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olePigeon · Oct 19, 2010, 11:25 PM

My boss uses Mobile Me for most of her emails and seems reluctant to switch to our email server (she's used Mobile Me since before I started working there, so nearly everyone contacts her through that, so it's understandable why she wouldn't move.)

She can not send email, it says that the smtp.me.com could not be located. It is set up correctly, exactly how Apple describes the setup, and it did used to work. If I delete the outgoing email server and re-add it, it'll work for a few emails, then go back to not working.

I haven't a clue why it doesn't work. Could the amount of email affect it? She has over 30,000 emails in her inbox, and over 17,000 emails in her outbox.

I also noticed she has Norton installed. I'm going to uninstall it. 99% of problems can be solved by getting rid of that hunk of crap, but just incase it's not causing the problem, I could use some advice.

besson3c · Oct 19, 2010, 11:57 PM

Can you contact the SMTP server by telnetting to it on port 25? If you can't reach it that way, the problem has nothing to do with your client, but is some sort of network problem. If you can, I'd check Mail's Activity Viewer. WIth my past experience Mail has proven to be complete ass with large mailboxes, so it is a possibility that its general chattiness is causing timeouts. If this is the case you should notice that the overall computer performance is not-so-great as well. If this is what is going on I'd definitely suggest using Postbox, it is much better with large mailboxes.

How can she have 17,000 unsent messages in her outbox? Do you mean sent messages folder?

olePigeon · Oct 20, 2010, 11:15 AM

Yeah, I meant Sent Messages.

I'm going to try and rebuild her inbox, see if that helps.

besson3c · Oct 20, 2010, 12:56 PM

Originally Posted by olePigeon

Yeah, I meant Sent Messages.

I'm going to try and rebuild her inbox, see if that helps.

In theory her mail store and connectivity to her IMAP/POP server should be a totally separate animal than her SMTP connectivity/authentication, so if this works this is pure OS X Mail voodoo and should not be settling to the stomach.

olePigeon · Oct 21, 2010, 08:33 PM

Well, I uninstalled Norton and had her rebuild her sent messages box before she left. Unfortunately I don't know if it worked because she was in meetings all day and I didn't have access to her computer.

I did solve the case of the missing emails. She had inadvertently clicked on the read/unread sort button instead of the Date Received, so it was sorting her emails in a really weird way. With 30,000+ emails, all her unread emails were just jumbled, so she could never find the emails she needed.

olePigeon · Oct 25, 2010, 10:20 AM

She still can't send emails via Mobile Me. It just dies.

So, I'm going to completely reset her Mail program. Delete all the Mail preferences, and have it redownload all her email this evening. It works on her laptop, just not on her desktop. It has to be a corrupted Mail preference or something.

Also, even though I deleted unneeded mail accounts and mail servers from Mail, they still show up as options as accounts and servers to use. I think it's just fubar.

olePigeon · Oct 26, 2010, 08:09 PM

OK, reset her email. Didn't fix the sending issue, but it did get rid of the rogue accounts and email servers, though. However, I did notice that after I telnet to smtp.me.com 587 at work, it didn't finish the connection. The second I typed anything in terminal it said connection terminated. However, when I got home and telnet in, I could run basic commands just like a shell account.

I've eliminated any problems with her computer or even Mail. I'm thinking it's the DNS server, so I'll fire off an email to the network admin.

besson3c · Oct 26, 2010, 10:52 PM

It's not a DNS issue. If you can't connect to the SMTP server via telnet at one location but you can the other, as long as smtp.me.com is resolving to the same IP address it is likely a block that Apple has put in place or else some sort of networking issue that is giving you connectivity problems. Have you tried investigating to see if your IP block or individual IP is on some sort of blacklist?

P · Oct 27, 2010, 02:25 AM

Originally Posted by olePigeon

However, I did notice that after I telnet to smtp.me.com 587 at work, it didn't finish the connection. The second I typed anything in terminal it said connection terminated. However, when I got home and telnet in, I could run basic commands just like a shell account.

Could just mean that Apple runs SMTP after POP.

besson3c · Oct 27, 2010, 02:52 AM

Originally Posted by P

Could just mean that Apple runs SMTP after POP.

Huh? I'm not following you here... What does POP have to do with this, if you don't mind me asking?

olePigeon · Oct 27, 2010, 11:20 AM

Originally Posted by besson3c

It's not a DNS issue. If you can't connect to the SMTP server via telnet at one location but you can the other, as long as smtp.me.com is resolving to the same IP address it is likely a block that Apple has put in place or else some sort of networking issue that is giving you connectivity problems. Have you tried investigating to see if your IP block or individual IP is on some sort of blacklist?

Almost! Turns out it was our 8e6 web filter blocking Mobile Me. They changed the filter and now it's working correctly.

P · Oct 27, 2010, 11:54 AM

Originally Posted by besson3c

Huh? I'm not following you here... What does POP have to do with this, if you don't mind me asking?

It's a configuration option on the SMTP server. Since SMTP does not include an authentication phase, and you don't want to let just anyone send email using your server for spam reasons, you can configure it to check if the client IP requesting access has used POP recently. If yes, allow connection - if no, disallow. It's more compatible than SMTP AUTH, which is what I think was assumed here from the 587 port.

I honestly don't know how Apple configured things, it's just a suggestion. It seems that olePigeon solved the problem now, though.