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Is it worth using SSL in Apple Mail?

Is it worth using SSL in Mail? I run a POP e-mail client, sending and receiving from e-mail servers (as opposed to me running e-mail in a browser).


I've heard that some people say that SSL mail is not much more secure than non-SSL, as the encryption's not fully end-to-end.


Is SSL-encrypted mail totally transparent to its recipient? By that, I mean that if I opt to use SSL in Mail, do all the recipients of my e-mail need also to be using SSL, or is it really true that the encryption operates only among the relaying servers?


What does SSL do? Does it encrypt the entire body of the message, or does it just encrypt the account password?

iMac (27-inch, Late 2013), OS X Mavericks (10.9.2)

Posted on Sep 3, 2015 5:25 AM

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20 replies

Sep 3, 2015 6:19 AM in response to carefulowner

SSL email connections to the mail server just means it is encrypted from the mail server to your Mac, and no one in between can read it.


However, unless you have some other email encryption package and the people you are sending/receiving email with are using the same encryption package, the email itself is not encrypted, and it is sitting in plain text on the mail server. Which means it is subject to hacking, dishonest employees of the mail server company, the government, etc...


So while the last leg of your email journey is now secure and a step in the right direction, it is not giving you total email security.

Sep 3, 2015 6:50 AM in response to BobHarris

Oh, okay, it sounds like I misunderstood what I'd previously heard about SSL. I'd been told that, if you use SSL, encrypted mail is carried through all servers between a pair of users and is only not encrypted in the last leg, between each user and his/her nearest server. This is the converse of what you understand is the position.


On the other hand, I've for a long time had a suspicion that, for SSL to be used with any great effect, the recipient had to be using the same encryption method as the sender, and you now seem to have confirmed that. Even if the e-mail stays in plaintext in a situation like that, would the password nonetheless be encrypted? If not, then it'd seem worthless using SSL at all unless you can guarantee that every individual and organisation with whom you communicate by e-mail also uses SSL.

Sep 3, 2015 8:23 AM in response to BobHarris

Ah, I meant to ask also whether SSL encryption is a separate exercise to authentication. In other words, when you configure Mail for SSL do you also have to set a specific authentication method to go with that? I seem to recall that, in my present non-SSL-configured account, the authentication is None in one direction, and Password in the other.

Sep 3, 2015 2:00 PM in response to carefulowner

I'd consider migrating my mail hosting away from any ISP that still provided non-SSL (TLS) access. That's just allowing connections from somebody doesn't intend to or that doesn't know any better — with a cleartext transport. Cleartext access is just not a good thing for an ISP to be supporting in this era. Why migrate providers? Because I'd wonder what else the ISP is letting slide here — maybe they're using cleartext password storage for their customer databases, or using a hash that's far too fast to calculate?

Sep 3, 2015 2:28 PM in response to MrHoffman

I agree with you. However, my current service provider is not the one I was with originally but instead was the provider that I defaulted to when my previous one sold their business a few years ago. I've been thinking of changing to an allegedly better provider for some considerable time and also upgrading the basic Internet service I get at the same time. However, a house move has been on the cards for some time, so it's not been sensible to make the change just yet. The current ISP just so happens to have been upgrading a few features of late, one of which has been to offer SSL e-mail. As you say, very late to the party, when you think about it. I was complaining to them very early on about the massive security holes in their e-mail service, such as transporting the password in plaintext and in one or two other ways it not being compatible with what Apple Mail normally expects. But my criticisms fell on deaf ears. Frankly, I don't think they're alone in lagging behind on these sorts of matters. But at least they've now made one small move toward improving it where e-mail's concerned.

Is it worth using SSL in Apple Mail?

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