diff --git a/packages/cli/package.json b/packages/cli/package.json
index d4deefab9e..59effb5357 100644
--- a/packages/cli/package.json
+++ b/packages/cli/package.json
@@ -46,6 +46,7 @@
     "ansi-escapes": "3.2.0",
     "async-file": "^2.0.2",
     "chalk": "^2.4.2",
+    "copy-paste": "^1.5.3",
     "date-fns": "^2.30.0",
     "debug": "4.1.1",
     "dotenv": "^16.3.1",
diff --git a/packages/cli/src/commands/doctor/ask.ts b/packages/cli/src/commands/doctor/ask.ts
new file mode 100644
index 0000000000..83e91598c9
--- /dev/null
+++ b/packages/cli/src/commands/doctor/ask.ts
@@ -0,0 +1,39 @@
+import color from '@heroku-cli/color'
+import {Command, flags} from '@heroku-cli/command'
+import * as Heroku from '@heroku-cli/schema'
+import {Args, ux} from '@oclif/core'
+// const Font = require('ascii-art-font')
+// Font.fontPath = '../../../lib/doctor/font'
+
+export default class DoctorAsk extends Command {
+  static description = 'recieve responses from HerokAI'
+  static topic = 'doctor'
+
+  static flags = {
+    interactive: flags.boolean({description: 'use interactive mode with HerokAI', required: false}),
+    json: flags.boolean({description: 'display doctor:ask input/output as json', required: false}),
+  }
+
+  static args = {
+    question: Args.string({description: 'question to ask HerokAI', required: true}),
+  }
+
+  async run() {
+    const {args, flags} = await this.parse(DoctorAsk)
+    const {body: user} = await this.heroku.get<Heroku.Account>('/account', {retryAuth: false})
+    const userName = (user && user.name) ? ` ${user.name}` : ''
+    const herokAIResponse = `${color.heroku(`${color.bold(`Hi${userName},`)} \n\nI'm just a concept right now. Remember? Maybe you can get some buy in during the demo?`)}`
+    const herokAIJsonResponse = `Hi${userName}, I'm just a concept right now. Remember? Maybe you can get some buy in during the demo?`
+
+    const dialogue = {
+      question: args.question,
+      response: herokAIJsonResponse,
+    }
+
+    if (flags.json) {
+      ux.styledJSON(dialogue)
+    } else {
+      ux.log(herokAIResponse)
+    }
+  }
+}
diff --git a/packages/cli/src/commands/doctor/diagnose.ts b/packages/cli/src/commands/doctor/diagnose.ts
new file mode 100644
index 0000000000..6d6e0ec72d
--- /dev/null
+++ b/packages/cli/src/commands/doctor/diagnose.ts
@@ -0,0 +1,42 @@
+import color from '@heroku-cli/color'
+import {Command, flags} from '@heroku-cli/command'
+import * as Heroku from '@heroku-cli/schema'
+import {Args, ux} from '@oclif/core'
+import * as lodash from 'lodash'
+const clipboard = require('copy-paste')
+const {exec} = require('child_process')
+const {promisify} = require('util')
+const execAsync = promisify(exec)
+
+export default class DoctorDiagnose extends Command {
+  static description = 'check the heroku cli build for errors'
+  static topic = 'doctor'
+
+  static args = {
+    command: Args.string({description: 'command to check for errors', required: false}),
+  }
+
+  static flags = {
+    all: flags.boolean({description: 'check all commands for errors', required: false, char: 'A'}),
+    build: flags.boolean({description: 'check entire heroku cli build for errors', required: false, char: 'b'}),
+    'copy-results': flags.boolean({description: 'copies results to clipboard', required: false, char: 'p'}),
+    json: flags.boolean({description: 'display as json', required: false}),
+  }
+
+  async run() {
+    const {args, flags} = await this.parse(DoctorDiagnose)
+    const errorMessage = 'H23'
+    const stackMessage = 'some/crazy/looking/stack/message'
+
+    ux.action.start(`${color.heroku(`Running diagnostics on ${color.cyan(`${args.command}`)}`)}`)
+    ux.action.stop()
+    ux.action.start(`${color.heroku(`Writing up report on ${color.cyan(`${args.command}`)}`)}`)
+    ux.action.stop()
+
+    ux.log('\n')
+    ux.log(`${color.bold(`${color.heroku('Report')}`)}`)
+    ux.log(`${color.bold(`${color.heroku('-------------------------------------------')}`)}`)
+    ux.log(`${color.cyan('Error:')} ${errorMessage}`)
+    ux.log(`${color.cyan('Stack:')} ${stackMessage}`)
+  }
+}
diff --git a/packages/cli/src/commands/doctor/recommend.ts b/packages/cli/src/commands/doctor/recommend.ts
new file mode 100644
index 0000000000..f63c3c0c8b
--- /dev/null
+++ b/packages/cli/src/commands/doctor/recommend.ts
@@ -0,0 +1,42 @@
+import color from '@heroku-cli/color'
+import {Command, flags} from '@heroku-cli/command'
+import * as Heroku from '@heroku-cli/schema'
+import {Args, ux} from '@oclif/core'
+import * as lodash from 'lodash'
+const clipboard = require('copy-paste')
+const {exec} = require('child_process')
+const {promisify} = require('util')
+const execAsync = promisify(exec)
+
+export default class DoctorRecommend extends Command {
+  static description = 'recieve the latest tips, general playbooks, and resources when encountering cli issues'
+  static topic = 'doctor'
+  static examples = [
+    '$ heroku doctor:recommend <command>',
+    '$ heroku doctor:recommend --type command "Command will not show output"',
+    '$ heroku doctor:recommend --type install "Cli is erroring during install"',
+    '$ heroku doctor:recommend --type error "I get an error when running..."',
+    '$ heroku doctor:recommend --type network "I can not push my latest release"',
+    '$ heroku doctor:recommend --type permissions "I cannot get access to..."',
+  ]
+
+  static args = {
+    statement: Args.string({description: 'statement of problem user is enountering', required: true}),
+  }
+
+  static flags = {
+    type: flags.string({description: 'type of help required', required: false}),
+    'copy-results': flags.boolean({description: 'copies results to clipboard', required: false}),
+  }
+
+  async run() {
+    const {flags} = await this.parse(DoctorRecommend)
+    ux.log(`${color.bold(`${color.heroku('Recommendations')}`)}`)
+    ux.log(`${color.bold(`${color.heroku('-------------------------------------------')}`)}`)
+    ux.log(`- Visit ${color.cyan('"https://devcenter.heroku.com/articles/heroku-cli"')} for more install information`)
+    ux.log('- Try reinstalling the heroku cli')
+    ux.log(`- Try running ${color.cyan('"$ heroku doctor:diagnose"')}`)
+    ux.log(`- Try running ${color.cyan('"$ heroku doctor:ask"')}`)
+    ux.log('- Check which version of the heroku cli your are running')
+  }
+}
diff --git a/packages/cli/src/commands/doctor/vitals.ts b/packages/cli/src/commands/doctor/vitals.ts
new file mode 100644
index 0000000000..0bfceaf426
--- /dev/null
+++ b/packages/cli/src/commands/doctor/vitals.ts
@@ -0,0 +1,127 @@
+import color from '@heroku-cli/color'
+import {Command, flags} from '@heroku-cli/command'
+import * as Heroku from '@heroku-cli/schema'
+import {ux} from '@oclif/core'
+import * as lodash from 'lodash'
+const clipboard = require('copy-paste')
+const {exec} = require('child_process')
+const {promisify} = require('util')
+const execAsync = promisify(exec)
+
+const getLocalNodeVersion = async () => {
+  const {stdout} = await execAsync('node -v')
+  return stdout
+}
+
+const getInstallMethod = () => {
+  return 'brew'
+}
+
+const getInstallLocation = async () => {
+  const {stdout} = await execAsync('which heroku')
+  const formattedOutput = stdout.replace(/\n/g, '')
+  return formattedOutput
+}
+
+const getLocalProxySettings = async (unmasked = false) => {
+  const command = `httpsProxy=$(scutil --proxy | awk -F': ' '/HTTPSProxy/ {print $2}')
+
+  # Check if HTTPSProxy has a value
+  if [ -n "$httpsProxy" ]; then
+    echo "$httpsProxy"
+  else
+    echo "no proxy set"
+  fi`
+
+  const {stdout} = await execAsync(command)
+  const hasProxySet = !stdout.includes('no proxy set')
+
+  if (unmasked) {
+    return stdout
+  }
+
+  return hasProxySet ? 'xxxxx\n' : stdout
+}
+
+const getInstalledPLugins = async () => {
+  const {stdout} = await execAsync('heroku plugins')
+  return stdout
+}
+
+const getHerokuStatus = async () => {
+  const {stdout} = await execAsync('heroku status')
+  return stdout
+}
+
+const copyToClipboard = async (value: any) => {
+  clipboard.copy(value)
+}
+
+export default class DoctorVitals extends Command {
+  static description = 'list local user setup for debugging'
+  static topic = 'doctor'
+
+  static flags = {
+    unmask: flags.boolean({description: 'unmasks fields heroku has deemed potentially sensitive', required: false}),
+    'copy-results': flags.boolean({description: 'copies results to clipboard', required: false}),
+    json: flags.boolean({description: 'display as json', required: false}),
+  }
+
+  async run() {
+    const {flags} = await this.parse(DoctorVitals)
+    const copyResults = flags['copy-results']
+    const time = new Date()
+    const dateChecked = time.toISOString().split('T')[0]
+    const cliInstallMethod = getInstallMethod()
+    const cliInstallLocation = await getInstallLocation()
+    const os = this.config.platform
+    const cliVersion = `v${this.config.version}`
+    const nodeVersion = await getLocalNodeVersion()
+    const networkConfig = {
+      httpsProxy: await getLocalProxySettings(flags.unmask),
+    }
+    const installedPlugins = await getInstalledPLugins()
+    const herokuStatus = await getHerokuStatus()
+
+    const isHerokuUp = true
+    let copiedResults = ''
+
+    ux.styledHeader(`${color.heroku('Heroku CLI Doctor')} · ${color.cyan(`User Local Setup on ${dateChecked}`)}`)
+    ux.log(`${color.cyan('CLI Install Method:')} ${cliInstallMethod}`)
+    ux.log(`${color.cyan('CLI Install Location:')} ${cliInstallLocation}`)
+    ux.log(`${color.cyan('OS:')} ${os}`)
+    ux.log(`${color.cyan('Heroku CLI Version:')} ${cliVersion}`)
+    ux.log(`${color.cyan('Node Version:')} ${nodeVersion}`)
+
+    ux.log(`${color.cyan('Network Config')}`)
+    ux.log(`HTTPSProxy: ${networkConfig.httpsProxy}`)
+
+    ux.log(`${color.cyan('Installed Plugins')}`)
+    ux.log(`${installedPlugins}`)
+
+    ux.log(`${color.bold(color.heroku('Heroku Status'))}`)
+    ux.log(`${color.bold(color.heroku('----------------------------------------'))}`)
+    ux.log(isHerokuUp ? color.green(herokuStatus) : color.red(herokuStatus))
+
+    if (copyResults) {
+      // copy results to clipboard here
+      copiedResults += `Heroku CLI Doctor · User Local Setup on ${dateChecked}\n`
+      copiedResults += `CLI Install Method: ${cliInstallMethod}\n`
+      copiedResults += `CLI Install Location: ${cliInstallLocation}\n`
+      copiedResults += `OS: ${os}\n`
+      copiedResults += `Heroku CLI Version: ${cliVersion}\n`
+      copiedResults += `Node Version: ${nodeVersion}\n`
+      copiedResults += 'Network Config\n'
+      copiedResults += `HTTPSProxy: ${networkConfig.httpsProxy}\n`
+      copiedResults += 'Installed Plugins\n'
+      copiedResults += `${installedPlugins}\n`
+      copiedResults += 'Heroku Status\n'
+      copiedResults += '----------------------------------------\n'
+      copiedResults += herokuStatus
+
+      ux.log(`\n${color.bold(`${color.heroku('Results copied to clipboard!')}`)}`)
+    }
+
+    await copyToClipboard(copiedResults)
+  }
+}
diff --git a/packages/cli/src/lib/doctor/font/README.md b/packages/cli/src/lib/doctor/font/README.md
new file mode 100644
index 0000000000..8203fbd72a
--- /dev/null
+++ b/packages/cli/src/lib/doctor/font/README.md
@@ -0,0 +1 @@
+This is just temporary proof of concept. Actual font should be imported via heroku's cdn.
\ No newline at end of file
diff --git a/packages/cli/src/lib/doctor/font/heroku.otf b/packages/cli/src/lib/doctor/font/heroku.otf
new file mode 100644
index 0000000000..68c339480a
Binary files /dev/null and b/packages/cli/src/lib/doctor/font/heroku.otf differ
diff --git a/yarn.lock b/yarn.lock
index 3abdab80d1..85a0282d33 100644
--- a/yarn.lock
+++ b/yarn.lock
@@ -6215,6 +6215,15 @@ __metadata:
   languageName: node
   linkType: hard
 
+"copy-paste@npm:^1.5.3":
+  version: 1.5.3
+  resolution: "copy-paste@npm:1.5.3"
+  dependencies:
+    iconv-lite: ^0.4.8
+  checksum: 97fac26ea222478e93f2177fdb29f4e90687698a600a128032aa96f15956afe45d03b4c226756264d9266ddee39926f177992cc1809cbfe659c622275095eddd
+  languageName: node
+  linkType: hard
+
 "core-util-is@npm:1.0.2, core-util-is@npm:~1.0.0":
   version: 1.0.2
   resolution: "core-util-is@npm:1.0.2"
@@ -9317,6 +9326,7 @@ __metadata:
     bats: ^1.1.0
     chai: ^4.2.0
     chalk: ^2.4.2
+    copy-paste: ^1.5.3
     date-fns: ^2.30.0
     debug: 4.1.1
     dotenv: ^16.3.1
@@ -9564,7 +9574,7 @@ __metadata:
   languageName: node
   linkType: hard
 
-"iconv-lite@npm:^0.4.17, iconv-lite@npm:^0.4.24":
+"iconv-lite@npm:^0.4.17, iconv-lite@npm:^0.4.24, iconv-lite@npm:^0.4.8":
   version: 0.4.24
   resolution: "iconv-lite@npm:0.4.24"
   dependencies: