Are Hotmail cutting their own throat


UPDATE: Email clients play a role too

While reading back through this article I noticed that it was totally server centric, with no consideration of what an individual email client might be doing to effect an emails deliverability to Hotmail. Email clients are responsible for adding header information which is widely used for aiding in anti spam purposes.

I started playing around with clients rather than concentrating on server setup, and I've had some interesting results. I can send to Hotmail without a problem using Outlook 2003, but no cigar with Mozilla Thunderbird. I haven't tested other email clients yet, but I think that this suggests that the headers the email clients add to an email also play a crucial role in determining if the mail gets through or not. This is BAD news because as a system admin there is generally very little you can do about this. I'll be interested to continue testing, especially with the user-agent and x-mailer headers.


This one should not be a hard one to come to. If people are not able to be confident that mail sent to Hotmail will get there, then why use their services? Especially when there are so many other players in the field. I have now configured rules for this website that ban the use of Hotmail addresses during signup, and have configured my email server to send a message to any of my users sending to a Hotmail account informing them that their email is unlikely to get through. I realise that me banning Hotmail is not going to make any difference, but get 1000, then 10,000 the 100,000 other webmasters just like me doing the same thing and you really have to ask yourself. Are Hotmail cutting their own throat?


Anonymous's picture

I can send now

After 3 months sending emails to microsoft's support, they finally removed my IP from their black list.
I did all the steps suggested in this pdf
except pay for third part white list, and they finally answered me with this:

"I am pleased to inform you that we have taken steps to implement a temporary mitigation to your mail delivery problem. The mitigation will take 24-48 hours to fully reflect in our system.

During the mitigation period your emails should not experience any issues arriving in Hotmail customer's inboxes. This period will also give our filters sufficient time to learn enough about your mailing practices that after the mitigation expires your mails shouldn't any issues with arriving in our Hotmail customer's inboxes. Hotmail has created group of programs that should benefit your mailings during this time. To help avoid future issues I would strongly suggest enrolling-in or implementing these if you have not already. "

So, never quit!

Anonymous's picture

Why doesn't Microsoft take this problem seriously?

I have several websites at different hosting companies. For the last two years I have gotten complaints from new users signing up who says they never receive verification e-mail (I use that to verify that the e-mail address is valid) and thus can't login for the first time. Everyone who has problems was using hotmail.
I haven't spent much time trying to get it working since the majority of users still have other e-mail providers.
But recently I set up two sites at the same hosting, therefore using the same mail server although different domains. One of them works without problems, even hotmail users recive notifications by mail.
But on the other mails disappear into the Hotmail Black Hole. No bouncing, no errors. Irony - all my websites run on Microsoft software...

I found this story and everything made sense. What strikes me is that these problems were reported to Microsoft early 2007 - and still almost a year later they have done NOTHING to take care of it?
I think that to few end users have been informed. To few website owners have started blocking hotmail users from signing up. Probably because MS help the bigger ones out and ignores the small.

Hosting companies have more or less given up since Microsoft only provide useless support as reported by many people on these forums. Even when supplied with sufficient evidence the support staff sends back "have you looked in the Junk folder?"-kind of replies.

What if all affected by this set up auto-replies "Unfortunately we cannot accept e-mail from until Microsoft accepts the e-mails we send out. Please contact Microsoft support. If they can't help you, here is a list of other great mail services that are free as well:"

Anonymous's picture

Why even honour them with

Why even honour them with specific mention of their name.
it'll only boost up their search engine results and make that retarded #opps#s look important.

back in the days, whenever there was a 'well known' problem with one of the crappy free mailers we just put them into the enemy list in the signup thing going 'we don't accept e-mail addresses from this country/company for technical reasons' or something like that, you don't specifically mention 'hotmail' on your sites, that will only give them a hard one.

as for the rest of it, we can pull m$ tricks as well but having sites going 'this site won't display unless you upgrade to a real operating system with a real browser' doesn't exactly help the cashflow process :P

although you could try to get microsoft to pay $1400 to be 'approved' to 'fix' the problems with their browsers/e-mail users/clients/etc :P

clearly these people still don't have any understanding about the concept 'internet' which includes that i allow you to transfer your data over my network and you allow me to transfer my data over yours, also on higher levels such as e-mail exchange.

oh well, in the end, most people using m$ crap are low-budget customers anyway, we don't really miss out on a lot of money if we would just block them all artificially (ip fingerprinting or useragent or mailheaders wise).

but #opps# it, they're a has-been anyway.

Anonymous's picture

Sending POP mail using hotmail

I collect all my POP3 mail using Windows Live Mail. Two of the sources do not allow sending so I want to set Hotmail as the sending server.

Is this possible? What are the encantations needed? Thanks

Anonymous's picture

Want to get your rivals website banned?

Here is the most ludicrous thing about Hotmail.

Set up a new Hotmail account, import about 100 hotmail addresses into the contact list and then send a message to all of them using BCC

In the message put your rival websites address. The idiot Hotmail program will then pick up the URL and do a reverse ip check and ban the ip address.

How do I know this? Well, I was stupid enough to send an email to all my contacts informing them that our domain name had changed. Hotmail decided I was spamming and banned the new domain's server ip address.

To this day I still can't send an email from the server to any hotmail address. They just vanish.

So if you really want to get rid of all your web rivals just do the same thing. If enough people do it then maybe Hotmail will wake up and realize how stupid it is to ban a site based on a single URL in an email sent to multiple users. (I could understand this if I sent it to like 2 or 3 thousand, but just a hundred users? Wake up Hotmail)

Anonymous's picture

No hotmail is allowed

I am going to prevent users to sign up with hotmail account at my site, and I will force existing members to change their email address

Anonymous's picture

Ban the Hotmail

In my opinion - Microsoft cashing in and will end up loosing out end of day

i have many servers, some work fine some get blackholed


Anonymous's picture

Stupid workaround

I've been plagued with the same issue since relocating to a new dedicated hosting provider. The company is reputable, more so than the last, and RDNS is setup. SPF isn't configured, but wasn't before either. Nothing has changed except the IP, which was not black listed, yet mails vanished into the ether. Hotmail happily accepts the email with a 250 return code but decides not to actually deliver it.

A simple Perl script is used to email users on signup, and also for password retrieval. Troubleshooting from my home DSL account showed the problem not to be with the IP, but the format of the email. Send the exact same text through a simple text email and it works, sending it via telnet (trying to put in all the correct "Reply-To" and "X-Mailer" headers) did not work.

While playing around I found out two things made the mail suddenly work.

Firstly, send it to more than one recipient. Whilst I think this makes it look more like spam, Hotmail likes it. I have the sendmail "To:" line have the user's email address and also the mail-out accounts address.

Secondly, don't make the sender's name look pretty. No "From: Firstname Lastname ", just "From: ". Again I think it makes the email more spam-like, but both of these were necessary to make the emails work.

For reference the sendmail mail commands look like:

To: <>, <>
From: <>
X-Mailer: My.TAG
Subject: Welcome to!

I've stopped new users signing up with hotmail accounts, but at least this precarious workaround lets existing hotmail users manage their accounts.


Anonymous's picture

Hotmail and

No, don't block Sympatico users as well!
I have a Hotmail and a Sympatico account and have the same problem with Hotmail - however, the same person who didn't receive my Hotmail messages, received the message when I sent it through Sympatico!
So, although these two email services are in kahoots, so to speak, the problem seems to be soley with Hotmail, not with Sympatico.

Anonymous's picture


I was so disappointed I have had the same MSN account & Password for years.Allof a suden nothing.I had several pages of e-mails were very valuable to me as I had cancer & they were sentimental & never cancelled them out & a lot of others also I lost all my contacts & everything.I think for a company to do such a horrible thing to people shows us what they are made of without letting us no they were going to do it & somehow we could have saved them