Hotmail Drops Email Sent by Thunderbird
I have been struggling with this problem for a number of months. Here are the symptoms:
- Email sent to Hotmail via my SMTP server and Thunderbird never arrives, but I get no bounce message.
- Strangely, email sent to Hotmail via my SMTP server and the “mail” command arrives perfectly.
- 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.
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.
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
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:
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?
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.
mails from thunderbird seem to go straight to junk mail folder in hotmail account
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.
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.
Are you still having this issue?
I am noticing emails being flagged as “bad” coming from Thunderbird 184.108.40.206 which have 2(!) To: headers in the email header.
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!).