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Guide or Outlook will not connect to Gmail

The most common reason that this isn’t working is Gmail is blocking the connection. Gmail has very high security settings by default that blocks all third-party applications from connecting to their email database. The process for fixing a Gmail account is as follows:

  1. In a web browser, go to gmail.com and log-in with the email address and password. If it lets you log on, progress to the next step. If you cannot log in, most likely the password is wrong and needs to be reset by going through the Forgot My Password link that Gmail provides. (Note: If you cannot satisfy the security questions, the email account must be abandoned unless the password is remembered.)
  2. Once logged in, see if there is a recent email from Gmail with a security alert. If it asks you if you recognize the activity, you want to choose “Yes.”
  3. 3. Turn on access by “less secure apps.” Gmail will warn you not to do this but it is required to connect to any email program. On the Gmail inbox screen find the circle icon in the upper right corner with the account’s first initial on it. Click on this and choose the “Google Account” button. On the next page, go to Security and scroll down to “Less secure app access.” Make sure this is turned on. If it is not, turn it on.
  4. Try to connect through Outlook or Guide again. If it is still failing, repeat steps 2 and 3, as sometimes Gmail likes to toggle off your settings.
  5. Try to connect again. If it still doesn’t work, go back to the Security page and make sure 2-factor authentication is NOT turned on. If it is turned on, you will need to generate an application-specific password for use with Outlook and Guide; the regular password will not work with this enhanced security setting.