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”

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  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:

  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?


  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 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 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!).