pages/api/auth/signup.ts
index f44c231fb3..7fd211dda6 100644
--- a/apps/web/pages/api/auth/signup.ts
+++ b/apps/web/pages/api/auth/signup.ts
@@ -1,210 +1,215 @@
-import type { NextApiRequest, NextApiResponse } from "next";
+import type { NextApiResponse } from "next";
 
-import dayjs from "@calcom/dayjs";
-import { checkPremiumUsername } from "@calcom/ee/common/lib/checkPremiumUsername";
+import stripe from "@calcom/app-store/stripepayment/lib/server";
+import { getPremiumMonthlyPlanPriceId } from "@calcom/app-store/stripepayment/lib/utils";
 import { hashPassword } from "@calcom/features/auth/lib/hashPassword";
 import { sendEmailVerification } from "@calcom/features/auth/lib/verifyEmail";
 import { IS_CALCOM } from "@calcom/lib/constants";
+import { WEBAPP_URL } from "@calcom/lib/constants";
+import { getLocaleFromRequest } from "@calcom/lib/getLocaleFromRequest";
+import { HttpError } from "@calcom/lib/http-error";
+import type { RequestWithUsernameStatus } from "@calcom/lib/server/username";
 import slugify from "@calcom/lib/slugify";
-import { closeComUpsertTeamUser } from "@calcom/lib/sync/SyncServiceManager";
-import { validateUsernameInTeam, validateUsername } from "@calcom/lib/validateUsername";
-import prisma from "@calcom/prisma";
-import { IdentityProvider } from "@calcom/prisma/enums";
+import { createWebUser as syncServicesCreateWebUser } from "@calcom/lib/sync/SyncServiceManager";
 import { signupSchema } from "@calcom/prisma/zod-utils";
-import { teamMetadataSchema } from "@calcom/prisma/zod-utils";
 
-export default async function handler(req: NextApiRequest, res: NextApiResponse) {
+export async function findExistingUser(username: string, email: string) {
+  const user = await prisma.user.findFirst({
+    where: {
+      OR: [
+        {
+          username,
+        },
+        {
+          email,
+        },
+      ],
+    },
+  });
+  if (user) {
+    throw new HttpError({
+      statusCode: 442,
+      message: "A user exists with that email address",
+    });
+  }
+}
+
+function ensurePostMethod(req: RequestWithUsernameStatus, res: NextApiResponse) {
   if (req.method !== "POST") {
-    return res.status(405).end();
+    throw new HttpError({
+      statusCode: 405,
+      message: "Method not allowed",
+    });
   }
+}
 
+function throwIfSignupIsDisabled() {
   if (process.env.NEXT_PUBLIC_DISABLE_SIGNUP === "true") {
-    res.status(403).json({ message: "Signup is disabled" });
-    return;
+    throw new HttpError({
+      statusCode: 403,
+      message: "Signup is disabled",
+    });
   }
+}
 
-  const data = req.body;
-  const { email, password, language, token } = signupSchema.parse(data);
-
-  const username = slugify(data.username);
-  const userEmail = email.toLowerCase();
-
-  if (!username) {
-    res.status(422).json({ message: "Invalid username" });
-    return;
+function parseSignupData(data: unknown) {
+  const parsedSchema = signupSchema.safeParse(data);
+  if (!parsedSchema.success) {
+    throw new HttpError({
+      statusCode: 422,
+      message: "Invalid input",
+    });
   }
+  return {
+    ...parsedSchema.data,
+    email: parsedSchema.data.email.toLowerCase(),
+    username: slugify(parsedSchema.data.username),
+  };
+}
 
-  let foundToken: { id: number; teamId: number | null; expires: Date } | null = null;
-  if (token) {
-    foundToken = await prisma.verificationToken.findFirst({
-      where: {
-        token,
-      },
-      select: {
-        id: true,
-        expires: true,
-        teamId: true,
-      },
+async function handlePremiumUsernameFlow({
+  email,
+  username,
+  premiumUsernameStatusCode,
+}: {
+  email: string;
+  username: string;
+  premiumUsernameStatusCode: number;
+}) {
+  if (!IS_CALCOM) return;
+  const metadata: {
+    stripeCustomerId?: string;
+    checkoutSessionId?: string;
+  } = {};
+
+  // Create the customer in Stripe
+  const customer = await stripe.customers.create({
+    email,
+    metadata: {
+      email /* Stripe customer email can be changed, so we add this to keep track of which email was used to signup */,
+      username,
+    },
+  });
+
+  const returnUrl = `${WEBAPP_URL}/api/integrations/stripepayment/paymentCallback?checkoutSessionId={CHECKOUT_SESSION_ID}&callbackUrl=/auth/verify?sessionId={CHECKOUT_SESSION_ID}`;
+
+  if (premiumUsernameStatusCode === 402) {
+    const checkoutSession = await stripe.checkout.sessions.create({
+      mode: "subscription",
+      payment_method_types: ["card"],
+      customer: customer.id,
+      line_items: [
+        {
+          price: getPremiumMonthlyPlanPriceId(),
+          quantity: 1,
+        },
+      ],
+      success_url: returnUrl,
+      cancel_url: returnUrl,
+      allow_promotion_codes: true,
     });
 
-    if (!foundToken) {
-      return res.status(401).json({ message: "Invalid Token" });
-    }
-
-    if (dayjs(foundToken?.expires).isBefore(dayjs())) {
-      return res.status(401).json({ message: "Token expired" });
-    }
-    if (foundToken?.teamId) {
-      const teamUserValidation = await validateUsernameInTeam(username, userEmail, foundToken?.teamId);
-      if (!teamUserValidation.isValid) {
-        return res.status(409).json({ message: "Username or email is already taken" });
-      }
-    }
-  } else {
-    const userValidation = await validateUsername(username, userEmail);
-    if (!userValidation.isValid) {
-      return res.status(409).json({ message: "Username or email is already taken" });
-    }
+    /** We create a username-less user until he pays */
+    metadata["stripeCustomerId"] = customer.id;
+    metadata["checkoutSessionId"] = checkoutSession.id;
   }
 
-  const hashedPassword = await hashPassword(password);
+  return metadata;
+}
 
-  if (foundToken && foundToken?.teamId) {
-    const team = await prisma.team.findUnique({
-      where: {
-        id: foundToken.teamId,
-      },
+function createUser({
+  username,
+  email,
+  hashedPassword,
+  metadata,
+}: {
+  username: string;
+  email: string;
+  hashedPassword: string;
+  metadata?: {
+    stripeCustomerId?: string;
+    checkoutSessionId?: string;
+  };
+}) {
+  return prisma.user.create({
+    data: {
+      username,
+      email,
+      password: hashedPassword,
+      metadata,
+    },
+  });
+}
+
+function syncServicesCreateUser(user: Awaited<ReturnType<typeof createUser>>) {
+  return IS_CALCOM && syncServicesCreateWebUser(user);
+}
+
+function sendVerificationEmail({
+  email,
+  language,
+  username,
+}: {
+  email: string;
+  language: string;
+  username: string;
+}) {
+  if (!IS_CALCOM) return;
+  return sendEmailVerification({
+    email,
+    language,
+    username: username || "",
+  });
+}
+
+export default async function handler(req: RequestWithUsernameStatus, res: NextApiResponse) {
+  try {
+    ensurePostMethod(req, res);
+    throwIfSignupIsDisabled();
+    const { email, password, language, token, username } = parseSignupData(req.body);
+    await findExistingUser(username, email);
+    const hashedPassword = await hashPassword(password);
+    const premiumUsernameMetadata = await handlePremiumUsernameFlow({
+      email,
+      username,
+      premiumUsernameStatusCode: req.usernameStatus.statusCode,
     });
-    if (team) {
-      const teamMetadata = teamMetadataSchema.parse(team?.metadata);
 
-      if (IS_CALCOM && (!teamMetadata?.isOrganization || !!team.parentId)) {
-        const checkUsername = await checkPremiumUsername(username);
-        if (checkUsername.premium) {
-          // This signup page is ONLY meant for team invites and local setup. Not for every day users.
-          // In singup redesign/refactor coming up @sean will tackle this to make them the same API/page instead of two.
-          return res.status(422).json({
-            message: "Sign up from https://cal.com/signup to claim your premium username",
-          });
-        }
-      }
-
-      const user = await prisma.user.upsert({
-        where: { email: userEmail },
-        update: {
-          username,
-          password: hashedPassword,
-          emailVerified: new Date(Date.now()),
-          identityProvider: IdentityProvider.CAL,
-        },
-        create: {
-          username,
-          email: userEmail,
-          password: hashedPassword,
-          identityProvider: IdentityProvider.CAL,
-        },
-      });
-
-      if (teamMetadata?.isOrganization) {
-        await prisma.user.update({
-          where: {
-            id: user.id,
-          },
-          data: {
-            organizationId: team.id,
-          },
-        });
-      }
-
-      const membership = await prisma.membership.update({
-        where: {
-          userId_teamId: { userId: user.id, teamId: team.id },
-        },
-        data: {
-          accepted: true,
-        },
-      });
-      closeComUpsertTeamUser(team, user, membership.role);
-
-      // Accept any child team invites for orgs.
-      if (team.parentId) {
-        // Join ORG
-        await prisma.user.update({
-          where: {
-            id: user.id,
-          },
-          data: {
-            organizationId: team.parentId,
-          },
-        });
-
-        /** We do a membership update twice so we can join the ORG invite if the user is invited to a team witin a ORG. */
-        await prisma.membership.updateMany({
-          where: {
-            userId: user.id,
-            team: {
-              id: team.parentId,
-            },
-            accepted: false,
-          },
-          data: {
-            accepted: true,
-          },
-        });
-
-        // Join any other invites
-        await prisma.membership.updateMany({
-          where: {
-            userId: user.id,
-            team: {
-              parentId: team.parentId,
-            },
-            accepted: false,
-          },
-          data: {
-            accepted: true,
-          },
-        });
-      }
-    }
-
-    // Cleanup token after use
-    await prisma.verificationToken.delete({
-      where: {
-        id: foundToken.id,
-      },
-    });
-  } else {
-    if (IS_CALCOM) {
-      const checkUsername = await checkPremiumUsername(username);
-      if (checkUsername.premium) {
-        res.status(422).json({
-          message: "Sign up from https://cal.com/signup to claim your premium username",
-        });
-        return;
-      }
-    }
-    await prisma.user.upsert({
-      where: { email: userEmail },
-      update: {
-        username,
-        password: hashedPassword,
-        emailVerified: new Date(Date.now()),
-        identityProvider: IdentityProvider.CAL,
-      },
-      create: {
-        username,
-        email: userEmail,
-        password: hashedPassword,
-        identityProvider: IdentityProvider.CAL,
-      },
+    // Create the user
+    const user = await createUser({
+      username,
+      email,
+      hashedPassword,
+      metadata: premiumUsernameMetadata,
     });
     await sendEmailVerification({
-      email: userEmail,
-      username,
-      language,
+      email,
+      language: await getLocaleFromRequest(req),
+      username: username || "",
     });
+    await syncServicesCreateUser(user);
+
+    if (IS_CALCOM && premiumUsernameMetadata) {
+      if (premiumUsernameMetadata.checkoutSessionId) {
+        return res.status(402).json({
+          message: "Created user but missing payment",
+          checkoutSessionId: premiumUsernameMetadata.checkoutSessionId,
+        });
+      }
+      return res
+        .status(201)
+        .json({ message: "Created user", stripeCustomerId: premiumUsernameMetadata.stripeCustomerId });
+    }
+  } catch (e) {
+    if (e instanceof HttpError) {
+      return res.status(e.statusCode).json({ message: e.message });
+    }
+    return res.status(500).json({ message: "Internal server error" });
   }
 
-  res.status(201).json({ message: "Created user" });
+  // if (IS_CALCOM) {
+  //   // return await hostedHandler(req, res);
+  // } else {
+  //   return await selfHostedHandler(req, res);
+  // }
 }
diff --git a/packages/lib/server/username.ts b/packages/lib/server/username.ts
new file mode 100644
index 0000000000..60c9d548e6
--- /dev/null
+++ b/packages/lib/server/username.ts
@@ -0,0 +1,126 @@
+import type { NextApiRequest, NextApiResponse } from "next";
+
+import slugify from "@calcom/lib/slugify";
+import prisma from "@calcom/prisma";
+
+import notEmpty from "../../../apps/website/lib/utils/notEmpty";
+import { wordlist } from "../../../apps/website/lib/utils/wordlist/wordlist";
+
+export type RequestWithUsernameStatus = NextApiRequest & {
+  usernameStatus: {
+    /**
+     * ```text
+     * 200: Username is available
+     * 402: Pro username, must be purchased
+     * 418: A user exists with that username
+     * ```
+     */
+    statusCode: 200 | 402 | 418;
+    requestedUserName: string;
+    json: {
+      available: boolean;
+      premium: boolean;
+      message?: string;
+      suggestion?: string;
+    };
+  };
+};
+
+type CustomNextApiHandler<T = unknown> = (
+  req: RequestWithUsernameStatus,
+  res: NextApiResponse<T>
+) => void | Promise<void>;
+
+export const isPremiumUserName = (username: string): boolean =>
+  username.length <= 4 || Object.prototype.hasOwnProperty.call(wordlist, username);
+
+const generateUsernameSuggestion = async (users: string[], username: string) => {
+  const limit = username.length < 2 ? 9999 : 999;
+  let rand = 1;
+  while (users.includes(username + String(rand).padStart(4 - rand.toString().length, "0"))) {
+    rand = Math.ceil(1 + Math.random() * (limit - 1));
+  }
+  return username + String(rand).padStart(4 - rand.toString().length, "0");
+};
+
+const usernameHandler =
+  (handler: CustomNextApiHandler) =>
+  async (req: RequestWithUsernameStatus, res: NextApiResponse): Promise<void> => {
+    const username = slugify(req.body.username);
+    const check = await usernameCheck(username);
+
+    req.usernameStatus = {
+      statusCode: 200,
+      requestedUserName: username,
+      json: {
+        available: true,
+        premium: false,
+        message: "Username is available",
+      },
+    };
+
+    if (check.premium) {
+      req.usernameStatus.statusCode = 402;
+      req.usernameStatus.json.premium = true;
+      req.usernameStatus.json.message = "This is a premium username.";
+    }
+
+    if (!check.available) {
+      req.usernameStatus.statusCode = 418;
+      req.usernameStatus.json.available = false;
+      req.usernameStatus.json.message = "A user exists with that username";
+    }
+
+    req.usernameStatus.json.suggestion = check.suggestedUsername;
+
+    return handler(req, res);
+  };
+
+const usernameCheck = async (usernameRaw: string) => {
+  const response = {
+    available: true,
+    premium: false,
+    suggestedUsername: "",
+  };
+
+  const username = slugify(usernameRaw);
+
+  const user = await prisma.user.findFirst({
+    where: { username, organizationId: null },
+    select: {
+      username: true,
+    },
+  });
+
+  if (user) {
+    response.available = false;
+  }
+
+  if (isPremiumUserName(username)) {
+    response.premium = true;
+  }
+
+  // get list of similar usernames in the db
+  const users = await prisma.user.findMany({
+    where: {
+      username: {
+        contains: username,
+      },
+    },
+    select: {
+      username: true,
+    },
+  });
+
+  // We only need suggestedUsername if the username is not available
+  if (!response.available) {
+    response.suggestedUsername = await generateUsernameSuggestion(
+      users.map((user) => user.username).filter(notEmpty),
+      username
+    );
+  }
+
+  return response;
+};
+
+export { usernameHandler, usernameCheck };
diff --git a/yarn.lock b/yarn.lock
index 3d6d9fa713..c8fef97305 100644
--- a/yarn.lock
+++ b/yarn.lock
@@ -197,25 +197,6 @@ __metadata:
   languageName: node
   linkType: hard
 
-"@auth/core@npm:^0.1.4":
-  version: 0.1.4
-  resolution: "@auth/core@npm:0.1.4"
-  dependencies:
-    "@panva/hkdf": 1.0.2
-    cookie: 0.5.0
-    jose: 4.11.1
-    oauth4webapi: 2.0.5
-    preact: 10.11.3
-    preact-render-to-string: 5.2.3
-  peerDependencies:
-    nodemailer: 6.8.0
-  peerDependenciesMeta:
-    nodemailer:
-      optional: true
-  checksum: 64854404ea1883e0deb5535b34bed95cd43fc85094aeaf4f15a79e14045020eb944f844defe857edfc8528a0a024be89cbb2a3069dedef0e9217a74ca6c3eb79
-  languageName: node
-  linkType: hard
-
 "@aws-crypto/ie11-detection@npm:^3.0.0":
   version: 3.0.0
   resolution: "@aws-crypto/ie11-detection@npm:3.0.0"
@@ -3221,41 +3202,6 @@ __metadata:
   languageName: unknown
   linkType: soft
 
-"@calcom/auth@workspace:apps/auth":
-  version: 0.0.0-use.local
-  resolution: "@calcom/auth@workspace:apps/auth"
-  dependencies:
-    "@auth/core": ^0.1.4
-    "@calcom/app-store": "*"
-    "@calcom/app-store-cli": "*"
-    "@calcom/config": "*"
-    "@calcom/core": "*"
-    "@calcom/dayjs": "*"
-    "@calcom/embed-core": "workspace:*"
-    "@calcom/embed-react": "workspace:*"
-    "@calcom/embed-snippet": "workspace:*"
-    "@calcom/features": "*"
-    "@calcom/lib": "*"
-    "@calcom/prisma": "*"
-    "@calcom/trpc": "*"
-    "@calcom/tsconfig": "*"
-    "@calcom/types": "*"
-    "@calcom/ui": "*"
-    "@types/node": 16.9.1
-    "@types/react": 18.0.26
-    "@types/react-dom": ^18.0.9
-    eslint: ^8.34.0
-    eslint-config-next: ^13.2.1
-    next: ^13.4.6
-    next-auth: ^4.22.1
-    postcss: ^8.4.18
-    react: ^18.2.0
-    react-dom: ^18.2.0
-    tailwindcss: ^3.3.1
-    typescript: ^4.9.4
-  languageName: unknown
-  linkType: soft
-
 "@calcom/basecamp3@workspace:packages/app-store/basecamp3":
   version: 0.0.0-use.local
   resolution: "@calcom/basecamp3@workspace:packages/app-store/basecamp3"
@@ -7653,13 +7599,6 @@ __metadata:
   languageName: node
   linkType: hard
 
-"@panva/hkdf@npm:1.0.2":
-  version: 1.0.2
-  resolution: "@panva/hkdf@npm:1.0.2"
-  checksum: 75183b4d5ea816ef516dcea70985c610683579a9e2ac540c2d59b9a3ed27eedaff830a43a1c43c1683556a457c92ac66e09109ee995ab173090e4042c4c4bb03
-  languageName: node
-  linkType: hard
-
 "@panva/hkdf@npm:^1.0.2":
   version: 1.0.4
   resolution: "@panva/hkdf@npm:1.0.4"
@@ -24677,13 +24616,6 @@ __metadata:
   languageName: node
   linkType: hard
 
-"jose@npm:4.11.1":
-  version: 4.11.1
-  resolution: "jose@npm:4.11.1"
-  checksum: cd15cba258d0fd20f6168631ce2e94fda8442df80e43c1033c523915cecdf390a1cc8efe0eab0c2d65935ca973d791c668aea80724d2aa9c2879d4e70f3081d7
-  languageName: node
-  linkType: hard
-
 "jose@npm:4.12.0":
   version: 4.12.0
   resolution: "jose@npm:4.12.0"
@@ -28758,13 +28690,6 @@ __metadata:
   languageName: node
   linkType: hard
 
-"oauth4webapi@npm:2.0.5":
-  version: 2.0.5
-  resolution: "oauth4webapi@npm:2.0.5"
-  checksum: 32d0cb7b1cca42d51dfb88075ca2d69fe33172a807e8ea50e317d17cab3bc80588ab8ebcb7eb4600c371a70af4674595b4b341daf6f3a655f1efa1ab715bb6c9
-  languageName: node
-  linkType: hard
-
 "oauth@npm:^0.9.15":
   version: 0.9.15
   resolution: "oauth@npm:0.9.15"
@@ -30535,17 +30460,6 @@ __metadata:
   languageName: node
   linkType: hard
 
-"preact-render-to-string@npm:5.2.3":
-  version: 5.2.3
-  resolution: "preact-render-to-string@npm:5.2.3"
-  dependencies:
-    pretty-format: ^3.8.0
-  peerDependencies:
-    preact: ">=10"
-  checksum: 6e46288d8956adde35b9fe3a21aecd9dea29751b40f0f155dea62f3896f27cb8614d457b32f48d33909d2da81135afcca6c55077520feacd7d15164d1371fb44
-  languageName: node
-  linkType: hard
-
 "preact-render-to-string@npm:^5.1.19":
   version: 5.2.6
   resolution: "preact-render-to-string@npm:5.2.6"
@@ -30557,7 +30471,7 @@ __metadata:
   languageName: node
   linkType: hard
 
-"preact@npm:10.11.3, preact@npm:^10.6.3":
+"preact@npm:^10.6.3":
   version: 10.11.3
   resolution: "preact@npm:10.11.3"
   checksum: 9387115aa0581e8226309e6456e9856f17dfc0e3d3e63f774de80f3d462a882ba7c60914c05942cb51d51e23e120dcfe904b8d392d46f29ad15802941fe7a367
@@ -39535,4 +39449,4 @@ __metadata:
   resolution: "zwitch@npm:2.0.4"
   checksum: f22ec5fc2d5f02c423c93d35cdfa83573a3a3bd98c66b927c368ea4d0e7252a500df2a90a6b45522be536a96a73404393c958e945fdba95e6832c200791702b6
   languageName: node
-  linkType: hard
\ No newline at end of file
+  linkType: hard