Dreamhost email via Gmail w/ SSL

Hello, appreciate anyone’s advice on this:

I am setting up a client’s (regular) Gmail account so it automatically fetches their emails from a specific Dreamhost-hosted email address.

Using the “Add a POP3 Account you Own” option in the settings, Gmail has no problem connecting to the Dreamhost server if I select Port 110 and uncheck the “Always use secure (SSL) when retrieving mail.”

Using these settings, is there a security risk, or is SSL protection already implied by using Dreamhost’s mail server?

(If I check SSL and switch the port to 995, I get the error:
[color=#FF0000]“Unable to establish secure SSL connection to mail.stlydias.org[/color])

(I am also able to connect to sub4.homie.mail.dreamhost.com)

Thank you

Panel > Mail > Manage Email

  • Edit account client@domain.tld

  • List all email addresses to forward to, one per line : client@gmail.com

  • Click Save Changes

As of December 2012 Google decided to up their security measures. They no longer support self-signed certificates. I had the same problem back in December. I had set up POP3 with my hosted email and gmail, and in December it broke. So far Dreamhost has not fixed the solution to this problem… Meaning, they are still using self-signed certificates on the webmail servers, or at least not valid enough certificates for Google.

Using sXi’s solution would be the best option. If you use POP3 without SSL you are opening yourself up for security risks. Without using SSL the data is sent across the internet unencrypted so anyone wanting to intercept your login information can do so and easily have your information.

Another option is to use a different email client. At work I use a Mac and have just set up my email with the Mac Mail Client. It also gives me a warning that the mail server may not have a valid certificate, but you can tell it to connect anyway knowing that the certificates Dreamhost uses are valid and safe.

For more information on the Dreamhost forums: https://discussion.dreamhost.com/thread-136654.html

Or google: http://support.google.com/mail/bin/answer.py?hl=en&answer=21291&ctx=gmail#strictSSL