Gmail from Outlook fails

Late 2016, this is happening more and more as they take steps to secure or lockdown the locations and devices which are used to access the account.

Refer to following article
https://support.google.com/mail/answer/7126229

Allow Less Secure Apps
https://support.google.com/accounts/answer/6010255
which leads to:
https://www.google.com/settings/security/lesssecureapps

or

Perform a captcha step
https://www.google.com/accounts/DisplayUnlockCaptcha