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Cannot access mail from iPhone or Mac Mail
https://forum.linode.com/viewtopic.php?f=11&t=8937		 Page 2 of 2
Author:  Dweeber [ Sat Jun 02, 2012 3:48 pm ]
Post subject: 
vonskippy wrote:
Dweeber wrote:
I've listened on 2025 as well as 25 for a very long time on servers that are for client access. It is easier for them to remember.


You have very weird (and stupid) clients if that is true.

Doh, I can't remember a two digit number "25", but I can remember a four digit number that ends in the same two digits that I can't remember.

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.
Author:  vonskippy [ Sat Jun 02, 2012 4:36 pm ]
Post subject: 
Must be symptomatic of living in the Arizona oven.

Code:
State Records

Ariz.    128°   June 29, 1994   Lake Havasu               505


Normal Day just outside of Phoenix
Image
Author:  pacothelovetaco [ Sat Jun 02, 2012 8:01 pm ]
Post subject: 
pclissold wrote:
Default SMTP setting for Mac Mail tries 25, 465, 587, in that order. Since it never receives a reply from your server saying that 25 is unavailable, it is probably timing out. Set its SMTP conf to use 465 instead of trying to figure out which port is available.


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.
Author:  richrad [ Sat Aug 25, 2012 1:41 pm ]
Post subject:  Re: Cannot access mail from iPhone or Mac Mail
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.
Author:  petarpetrovic [ Mon Nov 26, 2012 12:43 pm ]
Post subject:  Re: Cannot access mail from iPhone or Mac Mail
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.
Author:  baza207 [ Mon Dec 10, 2012 10:41 pm ]
Post subject:  Re: Cannot access mail from iPhone or Mac Mail
I'm having the same issue withSMTP in the Mail.app.

Quote:
So, just set up Postfix to use Dovecot's SSL certificate or the opposite, and you should be fine.

How would you do this?

Cheers :D
Author:  petarpetrovic [ Sat Dec 15, 2012 7:50 pm ]
Post subject:  Re: Cannot access mail from iPhone or Mac Mail
Simple. Open your /etc/postfix/main.cf file and change the following two parameters, like this:

Code:
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. :-)
Author:  Vance [ Sat Dec 15, 2012 11:54 pm ]
Post subject:  Re: Cannot access mail from iPhone or Mac Mail
petarpetrovic wrote:
Apple Mail doesn't work anymore even with these settings

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.
Author:  petarpetrovic [ Sun Dec 16, 2012 3:10 pm ]
Post subject:  Re: Cannot access mail from iPhone or Mac Mail
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.
Author:  Vance [ Sun Dec 16, 2012 10:59 pm ]
Post subject:  Re: Cannot access mail from iPhone or Mac Mail
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.)
Author:  sleddog [ Mon Dec 17, 2012 9:24 am ]
Post subject:  Re: Cannot access mail from iPhone or Mac Mail
petarpetrovic wrote:
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.


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 :)
Author:  petarpetrovic [ Thu Dec 20, 2012 12:53 pm ]
Post subject:  Re: Cannot access mail from iPhone or Mac Mail
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.
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