Hotmail Drops Email Sent by Thunderbird

I have been struggling with this problem for a number of months. Here are the symptoms:

  1. Email sent to Hotmail via my SMTP server and Thunderbird never arrives, but I get no bounce message.
  2. Strangely, email sent to Hotmail via my SMTP server and the “mail” command arrives perfectly.
  3. Email sent as a reply to a Hotmail message using Thunderbird arrives perfectly.

I played with SPF and lots of other Postfix and DNS settings hoping to fix things, but the problem persisted. I gained some hope when I read that this site was having the same problem.

I’m stuck scratching my head since it’s obviously not a server problem. I just can’t imagine what header Thunderbird is adding that Hotmail doesn’t like. I started this thread (continued here) on the Provo Linux Users Group hoping to get some answers. No luck yet.

10 comments to “Hotmail Drops Email Sent by Thunderbird”

You can leave a reply or Trackback this post.
  1. http://John says: -#1

    I am having the exact same problem. I have a fedora 7 machine with qmail installed. I am on a dynamic ip so I user smtproutes with a patch that allows me to auth/pass to an external mail server for forwarding to the outside world. It works fine on all systems (gmail, yahoo, other domains) except hotmail.

    Hotmail doesn’t receive my email if I use Thunderbird (Linux or Windows) but it will with mutt or sending from the command line.

  2. I am also having the same problem.

    I started to get some hints here and there.

    #1 hotmail sucks!

    #2 i was able to get one message through (and by “through” i mean to the “spam” box.. even though I have my own private server that is on no blacklist, is pretty new, and has never spammed, has reverse lookup, etc.) — i did this by sending the email has html and text (which you can only do if you add some formatting, like color or something). However, I could not repeat this success

    #3 i could not duplicate the “success” I had in #2 on subsequent tries

    #4 hotmail / msn f$$king sucks!

    #5 i just sent a plain text message from webmail (horde on my server) — it “arrived” to hotmail — but to spam box (Junk) — i stress, my IP address is incredibly “CLEAN” – never has been spammed from, not blacklisted

    #6 hotmail, yes, hotmail, it bites, yes it does

  3. I have the exact same problem.

    I can reply to emails sent to me from Hotmail, but I can’t Write and send a new message.

    I have found that if I reply to any message (doesn’t matter who sent it), and then change the To: email address to the Hotmail account I want to send to, it then works. Strange.

    I found that idea here:
    http://forums.mozillazine.org/viewtopic.php?t=435829

  4. Galahs,

    Does that mean that you can reply to a non-Hotmail message and then change the “To:” field to a Hotmail address, and it works?

    –Dave

  5. Through script you can try adding the following header:

    Content-Type: text/html; charset=iso-8859-1

    Note: Be sure to add the character set. I’m not sure if Thunderbird creates messages with the character set explicitly defined — if not this may help them.

  6. mails from thunderbird seem to go straight to junk mail folder in hotmail account

  7. Great article! I have been having exactly the same problem for well over a year now. Like you state, if you use pine/mutt and same smtp the e-mail is delivered. Using Thunderbird, it is not. Conspiracy..?

    As a result, I simply refuse to communicate with people using @hotmail.com. Why people use such an awful service, i have no idea.

  8. I’m seeing the same thing… it’s sporadic – sometimes it works for a while, and then stops again. I haven’t done any exhaustive testing, but a cause for this would be nice! Even nicer would be if everyone stopped using hotmail, but that’s not such an option, unfortunately.

  9. http://J.%20Roeleveld says: -#1

    Are you still having this issue?
    I am noticing emails being flagged as “bad” coming from Thunderbird 2.0.0.22 which have 2(!) To: headers in the email header.

  10. For the past year or so, Hotmail has been accepting all my Thunderbird emails. There’s only one person to whom I send email who uses Hotmail, so it may just be an isolated case.

    So for me, problem solved (not that I know how!).

Write a Reply or Comment

Your email address will not be published.