SSL Email

I’m trying to setup my email client to check my mail thru POP using SSL (port 995) and am having some difficulties. I had originally been trying thru Entourage with no success, and have now switched to Mail.App and still have no success. (I am running Mac OS X.)

When I check my mail, I get an error message complaining about the site’s certificate. I’m including the error message at the bottom of this post.

I contacted support over this while I was using Entourage and they suggested I try switching to Mail.App, which didn’t work. (However, I would like to stay with Mail.App, so I don’t really need to make Enoutrage work now.) Regarding certificates, I was told that they use self-signed certificates which apply to several different backend machines, which means that the IP and hostname might change while the certificate won’t–which is evidently what is causing problems with both Entourage and Mail.App. However, if that does cause an issue, then they consider it “officially unsupported” in those situations (though they do still try to help). He suggested I inquire on the boards here if I continued to run into problems.

So has anyone fought with this issue before and found a solution? I’d really like to use SSL, and I’d really prefer not to have to fight with those annoying certificate messages everytime I open Mail.App.

Thank you!!

Here’s the message it gives me:

Unable to verify SSL server

Mail was unable to verify the identity of this server, which has a certificate issued to “”. The error was:

The root certificate for this server could not be verified.

You might be connecting to a computer that is pretending to be “”, and putting your confidential information at risk. Would you like to continue anyway?

[Show certificate] [Cancel] [Continue]

I’m using mail right now and it is working. Just out of curiosity is your SSL webmail working?

SSL webmail gives a similar error when I try to access it. The message is below. Clicking continue allows me to view the page and login to my mail.


Here’s the error message (as given by Safari):

Safari could not verify the identiy of the website “”.

The website’s certificate was signed by an unknown certifying authority. You might be connecting to a website that is pretending to be “” which could put your confidential information at risk. Would you like to continue anyway?

[Cancel] [Continue]

yeah that error in Safari is normal. Only beacause dreamhost isn’t using one of those paid ones.

With webmail, if I click [Continue], it loads the login page for accessing webmail, and everything works alright from that point on.

With Mail.App, if I click [Continue], it downloads my email like it’s supposed to.

With both apps, they can re-access the servers repeatedly while the app is open without getting additional error messages, but if I close the app and then later re-open, I get the messages again.

When I click [Continue] and proceed to check my mail (thru either method), am I still getting a secure connection? If so, is there some way to make the error messages stop popping up; if it’s not secure, is there some way to make it work securely?

Thanks again,

DreamHost has good support for free SSL/TLS certificates Unless a site has specific cert requirements (extended certs, wildcards, etc), I’d recommend Let’s Encrypt.

with regards
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