Apple Event: May 7th at 7 am PT

Looks like no one’s replied in a while. To start the conversation again, simply ask a new question.

Where is the TLS option in Mail?

Hello,

I keep seeing thing on the net indicating that Mail supports TSL, yet I can't find the setting anywhere.

Thanks,

-Travis

Posted on Jul 21, 2008 10:38 AM

Reply
16 replies

Jul 21, 2008 11:30 AM in response to Travis B

No. No, it is not. I am not sure that Apple Mail can handle TLS. TLS is the follow-on or replacement for SSL. But, when I see SSL as an option with no explanation, it doesn't make me feel comfortable that the SSL option of Mail will support TLS 1.0 servers.

But, yes, Travis, I would assume that checking SSL will work with TLS servers..

-fred

Sep 30, 2008 4:47 PM in response to Travis B

You can't find it, because Mail is smart enough to figure out what you want to do, and do it, without being told.

TLS refers to the standardized version of SSL. However, in common usage, almost nobody uses the term 'TLS' as equivalent to 'SSL'. Instead, TLS is frequently used as shorthand for connections that start out unencrypted, and then use the StartTLS extension to various protocols to boot the connection to be encrypted.

So, in Mail, when you set the IMAP server port to '143' and check the 'Use SSL' box, Mail says "Oh, he wants me to connect unencrypted, then do StartTLS." The same thing for when you set up the SMTP server, set the port to '25' or '587', and click the 'Use SSL' box.

IMAP port 993 starts encrypted (SSL), then does IMAP inside that. The same for SMTPs port 465.

Oct 1, 2008 4:32 AM in response to Sunnnz

Well, considering probably millions of others, including me, have been using Mail just fine with Gmail for years, I'm not convinced that you have configured Gmail to turn on IMAP/SMTP or POP/SMTP support.

Gmail has a help page that will walk you through configuring Leopard or Tiger Mail. If that doesn't work for you, you probably need to tweak your firewall to allow outbound connections on the required ports.

Oct 1, 2008 6:56 AM in response to moulles

Ah, nope, it works in Thunderbird. It is definitely a problem with Apple Mail.

I haven't seen million of Mail users work, you are the only one who claimed it... so would you be glad to show what does one need to do in order to make Mail work?

And yes I have tried the Google documentation, Mail just refuse to work... that's why I Google about this and found this thread.

EDIT:

Here's the SMTP setting I have in Mail: (Mail - Preferences - Accounts - Outgoing Mail Server)

Description: Google
Server Name: smtp.gmail.com
Use Custom Port: 465
User SSL: Checked
Authentication: Passoword
User Name: username@gmail.com
Password: *****

I also have tried the same thing with port 587 and port 25. And yes I have verified that I have the correct username and password.

In "connection doctor" it said that it "Could not connect to this SMTP server", "check your connection", "if the SMTP server doesn't support SSL then uncheck SSL".

Of course there are nothing wrong with my connection, because thunderbird works. But again thunderbird explicitly stated that it will try TLS then SSL.

So it still seems like Mail is stupid with TLS.

Oct 1, 2008 7:08 AM in response to Sunnnz

There are definitely nothing wrong with the internet connection:

$ telnet smtp.gmail.com 587
Trying 209.85.199.111...
Connected to gmail-smtp-msa.l.google.com.
Escape character is '^]'.
220 mx.google.com ESMTP k41sm4265487rvb.9

$ telnet smtp.gmail.com 465
Trying 209.85.199.111...
Connected to gmail-smtp-msa.l.google.com.
Escape character is '^]'.

Oct 1, 2008 7:12 AM in response to Sunnnz

Greetings,

I have no idea why you are having an issue, but it has to be something hosed up on your Mac. I just let the Staff/Faculty Macs set themselves up, using the setup wizard, and the labs are just basic clones and they have to use the Web Mail for MobileMe users, as well as Outlook Web for those using Exchange.

If it were me, I'd trash all the Mail .plist files, and start over. That fixes most issues like this.

I just set up Thunderbird, for grins, and it also works with the same settings I have for Mac Mail.

Good Luck - Cheers,
M.
******

Where is the TLS option in Mail?

Welcome to Apple Support Community
A forum where Apple customers help each other with their products. Get started with your Apple ID.