Sending email fails when two factor authentication is on for Gmail

Question

I am using my Gmail account and smtp.gmail.com inside my web application to test and send email. when two factor authentication is ON for my Gmail account, it fails to send the email, however when I turn it off, the web application sends email successfully. Appreciate any kind of advice.

Answer 1

Create a custom app in you Gmail security settings.

1. Log-in into Gmail with your account
2. Navigate to https://security.google.com/settings/security/apppasswords
3. In 'select app' choose 'custom', give it an arbitrary name and press generate
4. It will give you 16 chars token.

Use the token as password in combination with your full Gmail account and two factor authentication will not be required.

Note: The link in step 2 will work only if you have 2-factor-authentication enabled.

Answer 2

If you are here because of difficulties with the ARQ backup app on Mac OSX, I found the following settings worked for me:

SMTP hostname: smtp.gmail.com SMTP Port: 587 Click: Enable SSL (STARTTLS) Authentication Type: Password (SASL PLAIN) User Name: <full Gmail email address> Password: <Google-generated app password> 

The Google-generated app password is generated as @stoyan-dimov suggests in his answer above, using the following URL:

https://security.google.com/settings/security/apppasswords

Choose to generate a 'Mail' password, and set the device as 'Custom' (I called mine "ARQ".)

Caveat: You must have two-factor authentication enabled on your Google account to get to the above URL.