diff --git a/bin/now-deploy.js b/bin/now-deploy.js
index c5ddcc4..e976813 100755
--- a/bin/now-deploy.js
+++ b/bin/now-deploy.js
@@ -14,6 +14,7 @@ const flatten = require('arr-flatten')
 const dotenv = require('dotenv')
 const { eraseLines } = require('ansi-escapes')
 const { write: copy } = require('clipboardy')
+const inquirer = require('inquirer')
 
 // Ours
 const login = require('../lib/login')
@@ -221,6 +222,37 @@ const stopDeployment = msg => {
   process.exit(1)
 }
 
+const envFields = async list => {
+  const questions = []
+
+  for (const field of list) {
+    questions.push({
+      name: field,
+      message: field
+    })
+  }
+
+  // eslint-disable-next-line import/no-unassigned-import
+  require('../lib/utils/input/patch-inquirer')
+
+  info('Please enter the values for the following environment variables:')
+  const answers = await inquirer.prompt(questions)
+
+  for (const answer in answers) {
+    if (!{}.hasOwnProperty.call(answers, answer)) {
+      continue
+    }
+
+    const content = answers[answer]
+
+    if (content === '') {
+      stopDeployment(`Enter a value for ${answer}`)
+    }
+  }
+
+  return answers
+}
+
 // Create a new deployment if user changed the name or made `_src` public.
 // This works fine because it doesn't force a new sync,
 // it just forces a new deployment.
@@ -415,12 +447,21 @@ async function sync({ token, config: { currentTeam, user } }) {
     dotenvConfig = dotenv.parse(dotenvFile)
   }
 
-  // Merge `now.env` from package.json with `-e` arguments.
   const pkgEnv = nowConfig && nowConfig.env
+  const argEnv = [].concat(argv.env || [])
+
+  if (pkgEnv && Array.isArray(nowConfig.env)) {
+    const defined = argEnv.join()
+    const askFor = nowConfig.env.filter(item => !defined.includes(`${item}=`))
+
+    nowConfig.env = await envFields(askFor)
+  }
+
+  // Merge `now.env` from package.json with `-e` arguments
   const envs = [
     ...Object.keys(dotenvConfig || {}).map(k => `${k}=${dotenvConfig[k]}`),
     ...Object.keys(pkgEnv || {}).map(k => `${k}=${pkgEnv[k]}`),
-    ...[].concat(argv.env || [])
+    ...argEnv
   ]
 
   let secrets
diff --git a/lib/utils/input/list.js b/lib/utils/input/list.js
index cfa648b..d6bf72b 100644
--- a/lib/utils/input/list.js
+++ b/lib/utils/input/list.js
@@ -1,19 +1,8 @@
-const chalk = require('chalk')
 const inquirer = require('inquirer')
 const stripAnsi = require('strip-ansi')
 
-/* eslint-disable no-multiple-empty-lines, no-var, no-undef, no-eq-null, eqeqeq, semi */
-inquirer.prompt.prompts.list.prototype.getQuestion = function() {
-  var message = chalk.bold('> ' + this.opt.message) + ' '
-
-  // Append the default if available, and if question isn't answered
-  if (this.opt.default != null && this.status !== 'answered') {
-    message += chalk.dim('(' + this.opt.default + ') ')
-  }
-
-  return message
-}
-/* eslint-enable */
+// eslint-disable-next-line import/no-unassigned-import
+require('./patch-inquirer')
 
 function getLength(string) {
   let biggestLength = 0
diff --git a/lib/utils/input/patch-inquirer.js b/lib/utils/input/patch-inquirer.js
new file mode 100644
index 0000000..a869c4f
--- /dev/null
+++ b/lib/utils/input/patch-inquirer.js
@@ -0,0 +1,20 @@
+const inquirer = require('inquirer')
+const chalk = require('chalk')
+
+// Here we patch inquirer to use a `>` instead of the ugly green `?`
+
+/* eslint-disable no-multiple-empty-lines, no-var, no-undef, no-eq-null, eqeqeq, semi */
+const getQuestion = function() {
+  var message = chalk.bold('> ' + this.opt.message) + ' '
+
+  // Append the default if available, and if question isn't answered
+  if (this.opt.default != null && this.status !== 'answered') {
+    message += chalk.dim('(' + this.opt.default + ') ')
+  }
+
+  return message
+}
+/* eslint-enable */
+
+inquirer.prompt.prompts.input.prototype.getQuestion = getQuestion
+inquirer.prompt.prompts.list.prototype.getQuestion = getQuestion