Seriously. When they can't use 25, 2025 is much easier to remember than 465. Also, I have been doing this since 1992, long before some of the other "common" ports or protocols even existed or were in common usage. Before that email was sent via UUCP which I did going back to the late 70's.

_________________
Kevin a.k.a. Dweeber

Must be symptomatic of living in the Arizona oven.

State Records

Ariz.    128°   June 29, 1994   Lake Havasu               505

Normal Day just outside of Phoenix

Ya, that's what I thought. I already tried it. I find this issue particularly odd. I figured it might be due to the fact that this account is virtually identical to the one on my last server. I had a feeling there might be some corrupt data in the preference files. I cleaned out mail preferences and all the keychain entries but to no avail. I don't even have the OS firewall on. Odd indeed.

So I thought I would bump this up just to see if anyone has worked out a solution. I've been having the same problem with my Apple devices and I still can't quite figure out what's up. I temporarily switched to Sparrow and it had no problem sending mail, but seeing as they're now out of development I'd really like to get Mail.app working right.

I don't know whether you've found a solution to your problem, but I had a similar issue with Apple Mail. Namely, for some reason, it doesn't like when Dovecot and Postfix have different SSL certificates. Yeah, you heard that right. So, just set up Postfix to use Dovecot's SSL certificate or the opposite, and you should be fine.

I'm having the same issue withSMTP in the Mail.app.


How would you do this?

Cheers

Simple. Open your /etc/postfix/main.cf file and change the following two parameters, like this:

smtpd_tls_cert_file=/etc/ssl/certs/dovecot.pem
smtpd_tls_key_file=/etc/ssl/private/dovecot.pem

This is my setup on my Ubuntu 12.04, it may be slightly different on other distros, though.

I must note that I was rebuilding my mail server recently, and Apple Mail doesn't work anymore even with these settings, so I've just switched to Thunderbird for the time being, until I get enough money to buy a proper SSL certificate. But you should try it, you don't have anything to lose.

Are you using a Startcom certificate? Even if your certificate's expiration date hasn't arrived yet, check to see if the certificate used to sign it has expired. That bit someone else I know.

No, I'm not using StartCom's certificate. I'm currently using a certificate that came with Postfix/Dovecot. But as I said, I am planning to buy a certificate from some CA, because Apple Mail doesn't work anymore with any settings.

You can get a certificate from Startcom at no cost, but it is limited to one year of validity. (I would presume that newly-issued ones wouldn't have the same problem with the signing certificate, but don't know for sure.)

That's probably your issue.

While testing a new mailserver setup I used a self-signed cert. Most mail apps would present a "do you want to accept this certificate?" dialog. iPhone mail would just spin until timeout, then give a generic "connection failed" message.

Once I installed a real cert, iPhone mail worked fine.

You only need one cert, put it somewhere (e.g., /etc/ssl/certs) and reference it in Dovecot and Postfix.

If you buy a ~$10 cert like StartSSL, make sure you chain it.

Use the SMTP submission port, 587. I've tested it with a wide variety of mail apps from Outlook Express to iPhone, and every one auto-detects it just fine -- assuming of course that your configuration is correct

_________________
sleddog

I've tested Apple Mail again, and this time it worked with a self - signed cert. I know that I can get a free one at StartCom, and actually I did get one, but then I forgot to back it up so now I need to wait a year before I can get it again.

But anyway, $10 for a SSL certificate isn't much, so I'll go that route for now.

Regarding iPhone, it just works even with the self signed cert, just issued a warning that it cannot verify the identity of the server, and that's it. So far, no problems any more.