Apple Mail won't recognize an SSL certificate as "Trusted"

Question

Level 1

8 points

Apple Mail won't recognize an SSL certificate as "Trusted"

When I open Mail I get a message saying my mail host's SSL certificate is untrusted. I have looked at the certificate (*.hostingplatform.com) and told my mac to always trust it. But the next time I open mail the process repeats. When I look at the certificate yet again, it even says it is always to be trusted. But the "no trust" message still appears every time I open Mail. How do I get rid of that message and just open my mail program "normally"? I use OSX 10.10.2 and Mail 8.2. The problems just started a few days ago.

iMac

Posted on Mar 22, 2015 8:54 AM

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Answer 1

Linc Davis

Level 10

209,739 points

Mar 22, 2015 11:50 AM in response to KenBures

First, you should never change the trust settings of any SSL certificate unless you created it yourself. Doing so can be very dangerous.

In the Advanced settings for the account in the Mail preferences window, check the box marked

Allow insecure authentication

Your password will be sent over the Internet in plain text every time you connect to the server. You should therefore have no expectation of privacy or security when using the mail account.

To edit the settings for an outgoing mail (SMTP) account, double-click it in the Connection Doctor window, which you can open under the Window menu.

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Answer 2

KenBures Author

Level 1

8 points

Mar 22, 2015 1:34 PM in response to Linc Davis

Thank you very much for your response. I have taken your advice of not changing a trust setting. But I think that allowing insecure authentication sounds even more risky. I called my email provider to see if they could explain why their certificate is causing this problem. The lady I talked to said I should go to Mail Preferences->Accounts->Advanced, and then uncheck "Use SSL" next to the Port number. She said I would still have a secure authentication even though this was unchecked. So I did that, and the troublesome Apple message has disappeared. Hopefully she is right about the security of the authentication. Any thoughts on this?

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Answer 3

Linc Davis

Level 10

209,739 points

Mar 22, 2015 2:23 PM in response to KenBures

She said I would still have a secure authentication even though this was unchecked.

That depends on the authentication method used, which you can see in the Advanced settings for the account. Regardless, even if authentication is secure, the message traffic is not, and you should still not expect privacy when using the account.

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