Apple Mail Issue - incorrectly reporting non-delivery

Discussion in 'Mac Apps and Mac App Store' started by jg87, Oct 5, 2011.

  1. jg87, Oct 5, 2011
    Last edited: Oct 5, 2011

    jg87 macrumors newbie

    Joined:
    Oct 5, 2011
    #1
    Hello all,

    I'm having a problem with Apple Mail that's been troubling me intermittently for quite a while. Often when sending an email from my domain name email account, Mail will report that it was unable to send and suggests that I select a different SMTP server from a list of my other email accounts.

    After trying with the same server a few times, I usually give up and send using my Hotmail server (this is annoying, as sometimes it tells the recipient that it's sent from my Hotmail account, sometimes not).

    The main issue is that I usually find out later that every email has actually sent, and the recipient now has three or four copies of the email in their account, despite Mail reporting that it was unable to send.

    I'm sure that my mail settings are correct, as this is an intermittent problem - sometimes there is no issue at all. It seems to occur more often if I'm sending an attachment with the message (although that might not be the case). I've yet to notice whether this occurs on other devices, but I will try to make it happen on my other laptop and phone.

    Obviously my main issue is that I have no way of telling whether my email has actually sent or not. Also I look like a massive noob when someone receives fifty identical emails from me, which is pretty unprofessional. I guess I could automatically Bcc myself in on every email I send, but obviously that wouldn't be overly practical.

    I'm running OS X 10.5.8 on a Macbook, and Mail version 3.6 (936). I would attach a screenshot of the message, but obviously now that I actually want the error to happen, it won't. If you need any more info I'd be happy to provide.

    I'd be really grateful to anyone who might be able to help with this.


    Edit: It's just happened again and managed to get a screenshot.

    Just to clarify, I'm not trying to send using my hotmail account, it's a personal domain that I've blurred for security.

    I can confirm that despite receiving the error message, I Bcc'ed the email to myself and it is in fact in my inbox.

    [​IMG]
     
  2. jg87 thread starter macrumors newbie

    Joined:
    Oct 5, 2011
    #2
    So um...apparently I'm not allowed to bring my thread to the attention of people who might have missed it.

    Better think of a way to disguise a bump as some new info.
    Users in other threads have mentioned repeatedly being asked to re-enter their password for an account. This happens to me regularly.
    My other Mac also has the same false non-delivery report issue.
    Perhaps it's an issue with the actual SMTP server?
     
  3. wrldwzrd89 macrumors G5

    wrldwzrd89

    Joined:
    Jun 6, 2003
    Location:
    Solon, OH
    #3
    Based on what information you have shared, I suggest going to your email provider's site and looking for the recommended server settings, then making sure yours match. What I suspect is going on is an authentication mismatch - this is correctly being reported to you as a failure. However, what happens after that isn't reported - Mail auto-negotiates with the server for the correct authentication settings, and sends the mail successfully that way.
     
  4. jg87 thread starter macrumors newbie

    Joined:
    Oct 5, 2011
    #4
    Interesting...

    I've checked the server setting so many times, so I'm pretty sure it's not that. Is there any way to view a log of the transaction, find out which settings Mail decides on?

    Cheers.
     
  5. wrldwzrd89 macrumors G5

    wrldwzrd89

    Joined:
    Jun 6, 2003
    Location:
    Solon, OH
    #5
    Yes! Check Console (in your Utilities folder) for any messages Mail may have logged.
     
  6. jg87 thread starter macrumors newbie

    Joined:
    Oct 5, 2011
    #6
    Thanks for your help with this. Sorry for the delayed reply, I've been unsuccessfully trying to replicate the problem with the log running (had to execute a mail log script...).

    However I'm now battling with a further problem, which seems to have replaced the initial issue. Messages seem to be intermittently not sending at all, with no error message popping up and an unhelpful delivery failure report 3-4 days later. It mentions a #4.4.2 error and displays the following message:

    "Connected to xxx.xx.xxx.xxx but connection died. Possible duplicate! (#4.4.2)
    I'm not going to try again; this message has been in the queue too long."

    I'm sure the problems must be connected somehow.
     
  7. wrldwzrd89 macrumors G5

    wrldwzrd89

    Joined:
    Jun 6, 2003
    Location:
    Solon, OH
    #7
    I'm confident that you are right - these problems must be connected. Just to rule out a bug in Mail, have you tried using Mozilla Thunderbird? Another useful tip for Console: There's a search option. It's very helpful when looking for logs generated by a specific application.
     
  8. jg87, Oct 21, 2011
    Last edited: Oct 21, 2011

    jg87 thread starter macrumors newbie

    Joined:
    Oct 5, 2011
    #8
    I tried Thunderbird a while ago but didn't stick with it...I don't remember exactly why but I have a feeling I tried it as a solution to the problem and it didn't solve it. I'll give it another go and see what happens.

    I've managed to recreate the initial problem, with the log running. I'm not entirely sure I want to post the whole thing becase firstly, there's a hell of a lot of data there and secondly, it contains quite a lot of personal info (email addresses, IP addresses etc.). Is there anything specific I should look for?


    EDIT: I think I've managed to isolate the info relating to sending and recieving (as opposed to message content). I've dumped it in a text file you can download here http://dl.dropbox.com/u/18140641/Mail log.rtf but if you'd rather I posted it in the thread I can do that. Personal data removed for obvious reasons.
     
  9. wrldwzrd89 macrumors G5

    wrldwzrd89

    Joined:
    Jun 6, 2003
    Location:
    Solon, OH
    #9
    How very odd! The log doesn't suggest any obvious cause, at least to me. :confused:
     
  10. jg87 thread starter macrumors newbie

    Joined:
    Oct 5, 2011
    #10
    That's a shame - I couldn't see anything obvious either :confused:

    Sorry about the delay - I've kind of given up to be honest. If I route it through my Hotmail SMTP it works ok, and as my web host renewal is coming up soon I'll try a different company and see if that fixes it.

    Thanks for your help with this anyway, I appreciate it.
     

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