I am using OS X 10.11.3 El Capitan and Mail 9.2
Whenever the computer is connected via PIA's VPN, Mail is unable to send email messages. Is there a work-around to resolve this issue? Please, let me know. Thank you!
iMac, OS X Yosemite (10.10.1)
There is not enough information here to determine what the problem is.
If you are using one of the many VPN services designed to let you mask your activity (supposedly), it's entirely possible that your email provider has locked down their servers to prevent spam from being sent by the criminals who often use such VPNs.
What did your email provider say when you contacted them and reported the problem.
when I use a vpn client to connect to my work then my computers network connection rights would be that of my work that the vpn tunnel all network activities to
so if the network you connect to is not open for the ports your mail providers smtp server use then you would not be able to send mails , but you should still be able to use their web client as all browser related stuff rely on port80 only
I didn't contact them, but maybe it's good idea - thank you for the hint!
Thank you for your reply. I understand it could be a port issue - do I have to assign another port (and which one?) or do some network tweaking in Preferences in order to allow for VPN and email being sent simultaneously?
OK, after consulting with PIA tech service, here are the why and how regarding sending email while using vpn:
Ist reply:
“Any VPN provider that does not retain logs must block SMTP traffic due to rampant spam associated with usage of VPN services. This is necessary for the security and privacy of our customers, and we apologize for any inconvenience this may cause.
With that said, we can whitelist any/all SMTP servers that require authentication, provided they are correctly setup so they are not open relays (we'll test them once we receive them from you). If you can provide us with the hostname of the outgoing (SMTP) server(s) you are using, we will be happy to whitelist these servers on our network, for you to use.”
2nd reply after I provided the server name:
“I have added your mail server(s) to our white list. Please allow up to 24 hours for this whitelisting to to update across all our servers.
Please also make these following changes in your mail client settings:
- Change the SMTP hostname from <SERVER NAME>, to the following IP: 209.169.131.140
- 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
- Make sure that SSL is not enabled
After it's setup, make sure to clear out your Outbox in your email client, and close/reopen the email program for everything to take effect.”
OK, after consulting with PIA tech service, here are the why and how regarding sending email while using vpn:
Ist reply:
“Any VPN provider that does not retain logs must block SMTP traffic due to rampant spam associated with usage of VPN services. This is necessary for the security and privacy of our customers, and we apologize for any inconvenience this may cause.
With that said, we can whitelist any/all SMTP servers that require authentication, provided they are correctly setup so they are not open relays (we'll test them once we receive them from you). If you can provide us with the hostname of the outgoing (SMTP) server(s) you are using, we will be happy to whitelist these servers on our network, for you to use.”
2nd reply after I provided the server name:
“I have added your mail server(s) to our white list. Please allow up to 24 hours for this whitelisting to to update across all our servers.
Please also make these following changes in your mail client settings:
- Change the SMTP hostname from <SERVER NAME>, to the following IP: 209.169.131.140
- 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
- Make sure that SSL is not enabled
After it's setup, make sure to clear out your Outbox in your email client, and close/reopen the email program for everything to take effect.”
Mail: cannot send email through VPN
