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Why am I unable to send emails when using the VPN? - Knowledgebase / Frequently Asked Questions - PIA Support Portal

Why am I unable to send emails when using the VPN?

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Sometimes VPN connections can interfere with the ability to send emails, and some email providers fully block VPN traffic.

If your email provider does not block VPN connections, and if possible to allow email traffic through an email client with the VPN active, you will need to have your email client set up to use either port 587 or 465. Depending upon which you are using, you will need to configure specific settings in your email client as follows: 

Port 587 

  • Change the SMTP server address from the hostname, to the whitelisted IP 

  • Ensure "Secure Password Authentication (SPA) is not enabled. 

  • Enable SMTP authentication 

  • Set the option to use the same login information as the incoming server 

  • Set the username as your full email address, instead of just the first part 

  • Set the outgoing port to 587 

 Port 465 

  • Keep the SMTP server address the same, do not change to the IP. 

  • Ensure Secure Password Authentication (SPA) is not enabled (applies to MS/Outlook only) 

  • Enable SMTP authentication 

  • Set the option to use the same login information as the incoming server 

  • Set the username as your full email address, instead of just the first part 

  • Set the outgoing port to 465 

 After performing this setup, make sure to clear your outbox in your email client, then close/reopen the email program for everything to take effect. 

 If you are still experiencing issues with this configuration, we may need to add your SMTP IP to the whitelist. In order for a SMTP server to be placed on the SMTP whitelist we must know the IP and confirm it is not an open relay. 

 

Please use command line to ping the smtp servers of the email addresses you use. For providers such as gmail or icloud, this will not be necessary, as we have already whitelisted major email providers. Once we have the required information, we will perform tests to confirm the server does not allow spam traffic. If this can be verified, we will add the server to our whitelist — it can sometimes take up to 48 hours to fully propagate across all of our servers. 

If your email client is configured properly, and the whitelisting process has not resolved this issue, your email provider has blocked VPN connections. If this is the case, you will need to use browser based email, add your email client to the split-tunnel feature in the software, disconnect the VPN when using your email client, or use a different email provider. 

If you think you may need to have your email provider whitelisted, please provide our support team with a screenshot(s) showing all of the following settings within your email provider's settings via a support ticket here:

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)

Once you have submitted the above setting information via support ticket, we will be able to confirm if we can whitelist your emails SMTP information.