diff --git a/.github/workflows/e2e.yml b/.github/workflows/e2e.yml
index ad5e089cba..fbc4663aa4 100644
--- a/.github/workflows/e2e.yml
+++ b/.github/workflows/e2e.yml
@@ -27,8 +27,9 @@ jobs:
         tailwind: ["true", "false"]
         nextAuth: ["true", "false"]
         prisma: ["true", "false"]
+        prettierAndExtendedEslint: ["true", "false"]
 
-    name: "Build and Start T3 App ${{ matrix.trpc }}-${{ matrix.tailwind }}-${{ matrix.nextAuth }}-${{ matrix.prisma }}"
+    name: "Build and Start T3 App ${{ matrix.trpc }}-${{ matrix.tailwind }}-${{ matrix.nextAuth }}-${{ matrix.prisma }}-${{ matrix.prettierAndExtendedEslint }}"
     steps:
       - uses: actions/checkout@v3
         with:
@@ -65,7 +66,7 @@ jobs:
       # has to be scaffolded outside the CLI project so that no lint/tsconfig are leaking
       # through. this way it ensures that it is the app's configs that are being used
       # FIXME: this is a bit hacky, would rather have --packages=trpc,tailwind,... but not sure how to setup the matrix for that
-      - run: cd cli && pnpm start ../../ci-${{ matrix.trpc }}-${{ matrix.tailwind }}-${{ matrix.nextAuth }}-${{ matrix.prisma }} --noGit --CI --trpc=${{ matrix.trpc }} --tailwind=${{ matrix.tailwind }} --nextAuth=${{ matrix.nextAuth }} --prisma=${{ matrix.prisma }}
-      - run: cd ../ci-${{ matrix.trpc }}-${{ matrix.tailwind }}-${{ matrix.nextAuth }}-${{ matrix.prisma }} && pnpm build
+      - run: cd cli && pnpm start ../../ci-${{ matrix.trpc }}-${{ matrix.tailwind }}-${{ matrix.nextAuth }}-${{ matrix.prisma }}-${{ matrix.prettierAndExtendedEslint }} --noGit --CI --trpc=${{ matrix.trpc }} --tailwind=${{ matrix.tailwind }} --nextAuth=${{ matrix.nextAuth }} --prisma=${{ matrix.prisma }} --prettier-and-extended-eslint=${{ matrix.prettierAndExtendedEslint }}
+      - run: cd ../ci-${{ matrix.trpc }}-${{ matrix.tailwind }}-${{ matrix.nextAuth }}-${{ matrix.prisma }}-${{ matrix.prettierAndExtendedEslint }} && pnpm build
         env:
           NEXTAUTH_SECRET: foo
diff --git a/cli/src/cli/index.ts b/cli/src/cli/index.ts
index 73c8833879..bc7e3b8e71 100644
--- a/cli/src/cli/index.ts
+++ b/cli/src/cli/index.ts
@@ -2,8 +2,10 @@ import chalk from "chalk";
 import { Command } from "commander";
 import inquirer from "inquirer";
 import { CREATE_T3_APP, DEFAULT_APP_NAME } from "~/consts.js";
-import { type AvailablePackages } from "~/installers/index.js";
-import { availablePackages } from "~/installers/index.js";
+import {
+  availablePackages,
+  type AvailablePackages,
+} from "~/installers/index.js";
 import { getVersion } from "~/utils/getT3Version.js";
 import { getUserPkgManager } from "~/utils/getUserPkgManager.js";
 import { logger } from "~/utils/logger.js";
@@ -15,6 +17,7 @@ interface CliFlags {
   noInstall: boolean;
   default: boolean;
   importAlias: string;
+  prettierAndExtendedEslint: boolean;
 
   /** @internal Used in CI. */
   CI: boolean;
@@ -47,6 +50,7 @@ const defaultOptions: CliResults = {
     prisma: false,
     nextAuth: false,
     importAlias: "~/",
+    prettierAndExtendedEslint: false,
   },
 };
 
@@ -114,6 +118,12 @@ export const runCli = async () => {
       "Explicitly tell the CLI to use a custom import alias",
       defaultOptions.flags.importAlias,
     )
+    /** @experimental - Used for CI E2E tests. Used in conjunction with `--CI` to skip prompting. */
+    .option(
+      "-p, --prettier-and-extended-eslint",
+      "Explicitly tell the CLI to use a custom import alias",
+      defaultOptions.flags.prettierAndExtendedEslint,
+    )
     /** END CI-FLAGS */
     .version(getVersion(), "-v, --version", "Display the version number")
     .addHelpText(
@@ -153,6 +163,9 @@ export const runCli = async () => {
     if (cliResults.flags.tailwind) cliResults.packages.push("tailwind");
     if (cliResults.flags.prisma) cliResults.packages.push("prisma");
     if (cliResults.flags.nextAuth) cliResults.packages.push("nextAuth");
+    if (cliResults.flags.prettierAndExtendedEslint) {
+      cliResults.flags.prettierAndExtendedEslint = true;
+    }
   }
 
   // Explained below why this is in a try/catch block
@@ -186,6 +199,9 @@ export const runCli = async () => {
       }
 
       cliResults.flags.importAlias = await promptImportAlias();
+
+      cliResults.flags.prettierAndExtendedEslint =
+        await promtPrettierAndExtendedEslint();
     }
   } catch (err) {
     // If the user is not calling create-t3-app from an interactive terminal, inquirer will throw an error with isTTYError = true
@@ -329,3 +345,16 @@ const promptImportAlias = async (): Promise<string> => {
 
   return importAlias;
 };
+
+const promtPrettierAndExtendedEslint = async (): Promise<boolean> => {
+  const { prettierAndExtendedEslint } = await inquirer.prompt<
+    Pick<CliFlags, "prettierAndExtendedEslint">
+  >({
+    name: "prettierAndExtendedEslint",
+    type: "confirm",
+    message: "Would you like to use prettier and extended eslint conifg?",
+    default: defaultOptions.flags.prettierAndExtendedEslint,
+  });
+
+  return prettierAndExtendedEslint;
+};
diff --git a/cli/src/helpers/createProject.ts b/cli/src/helpers/createProject.ts
index ea1e3942f4..fe2ca1560c 100644
--- a/cli/src/helpers/createProject.ts
+++ b/cli/src/helpers/createProject.ts
@@ -2,7 +2,9 @@ import path from "path";
 import { installPackages } from "~/helpers/installPackages.js";
 import { scaffoldProject } from "~/helpers/scaffoldProject.js";
 import { selectAppFile, selectIndexFile } from "~/helpers/selectBoilerplate.js";
+import { installExtendedEslint } from "~/installers/eslint.js";
 import { type PkgInstallerMap } from "~/installers/index.js";
+import { installPrettier } from "~/installers/prettier.js";
 import { getUserPkgManager } from "~/utils/getUserPkgManager.js";
 
 interface CreateProjectOptions {
@@ -10,12 +12,14 @@ interface CreateProjectOptions {
   packages: PkgInstallerMap;
   noInstall: boolean;
   importAlias: string;
+  prettierAndExtendedEslint: boolean;
 }
 
 export const createProject = async ({
   projectName,
   packages,
   noInstall,
+  prettierAndExtendedEslint,
 }: CreateProjectOptions) => {
   const pkgManager = getUserPkgManager();
   const projectDir = path.resolve(process.cwd(), projectName);
@@ -36,6 +40,16 @@ export const createProject = async ({
     noInstall,
   });
 
+  if (prettierAndExtendedEslint) {
+    const installArgs = {
+      projectDir,
+      pkgManager,
+      noInstall,
+    };
+    installPrettier(installArgs);
+    installExtendedEslint(installArgs);
+  }
+
   // TODO: Look into using handlebars or other templating engine to scaffold without needing to maintain multiple copies of the same file
   selectAppFile({ projectDir, packages });
   selectIndexFile({ projectDir, packages });
diff --git a/cli/src/index.ts b/cli/src/index.ts
index 66bca71a87..3e867b6e88 100644
--- a/cli/src/index.ts
+++ b/cli/src/index.ts
@@ -32,7 +32,7 @@ const main = async () => {
   const {
     appName,
     packages,
-    flags: { noGit, noInstall, importAlias },
+    flags: { noGit, noInstall, importAlias, prettierAndExtendedEslint },
   } = await runCli();
 
   const usePackages = buildPkgInstallerMap(packages);
@@ -45,6 +45,7 @@ const main = async () => {
     packages: usePackages,
     importAlias: importAlias,
     noInstall,
+    prettierAndExtendedEslint,
   });
 
   // Write name to package.json
@@ -67,10 +68,12 @@ const main = async () => {
   }
 
   // Rename _eslintrc.json to .eslintrc.json - we use _eslintrc.json to avoid conflicts with the monorepos linter
-  fs.renameSync(
-    path.join(projectDir, "_eslintrc.cjs"),
-    path.join(projectDir, ".eslintrc.cjs"),
-  );
+  if (fs.existsSync(path.join(projectDir, "_eslintrc.cjs"))) {
+    fs.renameSync(
+      path.join(projectDir, "_eslintrc.cjs"),
+      path.join(projectDir, ".eslintrc.cjs"),
+    );
+  }
 
   if (!noGit) {
     await initializeGit(projectDir);
diff --git a/cli/src/installers/dependencyVersionMap.ts b/cli/src/installers/dependencyVersionMap.ts
index dffeacc809..5fde931227 100644
--- a/cli/src/installers/dependencyVersionMap.ts
+++ b/cli/src/installers/dependencyVersionMap.ts
@@ -15,9 +15,6 @@ export const dependencyVersionMap = {
   tailwindcss: "^3.3.0",
   autoprefixer: "^10.4.14",
   postcss: "^8.4.21",
-  prettier: "^2.8.6",
-  "prettier-plugin-tailwindcss": "^0.2.6",
-  "@types/prettier": "^2.7.2",
 
   // tRPC
   "@trpc/client": "^10.18.0",
@@ -26,5 +23,14 @@ export const dependencyVersionMap = {
   "@trpc/next": "^10.18.0",
   "@tanstack/react-query": "^4.28.0",
   superjson: "1.12.2",
+
+  // Prettier
+  prettier: "^2.8.6",
+  "prettier-plugin-tailwindcss": "^0.2.6",
+  "@types/prettier": "^2.7.2",
+  "@ianvs/prettier-plugin-sort-imports": "^3.7.2",
+
+  // Eslint
+  "eslint-config-next": "^13.4.1",
 } as const;
 export type AvailableDependencies = keyof typeof dependencyVersionMap;
diff --git a/cli/src/installers/eslint.ts b/cli/src/installers/eslint.ts
new file mode 100644
index 0000000000..7c5536132b
--- /dev/null
+++ b/cli/src/installers/eslint.ts
@@ -0,0 +1,23 @@
+import { type Installer } from "./index.js";
+import fs from "fs-extra";
+import path from "path";
+import { PKG_ROOT } from "~/consts.js";
+import { addPackageDependency } from "~/utils/addPackageDependency.js";
+
+export const installExtendedEslint: Installer = ({ projectDir }) => {
+  addPackageDependency({
+    dependencies: ["eslint-config-next"],
+    devMode: true,
+    projectDir,
+  });
+
+  const configDir = path.join(PKG_ROOT, "template/extras/config");
+
+  // Remove the default config
+  fs.rmSync(path.join(projectDir, "_eslintrc.cjs"));
+
+  fs.copySync(
+    path.join(configDir, "_eslintrc.cjs"),
+    path.join(projectDir, ".eslintrc.cjs"),
+  );
+};
diff --git a/cli/src/installers/prettier.ts b/cli/src/installers/prettier.ts
new file mode 100644
index 0000000000..8b33d3b9d0
--- /dev/null
+++ b/cli/src/installers/prettier.ts
@@ -0,0 +1,55 @@
+import { type Installer } from "../installers/index.js";
+import { type AvailableDependencies } from "./dependencyVersionMap.js";
+import fs from "fs-extra";
+import path from "path";
+import { PKG_ROOT } from "~/consts.js";
+import { addPackageDependency } from "~/utils/addPackageDependency.js";
+import { addPackageScript } from "~/utils/addPackageScript.js";
+
+export const installPrettier: Installer = ({ projectDir, packages }) => {
+  const packeagesToInstall: AvailableDependencies[] = [
+    "prettier",
+    "@types/prettier",
+    "@ianvs/prettier-plugin-sort-imports",
+  ];
+
+  if (packages?.tailwind.inUse) {
+    packeagesToInstall.push("prettier-plugin-tailwindcss");
+  }
+
+  addPackageDependency({
+    projectDir,
+    dependencies: packeagesToInstall,
+    devMode: true,
+  });
+
+  addPackageScript({
+    projectDir,
+    scripts: [
+      {
+        name: "format",
+        value: "pnpm format:check --write",
+      },
+      {
+        name: "format:check",
+        value:
+          "pnpm prettier --check --plugin-search-dir=. **/*.{cjs,mjs,ts,tsx,md,json} --ignore-path ../.gitignore --ignore-unknown --no-error-on-unmatched-pattern",
+      },
+    ],
+  });
+
+  if (packages?.tailwind.inUse) {
+    fs.copySync(
+      path.join(
+        PKG_ROOT,
+        "template/extras/config/prettier-with-tailwind.config.cjs",
+      ),
+      path.join(projectDir, "prettier.config.cjs"),
+    );
+  } else {
+    fs.copySync(
+      path.join(PKG_ROOT, "template/extras/config/_prettier.config.cjs"),
+      path.join(projectDir, "prettier.config.cjs"),
+    );
+  }
+};
diff --git a/cli/src/installers/tailwind.ts b/cli/src/installers/tailwind.ts
index 10fd860a3c..681841b989 100644
--- a/cli/src/installers/tailwind.ts
+++ b/cli/src/installers/tailwind.ts
@@ -7,14 +7,7 @@ import { addPackageDependency } from "~/utils/addPackageDependency.js";
 export const tailwindInstaller: Installer = ({ projectDir }) => {
   addPackageDependency({
     projectDir,
-    dependencies: [
-      "tailwindcss",
-      "postcss",
-      "autoprefixer",
-      "prettier",
-      "prettier-plugin-tailwindcss",
-      "@types/prettier",
-    ],
+    dependencies: ["tailwindcss", "postcss", "autoprefixer"],
     devMode: true,
   });
 
@@ -26,16 +19,12 @@ export const tailwindInstaller: Installer = ({ projectDir }) => {
   const postcssCfgSrc = path.join(extrasDir, "config/postcss.config.cjs");
   const postcssCfgDest = path.join(projectDir, "postcss.config.cjs");
 
-  const prettierSrc = path.join(extrasDir, "config/prettier.config.cjs");
-  const prettierDest = path.join(projectDir, "prettier.config.cjs");
-
   const cssSrc = path.join(extrasDir, "src/styles/globals.css");
   const cssDest = path.join(projectDir, "src/styles/globals.css");
 
   fs.copySync(twCfgSrc, twCfgDest);
   fs.copySync(postcssCfgSrc, postcssCfgDest);
   fs.copySync(cssSrc, cssDest);
-  fs.copySync(prettierSrc, prettierDest);
 
   // Remove vanilla css file
   const indexModuleCss = path.join(projectDir, "src/pages/index.module.css");
diff --git a/cli/src/utils/addPackageScript.ts b/cli/src/utils/addPackageScript.ts
new file mode 100644
index 0000000000..6ad54b3e44
--- /dev/null
+++ b/cli/src/utils/addPackageScript.ts
@@ -0,0 +1,26 @@
+import fs from "fs-extra";
+import path from "path";
+import sortPackageJson from "sort-package-json";
+import { type PackageJson } from "type-fest";
+
+export const addPackageScript = (opts: {
+  scripts: { name: string; value: string }[];
+  projectDir: string;
+}) => {
+  const pkgJson = fs.readJSONSync(
+    path.join(opts.projectDir, "package.json"),
+  ) as PackageJson;
+
+  if (!pkgJson.scripts) {
+    pkgJson.scripts = {};
+  }
+
+  for (const script of opts.scripts) {
+    pkgJson.scripts[script.name] = script.value;
+  }
+  const sortedPkgJson = sortPackageJson(pkgJson);
+
+  fs.writeJSONSync(path.join(opts.projectDir, "package.json"), sortedPkgJson, {
+    spaces: 2,
+  });
+};
diff --git a/cli/template/base/_eslintrc.cjs b/cli/template/base/_eslintrc.cjs
index 8b7a0e8f9c..3733acb0cf 100644
--- a/cli/template/base/_eslintrc.cjs
+++ b/cli/template/base/_eslintrc.cjs
@@ -3,33 +3,11 @@ const path = require("path");
 
 /** @type {import("eslint").Linter.Config} */
 const config = {
-  overrides: [
-    {
-      extends: [
-        "plugin:@typescript-eslint/recommended-requiring-type-checking",
-      ],
-      files: ["*.ts", "*.tsx"],
-      parserOptions: {
-        project: path.join(__dirname, "tsconfig.json"),
-      },
-    },
-  ],
   parser: "@typescript-eslint/parser",
   parserOptions: {
     project: path.join(__dirname, "tsconfig.json"),
   },
   plugins: ["@typescript-eslint"],
-  extends: ["next/core-web-vitals", "plugin:@typescript-eslint/recommended"],
-  rules: {
-    "@typescript-eslint/consistent-type-imports": [
-      "warn",
-      {
-        prefer: "type-imports",
-        fixStyle: "inline-type-imports",
-      },
-    ],
-    "@typescript-eslint/no-unused-vars": ["warn", { argsIgnorePattern: "^_" }],
-  },
 };
 
 module.exports = config;
diff --git a/cli/template/base/package.json b/cli/template/base/package.json
index 23bb2c89da..104332ac5c 100644
--- a/cli/template/base/package.json
+++ b/cli/template/base/package.json
@@ -23,7 +23,6 @@
     "@typescript-eslint/eslint-plugin": "^5.56.0",
     "@typescript-eslint/parser": "^5.56.0",
     "eslint": "^8.36.0",
-    "eslint-config-next": "^13.4.1",
     "typescript": "^5.0.2"
   }
 }
diff --git a/cli/template/extras/config/_eslintrc.cjs b/cli/template/extras/config/_eslintrc.cjs
new file mode 100644
index 0000000000..758c95a7b3
--- /dev/null
+++ b/cli/template/extras/config/_eslintrc.cjs
@@ -0,0 +1,43 @@
+// eslint-disable-next-line @typescript-eslint/no-var-requires
+const path = require("path");
+
+/** @type {import("eslint").Linter.Config} */
+const config = {
+  overrides: [
+    {
+      extends: [
+        "plugin:@typescript-eslint/recommended-requiring-type-checking",
+      ],
+      files: ["*.ts", "*.tsx"],
+      parserOptions: {
+        project: path.join(__dirname, "tsconfig.json"),
+      },
+    },
+  ],
+  parser: "@typescript-eslint/parser",
+  parserOptions: {
+    project: path.join(__dirname, "tsconfig.json"),
+  },
+  plugins: ["@typescript-eslint"],
+  extends: ["next/core-web-vitals", "plugin:@typescript-eslint/recommended"],
+  rules: {
+    "@typescript-eslint/consistent-type-imports": [
+      "warn",
+      {
+        prefer: "type-imports",
+        fixStyle: "inline-type-imports",
+      },
+    ],
+    "@typescript-eslint/no-unused-vars": ["warn", { argsIgnorePattern: "^_" }],
+    "@typescript-eslint/no-misused-promises": [
+      2,
+      {
+        checksVoidReturn: {
+          attributes: false,
+        },
+      },
+    ],
+  },
+};
+
+module.exports = config;
diff --git a/cli/template/extras/config/prettier.config.cjs b/cli/template/extras/config/_prettier.config.cjs
similarity index 58%
rename from cli/template/extras/config/prettier.config.cjs
rename to cli/template/extras/config/_prettier.config.cjs
index ca28ed9e46..6058b6de93 100644
--- a/cli/template/extras/config/prettier.config.cjs
+++ b/cli/template/extras/config/_prettier.config.cjs
@@ -1,6 +1,6 @@
 /** @type {import("prettier").Config} */
 const config = {
-  plugins: [require.resolve("prettier-plugin-tailwindcss")],
+  plugins: ["@ianvs/prettier-plugin-sort-imports"],
 };
 
 module.exports = config;
diff --git a/cli/template/extras/config/prettier-with-tailwind.config.cjs b/cli/template/extras/config/prettier-with-tailwind.config.cjs
new file mode 100644
index 0000000000..f817bf3608
--- /dev/null
+++ b/cli/template/extras/config/prettier-with-tailwind.config.cjs
@@ -0,0 +1,9 @@
+/** @type {import("prettier").Config} */
+const config = {
+  plugins: [
+    "@ianvs/prettier-plugin-sort-imports",
+    "prettier-plugin-tailwindcss",
+  ],
+};
+
+module.exports = config;
diff --git a/www/.prettierrc.cjs b/www/.prettierrc.cjs
index 3dd61cf5bd..39a5ef01c8 100644
--- a/www/.prettierrc.cjs
+++ b/www/.prettierrc.cjs
@@ -5,6 +5,7 @@ const config = {
   plugins: [
     ...baseConfig.plugins,
     require.resolve("prettier-plugin-astro"),
+    require.resolve("@ianvs/prettier-plugin-sort-imports"),
     require.resolve("prettier-plugin-tailwindcss"), // MUST come last
   ],
   pluginSearchDirs: false,
diff --git a/www/src/pages/en/usage/tailwind.md b/www/src/pages/en/usage/tailwind.md
index bdb355a4b0..12e11a3521 100644
--- a/www/src/pages/en/usage/tailwind.md
+++ b/www/src/pages/en/usage/tailwind.md
@@ -74,7 +74,7 @@ Make sure you have editor plugins for Tailwind installed to improve your experie
 
 ### Formatting
 
-Tailwind CSS classes can easily get a bit messy, so a formatter for the classes is a must have. [Tailwind CSS Prettier Plugin](https://github.com/tailwindlabs/prettier-plugin-tailwindcss) sorts the classes in the [recommended order](https://tailwindcss.com/blog/automatic-class-sorting-with-prettier#how-classes-are-sorted) so that the classes match the outputted css bundle. When selecting Tailwind in the CLI, we will install and configure this for you.
+Tailwind CSS classes can easily get a bit messy, so a formatter for the classes is a must have. [Tailwind CSS Prettier Plugin](https://github.com/tailwindlabs/prettier-plugin-tailwindcss) sorts the classes in the [recommended order](https://tailwindcss.com/blog/automatic-class-sorting-with-prettier#how-classes-are-sorted) so that the classes match the outputted css bundle. When selecting Tailwind in the CLI, we will install and configure this for you when the prettier option is selected.
 
 ### Conditionally Applying Classes