diff --git a/packages/@vue/cli/__tests__/Upgrader.spec.js b/packages/@vue/cli-plugin-babel/__tests__/babelMigrator.spec.js
similarity index 54%
rename from packages/@vue/cli/__tests__/Upgrader.spec.js
rename to packages/@vue/cli-plugin-babel/__tests__/babelMigrator.spec.js
index 3b831296de..42414a9c9a 100644
--- a/packages/@vue/cli/__tests__/Upgrader.spec.js
+++ b/packages/@vue/cli-plugin-babel/__tests__/babelMigrator.spec.js
@@ -1,20 +1,7 @@
-const fs = require('fs')
-const path = require('path')
-const create = require('@vue/cli-test-utils/createTestProject')
+const create = require('@vue/cli-test-utils/createUpgradableProject')
 const { logs } = require('@vue/cli-shared-utils')
 
-const Upgrader = require('../lib/Upgrader')
-
 jest.setTimeout(300000)
-
-const outsideTestFolder = path.resolve(__dirname, '../../../../../vue-upgrade-tests')
-
-beforeAll(() => {
-  if (!fs.existsSync(outsideTestFolder)) {
-    fs.mkdirSync(outsideTestFolder)
-  }
-})
-
 beforeEach(() => {
   process.env.VUE_CLI_TEST_DO_INSTALL_PLUGIN = true
 })
@@ -26,12 +13,12 @@ test('upgrade: plugin-babel v3.5', async () => {
         version: '3.5.3'
       }
     }
-  }, outsideTestFolder)
+  })
 
   const pkg = JSON.parse(await project.read('package.json'))
   expect(pkg.dependencies).not.toHaveProperty('core-js')
 
-  await (new Upgrader(project.dir)).upgrade('babel', {})
+  await project.upgrade('babel')
 
   const updatedPkg = JSON.parse(await project.read('package.json'))
   expect(updatedPkg.dependencies).toHaveProperty('core-js')
@@ -49,31 +36,13 @@ test('upgrade: plugin-babel with core-js 2', async () => {
         version: '3.8.0'
       }
     }
-  }, outsideTestFolder)
+  })
 
   const pkg = JSON.parse(await project.read('package.json'))
   expect(pkg.dependencies['core-js']).toMatch('^2')
 
-  await (new Upgrader(project.dir)).upgrade('babel', {})
+  await project.upgrade('babel')
 
   const updatedPkg = JSON.parse(await project.read('package.json'))
   expect(updatedPkg.dependencies['core-js']).toMatch('^3')
 })
-
-test('upgrade: should add eslint to devDependencies', async () => {
-  const project = await create('plugin-eslint-v3.0', {
-    plugins: {
-      '@vue/cli-plugin-eslint': {
-        version: '3.0.0'
-      }
-    }
-  }, outsideTestFolder)
-
-  const pkg = JSON.parse(await project.read('package.json'))
-  expect(pkg.devDependencies).not.toHaveProperty('eslint')
-
-  await (new Upgrader(project.dir)).upgrade('eslint', {})
-
-  const updatedPkg = JSON.parse(await project.read('package.json'))
-  expect(updatedPkg.devDependencies.eslint).toMatch('^4')
-})
diff --git a/packages/@vue/cli-plugin-eslint/__tests__/eslintMigrator.spec.js b/packages/@vue/cli-plugin-eslint/__tests__/eslintMigrator.spec.js
new file mode 100644
index 0000000000..1a570e38cf
--- /dev/null
+++ b/packages/@vue/cli-plugin-eslint/__tests__/eslintMigrator.spec.js
@@ -0,0 +1,68 @@
+jest.setTimeout(300000)
+jest.mock('inquirer')
+
+beforeEach(() => {
+  process.env.VUE_CLI_TEST_DO_INSTALL_PLUGIN = true
+})
+
+const create = require('@vue/cli-test-utils/createUpgradableProject')
+const { expectPrompts } = require('inquirer')
+
+test('upgrade: should add eslint to devDependencies', async () => {
+  const project = await create('plugin-eslint-v3.0', {
+    plugins: {
+      '@vue/cli-plugin-eslint': {
+        version: '3.0.0'
+      }
+    }
+  })
+
+  const pkg = JSON.parse(await project.read('package.json'))
+  expect(pkg.devDependencies).not.toHaveProperty('eslint')
+
+  expectPrompts([
+    {
+      message: `Your current ESLint version is v4`,
+      confirm: false
+    }
+  ])
+
+  await project.upgrade('eslint')
+
+  const updatedPkg = JSON.parse(await project.read('package.json'))
+  expect(updatedPkg.devDependencies.eslint).toMatch('^4')
+})
+
+test.only('upgrade: should upgrade eslint from v5 to v6', async () => {
+  const project = await create('plugin-eslint-with-eslint-5', {
+    plugins: {
+      '@vue/cli-plugin-eslint': {
+        version: '3.12.1',
+        config: 'airbnb'
+      }
+    }
+  })
+
+  const pkg = JSON.parse(await project.read('package.json'))
+  expect(pkg.devDependencies.eslint).toMatch('^5')
+
+  expectPrompts([
+    {
+      message: `Your current ESLint version is v5`,
+      confirm: true
+    }
+  ])
+
+  try {
+    await project.upgrade('eslint')
+  } catch (e) {
+    // TODO:
+    // Currently the `afterInvoke` hook will fail,
+    // because deps are not correctly installed in test env.
+    // Need to fix later.
+  }
+
+  const updatedPkg = JSON.parse(await project.read('package.json'))
+  expect(updatedPkg.devDependencies.eslint).toMatch('^6')
+  expect(updatedPkg.devDependencies).toHaveProperty('eslint-plugin-import')
+})
diff --git a/packages/@vue/cli-plugin-eslint/eslintDeps.js b/packages/@vue/cli-plugin-eslint/eslintDeps.js
new file mode 100644
index 0000000000..80baf86200
--- /dev/null
+++ b/packages/@vue/cli-plugin-eslint/eslintDeps.js
@@ -0,0 +1,45 @@
+const DEPS_MAP = {
+  base: {
+    eslint: '^6.7.2',
+    'eslint-plugin-vue': '^6.1.2'
+  },
+  airbnb: {
+    '@vue/eslint-config-airbnb': '^5.0.1',
+    'eslint-plugin-import': '^2.18.2'
+  },
+  prettier: {
+    '@vue/eslint-config-prettier': '^6.0.0',
+    'eslint-plugin-prettier': '^3.1.1',
+    prettier: '^1.19.1'
+  },
+  standard: {
+    '@vue/eslint-config-standard': '^5.1.0',
+    'eslint-plugin-import': '^2.18.2',
+    'eslint-plugin-node': '^9.1.0',
+    'eslint-plugin-promise': '^4.2.1',
+    'eslint-plugin-standard': '^4.0.0'
+  },
+  typescript: {
+    '@vue/eslint-config-typescript': '^5.0.1',
+    '@typescript-eslint/eslint-plugin': '^2.10.0',
+    '@typescript-eslint/parser': '^2.10.0'
+  }
+}
+
+exports.DEPS_MAP = DEPS_MAP
+
+exports.getDeps = function (api, preset) {
+  const deps = Object.assign({}, DEPS_MAP.base, DEPS_MAP[preset])
+
+  if (api.hasPlugin('typescript')) {
+    Object.assign(deps, DEPS_MAP.typescript)
+  }
+
+  if (api.hasPlugin('babel') && !api.hasPlugin('typescript')) {
+    Object.assign(deps, {
+      'babel-eslint': '^10.0.3'
+    })
+  }
+
+  return deps
+}
diff --git a/packages/@vue/cli-plugin-eslint/eslintOptions.js b/packages/@vue/cli-plugin-eslint/eslintOptions.js
index c278c036a4..4f4c528ba1 100644
--- a/packages/@vue/cli-plugin-eslint/eslintOptions.js
+++ b/packages/@vue/cli-plugin-eslint/eslintOptions.js
@@ -1,4 +1,4 @@
-exports.config = api => {
+exports.config = (api, preset) => {
   const config = {
     root: true,
     env: { node: true },
@@ -11,11 +11,35 @@ exports.config = api => {
       'no-debugger': makeJSOnlyValue(`process.env.NODE_ENV === 'production' ? 'error' : 'off'`)
     }
   }
+
   if (api.hasPlugin('babel') && !api.hasPlugin('typescript')) {
     config.parserOptions = {
       parser: 'babel-eslint'
     }
   }
+
+  if (preset === 'airbnb') {
+    config.extends.push('@vue/airbnb')
+  } else if (preset === 'standard') {
+    config.extends.push('@vue/standard')
+  } else if (preset === 'prettier') {
+    config.extends.push(...['eslint:recommended', '@vue/prettier'])
+  } else {
+    // default
+    config.extends.push('eslint:recommended')
+  }
+
+  if (api.hasPlugin('typescript')) {
+    // typically, typescript ruleset should be appended to the end of the `extends` array
+    // but that is not the case for prettier, as there are conflicting rules
+    if (preset === 'prettier') {
+      config.extends.pop()
+      config.extends.push(...['@vue/typescript/recommended', '@vue/prettier', '@vue/prettier/@typescript-eslint'])
+    } else {
+      config.extends.push('@vue/typescript/recommended')
+    }
+  }
+
   return config
 }
 
diff --git a/packages/@vue/cli-plugin-eslint/generator/index.js b/packages/@vue/cli-plugin-eslint/generator/index.js
index b6a4b76e84..042c4fdf56 100644
--- a/packages/@vue/cli-plugin-eslint/generator/index.js
+++ b/packages/@vue/cli-plugin-eslint/generator/index.js
@@ -2,74 +2,15 @@ const fs = require('fs')
 const path = require('path')
 
 module.exports = (api, { config, lintOn = [] }, _, invoking) => {
-  const eslintConfig = require('../eslintOptions').config(api)
-  const extentions = require('../eslintOptions').extensions(api)
-    .map(ext => ext.replace(/^\./, ''))  // remove the leading `.`
+  const eslintConfig = require('../eslintOptions').config(api, config)
+  const devDependencies = require('../eslintDeps').getDeps(api, config)
 
   const pkg = {
     scripts: {
       lint: 'vue-cli-service lint'
     },
     eslintConfig,
-    devDependencies: {
-      eslint: '^6.7.2',
-      'eslint-plugin-vue': '^6.1.2'
-    }
-  }
-
-  if (api.hasPlugin('babel') && !api.hasPlugin('typescript')) {
-    pkg.devDependencies['babel-eslint'] = '^10.0.3'
-  }
-
-  switch (config) {
-  case 'airbnb':
-    eslintConfig.extends.push('@vue/airbnb')
-    Object.assign(pkg.devDependencies, {
-      '@vue/eslint-config-airbnb': '^5.0.1',
-      'eslint-plugin-import': '^2.18.2'
-    })
-    break
-  case 'standard':
-    eslintConfig.extends.push('@vue/standard')
-    Object.assign(pkg.devDependencies, {
-      '@vue/eslint-config-standard': '^5.1.0',
-      'eslint-plugin-import': '^2.18.2',
-      'eslint-plugin-node': '^9.1.0',
-      'eslint-plugin-promise': '^4.2.1',
-      'eslint-plugin-standard': '^4.0.0'
-    })
-    break
-  case 'prettier':
-    eslintConfig.extends.push(
-      ...(api.hasPlugin('typescript')
-        ? ['eslint:recommended', '@vue/typescript/recommended', '@vue/prettier', '@vue/prettier/@typescript-eslint']
-        : ['eslint:recommended', '@vue/prettier']
-      )
-    )
-    Object.assign(pkg.devDependencies, {
-      '@vue/eslint-config-prettier': '^6.0.0',
-      'eslint-plugin-prettier': '^3.1.1',
-      prettier: '^1.19.1'
-    })
-    break
-  default:
-    // default
-    eslintConfig.extends.push('eslint:recommended')
-    break
-  }
-
-  // typescript support
-  if (api.hasPlugin('typescript')) {
-    Object.assign(pkg.devDependencies, {
-      '@vue/eslint-config-typescript': '^5.0.1',
-      '@typescript-eslint/eslint-plugin': '^2.10.0',
-      '@typescript-eslint/parser': '^2.10.0'
-    })
-    if (config !== 'prettier') {
-      // for any config other than `prettier`,
-      // typescript ruleset should be appended to the end of the `extends` array
-      eslintConfig.extends.push('@vue/typescript/recommended')
-    }
+    devDependencies
   }
 
   const editorConfigTemplatePath = path.resolve(__dirname, `./template/${config}/_editorconfig`)
@@ -102,6 +43,8 @@ module.exports = (api, { config, lintOn = [] }, _, invoking) => {
     pkg.gitHooks = {
       'pre-commit': 'lint-staged'
     }
+    const extentions = require('../eslintOptions').extensions(api)
+      .map(ext => ext.replace(/^\./, ''))  // remove the leading `.`
     pkg['lint-staged'] = {
       [`*.{${extentions.join(',')}}`]: ['vue-cli-service lint', 'git add']
     }
@@ -157,10 +100,6 @@ module.exports.applyTS = api => {
         parser: '@typescript-eslint/parser'
       }
     },
-    devDependencies: {
-      '@vue/eslint-config-typescript': '^5.0.1',
-      '@typescript-eslint/eslint-plugin': '^2.7.0',
-      '@typescript-eslint/parser': '^2.7.0'
-    }
+    devDependencies: require('../eslintDeps').DEPS_MAP.typescript
   })
 }
diff --git a/packages/@vue/cli-plugin-eslint/migrator/index.js b/packages/@vue/cli-plugin-eslint/migrator/index.js
index a1915af9d3..fe5caa41e8 100644
--- a/packages/@vue/cli-plugin-eslint/migrator/index.js
+++ b/packages/@vue/cli-plugin-eslint/migrator/index.js
@@ -1,26 +1,74 @@
-module.exports = (api) => {
+const inquirer = require('inquirer')
+const { semver } = require('@vue/cli-shared-utils')
+
+module.exports = async (api) => {
+  const pkg = require(api.resolve('package.json'))
+
+  let localESLintRange = pkg.devDependencies.eslint
+
   // if project is scaffolded by Vue CLI 3.0.x or earlier,
   // the ESLint dependency (ESLint v4) is inside @vue/cli-plugin-eslint;
   // in Vue CLI v4 it should be extracted to the project dependency list.
-  if (api.fromVersion('^3')) {
-    const pkg = require(api.resolve('package.json'))
-    const hasESLint = [
-      'dependencies',
-      'devDependencies',
-      'peerDependencies',
-      'optionalDependencies'
-    ].some(depType =>
-      Object.keys(pkg[depType] || {}).includes('eslint')
+  if (api.fromVersion('^3') && !localESLintRange) {
+    localESLintRange = '^4.19.1'
+    api.extendPackage({
+      devDependencies: {
+        eslint: localESLintRange,
+        'babel-eslint': '^8.2.5',
+        'eslint-plugin-vue': '^4.5.0'
+      }
+    })
+  }
+
+  const localESLintMajor = semver.major(
+    semver.maxSatisfying(
+      ['4.99.0', '5.99.0', '6.99.0'],
+      localESLintRange
     )
+  )
+
+  if (localESLintMajor === 6) {
+    return
+  }
+
+  const { confirmUpgrade } = await inquirer.prompt([{
+    name: 'confirmUpgrade',
+    type: 'confirm',
+    message:
+    `Your current ESLint version is v${localESLintMajor}.` +
+    `The lastest major version is v6.\n` +
+    `Do you want to upgrade? (May contain breaking changes)\n`
+  }])
+
+  if (confirmUpgrade) {
+    const { getDeps } = require('../eslintDeps')
+
+    const newDeps = getDeps(api)
+    if (pkg.devDependencies['@vue/eslint-config-airbnb']) {
+      Object.assign(newDeps, getDeps(api, 'airbnb'))
+    }
+    if (pkg.devDependencies['@vue/eslint-config-standard']) {
+      Object.assign(newDeps, getDeps(api, 'standard'))
+    }
+    if (pkg.devDependencies['@vue/eslint-config-prettier']) {
+      Object.assign(newDeps, getDeps(api, 'prettier'))
+    }
+
+    api.extendPackage({ devDependencies: newDeps })
 
-    if (!hasESLint) {
+    // in case anyone's upgrading from the legacy `typescript-eslint-parser`
+    if (api.hasPlugin('typescript')) {
       api.extendPackage({
-        devDependencies: {
-          eslint: '^4.19.1'
+        eslintConfig: {
+          parserOptions: {
+            parser: '@typescript-eslint/parser'
+          }
         }
       })
     }
 
-    // TODO: add a prompt for users to optionally upgrade their eslint configs to a new major version
+    // TODO:
+    // transform `@vue/prettier` to `eslint:recommended` + `@vue/prettier`
+    // transform `@vue/typescript` to `@vue/typescript/recommended` and also fix prettier compatibility for it
   }
 }
diff --git a/packages/@vue/cli-plugin-eslint/package.json b/packages/@vue/cli-plugin-eslint/package.json
index 080f777e87..d49e8c4359 100644
--- a/packages/@vue/cli-plugin-eslint/package.json
+++ b/packages/@vue/cli-plugin-eslint/package.json
@@ -26,6 +26,7 @@
     "@vue/cli-shared-utils": "^4.1.2",
     "eslint-loader": "^2.1.2",
     "globby": "^9.2.0",
+    "inquirer": "^6.3.1",
     "webpack": "^4.0.0",
     "yorkie": "^2.0.0"
   },
diff --git a/packages/@vue/cli-test-utils/createUpgradableProject.js b/packages/@vue/cli-test-utils/createUpgradableProject.js
new file mode 100644
index 0000000000..37b62c9755
--- /dev/null
+++ b/packages/@vue/cli-test-utils/createUpgradableProject.js
@@ -0,0 +1,24 @@
+const fs = require('fs')
+const path = require('path')
+
+const createTestProject = require('./createTestProject')
+const Upgrader = require('@vue/cli/lib/Upgrader')
+
+const outsideTestFolder = path.resolve(__dirname, '../../../../vue-upgrade-tests')
+
+module.exports = async function createUpgradableProject (...args) {
+  if (!fs.existsSync(outsideTestFolder)) {
+    fs.mkdirSync(outsideTestFolder)
+  }
+  process.env.VUE_CLI_TEST_DO_INSTALL_PLUGIN = true
+
+  const project = await createTestProject(...args, outsideTestFolder)
+  const upgrade = async function upgrade (pluginName, options) {
+    return (new Upgrader(project.dir)).upgrade(pluginName, options || {})
+  }
+
+  return {
+    ...project,
+    upgrade
+  }
+}