diff --git a/packages/cli/src/lib/container/docker_helper.ts b/packages/cli/src/lib/container/docker_helper.ts
index f3b3043b97..ba154c1e5d 100644
--- a/packages/cli/src/lib/container/docker_helper.ts
+++ b/packages/cli/src/lib/container/docker_helper.ts
@@ -4,6 +4,7 @@ import * as glob from 'glob'
 import * as Path from 'path'
 import * as inquirer from 'inquirer'
 import * as os from 'os'
+import {ux} from '@oclif/core'
 
 const DOCKERFILE_REGEX = /\bDockerfile(.\w*)?$/
 
@@ -140,6 +141,11 @@ export const chooseJobs = async function (jobs: groupedDockerJobs) {
   for (const processType in jobs) {
     if (Object.prototype.hasOwnProperty.call(jobs, processType)) {
       const group = jobs[processType]
+      if (group === undefined) {
+        ux.warn(`Dockerfile.${processType} not found`)
+        continue
+      }
+
       if (group.length > 1) {
         const prompt = [{
           type: 'list',
diff --git a/packages/cli/test/unit/commands/container/push.unit.test.ts b/packages/cli/test/unit/commands/container/push.unit.test.ts
index bd35470a11..80fa972000 100644
--- a/packages/cli/test/unit/commands/container/push.unit.test.ts
+++ b/packages/cli/test/unit/commands/container/push.unit.test.ts
@@ -1,4 +1,4 @@
-import {stdout} from 'stdout-stderr'
+import {stdout, stderr} from 'stdout-stderr'
 import Cmd from '../../../../src/commands/container/push'
 import runCommand from '../../../helpers/runCommand'
 import {expect} from 'chai'
@@ -198,6 +198,32 @@ describe('container push', function () {
       sandbox.assert.calledTwice(push)
     })
 
+    it('warns when a specified Dockerfile is missing', async function () {
+      const dockerfiles = sandbox.stub(DockerHelper, 'getDockerfiles')
+        .returns(['/path/to/Dockerfile.web'])
+      const build = sandbox.stub(DockerHelper, 'buildImage')
+      build.withArgs('/path/to/Dockerfile.web', 'registry.heroku.com/testapp/web', [])
+      build.withArgs('/path/to/Dockerfile.worker', 'registry.heroku.com/testapp/worker', [])
+      const push = sandbox.stub(DockerHelper, 'pushImage')
+      push.withArgs('registry.heroku.com/testapp/web')
+      push.withArgs('registry.heroku.com/testapp/worker')
+
+      await runCommand(Cmd, [
+        '--app',
+        'testapp',
+        '--recursive',
+        'web',
+        'worker',
+      ])
+
+      expect(stdout.output).to.contain('Building web (/path/to/Dockerfile.web)')
+      expect(stdout.output).to.contain('Pushing web (/path/to/Dockerfile.web)')
+      expect(stderr.output).to.contain('Dockerfile.worker not found')
+      sandbox.assert.calledOnce(dockerfiles)
+      sandbox.assert.calledOnce(build)
+      sandbox.assert.calledOnce(push)
+    })
+
     it('pushes all dockerfiles recursively when process types are not specified', async function () {
       const dockerfiles = sandbox.stub(DockerHelper, 'getDockerfiles')
         .returns(['/path/to/Dockerfile.web', '/path/to/Dockerfile.worker'])