diff --git a/src/cli/commands/auth/index.ts b/src/cli/commands/auth/index.ts
index 91827159a4..957c901499 100644
--- a/src/cli/commands/auth/index.ts
+++ b/src/cli/commands/auth/index.ts
@@ -7,6 +7,7 @@ import { Spinner } from 'cli-spinner';
 import * as snyk from '../../../lib';
 import { verifyAPI } from './is-authed';
 import { isCI } from '../../../lib/is-ci';
+import { isDocker } from '../../../lib/is-docker';
 import { args as argsLib } from '../../args';
 import * as config from '../../../lib/config';
 import request = require('../../../lib/request');
@@ -25,7 +26,7 @@ const debug = Debug('snyk-auth');
 let attemptsLeft = 0;
 
 function resetAttempts() {
-  attemptsLeft = 30;
+  attemptsLeft = isDocker() ? 60 : 30;
 }
 
 type AuthCliCommands = 'wizard' | 'ignore';
@@ -50,16 +51,9 @@ async function webAuth(via: AuthCliCommands) {
     urlStr += '&redirectUri=' + Buffer.from(redirects[via]).toString('base64');
   }
 
-  const msg =
-    '\nNow redirecting you to our auth page, go ahead and log in,\n' +
-    "and once the auth is complete, return to this prompt and you'll\n" +
-    "be ready to start using snyk.\n\nIf you can't wait use this url:\n" +
-    urlStr +
-    '\n';
-
   // suppress this message in CI
   if (!isCI()) {
-    console.log(msg);
+    console.log(browserAuthPrompt(isDocker(), urlStr));
   } else {
     return Promise.reject(MisconfiguredAuthInCI());
   }
@@ -70,9 +64,11 @@ async function webAuth(via: AuthCliCommands) {
 
   try {
     spinner.start();
-    await setTimeout(() => {
-      open(urlStr);
-    }, 0);
+    if (!isDocker()) {
+      await setTimeout(() => {
+        open(urlStr);
+      }, 0);
+    }
 
     return await testAuthComplete(token, ipFamily);
   } finally {
@@ -190,3 +186,23 @@ async function getIpFamily(): Promise<6 | undefined> {
     return undefined;
   }
 }
+
+function browserAuthPrompt(isDocker: boolean, urlStr: string): string {
+  if (isDocker) {
+    return (
+      '\nTo authenticate your account, open the below URL in your browser.\n' +
+      'After your authentication is complete, return to this prompt to ' +
+      'start using Snyk.\n\n' +
+      urlStr +
+      '\n'
+    );
+  } else {
+    return (
+      '\nNow redirecting you to our auth page, go ahead and log in,\n' +
+      "and once the auth is complete, return to this prompt and you'll\n" +
+      "be ready to start using snyk.\n\nIf you can't wait use this url:\n" +
+      urlStr +
+      '\n'
+    );
+  }
+}
diff --git a/test/smoke/spec/snyk_auth_spec.sh b/test/smoke/spec/snyk_auth_spec.sh
index 75402c6613..9e582de4ca 100644
--- a/test/smoke/spec/snyk_auth_spec.sh
+++ b/test/smoke/spec/snyk_auth_spec.sh
@@ -25,7 +25,7 @@ Describe "Snyk CLI Authorization"
 
       # Using timeout to not wait for browser confirmation
       When run timeout 5 snyk auth
-      The output should include "Now redirecting you to our auth page, go ahead and log in,"
+      The output should include "To authenticate your account, open the below URL in your browser."
       The result of function verify_login_url should include "snyk.io/login?token=" # URL found
       The status should be failure
       # TODO: unusable with our current docker issues
diff --git a/test/system/cli.test.ts b/test/system/cli.test.ts
index 722ca21bd2..26a962e2a8 100644
--- a/test/system/cli.test.ts
+++ b/test/system/cli.test.ts
@@ -2,6 +2,7 @@ import * as util from 'util';
 import * as _ from 'lodash';
 import { test } from 'tap';
 import * as ciChecker from '../../src/lib/is-ci';
+import * as dockerChecker from '../../src/lib/is-docker';
 import { makeTmpDirectory, silenceLog } from '../utils';
 import * as sinon from 'sinon';
 import * as proxyquire from 'proxyquire';
@@ -101,6 +102,8 @@ test('auth with no args', async (t) => {
   const auth = proxyquire('../../src/cli/commands/auth', { open });
   // stub CI check (ensure returns false for system test)
   const ciStub = sinon.stub(ciChecker, 'isCI').returns(false);
+  // ensure this works on circleCI as when running outside of a container
+  const dockerStub = sinon.stub(dockerChecker, 'isDocker').returns(false);
   // disable console.log
   const enableLog = silenceLog();
   try {
@@ -117,6 +120,7 @@ test('auth with no args', async (t) => {
       'opens login with token param',
     );
     ciStub.restore();
+    dockerStub.restore();
   } catch (e) {
     t.threw(e);
   }
@@ -130,6 +134,8 @@ test('auth with UTMs in environment variables', async (t) => {
   const auth = proxyquire('../../src/cli/commands/auth', { open });
   // stub CI check (ensure returns false for system test)
   const ciStub = sinon.stub(ciChecker, 'isCI').returns(false);
+  // ensure this works on circleCI as when running outside of a container
+  const dockerStub = sinon.stub(dockerChecker, 'isDocker').returns(false);
 
   // read data from console.log
   let stdoutMessages = '';
@@ -161,6 +167,7 @@ test('auth with UTMs in environment variables', async (t) => {
     delete process.env.SNYK_UTM_CAMPAIGN;
     // clean up stubs
     ciStub.restore();
+    dockerStub.restore();
 
     // restore original console.log
     console.log = origConsoleLog;