diff --git a/packages/cli/package.json b/packages/cli/package.json
index 1644c69d0c..afc6a2c813 100644
--- a/packages/cli/package.json
+++ b/packages/cli/package.json
@@ -45,7 +45,9 @@
     "pouchdb": "7.3.0",
     "pouchdb-replication-stream": "1.2.9",
     "randomstring": "1.1.5",
-    "tar": "6.1.11"
+    "tar": "6.1.11",
+    "yaml": "^2.1.1",
+    "find-free-port": "^2.0.0"
   },
   "devDependencies": {
     "copyfiles": "^2.4.1",
diff --git a/packages/cli/src/hosting/genUser.js b/packages/cli/src/hosting/genUser.js
new file mode 100644
index 0000000000..b6e078c8bd
--- /dev/null
+++ b/packages/cli/src/hosting/genUser.js
@@ -0,0 +1,17 @@
+const { success } = require("../utils")
+const { updateDockerComposeService } = require("./utils")
+const randomString = require("randomstring")
+
+exports.generateUser = async () => {
+  const email = "admin@admin.com"
+  const password = randomString.generate({ length: 6 })
+  updateDockerComposeService(service => {
+    service.environment["BB_ADMIN_USER_EMAIL"] = email
+    service.environment["BB_ADMIN_USER_PASSWORD"] = password
+  })
+  console.log(
+    success(
+      `User admin credentials configured, access with email: ${email} - password: ${password}`
+    )
+  )
+}
diff --git a/packages/cli/src/hosting/index.js b/packages/cli/src/hosting/index.js
index ae62c45992..d8133c4959 100644
--- a/packages/cli/src/hosting/index.js
+++ b/packages/cli/src/hosting/index.js
@@ -1,164 +1,18 @@
 const Command = require("../structures/Command")
-const { CommandWords, InitTypes, AnalyticsEvents } = require("../constants")
-const { lookpath } = require("lookpath")
-const {
-  downloadFile,
-  logErrorToFile,
-  success,
-  info,
-  parseEnv,
-} = require("../utils")
-const { confirmation } = require("../questions")
-const fs = require("fs")
-const compose = require("docker-compose")
-const makeEnv = require("./makeEnv")
-const axios = require("axios")
-const { captureEvent } = require("../events")
-
-const BUDIBASE_SERVICES = ["app-service", "worker-service", "proxy-service"]
-const ERROR_FILE = "docker-error.log"
-const FILE_URLS = [
-  "https://raw.githubusercontent.com/Budibase/budibase/master/hosting/docker-compose.yaml",
-]
-const DO_USER_DATA_URL = "http://169.254.169.254/metadata/v1/user-data"
-
-async function downloadFiles() {
-  const promises = []
-  for (let url of FILE_URLS) {
-    const fileName = url.split("/").slice(-1)[0]
-    promises.push(downloadFile(url, `./${fileName}`))
-  }
-  await Promise.all(promises)
-}
-
-async function checkDockerConfigured() {
-  const error =
-    "docker/docker-compose has not been installed, please follow instructions at: https://docs.budibase.com/docs/docker-compose"
-  const docker = await lookpath("docker")
-  const compose = await lookpath("docker-compose")
-  if (!docker || !compose) {
-    throw error
-  }
-}
-
-function checkInitComplete() {
-  if (!fs.existsSync(makeEnv.filePath)) {
-    throw "Please run the hosting --init command before any other hosting command."
-  }
-}
-
-async function handleError(func) {
-  try {
-    await func()
-  } catch (err) {
-    if (err && err.err) {
-      logErrorToFile(ERROR_FILE, err.err)
-    }
-    throw `Failed to start - logs written to file: ${ERROR_FILE}`
-  }
-}
-
-async function init(type) {
-  const isQuick = type === InitTypes.QUICK || type === InitTypes.DIGITAL_OCEAN
-  await checkDockerConfigured()
-  if (!isQuick) {
-    const shouldContinue = await confirmation(
-      "This will create multiple files in current directory, should continue?"
-    )
-    if (!shouldContinue) {
-      console.log("Stopping.")
-      return
-    }
-  }
-  captureEvent(AnalyticsEvents.SelfHostInit, {
-    type,
-  })
-  await downloadFiles()
-  const config = isQuick ? makeEnv.QUICK_CONFIG : {}
-  if (type === InitTypes.DIGITAL_OCEAN) {
-    try {
-      const output = await axios.get(DO_USER_DATA_URL)
-      const response = parseEnv(output.data)
-      for (let [key, value] of Object.entries(makeEnv.ConfigMap)) {
-        if (response[key]) {
-          config[value] = response[key]
-        }
-      }
-    } catch (err) {
-      // don't need to handle error, just don't do anything
-    }
-  }
-  await makeEnv.make(config)
-}
-
-async function start() {
-  await checkDockerConfigured()
-  checkInitComplete()
-  console.log(
-    info(
-      "Starting services, this may take a moment - first time this may take a few minutes to download images."
-    )
-  )
-  const port = makeEnv.get("MAIN_PORT")
-  await handleError(async () => {
-    // need to log as it makes it more clear
-    await compose.upAll({ cwd: "./", log: true })
-  })
-  console.log(
-    success(
-      `Services started, please go to http://localhost:${port} for next steps.`
-    )
-  )
-}
-
-async function status() {
-  await checkDockerConfigured()
-  checkInitComplete()
-  console.log(info("Budibase status"))
-  await handleError(async () => {
-    const response = await compose.ps()
-    console.log(response.out)
-  })
-}
-
-async function stop() {
-  await checkDockerConfigured()
-  checkInitComplete()
-  console.log(info("Stopping services, this may take a moment."))
-  await handleError(async () => {
-    await compose.stop()
-  })
-  console.log(success("Services have been stopped successfully."))
-}
-
-async function update() {
-  await checkDockerConfigured()
-  checkInitComplete()
-  if (await confirmation("Do you wish to update you docker-compose.yaml?")) {
-    await downloadFiles()
-  }
-  await handleError(async () => {
-    const status = await compose.ps()
-    const parts = status.out.split("\n")
-    const isUp = parts[2] && parts[2].indexOf("Up") !== -1
-    if (isUp) {
-      console.log(info("Stopping services, this may take a moment."))
-      await compose.stop()
-    }
-    console.log(info("Beginning update, this may take a few minutes."))
-    await compose.pullMany(BUDIBASE_SERVICES, { log: true })
-    if (isUp) {
-      console.log(success("Update complete, restarting services..."))
-      await start()
-    }
-  })
-}
+const { CommandWords } = require("../constants")
+const { init } = require("./init")
+const { start } = require("./start")
+const { stop } = require("./stop")
+const { status } = require("./status")
+const { update } = require("./update")
+const { generateUser } = require("./genUser")
+const { watchPlugins } = require("./watch")
 
 const command = new Command(`${CommandWords.HOSTING}`)
   .addHelp("Controls self hosting on the Budibase platform.")
   .addSubOption(
     "--init [type]",
-    "Configure a self hosted platform in current directory, type can be unspecified or 'quick'.",
+    "Configure a self hosted platform in current directory, type can be unspecified, 'quick' or 'single'.",
     init
   )
   .addSubOption(
@@ -181,5 +35,16 @@ const command = new Command(`${CommandWords.HOSTING}`)
     "Update the Budibase images to the latest version.",
     update
   )
+  .addSubOption(
+    "--watch-plugin-dir [directory]",
+    "Add plugin directory watching to a Budibase install.",
+    watchPlugins
+  )
+  .addSubOption(
+    "--gen-user",
+    "Create an admin user automatically as part of first start.",
+    generateUser
+  )
+  .addSubOption("--single", "Specify this with init to use the single image.")
 
 exports.command = command
diff --git a/packages/cli/src/hosting/init.js b/packages/cli/src/hosting/init.js
new file mode 100644
index 0000000000..37dfe9b4db
--- /dev/null
+++ b/packages/cli/src/hosting/init.js
@@ -0,0 +1,73 @@
+const { InitTypes, AnalyticsEvents } = require("../constants")
+const { confirmation } = require("../questions")
+const { captureEvent } = require("../events")
+const makeFiles = require("./makeFiles")
+const axios = require("axios")
+const { parseEnv } = require("../utils")
+const { checkDockerConfigured, downloadFiles } = require("./utils")
+const { watchPlugins } = require("./watch")
+const { generateUser } = require("./genUser")
+
+const DO_USER_DATA_URL = "http://169.254.169.254/metadata/v1/user-data"
+
+async function getInitConfig(type, isQuick, port) {
+  const config = isQuick ? makeFiles.QUICK_CONFIG : {}
+  if (type === InitTypes.DIGITAL_OCEAN) {
+    try {
+      const output = await axios.get(DO_USER_DATA_URL)
+      const response = parseEnv(output.data)
+      for (let [key, value] of Object.entries(makeFiles.ConfigMap)) {
+        if (response[key]) {
+          config[value] = response[key]
+        }
+      }
+    } catch (err) {
+      // don't need to handle error, just don't do anything
+    }
+  }
+  // override port
+  if (port) {
+    config[makeFiles.ConfigMap.MAIN_PORT] = port
+  }
+  return config
+}
+
+exports.init = async opts => {
+  let type, isSingle, watchDir, genUser, port
+  if (typeof opts === "string") {
+    type = opts
+  } else {
+    type = opts["init"]
+    isSingle = opts["single"]
+    watchDir = opts["watchPluginDir"]
+    genUser = opts["genUser"]
+    port = opts["port"]
+  }
+  const isQuick = type === InitTypes.QUICK || type === InitTypes.DIGITAL_OCEAN
+  await checkDockerConfigured()
+  if (!isQuick) {
+    const shouldContinue = await confirmation(
+      "This will create multiple files in current directory, should continue?"
+    )
+    if (!shouldContinue) {
+      console.log("Stopping.")
+      return
+    }
+  }
+  captureEvent(AnalyticsEvents.SelfHostInit, {
+    type,
+  })
+  const config = await getInitConfig(type, isQuick, port)
+  if (!isSingle) {
+    await downloadFiles()
+    await makeFiles.makeEnv(config)
+  } else {
+    await makeFiles.makeSingleCompose(config)
+  }
+  if (watchDir) {
+    await watchPlugins(watchDir)
+  }
+  if (genUser) {
+    await generateUser()
+  }
+}
diff --git a/packages/cli/src/hosting/makeEnv.js b/packages/cli/src/hosting/makeEnv.js
deleted file mode 100644
index d1d23999f8..0000000000
--- a/packages/cli/src/hosting/makeEnv.js
+++ /dev/null
@@ -1,66 +0,0 @@
-const { number } = require("../questions")
-const { success } = require("../utils")
-const fs = require("fs")
-const path = require("path")
-const randomString = require("randomstring")
-
-const FILE_PATH = path.resolve("./.env")
-
-function getContents(port) {
-  return `
-# Use the main port in the builder for your self hosting URL, e.g. localhost:10000
-MAIN_PORT=${port}
-
-# This section contains all secrets pertaining to the system
-JWT_SECRET=${randomString.generate()}
-MINIO_ACCESS_KEY=${randomString.generate()}
-MINIO_SECRET_KEY=${randomString.generate()}
-COUCH_DB_PASSWORD=${randomString.generate()}
-COUCH_DB_USER=${randomString.generate()}
-REDIS_PASSWORD=${randomString.generate()}
-INTERNAL_API_KEY=${randomString.generate()}
-
-# This section contains variables that do not need to be altered under normal circumstances
-APP_PORT=4002
-WORKER_PORT=4003
-MINIO_PORT=4004
-COUCH_DB_PORT=4005
-REDIS_PORT=6379
-WATCHTOWER_PORT=6161
-BUDIBASE_ENVIRONMENT=PRODUCTION`
-}
-
-module.exports.filePath = FILE_PATH
-module.exports.ConfigMap = {
-  MAIN_PORT: "port",
-}
-module.exports.QUICK_CONFIG = {
-  key: "budibase",
-  port: 10000,
-}
-
-module.exports.make = async (inputs = {}) => {
-  const hostingPort =
-    inputs.port ||
-    (await number(
-      "Please enter the port on which you want your installation to run: ",
-      10000
-    ))
-  const fileContents = getContents(hostingPort)
-  fs.writeFileSync(FILE_PATH, fileContents)
-  console.log(
-    success(
-      "Configuration has been written successfully - please check .env file for more details."
-    )
-  )
-}
-
-module.exports.get = property => {
-  const props = fs.readFileSync(FILE_PATH, "utf8").split(property)
-  if (props[0].charAt(0) === "=") {
-    property = props[0]
-  } else {
-    property = props[1]
-  }
-  return property.split("=")[1].split("\n")[0]
-}
diff --git a/packages/cli/src/hosting/makeFiles.js b/packages/cli/src/hosting/makeFiles.js
new file mode 100644
index 0000000000..0723d5e03d
--- /dev/null
+++ b/packages/cli/src/hosting/makeFiles.js
@@ -0,0 +1,135 @@
+const { number } = require("../questions")
+const { success, stringifyToDotEnv } = require("../utils")
+const fs = require("fs")
+const path = require("path")
+const randomString = require("randomstring")
+const yaml = require("yaml")
+const { getAppService } = require("./utils")
+
+const SINGLE_IMAGE = "budibase/budibase:latest"
+const VOL_NAME = "budibase_data"
+const COMPOSE_PATH = path.resolve("./docker-compose.yaml")
+const ENV_PATH = path.resolve("./.env")
+
+function getSecrets(opts = { single: false }) {
+  const secrets = [
+    "JWT_SECRET",
+    "MINIO_ACCESS_KEY",
+    "MINIO_SECRET_KEY",
+    "REDIS_PASSWORD",
+    "INTERNAL_API_KEY",
+  ]
+  const obj = {}
+  secrets.forEach(secret => (obj[secret] = randomString.generate()))
+  // setup couch creds separately
+  if (opts && opts.single) {
+    obj["COUCHDB_USER"] = "admin"
+    obj["COUCHDB_PASSWORD"] = randomString.generate()
+  } else {
+    obj["COUCH_DB_USER"] = "admin"
+    obj["COUCH_DB_PASSWORD"] = randomString.generate()
+  }
+  return obj
+}
+
+function getSingleCompose(port) {
+  const singleComposeObj = {
+    version: "3",
+    services: {
+      budibase: {
+        restart: "unless-stopped",
+        image: SINGLE_IMAGE,
+        ports: [`${port}:80`],
+        environment: getSecrets({ single: true }),
+        volumes: [`${VOL_NAME}:/data`],
+      },
+    },
+    volumes: {
+      [VOL_NAME]: {
+        driver: "local",
+      },
+    },
+  }
+  return yaml.stringify(singleComposeObj)
+}
+
+function getEnv(port) {
+  const partOne = stringifyToDotEnv({
+    MAIN_PORT: port,
+  })
+  const partTwo = stringifyToDotEnv(getSecrets())
+  const partThree = stringifyToDotEnv({
+    APP_PORT: 4002,
+    WORKER_PORT: 4003,
+    MINIO_PORT: 4004,
+    COUCH_DB_PORT: 4005,
+    REDIS_PORT: 6379,
+    WATCHTOWER_PORT: 6161,
+    BUDIBASE_ENVIRONMENT: "PRODUCTION",
+  })
+  return [
+    "# Use the main port in the builder for your self hosting URL, e.g. localhost:10000",
+    partOne,
+    "# This section contains all secrets pertaining to the system",
+    partTwo,
+    "# This section contains variables that do not need to be altered under normal circumstances",
+    partThree,
+  ].join("\n")
+}
+
+exports.ENV_PATH = ENV_PATH
+exports.COMPOSE_PATH = COMPOSE_PATH
+
+module.exports.ConfigMap = {
+  MAIN_PORT: "port",
+}
+
+module.exports.QUICK_CONFIG = {
+  key: "budibase",
+  port: 10000,
+}
+
+async function make(path, contentsFn, inputs = {}) {
+  const port =
+    inputs.port ||
+    (await number(
+      "Please enter the port on which you want your installation to run: ",
+      10000
+    ))
+  const fileContents = contentsFn(port)
+  fs.writeFileSync(path, fileContents)
+  console.log(
+    success(
+      `Configuration has been written successfully - please check ${path} for more details.`
+    )
+  )
+}
+
+module.exports.makeEnv = async (inputs = {}) => {
+  return make(ENV_PATH, getEnv, inputs)
+}
+
+module.exports.makeSingleCompose = async (inputs = {}) => {
+  return make(COMPOSE_PATH, getSingleCompose, inputs)
+}
+
+module.exports.getEnvProperty = property => {
+  const props = fs.readFileSync(ENV_PATH, "utf8").split(property)
+  if (props[0].charAt(0) === "=") {
+    property = props[0]
+  } else {
+    property = props[1]
+  }
+  return property.split("=")[1].split("\n")[0]
+}
+
+module.exports.getComposeProperty = property => {
+  const { service } = getAppService(COMPOSE_PATH)
+  if (property === "port" && Array.isArray(service.ports)) {
+    const port = service.ports[0]
+    return port.split(":")[0]
+  } else if (service.environment) {
+    return service.environment[property]
+  }
+  return null
+}
diff --git a/packages/cli/src/hosting/start.js b/packages/cli/src/hosting/start.js
new file mode 100644
index 0000000000..33b5eb92ce
--- /dev/null
+++ b/packages/cli/src/hosting/start.js
@@ -0,0 +1,34 @@
+const {
+  checkDockerConfigured,
+  checkInitComplete,
+  handleError,
+} = require("./utils")
+const { info, success } = require("../utils")
+const makeFiles = require("./makeFiles")
+const compose = require("docker-compose")
+const fs = require("fs")
+
+exports.start = async () => {
+  await checkDockerConfigured()
+  checkInitComplete()
+  console.log(
+    info(
+      "Starting services, this may take a moment - first time this may take a few minutes to download images."
+    )
+  )
+  let port
+  if (fs.existsSync(makeFiles.ENV_PATH)) {
+    port = makeFiles.getEnvProperty("MAIN_PORT")
+  } else {
+    port = makeFiles.getComposeProperty("port")
+  }
+  await handleError(async () => {
+    // need to log as it makes it more clear
+    await compose.upAll({ cwd: "./", log: true })
+  })
+  console.log(
+    success(
+      `Services started, please go to http://localhost:${port} for next steps.`
+    )
+  )
+}
diff --git a/packages/cli/src/hosting/status.js b/packages/cli/src/hosting/status.js
new file mode 100644
index 0000000000..2b98392133
--- /dev/null
+++ b/packages/cli/src/hosting/status.js
@@ -0,0 +1,17 @@
+const {
+  checkDockerConfigured,
+  checkInitComplete,
+  handleError,
+} = require("./utils")
+const { info } = require("../utils")
+const compose = require("docker-compose")
+
+exports.status = async () => {
+  await checkDockerConfigured()
+  checkInitComplete()
+  console.log(info("Budibase status"))
+  await handleError(async () => {
+    const response = await compose.ps()
+    console.log(response.out)
+  })
+}
diff --git a/packages/cli/src/hosting/stop.js b/packages/cli/src/hosting/stop.js
new file mode 100644
index 0000000000..5f38c93484
--- /dev/null
+++ b/packages/cli/src/hosting/stop.js
@@ -0,0 +1,17 @@
+const {
+  checkDockerConfigured,
+  checkInitComplete,
+  handleError,
+} = require("./utils")
+const { info, success } = require("../utils")
+const compose = require("docker-compose")
+
+exports.stop = async () => {
+  await checkDockerConfigured()
+  checkInitComplete()
+  console.log(info("Stopping services, this may take a moment."))
+  await handleError(async () => {
+    await compose.stop()
+  })
+  console.log(success("Services have been stopped successfully."))
+}
diff --git a/packages/cli/src/hosting/update.js b/packages/cli/src/hosting/update.js
new file mode 100644
index 0000000000..7d3367ce57
--- /dev/null
+++ b/packages/cli/src/hosting/update.js
@@ -0,0 +1,49 @@
+const {
+  checkDockerConfigured,
+  checkInitComplete,
+  downloadFiles,
+  handleError,
+  getServices,
+} = require("./utils")
+const { confirmation } = require("../questions")
+const compose = require("docker-compose")
+const { COMPOSE_PATH } = require("./makeFiles")
+const { info, success } = require("../utils")
+const { start } = require("./start")
+
+const BB_COMPOSE_SERVICES = ["app-service", "worker-service", "proxy-service"]
+const BB_SINGLE_SERVICE = ["budibase"]
+
+exports.update = async () => {
+  const { services } = getServices(COMPOSE_PATH)
+  const isSingle = Object.keys(services).length === 1
+  await checkDockerConfigured()
+  checkInitComplete()
+  if (
+    !isSingle &&
+    (await confirmation("Do you wish to update you docker-compose.yaml?"))
+  ) {
+    await downloadFiles()
+  }
+  await handleError(async () => {
+    const status = await compose.ps()
+    const parts = status.out.split("\n")
+    const isUp = parts[2] && parts[2].indexOf("Up") !== -1
+    if (isUp) {
+      console.log(info("Stopping services, this may take a moment."))
+      await compose.stop()
+    }
+    console.log(info("Beginning update, this may take a few minutes."))
+    let services
+    if (isSingle) {
+      services = BB_SINGLE_SERVICE
+    } else {
+      services = BB_COMPOSE_SERVICES
+    }
+    await compose.pullMany(services, { log: true })
+    if (isUp) {
+      console.log(success("Update complete, restarting services..."))
+      await start()
+    }
+  })
+}
diff --git a/packages/cli/src/hosting/utils.js b/packages/cli/src/hosting/utils.js
new file mode 100644
index 0000000000..952974ee83
--- /dev/null
+++ b/packages/cli/src/hosting/utils.js
@@ -0,0 +1,87 @@
+const { lookpath } = require("lookpath")
+const fs = require("fs")
+const makeFiles = require("./makeFiles")
+const { logErrorToFile, downloadFile, error } = require("../utils")
+const yaml = require("yaml")
+
+const ERROR_FILE = "docker-error.log"
+const FILE_URLS = [
+  "https://raw.githubusercontent.com/Budibase/budibase/master/hosting/docker-compose.yaml",
+]
+
+exports.downloadFiles = async () => {
+  const promises = []
+  for (let url of FILE_URLS) {
+    const fileName = url.split("/").slice(-1)[0]
+    promises.push(downloadFile(url, `./${fileName}`))
+  }
+  await Promise.all(promises)
+}
+
+exports.checkDockerConfigured = async () => {
+  const error =
+    "docker/docker-compose has not been installed, please follow instructions at: https://docs.budibase.com/docs/docker-compose"
+  const docker = await lookpath("docker")
+  const compose = await lookpath("docker-compose")
+  if (!docker || !compose) {
+    throw error
+  }
+}
+
+exports.checkInitComplete = () => {
+  if (
+    !fs.existsSync(makeFiles.ENV_PATH) &&
+    !fs.existsSync(makeFiles.COMPOSE_PATH)
+  ) {
+    throw "Please run the hosting --init command before any other hosting command."
+  }
+}
+
+exports.handleError = async func => {
+  try {
+    await func()
+  } catch (err) {
+    if (err && err.err) {
+      logErrorToFile(ERROR_FILE, err.err)
+    }
+    throw `Failed to start - logs written to file: ${ERROR_FILE}`
+  }
+}
+
+exports.getServices = path => {
+  const dockerYaml = fs.readFileSync(path, "utf8")
+  const parsedYaml = yaml.parse(dockerYaml)
+  return { yaml: parsedYaml, services: parsedYaml.services }
+}
+
+exports.getAppService = path => {
+  const { yaml, services } = exports.getServices(path),
+    serviceList = Object.keys(services)
+  let service
+  if (services["app-service"]) {
+    service = services["app-service"]
+  } else if (serviceList.length === 1) {
+    service = services[serviceList[0]]
+  }
+  return { yaml, service }
+}
+
+exports.updateDockerComposeService = updateFn => {
+  const opts = ["docker-compose.yaml", "docker-compose.yml"]
+  const dockerFilePath = opts.find(name => fs.existsSync(name))
+  if (!dockerFilePath) {
+    console.log(error("Unable to locate docker-compose YAML."))
+    return
+  }
+  const { yaml: parsedYaml, service } = exports.getAppService(dockerFilePath)
+  if (!service) {
+    console.log(
+      error(
+        "Unable to locate service within compose file, is it a valid Budibase configuration?"
+      )
+    )
+    return
+  }
+  updateFn(service)
+  fs.writeFileSync(dockerFilePath, yaml.stringify(parsedYaml))
+}
diff --git a/packages/cli/src/hosting/watch.js b/packages/cli/src/hosting/watch.js
new file mode 100644
index 0000000000..fb51aa9ad8
--- /dev/null
+++ b/packages/cli/src/hosting/watch.js
@@ -0,0 +1,34 @@
+const { resolve } = require("path")
+const fs = require("fs")
+const { error, success } = require("../utils")
+const { updateDockerComposeService } = require("./utils")
+
+exports.watchPlugins = async pluginPath => {
+  const PLUGIN_PATH = "/plugins"
+  // get absolute path
+  pluginPath = resolve(pluginPath)
+  if (!fs.existsSync(pluginPath)) {
+    console.log(
+      error(
+        `The directory "${pluginPath}" does not exist, please create and then try again.`
+      )
+    )
+    return
+  }
+  updateDockerComposeService(service => {
+    // set environment variable
+    service.environment["PLUGINS_DIR"] = PLUGIN_PATH
+    // add volumes to parsed yaml
+    if (!service.volumes) {
+      service.volumes = []
+    }
+    const found = service.volumes.find(vol => vol.includes(PLUGIN_PATH))
+    if (found) {
+      service.volumes.splice(service.volumes.indexOf(found), 1)
+    }
+    service.volumes.push(`${pluginPath}:${PLUGIN_PATH}`)
+  })
+  console.log(
+    success(`Docker compose configured to watch directory: ${pluginPath}`)
+  )
+}
diff --git a/packages/cli/src/plugins/index.js b/packages/cli/src/plugins/index.js
index 66cca8c19d..1057ca9aaa 100644
--- a/packages/cli/src/plugins/index.js
+++ b/packages/cli/src/plugins/index.js
@@ -1,5 +1,5 @@
 const Command = require("../structures/Command")
-const { CommandWords, AnalyticsEvents } = require("../constants")
+const { CommandWords, AnalyticsEvents, InitTypes } = require("../constants")
 const { getSkeleton, fleshOutSkeleton } = require("./skeleton")
 const questions = require("../questions")
 const fs = require("fs")
@@ -9,6 +9,9 @@ const { runPkgCommand } = require("../exec")
 const { join } = require("path")
 const { success, error, info, moveDirectory } = require("../utils")
 const { captureEvent } = require("../events")
+const fp = require("find-free-port")
+const { init: hostingInit } = require("../hosting/init")
+const { start: hostingStart } = require("../hosting/start")
 
 function checkInPlugin() {
   if (!fs.existsSync("package.json")) {
@@ -141,6 +144,19 @@ async function watch() {
   }
 }
 
+async function dev() {
+  const pluginDir = await questions.string("Directory to watch", "./")
+  const [port] = await fp(10000)
+  await hostingInit({
+    init: InitTypes.QUICK,
+    single: true,
+    watchPluginDir: pluginDir,
+    genUser: true,
+    port,
+  })
+  await hostingStart()
+}
+
 const command = new Command(`${CommandWords.PLUGIN}`)
   .addHelp(
     "Custom plugins for Budibase, init, build and verify your components and datasources with this tool."
@@ -160,5 +176,10 @@ const command = new Command(`${CommandWords.PLUGIN}`)
     "Automatically build any changes to your plugin.",
     watch
   )
+  .addSubOption(
+    "--dev",
+    "Run a development environment which automatically watches the current directory.",
+    dev
+  )
 
 exports.command = command
diff --git a/packages/cli/src/structures/Command.js b/packages/cli/src/structures/Command.js
index dfce96504d..e383c14263 100644
--- a/packages/cli/src/structures/Command.js
+++ b/packages/cli/src/structures/Command.js
@@ -1,4 +1,9 @@
-const { getSubHelpDescription, getHelpDescription, error } = require("../utils")
+const {
+  getSubHelpDescription,
+  getHelpDescription,
+  error,
+  capitaliseFirstLetter,
+} = require("../utils")
 
 class Command {
   constructor(command, func = null) {
@@ -8,6 +13,15 @@ class Command {
     this.func = func
   }
 
+  convertToCommander(lookup) {
+    const parts = lookup.toLowerCase().split("-")
+    // camel case, separate out first
+    const first = parts.shift()
+    return [first]
+      .concat(parts.map(part => capitaliseFirstLetter(part)))
+      .join("")
+  }
+
   addHelp(help) {
     this.help = help
     return this
@@ -25,10 +39,7 @@ class Command {
       command = command.description(getHelpDescription(thisCmd.help))
     }
     for (let opt of thisCmd.opts) {
-      command = command.option(
-        `${opt.command}`,
-        getSubHelpDescription(opt.help)
-      )
+      command = command.option(opt.command, getSubHelpDescription(opt.help))
     }
     command.helpOption(
       "--help",
@@ -36,17 +47,25 @@ class Command {
     )
     command.action(async options => {
       try {
-        let executed = false
+        let executed = false,
+          found = false
         for (let opt of thisCmd.opts) {
-          const lookup = opt.command.split(" ")[0].replace("--", "")
-          if (!executed && options[lookup]) {
+          let lookup = opt.command.split(" ")[0].replace("--", "")
+          // need to handle how commander converts watch-plugin-dir to watchPluginDir
+          lookup = this.convertToCommander(lookup)
+          found = !executed && options[lookup]
+          if (found && opt.func) {
             const input =
               Object.keys(options).length > 1 ? options : options[lookup]
             await opt.func(input)
             executed = true
           }
         }
-        if (!executed) {
+        if (found && !executed) {
+          console.log(
+            error(`${Object.keys(options)[0]} is an option, not an operation.`)
+          )
+        } else if (!executed) {
           console.log(error(`Unknown ${this.command} option.`))
           command.help()
         }
diff --git a/packages/cli/src/structures/ConfigManager.js b/packages/cli/src/structures/ConfigManager.js
index 04b7875b57..35799b8e92 100644
--- a/packages/cli/src/structures/ConfigManager.js
+++ b/packages/cli/src/structures/ConfigManager.js
@@ -33,11 +33,10 @@ class ConfigManager {
   }
 
   setValue(key, value) {
-    const updated = {
+    this.config = {
       ...this.config,
       [key]: value,
     }
-    this.config = updated
   }
 
   removeKey(key) {
diff --git a/packages/cli/src/utils.js b/packages/cli/src/utils.js
index 91f3263cc1..ba793420e7 100644
--- a/packages/cli/src/utils.js
+++ b/packages/cli/src/utils.js
@@ -84,3 +84,15 @@ exports.moveDirectory = (oldPath, newPath) => {
   }
   fs.rmdirSync(oldPath)
 }
+
+exports.capitaliseFirstLetter = str => {
+  return str.charAt(0).toUpperCase() + str.slice(1)
+}
+
+exports.stringifyToDotEnv = json => {
+  let str = ""
+  for (let [key, value] of Object.entries(json)) {
+    str += `${key}=${value}\n`
+  }
+  return str
+}
diff --git a/packages/cli/yarn.lock b/packages/cli/yarn.lock
index 547e9fd3e2..0850f94154 100644
--- a/packages/cli/yarn.lock
+++ b/packages/cli/yarn.lock
@@ -1113,6 +1113,11 @@ fill-range@^7.0.1:
   dependencies:
     to-regex-range "^5.0.1"
 
+find-free-port@^2.0.0:
+  version "2.0.0"
+  resolved "https://registry.yarnpkg.com/find-free-port/-/find-free-port-2.0.0.tgz#4b22e5f6579eb1a38c41ac6bcb3efed1b6da9b1b"
+  integrity sha512-J1j8gfEVf5FN4PR5w5wrZZ7NYs2IvqsHcd03cAeQx3Ec/mo+lKceaVNhpsRKoZpZKbId88o8qh+dwUwzBV6WCg==
+
 find-replace@^3.0.0:
   version "3.0.0"
   resolved "https://registry.yarnpkg.com/find-replace/-/find-replace-3.0.0.tgz#3e7e23d3b05167a76f770c9fbd5258b0def68c38"
@@ -3080,6 +3085,11 @@ yallist@^4.0.0:
   resolved "https://registry.yarnpkg.com/yallist/-/yallist-4.0.0.tgz#9bb92790d9c0effec63be73519e11a35019a3a72"
   integrity sha512-3wdGidZyq5PB084XLES5TpOSRA3wjXAlIWMhum2kRcv/41Sn2emQ0dycQW4uZXLejwKvg6EsvbdlVL+FYEct7A==
 
+yaml@^2.1.1:
+  version "2.1.1"
+  resolved "https://registry.yarnpkg.com/yaml/-/yaml-2.1.1.tgz#1e06fb4ca46e60d9da07e4f786ea370ed3c3cfec"
+  integrity sha512-o96x3OPo8GjWeSLF+wOAbrPfhFOGY0W00GNaxCDv+9hkcDJEnev1yh8S7pgHF0ik6zc8sQLuL8hjHjJULZp8bw==
+
 yargs-parser@^20.2.2:
   version "20.2.9"
   resolved "https://registry.yarnpkg.com/yargs-parser/-/yargs-parser-20.2.9.tgz#2eb7dc3b0289718fc295f362753845c41a0c94ee"