Are your emails failing to send with the "mailbox has not recently been synced" error even though your mailbox appears to be sending and syncing? Is your mailbox connected using Gmail OAuth2? If you answered yes to both of these, Gmail may have revoked your OAuth2 Token or it may have expired.
How to fix it:
- Go to Settings >> You >> Mailboxes >> Edit.
- Click into your mailbox and select 'disconnect'. The Gmail connection box should turn grey.
- Reconnect your mailbox by clicking on 'Connect to Gmail' and entering your Gmail email and password. This should turn blue.
- Turn on your sending and syncing toggles. These should turn green.
- Don't forget to hit save!
- Once reconnected, you can retry any failed emails from the Outreach outbox.
Why it happened:
When your Outreach mailbox is connected through Gmail's OAuth2 token, your Gmail account grants Outreach limited access to your mailbox. With this token, we send emails on your behalf, sync messages into Outreach, and notice when a prospect responds. These tokens expire and can be revoked by Gmail for several reasons. The most common reasons are:
- A large amount of emails sent from your email address at a high velocity. You can change the rate at which emails send in your 'advanced send settings' within your Mailbox Settings
- Your Gmail password has been updated, or 2-step authentication has been enabled
- Google has throttled your account. You can see Gmail sending limits here: https://support.google.com/a/answer/166852?hl=en
- Access to our app was revoked from the apps permission page in Gmail: https://security.google.com/settings/security/permissions
- Okta (or another iDP provider) can be set to automatically syncs its passwords into Gmail. https://support.okta.com/help/Documentation/Knowledge_Article/Google-Apps-Deployment-Guide (see "Managing Users" section)
- Okta (or other iDP providers) periodically forcs users to change their passwords.
You’ll know your Gmail token has been revoked if you see emails failing consistently. The failure message will most likely indicate that your mailbox has not recently been synced or is disconnected. Your mailbox will likely look like it is still sending and syncing properly.
NOTE: When an Okta (or other IDP provider) password expires, it is changed, and this change revokes Outreach's access to Gmail inboxes.