Mail not sending one week after Mountain Lion upgrade

Question

Mail not sending one week after Mountain Lion upgrade

Hi

Would really appreciate some help if possible please 🙂

Mail has all of a sudden stopped sending mail in one of my accounts and after consulting with some of the helpfiles online and trying the suggested solutions - nothing works.

I upgraded my macbook air to mountain lion a week ago and since then have had no problems whatsoever until today. Literally mail stopped sending emails today from just one account whilst the mail application was open. I've not made any changes to the settings etc and the relevant mail account is working fine on my iphone.

I've tried changing the port to 587 as suggested by some people on here and that doesn't work. I've followed the apple support page http://support.apple.com/kb/TS3276?viewlocale=en_US&locale=en_US about troubleshooting mail problems and checking everything is configured correctly.

It's weird that it's been working fine since I upgraded and literally stopped working whilst I was in the mail application today - one minute I could send mail from the account, and then it stopped and the email started piling up in the outbox. I've checked the connection doctor and it gives me little green lights to every account. The error message I get is: "Cannot send message using the server mail.mydomain.com. Verify that you have addressed this message correctly. Check your SMTP server settings in Mail preferences and verify any advanced settings with your system administrator. Select a different outgoing mail server from the list below or click Try Later to leave the message in your Outbox until it can be sent."

I can see that a few people are having similar problems after upgrading but it's so strange that it seems to have worked fine since the upgrade then nothing apparent has changed and it's now not working.

If anyone has any ideas/suggestions or has experienced this problem also I would be really grateful for your help and advice.

Many thanks

MacBook Air (11-INCH, MID 2011)

Posted on Nov 24, 2012 9:35 AM

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Answer 1

Eric Root

Level 10

684,027 points

Nov 24, 2012 9:46 AM in response to FrancescaBucci

Have you looked at this Apple article? There are others at the bottom of the article. The article stated it is for 10.6 and 10.7, but it appears to apply to 10.8 as well.

http://support.apple.com/kb/TS3276?viewlocale=en_US&locale=en_US

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Answer 2

Nov 24, 2012 9:50 AM in response to Eric Root

Hi

Yes unfortunately, I've tried this and everything that is suggests might be a problem is ok for me. Thanks for the suggestion though!

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Answer 3

Eric Root

Level 10

684,027 points

Nov 24, 2012 4:38 PM in response to FrancescaBucci

You are welcome. I wish it had solved your problem.

What type of mail account is it? I've read other people are having trouble with Gmail accounts. If it is a Gmail account, you might want to check the Gmail website. I've seen links posted to a discussion there.

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Answer 4

LousyFool

Level 4

2,662 points

Nov 25, 2012 10:23 AM in response to FrancescaBucci

There has been at least one case where the authentication for the SMTP server "got lost". I'm neither saying it was the OS, nor am I pointing at the user, but fact is it went missing. Fact is also it's a bit hidden and can easily be overlooked.

Let's see:

In Mail -> Preferences -> Accounts -> "your problematic account" -> Account Information tab, click onto the the entry next to Outgoing Mail Server (SMTP), then onto Edit SMTP Server List. Make sure the correct server for the account is selected, then cllck on Advanced. Other than a quick check of port and SSL, make sure that the correct authentication is selected. For most servers it's Password, and the user name and password must be entered.

Hmmm?

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Answer 5

Nov 25, 2012 1:09 PM in response to LousyFool

Hi

Thanks for your replies. It isn't a gmail account - it's a domain account hosted by Domainmonster. Also my iCloud email is now intermittent :(

I've checked the SSL settings/authentication settings and everything is as it should be according to the email provider. It's frustrating as it was working fine for exactly a week following the upgrade and then just stopped sending mail. Also, the intermittent nature of the problem on the iCloud account now suggests to me at least that this is a problem that isn't the users fault?

I've downloaded thunderbird and all my accounts are working perfectly through that so for the time being at least I'm staying with the upgrade and hoping that a future apple update might address the issue. From the reading around I've done this seems to be a problem some people are having that tends to be intermittent in nature and resolved temporarily but not completely at the users end of things.

I've given up for now thanks to the fact that Thunderbird is working and I can still access my accounts on my iPhone. Very frustrating though when things don't make sense :) I mean, if it was going to stop working I would expect it to have stopped when I upgraded - not functioned fine for a while afterwards and then just literally send a mail one minute and refuse to send the next five minutes later. Also with my new problem today of Mail and my .me account - randomly sending mail when it feels like it and stacking mails up in the outbox the next - just doesn't make sense to me :)

If anyone does figure out what's going on I'd be grateful for any ideas/suggestions. Seems weird that all the email accounts function fine through thunderbird but not Mail. So far anyway :)

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Answer 6

Eric Root

Level 10

684,027 points

Nov 25, 2012 1:17 PM in response to FrancescaBucci

Have you tried running Disk Utility,Repair Permissions and/or deleting the .plist for mail? See this thread. Maybe it will help.

https://discussions.apple.com/thread/4412019

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Answer 7

Dec 28, 2012 8:54 PM in response to FrancescaBucci

I'm going to ditto this - ongoing problems with email not sending or receiving - and it varies between accounts. There doesn't seem to be any pattern, and I can never tell which account or servers are going to be out today. I've tried all of the help tips but had changed nothing before this. I have about 7 email accounts on 3 spearate servers - all worked until the upgrade and icloud. Not impressed! The whole deal with Apple is that things are suppose to work!

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