GMAIL – Adding to Outlook for MAC with two-step authentication

IMAP applications like Outlook do not support two-step verification like the Gmail website. For these applications you will need to create an application specific password.

Generate App Security Password
Visit your App passwords page. You may be asked to sign in to your Google Account.

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

At the bottom, click Select app and choose the app you’re using.
Click Select device and choose the device you’re using.

Select Generate.

Follow the instructions to enter the App password (the 16 character code in the yellow bar) on your device.

Select Done.

Configure Gmail Setting in browser
After logging in to your Gmail account, select Settings under the gear in the upper right corner of the page.

Select: Forwarding and POP/IMAP” tab
Enable IMAP on your Gmail account
Recommended: disable POP
Use default setting for Trash
Click the Save Changes button.

Configuring Outlook
Go to Mail menu bar, choose add account.
Instead of selecting Google, choose add other account.
Enter the full email address and password for the account however hold the option key, the create button switches to next. Which will initiate the manual setup of the account.
Choose IMAP as the account type or POP depending on what you want.

Incoming Mail (IMAP) Server – requires SSL: imap.gmail.com
Use SSL: Yes
Port: 993
Outgoing Mail (SMTP) Server – requires TLS or SSL: smtp.gmail.com
Use Authentication: Yes
Port for TLS/STARTTLS: 587
Port for SSL: 465

Enabled Automatically detect and maintain settings.
Deselect allow insecure authentication.
Full Name or Display Name: [your name]
Account Name or User Name: your full email address (including @gmail.com or @your_domain.com)
Email Address: your email address (username@gmail.com or username@your_domain.com)
Password: your Gmail Application Password

Incoming Mail (IMAP) Server – requires SSL: imap.gmail.com
Use SSL: Yes
Port: 995
Outgoing Mail (SMTP) Server – requires TLS or SSL: smtp.gmail.com
Use Authentication: Yes
Port for TLS/STARTTLS: 587
Port for SSL: 465
Full Name or Display Name: [your name]
Account Name or User Name: your full email address (including @gmail.com or @your_domain.com)
Email Address: your email address (username@gmail.com or username@your_domain.com)
Password: your Gmail password

Create the account and check that the outgoing server settings don’t have authentication set to none. If it has authentication on the outgoing server set to none change it to password and add your email address and password for gmail.

References:
Sign in using App Passwords
https://support.google.com/accounts/answer/185833?hl=en&rd=1

Google 2-step verification failing in 10.10.3 ‘Internet Accounts’
https://discussions.apple.com/thread/6984508?tstart=0

Connect Outlook for Mac 2011 to Gmail’s IMAP service

Connect Outlook for Mac 2011 to Gmail’s IMAP service

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