Hello everyone,
I know this post is little bit old, but I'll try to leave here my contribution.
I faced the same problem in another e-mail server, actually using POP3 with TLS and port 995.
I checked everything like firewall open ports, server configuration, different connections and ports and nothing works.
Taking a look at the HESK code, in the file inc/mail/pop3.php, it's using fsockopen do connected the POP3 and there's a verification if the TLS is actived and if so, it puts the "tls://" suffix in the host name, and than to fix the problem I just changed it to "ssl://" and Eureka, it worked fine with my sever and probability will work with the GMAIL POP3.
I leave here a suggestion to the HESK team, to change the code and put two options, where the user can choose "TLS" or "SSL" protocol, for fsockopen, it makes a big difference.
If someone test it with Gmail, please let me know if it'll work fine.
Best Regards,
