Unable to access Gmail via Outlook

RobbieGRobbieG
in Other Software Support
I have two gmail accounts I access via Outlook (using IMAP). They work flawlessly when my PIA is not connected.
Once PIA is connected, I am prompted repeatedly to enter my gmail password, followed by two factor authentication, which then fails.
This issue has started over the past week. I can access the email from gmail online just fine, and there are no warnings or security alerts in my inbox.

Comments

  • Omnibus_IVOmnibus_IV
    I had the same problem a few years ago when I first joined PIA. I think the issue was a mismatch of IP address. It seems that GMail (from any other mail client) likes to see continuity. I believe the problem was solved with I was on PIA and rebuilt my Outlook Gmail account, It has been too long since I had this problem.

    One thing to be aware of. Don't start jumping from server to server and use outlook.Gmail will think you are a hacker and block your account.
  • [Deleted User][Deleted User]
    Hello RobbieG,

    Thank you for the inquiry. This link may be of some use to you: https://seed4.me/blog/thunderbird-gmail-for-vpn-connection/. It if for Thunderbird and Gmail, but the steps should be relatively close for Outlook. However, have you completed the whilelisting process? In order to assist you with whitelisting your SMTP server, please provide us with screenshots showing all of the following settings within your email provider's settings:

    1. The email address(es) being blocked
    2. The SMTP/outgoing email server name for the above address(es) (e.g. smtp.mail.com, mail.example.net)
    3. The Port number used to connect to the mail server (e.g. 587, 465, 25...)
    4. The SSL setting (enabled/disabled - may appear as TLS/SSL)
    However - there are multiple reasons behind why you may not be able to use your email client when connected to VPN. Email is extremely tricky when using a VPN. It could be because your email client application is using port 25, which is blocked by our VPN to prevent spam. This can happen especially with old email applications. To resolve the issue: 

    • Allow access to local network. This can be done on your app. 

    If the above step do not work, you may need to:

    • Switch to a newer email client such as Outlook or Thunderbird, or manually configure your email client to use port 587 instead of port 25. Outlook users will need to select the type of encrypted connection for the outgoing server before entering 587 for the Outgoing server (SMTP) port number. See details here.
    • Disconnect from our VPN to access your email. This may be necessary if you are using your ISP’s email server and it blocks email traffic coming from outside of its own network. If this is the case I sincerely apologize for the inconvenience
    If you need more assistance, let us know! - PIA CS TEAM
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