diff --git a/packages/cli/src/commands/doctor/ask.ts b/packages/cli/src/commands/doctor/ask.ts
new file mode 100644
index 0000000000..b4f947c609
--- /dev/null
+++ b/packages/cli/src/commands/doctor/ask.ts
@@ -0,0 +1,36 @@
+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'
+
+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(`Hi${userName},`)} \n\nI'm just a concept right now. Remember?`
+
+    const dialogue = {
+      question: args.question,
+      response: herokAIResponse,
+    }
+
+    if (flags.json) {
+      ux.styledJSON(dialogue)
+    } else {
+      ux.log(herokAIResponse)
+    }
+  }
+}
diff --git a/packages/cli/src/commands/doctor/diagnose.ts b/packages/cli/src/commands/doctor/diagnose.ts
new file mode 100644
index 0000000000..061d38550a
--- /dev/null
+++ b/packages/cli/src/commands/doctor/diagnose.ts
@@ -0,0 +1,125 @@
+import color from '@heroku-cli/color'
+import {Command, flags} from '@heroku-cli/command'
+import * as Heroku from '@heroku-cli/schema'
+import {ux} from '@oclif/core'
+import * as lodash from 'lodash'
+const clipboard = require('copy-paste')
+const {exec} = require('child_process')
+const {promisify} = require('util')
+const execAsync = promisify(exec)
+
+const getLocalNodeVersion = async () => {
+  const {stdout} = await execAsync('node -v')
+  return stdout
+}
+
+const getInstallMethod = () => {
+  return 'brew'
+}
+
+const getInstallLocation = async () => {
+  const {stdout} = await execAsync('which heroku')
+  const formattedOutput = stdout.replace(/\n/g, '')
+  return formattedOutput
+}
+
+const getLocalProxySettings = async (unmasked = false) => {
+  const command = `httpsProxy=$(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
+    }
+
+    await copyToClipboard(copiedResults)
+  }
+}
diff --git a/packages/cli/src/commands/doctor/recommend.ts b/packages/cli/src/commands/doctor/recommend.ts
new file mode 100644
index 0000000000..061d38550a
--- /dev/null
+++ b/packages/cli/src/commands/doctor/recommend.ts
@@ -0,0 +1,125 @@
+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
+    }
+
+    await copyToClipboard(copiedResults)
+  }
+}
diff --git a/packages/cli/src/lib/doctor/font/BentonSans Regular Regular.otf b/packages/cli/src/lib/doctor/font/BentonSans Regular Regular.otf
new file mode 100644
index 0000000000..68c339480a
Binary files /dev/null and b/packages/cli/src/lib/doctor/font/BentonSans Regular Regular.otf differ
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