diff --git a/packages/build-utils/src/types.ts b/packages/build-utils/src/types.ts
index 40d97737d..23564ce8f 100644
--- a/packages/build-utils/src/types.ts
+++ b/packages/build-utils/src/types.ts
@@ -335,6 +335,7 @@ export interface ProjectSettings {
   directoryListing?: boolean;
   gitForkProtection?: boolean;
   commandForIgnoringBuildStep?: string | null;
+  skipGitConnectDuringLink?: boolean;
 }
 
 export interface BuilderV2 {
diff --git a/packages/cli/src/commands/git/connect.ts b/packages/cli/src/commands/git/connect.ts
index 1a6490b81..10d556733 100644
--- a/packages/cli/src/commands/git/connect.ts
+++ b/packages/cli/src/commands/git/connect.ts
@@ -12,7 +12,7 @@ import {
   connectGitProvider,
   disconnectGitProvider,
   formatProvider,
-  ParsedRepoUrl,
+  RepoInfo,
   parseRepoUrl,
   printRemoteUrls,
 } from '../../util/git/connect-git-provider';
@@ -35,7 +35,7 @@ interface ConnectArgParams {
   org: Org;
   project: Project;
   confirm: boolean;
-  repoInfo: ParsedRepoUrl;
+  repoInfo: RepoInfo;
 }
 
 interface ConnectGitArgParams extends ConnectArgParams {
@@ -45,7 +45,7 @@ interface ConnectGitArgParams extends ConnectArgParams {
 interface PromptConnectArgParams {
   client: Client;
   yes: boolean;
-  repoInfo: ParsedRepoUrl;
+  repoInfo: RepoInfo;
   remoteUrls: Dictionary<string>;
 }
 
@@ -155,8 +155,8 @@ export default async function connect(
 
   output.log(`Connecting Git remote: ${link(remoteUrl)}`);
 
-  const parsedUrl = parseRepoUrl(remoteUrl);
-  if (!parsedUrl) {
+  const repoInfo = parseRepoUrl(remoteUrl);
+  if (!repoInfo) {
     output.error(
       `Failed to parse Git repo data from the following remote URL: ${link(
         remoteUrl
@@ -164,7 +164,7 @@ export default async function connect(
     );
     return 1;
   }
-  const { provider, org: gitOrg, repo } = parsedUrl;
+  const { provider, org: gitOrg, repo } = repoInfo;
   const repoPath = `${gitOrg}/${repo}`;
 
   const checkAndConnect = await checkExistsAndConnect({
diff --git a/packages/cli/src/util/git/connect-git-provider.ts b/packages/cli/src/util/git/connect-git-provider.ts
index 8bd1bc95d..d185dd7db 100644
--- a/packages/cli/src/util/git/connect-git-provider.ts
+++ b/packages/cli/src/util/git/connect-git-provider.ts
@@ -4,10 +4,10 @@ import { Org } from '../../types';
 import chalk from 'chalk';
 import link from '../output/link';
 import { isAPIError } from '../errors-ts';
-import { Dictionary } from '@vercel/client';
 import { Output } from '../output';
+import { Dictionary } from '@vercel/client';
 
-export interface ParsedRepoUrl {
+export interface RepoInfo {
   url: string;
   provider: string;
   org: string;
@@ -19,7 +19,7 @@ export async function disconnectGitProvider(
   org: Org,
   projectId: string
 ) {
-  const fetchUrl = `/v4/projects/${projectId}/link?${stringify({
+  const fetchUrl = `/v9/projects/${projectId}/link?${stringify({
     teamId: org.type === 'team' ? org.id : undefined,
   })}`;
   return client.fetch(fetchUrl, {
@@ -37,7 +37,7 @@ export async function connectGitProvider(
   type: string,
   repo: string
 ) {
-  const fetchUrl = `/v4/projects/${projectId}/link?${stringify({
+  const fetchUrl = `/v9/projects/${projectId}/link?${stringify({
     teamId: org.type === 'team' ? org.id : undefined,
   })}`;
   try {
@@ -52,22 +52,21 @@ export async function connectGitProvider(
       }),
     });
   } catch (err: unknown) {
-    if (isAPIError(err)) {
-      if (
-        err.action === 'Install GitHub App' ||
-        err.code === 'repo_not_found'
-      ) {
-        client.output.error(
-          `Failed to link ${chalk.cyan(
-            repo
-          )}. Make sure there aren't any typos and that you have access to the repository if it's private.`
-        );
-      } else if (err.action === 'Add a Login Connection') {
-        client.output.error(
-          err.message.replace(repo, chalk.cyan(repo)) +
-            `\nVisit ${link(err.link)} for more information.`
-        );
-      }
+    const apiError = isAPIError(err);
+    if (
+      apiError &&
+      (err.action === 'Install GitHub App' || err.code === 'repo_not_found')
+    ) {
+      client.output.error(
+        `Failed to link ${chalk.cyan(
+          repo
+        )}. Make sure there aren't any typos and that you have access to the repository if it's private.`
+      );
+    } else if (apiError && err.action === 'Add a Login Connection') {
+      client.output.error(
+        err.message.replace(repo, chalk.cyan(repo)) +
+          `\nVisit ${link(err.link)} for more information.`
+      );
     } else {
       client.output.error(
         `Failed to connect the ${formatProvider(
@@ -92,7 +91,7 @@ export function formatProvider(type: string): string {
   }
 }
 
-export function parseRepoUrl(originUrl: string): ParsedRepoUrl | null {
+export function parseRepoUrl(originUrl: string): RepoInfo | null {
   const isSSH = originUrl.startsWith('git@');
   // Matches all characters between (// or @) and (.com or .org)
   // eslint-disable-next-line prefer-named-capture-group
@@ -126,7 +125,6 @@ export function parseRepoUrl(originUrl: string): ParsedRepoUrl | null {
     repo,
   };
 }
-
 export function printRemoteUrls(
   output: Output,
   remoteUrls: Dictionary<string>
diff --git a/packages/cli/src/util/link/add-git-connection.ts b/packages/cli/src/util/link/add-git-connection.ts
new file mode 100644
index 000000000..08c951f87
--- /dev/null
+++ b/packages/cli/src/util/link/add-git-connection.ts
@@ -0,0 +1,107 @@
+import { Dictionary } from '@vercel/client';
+import { parseRepoUrl } from '../git/connect-git-provider';
+import Client from '../client';
+import { Org, Project, ProjectSettings } from '../../types';
+import { handleOptions } from './handle-options';
+import {
+  promptGitConnectMultipleUrls,
+  promptGitConnectSingleUrl,
+} from './git-connect-prompts';
+
+function getProjectSettings(project: Project): ProjectSettings {
+  return {
+    createdAt: project.createdAt,
+    framework: project.framework,
+    devCommand: project.devCommand,
+    installCommand: project.installCommand,
+    buildCommand: project.buildCommand,
+    outputDirectory: project.outputDirectory,
+    rootDirectory: project.rootDirectory,
+    directoryListing: project.directoryListing,
+    nodeVersion: project.nodeVersion,
+    skipGitConnectDuringLink: project.skipGitConnectDuringLink,
+  };
+}
+
+export async function addGitConnection(
+  client: Client,
+  org: Org,
+  project: Project,
+  remoteUrls: Dictionary<string>,
+  settings?: ProjectSettings
+): Promise<number | void> {
+  if (!settings) {
+    settings = getProjectSettings(project);
+  }
+  if (Object.keys(remoteUrls).length === 1) {
+    return addSingleGitRemote(
+      client,
+      org,
+      project,
+      remoteUrls,
+      settings || project
+    );
+  } else if (Object.keys(remoteUrls).length > 1 && !project.link) {
+    return addMultipleGitRemotes(
+      client,
+      org,
+      project,
+      remoteUrls,
+      settings || project
+    );
+  }
+}
+
+async function addSingleGitRemote(
+  client: Client,
+  org: Org,
+  project: Project,
+  remoteUrls: Dictionary<string>,
+  settings: ProjectSettings
+) {
+  const [remoteName, remoteUrl] = Object.entries(remoteUrls)[0];
+  const repoInfo = parseRepoUrl(remoteUrl);
+  if (!repoInfo) {
+    client.output.debug(`Could not parse repo url ${repoInfo}.`);
+    return 1;
+  }
+  const { org: parsedOrg, repo, provider } = repoInfo;
+  const alreadyLinked =
+    project.link &&
+    project.link.org === parsedOrg &&
+    project.link.repo === repo &&
+    project.link.type === provider;
+  if (alreadyLinked) {
+    client.output.debug('Project already linked. Skipping...');
+    return;
+  }
+
+  const replace =
+    project.link &&
+    (project.link.org !== parsedOrg ||
+      project.link.repo !== repo ||
+      project.link.type !== provider);
+  const shouldConnect = await promptGitConnectSingleUrl(
+    client,
+    project,
+    remoteName,
+    remoteUrl,
+    replace
+  );
+  return handleOptions(shouldConnect, client, org, project, settings, repoInfo);
+}
+
+async function addMultipleGitRemotes(
+  client: Client,
+  org: Org,
+  project: Project,
+  remoteUrls: Dictionary<string>,
+  settings: ProjectSettings
+) {
+  client.output.log('Found multiple Git remote URLs in Git config.');
+  const remoteUrlOrOptions = await promptGitConnectMultipleUrls(
+    client,
+    remoteUrls
+  );
+  return handleOptions(remoteUrlOrOptions, client, org, project, settings);
+}
diff --git a/packages/cli/src/util/link/git-connect-prompts.ts b/packages/cli/src/util/link/git-connect-prompts.ts
new file mode 100644
index 000000000..db6ef06be
--- /dev/null
+++ b/packages/cli/src/util/link/git-connect-prompts.ts
@@ -0,0 +1,86 @@
+import { Dictionary } from '@vercel/client';
+import chalk from 'chalk';
+import { Project } from '../../types';
+import Client from '../client';
+import { formatProvider } from '../git/connect-git-provider';
+import list from '../input/list';
+export async function promptGitConnectSingleUrl(
+  client: Client,
+  project: Project,
+  remoteName: string,
+  remoteUrl: string,
+  hasDiffConnectedProvider = false
+) {
+  const { output } = client;
+  if (hasDiffConnectedProvider) {
+    const currentRepoPath = `${project.link!.org}/${project.link!.repo}`;
+    const currentProvider = project.link!.type;
+    output.print('\n');
+    output.log(
+      `Found Git remote URL ${chalk.cyan(
+        remoteUrl
+      )}, which is different from the connected ${formatProvider(
+        currentProvider
+      )} repository ${chalk.cyan(currentRepoPath)}.`
+    );
+  } else {
+    output.print('\n');
+    output.log(
+      `Found local Git remote "${remoteName}": ${chalk.cyan(remoteUrl)}`
+    );
+  }
+  return await list(client, {
+    message: hasDiffConnectedProvider
+      ? 'Do you want to replace it?'
+      : `Do you want to connect "${remoteName}" to your Vercel project?`,
+    choices: [
+      {
+        name: 'Yes',
+        value: 'yes',
+        short: 'yes',
+      },
+      {
+        name: 'No',
+        value: 'no',
+        short: 'no',
+      },
+      {
+        name: 'Do not ask again for this project',
+        value: 'opt-out',
+        short: 'no (opt out)',
+      },
+    ],
+  });
+}
+
+export async function promptGitConnectMultipleUrls(
+  client: Client,
+  remoteUrls: Dictionary<string>
+) {
+  const staticOptions = [
+    {
+      name: 'No',
+      value: 'no',
+      short: 'no',
+    },
+    {
+      name: 'Do not ask again for this project',
+      value: 'opt-out',
+      short: 'no (opt out)',
+    },
+  ];
+  let choices = [];
+  for (const url of Object.values(remoteUrls)) {
+    choices.push({
+      name: url,
+      value: url,
+      short: url,
+    });
+  }
+  choices = choices.concat(staticOptions);
+
+  return await list(client, {
+    message: 'Do you want to connect a Git repository to your Vercel project?',
+    choices,
+  });
+}
diff --git a/packages/cli/src/util/link/handle-options.ts b/packages/cli/src/util/link/handle-options.ts
new file mode 100644
index 000000000..06239deaf
--- /dev/null
+++ b/packages/cli/src/util/link/handle-options.ts
@@ -0,0 +1,98 @@
+import chalk from 'chalk';
+import { Org, Project, ProjectSettings } from '../../types';
+import Client from '../client';
+import {
+  connectGitProvider,
+  disconnectGitProvider,
+  formatProvider,
+  RepoInfo,
+  parseRepoUrl,
+} from '../git/connect-git-provider';
+import { Output } from '../output';
+import { getCommandName } from '../pkg-name';
+import updateProject from '../projects/update-project';
+
+export async function handleOptions(
+  option: string,
+  client: Client,
+  org: Org,
+  project: Project,
+  settings: ProjectSettings,
+  repoInfo?: RepoInfo
+) {
+  const { output } = client;
+  if (option === 'no') {
+    skip(output);
+    return;
+  } else if (option === 'opt-out') {
+    optOut(client, project, settings);
+    return;
+  } else if (option !== '') {
+    // Option is "yes" or a URL
+
+    // Ensure parsed url exists
+    if (!repoInfo) {
+      const _repoInfo = parseRepoUrl(option);
+      if (!_repoInfo) {
+        output.debug(`Could not parse repo url ${option}.`);
+        return 1;
+      }
+      repoInfo = _repoInfo;
+    }
+    return connect(client, org, project, repoInfo);
+  }
+}
+
+async function optOut(
+  client: Client,
+  project: Project,
+  settings: ProjectSettings
+) {
+  settings.skipGitConnectDuringLink = true;
+  await updateProject(client, project.name, settings);
+  client.output
+    .log(`Opted out. You can re-enable this prompt by visiting the Settings > Git page on the
+  dashboard for this Project.`);
+}
+
+function skip(output: Output) {
+  output.log('Skipping...');
+  output.log(
+    `You can connect a Git repository in the future by running ${getCommandName(
+      'git connect'
+    )}.`
+  );
+}
+
+async function connect(
+  client: Client,
+  org: Org,
+  project: Project,
+  repoInfo: RepoInfo
+): Promise<number | void> {
+  const { output } = client;
+  const { provider, org: parsedOrg, repo } = repoInfo;
+  const repoPath = `${parsedOrg}/${repo}`;
+
+  output.log('Connecting...');
+
+  if (project.link) {
+    await disconnectGitProvider(client, org, project.id);
+  }
+  const connect = await connectGitProvider(
+    client,
+    org,
+    project.id,
+    provider,
+    repoPath
+  );
+  if (connect !== 1) {
+    output.log(
+      `Connected ${formatProvider(provider)} repository ${chalk.cyan(
+        repoPath
+      )}!`
+    );
+  } else {
+    return connect;
+  }
+}
diff --git a/packages/cli/src/util/link/setup-and-link.ts b/packages/cli/src/util/link/setup-and-link.ts
index 3e4ad3d22..fc83cf05f 100644
--- a/packages/cli/src/util/link/setup-and-link.ts
+++ b/packages/cli/src/util/link/setup-and-link.ts
@@ -28,6 +28,8 @@ import { EmojiLabel } from '../emoji';
 import createDeploy from '../deploy/create-deploy';
 import Now, { CreateOptions } from '../index';
 import { isAPIError } from '../errors-ts';
+import { getRemoteUrls } from '../create-git-meta';
+import { addGitConnection } from './add-git-connection';
 
 export interface SetupAndLinkOptions {
   forceDelete?: boolean;
@@ -128,6 +130,19 @@ export default async function setupAndLink(
   } else {
     const project = projectOrNewProjectName;
 
+    const remoteUrls = await getRemoteUrls(join(path, '.git/config'), output);
+    if (remoteUrls && !project.skipGitConnectDuringLink) {
+      const connectGit = await addGitConnection(
+        client,
+        org,
+        project,
+        remoteUrls
+      );
+      if (typeof connectGit === 'number') {
+        return { status: 'error', exitCode: connectGit };
+      }
+    }
+
     await linkFolderToProject(
       output,
       path,
@@ -241,6 +256,21 @@ export default async function setupAndLink(
     }
 
     const project = await createProject(client, newProjectName);
+
+    const remoteUrls = await getRemoteUrls(join(path, '.git/config'), output);
+    if (remoteUrls) {
+      const connectGit = await addGitConnection(
+        client,
+        org,
+        project,
+        remoteUrls,
+        settings
+      );
+      if (typeof connectGit === 'number') {
+        return { status: 'error', exitCode: connectGit };
+      }
+    }
+
     await updateProject(client, project.id, settings);
     Object.assign(project, settings);
 
diff --git a/packages/cli/src/util/projects/create-project.ts b/packages/cli/src/util/projects/create-project.ts
index 19bd8d053..6eaa86556 100644
--- a/packages/cli/src/util/projects/create-project.ts
+++ b/packages/cli/src/util/projects/create-project.ts
@@ -7,7 +7,7 @@ export default async function createProject(
 ) {
   const project = await client.fetch<Project>('/v1/projects', {
     method: 'POST',
-    body: JSON.stringify({ name: projectName }),
+    body: { name: projectName },
   });
   return project;
 }
diff --git a/packages/cli/src/util/projects/update-project.ts b/packages/cli/src/util/projects/update-project.ts
index e96d9c27f..77879938a 100644
--- a/packages/cli/src/util/projects/update-project.ts
+++ b/packages/cli/src/util/projects/update-project.ts
@@ -1,5 +1,5 @@
 import Client from '../client';
-import { ProjectSettings } from '../../types';
+import type { JSONObject, ProjectSettings } from '../../types';
 
 interface ProjectSettingsResponse extends ProjectSettings {
   id: string;
@@ -13,11 +13,14 @@ export default async function updateProject(
   prjNameOrId: string,
   settings: ProjectSettings
 ) {
+  // `ProjectSettings` is technically compatible with JSONObject
+  const body = settings as JSONObject;
+
   const res = await client.fetch<ProjectSettingsResponse>(
     `/v2/projects/${encodeURIComponent(prjNameOrId)}`,
     {
       method: 'PATCH',
-      body: JSON.stringify(settings),
+      body,
     }
   );
   return res;
diff --git a/packages/cli/test/fixtures/unit/link-connect-git/multiple-remotes/.gitignore b/packages/cli/test/fixtures/unit/link-connect-git/multiple-remotes/.gitignore
new file mode 100644
index 000000000..7b54c6705
--- /dev/null
+++ b/packages/cli/test/fixtures/unit/link-connect-git/multiple-remotes/.gitignore
@@ -0,0 +1,2 @@
+!.vercel
+.vercel
diff --git a/packages/cli/test/fixtures/unit/link-connect-git/multiple-remotes/git/config b/packages/cli/test/fixtures/unit/link-connect-git/multiple-remotes/git/config
new file mode 100644
index 000000000..c2c0dba42
--- /dev/null
+++ b/packages/cli/test/fixtures/unit/link-connect-git/multiple-remotes/git/config
@@ -0,0 +1,16 @@
+[core]
+        repositoryformatversion = 0
+        filemode = true
+        bare = false
+        logallrefupdates = true
+        ignorecase = true
+        precomposeunicode = true
+[remote "origin"]
+        url = https://github.com/user/repo.git
+        fetch = +refs/heads/*:refs/remotes/origin/*
+[remote "secondary"]
+        url = https://github.com/user2/repo2.git
+        fetch = +refs/heads/*:refs/remotes/secondary/*
+[remote "gitlab"]
+        url = https://gitlab.com/user/repo.git
+        fetch = +refs/heads/*:refs/remotes/gitlab/*
\ No newline at end of file
diff --git a/packages/cli/test/fixtures/unit/link-connect-git/single-remote-existing-link/.gitignore b/packages/cli/test/fixtures/unit/link-connect-git/single-remote-existing-link/.gitignore
new file mode 100644
index 000000000..7b54c6705
--- /dev/null
+++ b/packages/cli/test/fixtures/unit/link-connect-git/single-remote-existing-link/.gitignore
@@ -0,0 +1,2 @@
+!.vercel
+.vercel
diff --git a/packages/cli/test/fixtures/unit/link-connect-git/single-remote-existing-link/git/config b/packages/cli/test/fixtures/unit/link-connect-git/single-remote-existing-link/git/config
new file mode 100644
index 000000000..fd945011a
--- /dev/null
+++ b/packages/cli/test/fixtures/unit/link-connect-git/single-remote-existing-link/git/config
@@ -0,0 +1,13 @@
+[core]
+        repositoryformatversion = 0
+        filemode = true
+        bare = false
+        logallrefupdates = true
+        ignorecase = true
+        precomposeunicode = true
+[remote "origin"]
+        url = https://github.com/user2/repo2.git
+        fetch = +refs/heads/*:refs/remotes/origin/*
+[branch "master"]
+        remote = origin
+        merge = refs/heads/master
\ No newline at end of file
diff --git a/packages/cli/test/fixtures/unit/link-connect-git/single-remote/.gitignore b/packages/cli/test/fixtures/unit/link-connect-git/single-remote/.gitignore
new file mode 100644
index 000000000..7b54c6705
--- /dev/null
+++ b/packages/cli/test/fixtures/unit/link-connect-git/single-remote/.gitignore
@@ -0,0 +1,2 @@
+!.vercel
+.vercel
diff --git a/packages/cli/test/fixtures/unit/link-connect-git/single-remote/git/config b/packages/cli/test/fixtures/unit/link-connect-git/single-remote/git/config
new file mode 100644
index 000000000..887a8b0e1
--- /dev/null
+++ b/packages/cli/test/fixtures/unit/link-connect-git/single-remote/git/config
@@ -0,0 +1,13 @@
+[core]
+        repositoryformatversion = 0
+        filemode = true
+        bare = false
+        logallrefupdates = true
+        ignorecase = true
+        precomposeunicode = true
+[remote "origin"]
+        url = https://github.com/user/repo.git
+        fetch = +refs/heads/*:refs/remotes/origin/*
+[branch "master"]
+        remote = origin
+        merge = refs/heads/master
\ No newline at end of file
diff --git a/packages/cli/test/mocks/deployment.ts b/packages/cli/test/mocks/deployment.ts
index 607f051f7..6ca4daf81 100644
--- a/packages/cli/test/mocks/deployment.ts
+++ b/packages/cli/test/mocks/deployment.ts
@@ -49,6 +49,43 @@ export function useDeployment({
   return deployment;
 }
 
+export function useDeploymentMissingProjectSettings() {
+  client.scenario.post('/:version/deployments', (_req, res) => {
+    res.status(400).json({
+      error: {
+        code: 'missing_project_settings',
+        message:
+          'The `projectSettings` object is required for new projects, but is missing in the deployment payload',
+        framework: {
+          name: 'Other',
+          slug: null,
+          logo: 'https://raw.githubusercontent.com/vercel/vercel/main/packages/frameworks/logos/other.svg',
+          description: 'No framework or an unoptimized framework.',
+          settings: {
+            installCommand: {
+              placeholder: '`yarn install`, `pnpm install`, or `npm install`',
+            },
+            buildCommand: {
+              placeholder: '`npm run vercel-build` or `npm run build`',
+              value: null,
+            },
+            devCommand: { placeholder: 'None', value: null },
+            outputDirectory: { placeholder: '`public` if it exists, or `.`' },
+          },
+        },
+        projectSettings: {
+          devCommand: null,
+          installCommand: null,
+          buildCommand: null,
+          outputDirectory: null,
+          rootDirectory: null,
+          framework: null,
+        },
+      },
+    });
+  });
+}
+
 beforeEach(() => {
   deployments = new Map();
   deploymentBuilds = new Map();
diff --git a/packages/cli/test/mocks/project.ts b/packages/cli/test/mocks/project.ts
index 9edefcd72..76c362577 100644
--- a/packages/cli/test/mocks/project.ts
+++ b/packages/cli/test/mocks/project.ts
@@ -131,6 +131,70 @@ export const defaultProject = {
   ],
 };
 
+/**
+ * Responds to any GET for a project with a 404.
+ * `useUnknownProject` should always come after `useProject`, if any,
+ * to allow `useProject` responses to still happen.
+ */
+export function useUnknownProject() {
+  let project: Project;
+  client.scenario.get(`/v8/projects/:projectNameOrId`, (_req, res) => {
+    res.status(404).send();
+  });
+  client.scenario.post(`/:version/projects`, (req, res) => {
+    const { name } = req.body;
+    project = {
+      ...defaultProject,
+      name,
+      id: name,
+    };
+    res.json(project);
+  });
+  client.scenario.post(`/v9/projects/:projectNameOrId/link`, (req, res) => {
+    const { type, repo, org } = req.body;
+    const projName = req.params.projectNameOrId;
+    if (projName !== project.name && projName !== project.id) {
+      return res.status(404).send('Invalid Project name or ID');
+    }
+    if (
+      (type === 'github' || type === 'gitlab' || type === 'bitbucket') &&
+      (repo === 'user/repo' || repo === 'user2/repo2')
+    ) {
+      project.link = {
+        type,
+        repo,
+        repoId: 1010,
+        org,
+        gitCredentialId: '',
+        sourceless: true,
+        createdAt: 1656109539791,
+        updatedAt: 1656109539791,
+      };
+      res.json(project);
+    } else {
+      if (type === 'github') {
+        res.status(400).json({
+          message: `To link a GitHub repository, you need to install the GitHub integration first. (400)\nInstall GitHub App: https://github.com/apps/vercel`,
+          action: 'Install GitHub App',
+          link: 'https://github.com/apps/vercel',
+          repo,
+        });
+      } else {
+        res.status(400).json({
+          code: 'repo_not_found',
+          message: `The repository "${repo}" couldn't be found in your linked ${formatProvider(
+            type
+          )} account.`,
+        });
+      }
+    }
+  });
+  client.scenario.patch(`/:version/projects/:projectNameOrId`, (req, res) => {
+    Object.assign(project, req.body);
+    res.json(project);
+  });
+}
+
 export function useProject(project: Partial<Project> = defaultProject) {
   client.scenario.get(`/v8/projects/${project.name}`, (_req, res) => {
     res.json(project);
@@ -138,6 +202,10 @@ export function useProject(project: Partial<Project> = defaultProject) {
   client.scenario.get(`/v8/projects/${project.id}`, (_req, res) => {
     res.json(project);
   });
+  client.scenario.patch(`/:version/projects/${project.id}`, (req, res) => {
+    Object.assign(project, req.body);
+    res.json(project);
+  });
   client.scenario.get(
     `/v6/projects/${project.id}/system-env-values`,
     (_req, res) => {
@@ -183,7 +251,7 @@ export function useProject(project: Partial<Project> = defaultProject) {
       res.json(envs);
     }
   );
-  client.scenario.post(`/v4/projects/${project.id}/link`, (req, res) => {
+  client.scenario.post(`/v9/projects/${project.id}/link`, (req, res) => {
     const { type, repo, org } = req.body;
     if (
       (type === 'github' || type === 'gitlab' || type === 'bitbucket') &&
@@ -218,7 +286,7 @@ export function useProject(project: Partial<Project> = defaultProject) {
       }
     }
   });
-  client.scenario.delete(`/v4/projects/${project.id}/link`, (_req, res) => {
+  client.scenario.delete(`/v9/projects/${project.id}/link`, (_req, res) => {
     if (project.link) {
       project.link = undefined;
     }
diff --git a/packages/cli/test/unit/commands/git.test.ts b/packages/cli/test/unit/commands/git.test.ts
index 14dbb3ae2..6863fc2cd 100644
--- a/packages/cli/test/unit/commands/git.test.ts
+++ b/packages/cli/test/unit/commands/git.test.ts
@@ -39,6 +39,11 @@ describe('git', () => {
         await expect(client.stderr).toOutput('Found project');
         client.stdin.write('y\n');
 
+        await expect(client.stderr).toOutput(
+          'Do you want to connect "origin" to your Vercel project?'
+        );
+        client.stdin.write('n\n');
+
         await expect(client.stderr).toOutput(
           `Connecting Git remote: https://github.com/user/repo.git`
         );
diff --git a/packages/cli/test/unit/commands/link.test.ts b/packages/cli/test/unit/commands/link.test.ts
new file mode 100644
index 000000000..c48ddbfc7
--- /dev/null
+++ b/packages/cli/test/unit/commands/link.test.ts
@@ -0,0 +1,310 @@
+import { join } from 'path';
+import fs from 'fs-extra';
+import link from '../../../src/commands/link';
+import { useUser } from '../../mocks/user';
+import { useTeams } from '../../mocks/team';
+import {
+  defaultProject,
+  useUnknownProject,
+  useProject,
+} from '../../mocks/project';
+import { client } from '../../mocks/client';
+import { useDeploymentMissingProjectSettings } from '../../mocks/deployment';
+import { Project } from '../../../src/types';
+
+describe('link', () => {
+  describe('git prompt', () => {
+    const originalCwd = process.cwd();
+    const fixture = (name: string) =>
+      join(__dirname, '../../fixtures/unit/link-connect-git', name);
+
+    it('should prompt to connect a new project with a single remote', async () => {
+      const cwd = fixture('single-remote');
+      try {
+        process.chdir(cwd);
+        await fs.rename(join(cwd, 'git'), join(cwd, '.git'));
+        useUser();
+        useUnknownProject();
+        useDeploymentMissingProjectSettings();
+        useTeams('team_dummy');
+        const linkPromise = link(client);
+
+        await expect(client.stderr).toOutput('Set up');
+        client.stdin.write('y\n');
+        await expect(client.stderr).toOutput('Which scope');
+        client.stdin.write('\r');
+        await expect(client.stderr).toOutput('Link to existing project?');
+        client.stdin.write('n\n');
+        await expect(client.stderr).toOutput('What’s your project’s name?');
+        client.stdin.write('\r');
+        await expect(client.stderr).toOutput(
+          'In which directory is your code located?'
+        );
+        client.stdin.write('\r');
+        await expect(client.stderr).toOutput('Want to modify these settings?');
+        client.stdin.write('n\n');
+
+        await expect(client.stderr).toOutput(
+          'Found local Git remote "origin": https://github.com/user/repo.git'
+        );
+        await expect(client.stderr).toOutput(
+          'Do you want to connect "origin" to your Vercel project?'
+        );
+        client.stdin.write('\r');
+        await expect(client.stderr).toOutput(
+          'Connected GitHub repository user/repo!'
+        );
+        await expect(client.stderr).toOutput('Linked to');
+        await expect(linkPromise).resolves.toEqual(0);
+      } finally {
+        await fs.rename(join(cwd, '.git'), join(cwd, 'git'));
+        process.chdir(originalCwd);
+      }
+    });
+
+    it('should prompt to connect an existing project with a single remote to git', async () => {
+      const cwd = fixture('single-remote');
+      try {
+        process.chdir(cwd);
+        await fs.rename(join(cwd, 'git'), join(cwd, '.git'));
+        useUser();
+        useProject({
+          ...defaultProject,
+          name: 'single-remote',
+          id: 'single-remote',
+        });
+        useTeams('team_dummy');
+        const linkPromise = link(client);
+
+        await expect(client.stderr).toOutput('Set up');
+        client.stdin.write('y\n');
+        await expect(client.stderr).toOutput('Which scope');
+        client.stdin.write('\r');
+        await expect(client.stderr).toOutput('Found project');
+        client.stdin.write('y\n');
+
+        await expect(client.stderr).toOutput(
+          'Found local Git remote "origin": https://github.com/user/repo.git'
+        );
+        await expect(client.stderr).toOutput(
+          'Do you want to connect "origin" to your Vercel project?'
+        );
+        client.stdin.write('\r');
+        await expect(client.stderr).toOutput(
+          'Connected GitHub repository user/repo!'
+        );
+        await expect(client.stderr).toOutput('Linked to');
+
+        await expect(linkPromise).resolves.toEqual(0);
+      } finally {
+        await fs.rename(join(cwd, '.git'), join(cwd, 'git'));
+        process.chdir(originalCwd);
+      }
+    });
+    it('should prompt to replace a connected repository if there is one remote', async () => {
+      const cwd = fixture('single-remote-existing-link');
+      try {
+        process.chdir(cwd);
+        await fs.rename(join(cwd, 'git'), join(cwd, '.git'));
+        useUser();
+        const project = useProject({
+          ...defaultProject,
+          name: 'single-remote-existing-link',
+          id: 'single-remote-existing-link',
+        });
+        useTeams('team_dummy');
+        project.project.link = {
+          type: 'github',
+          org: 'user',
+          repo: 'repo',
+          repoId: 1010,
+          gitCredentialId: '',
+          sourceless: true,
+          createdAt: 1656109539791,
+          updatedAt: 1656109539791,
+        };
+
+        const linkPromise = link(client);
+
+        await expect(client.stderr).toOutput('Set up');
+        client.stdin.write('y\n');
+        await expect(client.stderr).toOutput('Which scope');
+        client.stdin.write('\r');
+        await expect(client.stderr).toOutput('Found project');
+        client.stdin.write('y\n');
+
+        await expect(client.stderr).toOutput(
+          `Found Git remote URL https://github.com/user2/repo2.git, which is different from the connected GitHub repository user/repo.`
+        );
+        await expect(client.stderr).toOutput('Do you want to replace it?');
+        client.stdin.write('\r');
+        await expect(client.stderr).toOutput(
+          'Connected GitHub repository user2/repo2!'
+        );
+        await expect(client.stderr).toOutput('Linked to');
+
+        await expect(linkPromise).resolves.toEqual(0);
+      } finally {
+        await fs.rename(join(cwd, '.git'), join(cwd, 'git'));
+        process.chdir(originalCwd);
+      }
+    });
+    it('should prompt to connect an existing project with multiple remotes', async () => {
+      const cwd = fixture('multiple-remotes');
+      try {
+        process.chdir(cwd);
+        await fs.rename(join(cwd, 'git'), join(cwd, '.git'));
+
+        useUser();
+        useProject({
+          ...defaultProject,
+          name: 'multiple-remotes',
+          id: 'multiple-remotes',
+        });
+        useTeams('team_dummy');
+
+        const linkPromise = link(client);
+
+        await expect(client.stderr).toOutput('Set up');
+        client.stdin.write('y\n');
+        await expect(client.stderr).toOutput('Which scope');
+        client.stdin.write('\r');
+        await expect(client.stderr).toOutput('Found project');
+        client.stdin.write('y\n');
+
+        await expect(client.stderr).toOutput(
+          `> Do you want to connect a Git repository to your Vercel project?`
+        );
+        client.stdin.write('\r');
+        await expect(client.stderr).toOutput(
+          'Connected GitHub repository user/repo!'
+        );
+        await expect(client.stderr).toOutput('Linked to');
+
+        await expect(linkPromise).resolves.toEqual(0);
+      } finally {
+        await fs.rename(join(cwd, '.git'), join(cwd, 'git'));
+        process.chdir(originalCwd);
+      }
+    });
+    it('should not prompt to replace a connected repository if there is more than one remote', async () => {
+      const cwd = fixture('multiple-remotes');
+      try {
+        process.chdir(cwd);
+        await fs.rename(join(cwd, 'git'), join(cwd, '.git'));
+
+        useUser();
+        const project = useProject({
+          ...defaultProject,
+          name: 'multiple-remotes',
+          id: 'multiple-remotes',
+        });
+        useTeams('team_dummy');
+        project.project.link = {
+          type: 'github',
+          org: 'user',
+          repo: 'repo',
+          repoId: 1010,
+          gitCredentialId: '',
+          sourceless: true,
+          createdAt: 1656109539791,
+          updatedAt: 1656109539791,
+        };
+
+        const linkPromise = link(client);
+
+        await expect(client.stderr).toOutput('Set up');
+        client.stdin.write('y\n');
+        await expect(client.stderr).toOutput('Which scope');
+        client.stdin.write('\r');
+        await expect(client.stderr).toOutput('Found project');
+        client.stdin.write('y\n');
+
+        expect(client.stderr).not.toOutput('Found multiple Git remote URLs');
+        await expect(client.stderr).toOutput('Linked to');
+
+        await expect(linkPromise).resolves.toEqual(0);
+      } finally {
+        await fs.rename(join(cwd, '.git'), join(cwd, 'git'));
+        process.chdir(originalCwd);
+      }
+    });
+    it('should set a project setting if user opts out', async () => {
+      const cwd = fixture('single-remote');
+      try {
+        process.chdir(cwd);
+        await fs.rename(join(cwd, 'git'), join(cwd, '.git'));
+
+        useUser();
+        useProject({
+          ...defaultProject,
+          name: 'single-remote',
+          id: 'single-remote',
+        });
+        useTeams('team_dummy');
+        const linkPromise = link(client);
+
+        await expect(client.stderr).toOutput('Set up');
+        client.stdin.write('y\n');
+        await expect(client.stderr).toOutput('Which scope');
+        client.stdin.write('\r');
+        await expect(client.stderr).toOutput('Found project');
+        client.stdin.write('y\n');
+
+        await expect(client.stderr).toOutput(
+          'Found local Git remote "origin": https://github.com/user/repo.git'
+        );
+        await expect(client.stderr).toOutput(
+          'Do you want to connect "origin" to your Vercel project?'
+        );
+        client.stdin.write('\x1B[B'); // Down arrow
+        client.stdin.write('\x1B[B');
+        client.stdin.write('\r'); // Opt out
+
+        await expect(client.stderr).toOutput(`Opted out.`);
+        await expect(client.stderr).toOutput('Linked to');
+        await expect(linkPromise).resolves.toEqual(0);
+
+        const newProjectData: Project = await client.fetch(
+          `/v8/projects/single-remote`
+        );
+        expect(newProjectData.skipGitConnectDuringLink).toBeTruthy();
+      } finally {
+        await fs.rename(join(cwd, '.git'), join(cwd, 'git'));
+        process.chdir(originalCwd);
+      }
+    });
+    it('should not prompt to connect git if the project has skipGitConnectDuringLink property', async () => {
+      const cwd = fixture('single-remote');
+      try {
+        process.chdir(cwd);
+        await fs.rename(join(cwd, 'git'), join(cwd, '.git'));
+
+        useUser();
+        const project = useProject({
+          ...defaultProject,
+          name: 'single-remote',
+          id: 'single-remote',
+        });
+        useTeams('team_dummy');
+        project.project.skipGitConnectDuringLink = true;
+        const linkPromise = link(client);
+
+        await expect(client.stderr).toOutput('Set up');
+        client.stdin.write('y\n');
+        await expect(client.stderr).toOutput('Which scope');
+        client.stdin.write('\r');
+        await expect(client.stderr).toOutput('Found project');
+        client.stdin.write('y\n');
+
+        expect(client.stderr).not.toOutput('Found local Git remote "origin"');
+
+        await expect(client.stderr).toOutput('Linked to');
+        await expect(linkPromise).resolves.toEqual(0);
+      } finally {
+        await fs.rename(join(cwd, '.git'), join(cwd, 'git'));
+        process.chdir(originalCwd);
+      }
+    });
+  });
+});
diff --git a/packages/cli/test/unit/util/deploy/create-git-meta.test.ts b/packages/cli/test/unit/util/deploy/create-git-meta.test.ts
index 6f2d31d96..4a8e3f612 100644
--- a/packages/cli/test/unit/util/deploy/create-git-meta.test.ts
+++ b/packages/cli/test/unit/util/deploy/create-git-meta.test.ts
@@ -58,92 +58,92 @@ describe('getRemoteUrls', () => {
 
 describe('parseRepoUrl', () => {
   it('should be null when a url does not match the regex', () => {
-    const parsedUrl = parseRepoUrl('https://examplecom/foo');
-    expect(parsedUrl).toBeNull();
+    const repoInfo = parseRepoUrl('https://examplecom/foo');
+    expect(repoInfo).toBeNull();
   });
   it('should be null when a url does not contain org and repo data', () => {
-    const parsedUrl = parseRepoUrl('https://github.com/borked');
-    expect(parsedUrl).toBeNull();
+    const repoInfo = parseRepoUrl('https://github.com/borked');
+    expect(repoInfo).toBeNull();
   });
   it('should parse url with a period in the repo name', () => {
-    const parsedUrl = parseRepoUrl('https://github.com/vercel/next.js');
-    expect(parsedUrl).toBeDefined();
-    expect(parsedUrl?.provider).toEqual('github');
-    expect(parsedUrl?.org).toEqual('vercel');
-    expect(parsedUrl?.repo).toEqual('next.js');
+    const repoInfo = parseRepoUrl('https://github.com/vercel/next.js');
+    expect(repoInfo).toBeDefined();
+    expect(repoInfo?.provider).toEqual('github');
+    expect(repoInfo?.org).toEqual('vercel');
+    expect(repoInfo?.repo).toEqual('next.js');
   });
   it('should parse url that ends with .git', () => {
-    const parsedUrl = parseRepoUrl('https://github.com/vercel/next.js.git');
-    expect(parsedUrl).toBeDefined();
-    expect(parsedUrl?.provider).toEqual('github');
-    expect(parsedUrl?.org).toEqual('vercel');
-    expect(parsedUrl?.repo).toEqual('next.js');
+    const repoInfo = parseRepoUrl('https://github.com/vercel/next.js.git');
+    expect(repoInfo).toBeDefined();
+    expect(repoInfo?.provider).toEqual('github');
+    expect(repoInfo?.org).toEqual('vercel');
+    expect(repoInfo?.repo).toEqual('next.js');
   });
   it('should parse github https url', () => {
-    const parsedUrl = parseRepoUrl('https://github.com/vercel/vercel.git');
-    expect(parsedUrl).toBeDefined();
-    expect(parsedUrl?.provider).toEqual('github');
-    expect(parsedUrl?.org).toEqual('vercel');
-    expect(parsedUrl?.repo).toEqual('vercel');
+    const repoInfo = parseRepoUrl('https://github.com/vercel/vercel.git');
+    expect(repoInfo).toBeDefined();
+    expect(repoInfo?.provider).toEqual('github');
+    expect(repoInfo?.org).toEqual('vercel');
+    expect(repoInfo?.repo).toEqual('vercel');
   });
   it('should parse github https url without the .git suffix', () => {
-    const parsedUrl = parseRepoUrl('https://github.com/vercel/vercel');
-    expect(parsedUrl).toBeDefined();
-    expect(parsedUrl?.provider).toEqual('github');
-    expect(parsedUrl?.org).toEqual('vercel');
-    expect(parsedUrl?.repo).toEqual('vercel');
+    const repoInfo = parseRepoUrl('https://github.com/vercel/vercel');
+    expect(repoInfo).toBeDefined();
+    expect(repoInfo?.provider).toEqual('github');
+    expect(repoInfo?.org).toEqual('vercel');
+    expect(repoInfo?.repo).toEqual('vercel');
   });
   it('should parse github git url', () => {
-    const parsedUrl = parseRepoUrl('git://github.com/vercel/vercel.git');
-    expect(parsedUrl).toBeDefined();
-    expect(parsedUrl?.provider).toEqual('github');
-    expect(parsedUrl?.org).toEqual('vercel');
-    expect(parsedUrl?.repo).toEqual('vercel');
+    const repoInfo = parseRepoUrl('git://github.com/vercel/vercel.git');
+    expect(repoInfo).toBeDefined();
+    expect(repoInfo?.provider).toEqual('github');
+    expect(repoInfo?.org).toEqual('vercel');
+    expect(repoInfo?.repo).toEqual('vercel');
   });
   it('should parse github ssh url', () => {
-    const parsedUrl = parseRepoUrl('git@github.com:vercel/vercel.git');
-    expect(parsedUrl).toBeDefined();
-    expect(parsedUrl?.provider).toEqual('github');
-    expect(parsedUrl?.org).toEqual('vercel');
-    expect(parsedUrl?.repo).toEqual('vercel');
+    const repoInfo = parseRepoUrl('git@github.com:vercel/vercel.git');
+    expect(repoInfo).toBeDefined();
+    expect(repoInfo?.provider).toEqual('github');
+    expect(repoInfo?.org).toEqual('vercel');
+    expect(repoInfo?.repo).toEqual('vercel');
   });
 
   it('should parse gitlab https url', () => {
-    const parsedUrl = parseRepoUrl(
+    const repoInfo = parseRepoUrl(
       'https://gitlab.com/gitlab-examples/knative-kotlin-app.git'
     );
-    expect(parsedUrl).toBeDefined();
-    expect(parsedUrl?.provider).toEqual('gitlab');
-    expect(parsedUrl?.org).toEqual('gitlab-examples');
-    expect(parsedUrl?.repo).toEqual('knative-kotlin-app');
+    expect(repoInfo).toBeDefined();
+    expect(repoInfo?.provider).toEqual('gitlab');
+    expect(repoInfo?.org).toEqual('gitlab-examples');
+    expect(repoInfo?.repo).toEqual('knative-kotlin-app');
   });
   it('should parse gitlab ssh url', () => {
-    const parsedUrl = parseRepoUrl(
+    const repoInfo = parseRepoUrl(
       'git@gitlab.com:gitlab-examples/knative-kotlin-app.git'
     );
-    expect(parsedUrl).toBeDefined();
-    expect(parsedUrl?.provider).toEqual('gitlab');
-    expect(parsedUrl?.org).toEqual('gitlab-examples');
-    expect(parsedUrl?.repo).toEqual('knative-kotlin-app');
+    expect(repoInfo).toBeDefined();
+    expect(repoInfo?.provider).toEqual('gitlab');
+    expect(repoInfo?.org).toEqual('gitlab-examples');
+    expect(repoInfo?.repo).toEqual('knative-kotlin-app');
   });
 
   it('should parse bitbucket https url', () => {
-    const parsedUrl = parseRepoUrl(
+    const repoInfo = parseRepoUrl(
       'https://bitbucket.org/atlassianlabs/maven-project-example.git'
     );
-    expect(parsedUrl).toBeDefined();
-    expect(parsedUrl?.provider).toEqual('bitbucket');
-    expect(parsedUrl?.org).toEqual('atlassianlabs');
-    expect(parsedUrl?.repo).toEqual('maven-project-example');
+    expect(repoInfo).toBeDefined();
+    expect(repoInfo?.provider).toEqual('bitbucket');
+    expect(repoInfo?.org).toEqual('atlassianlabs');
+    expect(repoInfo?.repo).toEqual('maven-project-example');
   });
   it('should parse bitbucket ssh url', () => {
-    const parsedUrl = parseRepoUrl(
+    const repoInfo = parseRepoUrl(
       'git@bitbucket.org:atlassianlabs/maven-project-example.git'
     );
-    expect(parsedUrl).toBeDefined();
-    expect(parsedUrl?.provider).toEqual('bitbucket');
-    expect(parsedUrl?.org).toEqual('atlassianlabs');
-    expect(parsedUrl?.repo).toEqual('maven-project-example');
+    expect(repoInfo).toBeDefined();
+    expect(repoInfo?.provider).toEqual('bitbucket');
+    expect(repoInfo?.org).toEqual('atlassianlabs');
+    expect(repoInfo?.repo).toEqual('maven-project-example');
   });
   it('should parse url without a scheme', () => {
     const parsedUrl = parseRepoUrl('github.com/user/repo');