I cant send emails to any hotmail account...
I figured out that hotmail blacklisted my ip, domain, and/or email...

The thing that allows the replies to work is a header in the response mail taken from the original mail that is:
References:

If this reference is equal to the email previous send it passes with out problems...

If you are blacklisted and you have to send a email to a hotmail account the only way is opening a hotmail account and send the email.

If you want that your email appears from your usually email you can change the "Reply-To Address" in the options (Message Replies)

Well, my conclusion, hotmail SUCKS.
Octavio.

I am hosting provider, and my setup is the same, I loose a lot of time in reading their troubleshootings, and submiting them tickets, and finally there is no result.

If you create an account:

xxxxxx@mail.iis-aid.com
Hotmail will receive it without problem, because of existing PTR (reverse DNS)

But it is impossible to configureall virtual server domains that are hosted from one IP with PTR (reverse DNS),bBecause for one IP there is one domain name, so all Virtual Architectires will be silently not deleivered by Hotmail.
So Hotmail really SUCKS.

Yeah, I think before too long Microsoft will have take a step back from this or it will hurt them. Non delivered mail with and NDR is one thing, but when a considerable amount of email disappears into the ether it will damage users trust in their services, and when they lose that custom it will be very hard to get it back. Since writing this article I've done some poking around the web, and it is amazing just how many other people are having issues with Hotmail since late last year.

I just experienced the same issue you described. I own a personal domain, to help keep my skills in check, and use it to maintain contact with friends and family. My SPF record is rock-solid, and no one has any issues receiving mail from my domain except Hotmail/MSN.

I jumped through the same hoops, and received the identical canned response from Microsoft support, recommending I spend the up to $1400 to be Sender Score certified.

Why would this "SmartScreen" consider any messages from a personal domain, with no signatures containing hyperlinks or images, spam? I look at my test Hotmail account, and see the dozens of spam received in the INBOX every day. How is it that SmartScreen doesn't filter out that garbage? I'll tell you why, because the spammers themselves are probably Sender Score certified. Nice. They make millions a year, what's $400 to them?

I'm beginning to think that this Sender Score certified idea is a racket. "Hey, pal. Would be a shame if something happened to yous nice little domain, wouldn't it? You need protection - pony up!"

What a damn shame. I'm telling everyone I know to move to Yahoo or Gmail. I'm disgusted by Microsoft's IdiotScreen technology. BOOOOOOO!

The problems you are describing go back further than last year. More like 2 to 3 years ago.

Bell Canada operates an Internet service called Sympatico. A couple of years ago they teamed up with Microsoft and are doing some co-branding. The Sympatico email accounts are now hosted on a server that uses the Hotmail system. You can log into it through your browser and it looks exactly like Hotmail, however Sympatico is the logo they use of course. You can also set up your email client if you prefer using it. The SMTP server is called smtphm.sympatico.ca. (the "hm" is for Hotmail). I found out that if you send email to a Hotmail account through this SMTP server, your email will almost never arrive. This is kind of ridiculous when you think about it. I haven't tried it from the Webmail interface yet. Nevertheless, this is basically a complete stupidity. I kept sending emails to people and they never received them. I was also using a non "sympatico.ca" email address as the sender. Perhaps if I had used the email address it might have worked. I guess their stupid SmartScreen technology flagged my emails as spam. I then found out that Bell Canada was still using their former SMTP server smtp1.sympatico.ca, so I switched to that and now approximately half of the emails arrive in Hotmail accounts. Still not great of course.

The other stupidity with Hotmail is that you cannot send people most types of attachments (especially EXE files). The attachment arrives and is displayed, but it's greyed out and you cannot open or download it. You can't even open something as simple as JPG's much of the time.

I tell people to use Yahoo instead, because Yahoo accepts all attachments and the email almost always arrive. Their spam filter seems to work better! I've been told that even the Gmail spam filter works better than Hotmail.

You know, the bottom line is that Microsoft is a crappy software company and almost anything they touch or do has enormous problems. When Hotmail was stilled owned by the original founders it functioned much better. I used to have an account and it was a real pleasure to use. It was even possible to use a 3rd-party software to download emails into your email client. Since Microsoft took over it's become another crappy, bug-infested behemoth like their operating systems and other products.

Thanks for the article, it's nice to know there are (many) other people out there having this issue. We have tried everything to fix this issue and it now seems there is no fix.

As a webmaster it looks like I have no option but to prevent anyone one with a hotmail address from joining our site and instead promote other free email services.

What, Microsoft block email sent via a competitors product? Surely not! Why, that would make their competitors product look unreliable, so I can't see why they would want to do that.....

I also having the same trouble and now have a policy of warning all hotmail user that my CMS will not accept them on hotmail accounts and that they should use gmail or yahoo. In some cases I have issued mail accounts to some of my users (critical) to ensure they get any email I send out.

I've been configuring our email server recently trying to get our emails to Hotmail accounts to work and also discovered that we can send a message using Outlook with no problems at all, but the identical message sent from Thunderbird or Eudora is silently eaten by the Hotmail mail server.

I too also noticed that Bell Sympatico uses Hotmail under the covers recently as I've been looking more closely at email headers in messages I received and discovered hotmail lurking in the headers of a message sent to me from a bell sympatico email account.

I've suggested this issue as a story to BBC's Click Online program and I recommend that anyone else that comes across this repeat it elsewhere prominently as well, people really need to be aware of this problem.

In the meantime I will do as this author has done and warn people away from it on our web page and provide links back to this and the "The Register" article that brought me here:
http://www.theregister.com/2007/05/01/hotmail_friendly_fire/

Sympatico users suffer from this as well since Bell-Sympatico "upgraded" its Email platform to hotmail/MSN. Now there are a whole variety of problems with disappearing Emails.

You might as well ban the "Sympatico.ca" domain as well since it it now hotmail.

Remove SmartScreen technology from Hotmail & Windows Live Mail.

Sign the petition right here:
http://www.petitiononline.com/notsmart/

I have had same issue with hotmail. After weeks of negotiations with the hotmail technical support, problem has been solved.
But, in any case, I do not recommend to "communicate" with them. Always inform users about possible disruptions in sending mail from your servers to hotmail accounts (through hotmail faults).

I'm no sysadmin but I fill the shoes at our office and at home. I had come to the conclusion that it wasn't my relative lack of knowledge but actually hotmail blocking my messages. Now all is confirmed. Outlook & Outlook expr, both work to hotmail, but no-go with T-bird. I finally dumped that waste of money ISP Sympatico also. Went with Velcom and a static IP for $20 bucks less a month than Sympatico. Symp want (I think) around $90 cdn a month for a static IP!!!! Down with the big boys!

Sender Score Certified is an independent 3rd part that maintains the whitelist that is used by 100's of other ISP's. I would not be surprised if you start seeing the other big boys behaving like this as well.

Sender Score Certified might be an independent 3rd party, but regardless of how it is put forward it still spells trouble for small/medium business with their own messaging infrastructure who cannot afford to pay upwards of $1000USD a year to maintain membership. I'd also be hesitant to use such as system as it bypasses your SPAM filters, especially when commercial entities can still send unlimited and unsolicited emails for $20,000 a year. Just sounds like it is a lot more about making money than stopping spam, especially with comments such as this in their FAQ;

Define legitimate email, and what is a negligible complaint rate? This description is a little bit too loose I think, especially when Return Path stand to make a lot of money by letting their certified customers send more email.

Hi Everyone,
Can you pls help. I a have a Hotmail account but had not accesed it for some time. Last night I wanted to have a look at my previously save folders and I was asked to re-activate the account, which I did but WHERE is my important folders and files gone? Can I ever recover these?
Pls help.
Thanks
Korehan

That's happened to me a few times in the 8 years I've hat my hotmail account Korehan, and another reason not to use Hotmail for important communications. Unfortunately I would say that all your data is gone. You could try contacting Hotmail support, but I don't like your chances of being able to get anything back from one of their free accounts.

How I wish I had found this article sooner. Just 2 questions to anyone listening.

1. Will changing the IP of my mailserver to a 'clean' IP address solve the problem of being blocked

and

2. How do we start the revolution to get hotmail to sort their act out? Where do I sign up. As webmasters we have the power to make ourselves be heard. Hotmail MUST listen.

1) I would say probably not, but can't be sure. My mail server has two IP addresses and after being blocked I changed the IP my mail server was bound to. This fixed the problem for a couple of days before it was blocked as well. This might have been because the two IP's I used were on the same subnet, but who knows. I personally doubt that.

2) Microsoft will have invested a massive amount of money and energy into their SenderID / SmartScreen screen technologies, so I very much doubt that they will let go of that easily. About the only thing you can do for now is spread the word and ban hotmail addresses from your site. If the combined reaction is greater than any benefit Microsoft can possibly attribute to their SenderID / SmartScreen (i.e it starts costing them money and/or users in a big way), then they may reconsider.

After a week of investigation, still no clue.. all my mails goes into Junk

SPF are done, contacted MS support and cache are refreshed..

I tried to find solution on IIS part, and read the article on this page. Honestly it helped a lot.

The problem is not IIS SMTP settings. After I read here, I tried my IIS with my outlook, and hotmail received my messages. But hotmail doesn't receive messages from WEB application which is ASP.NET. God sake it is a Microsoft product.

Anyways:

After I added headers to my message from my ASP.Net application, hotmail started to receive my emails. I don't know how long it will continue. I just post here immediatelly, so you guys don't have to struggle like me any more.

Here is How I added headers to my outgoing email:

-----------------------------------------------------------------
Dim objMail As New System.Web.Mail.MailMessage

objMail.From = "me@mydomain.com"
objMail.To = "you@hotmail.com"

objMail.Subject = "Subject line comes here"
objMail.Body = "Message body goes here"

objMail.BodyFormat = Mail.MailFormat.Text

objMail.Headers.Add("X-Mailer", "ASP.NET")
SmtpMail.SmtpServer = "My Local SMTP Server Address"

SmtpMail.Send(objMail)
-----------------------------------------------------------------

Hope it helps;

Emin Pala

Not only is the client the main error in hotmail's pathetic SILENT deletion of incoming mail, such as the thunderbird version you tested, but my own tests show that emial sent from an equally non-spamming small server 100% configured correctly also is lost, so long as the CLIENT email program used to create the mail is Microsofts own Mac version of the older Outlook Express 5.0

So the client creates the spam score. The same exact email sent other ways goes through.

insane!

I will direct everyone to this page to now say goodbye to hotmail.

Hotmail (which microsoft paid nearly a billion dollars for I think) is as of this month, a dead service.

Long live Yahoo (gmail is better but archives your emails).

CRAZY microsoft! What were they thinking?

I might consider trying to add a different X-Mailer header as suggested on the email server to overcome microsofts retardation.

I have what appears to be the exact same problem. Thanks for the write up!

--Dave

I've been embroiled in this hotmail cr*p for the past month.
Countless hours lost. And still no resolution.
Here are some things we've discovered:

-If a hotmail users sends an email, and the recepient replies, the email will make it through.
-There was some success with the following header:
To: "Test User{or the actual display name of the user}"
versus the usual:
To:
-Someone in the company discovered that sending as html (Content-Type: multipart/alternative) was successful 70% of the time. Sending as text/plain went to spam folder everytime.

Interesting comments ab't Hotmail...my service has been nil for weeks...while looking into the problelm, I stumbled on your site...I am an illiterate ludite..what can i do? I am taking my hard drive to an"expert" and seeing if there is any hope for me and my "toweer of power"!!!! Moreabout this later... if me and my computer survive...or it will be an Apple for me!! dont know how to sign off, except :
Hoping to communicate with you soon. BP Canada

E-mail sent from a HotPOP account to Hotmail are also lost into oblivion.

Hotmail also stoped working with Entourage 2001and OE5 Mac. I can get e-mails but not send.

I am having exactly the same problem. Outlooks arrives, mutt arrives, CLI arrives, thunderbird, evolution, squirrel mail don't.

But, if I send the same email to a gmail account and hotmail account at the same time (by filling out 2 to: fields) it gets through!

Also, as you said, replying to a hotmail message also gets through.

Two months ago, i've started a few sites. Sometimes i would send out a few emails not only to test the server, but also to test some site features (formmails, newsletters,...). Those emails were sent to Hotmail and other email services (only to accounts owned by me).

Even though some mail was being marked as spam, all messages were arriving without any issues. But since September 1st, email sent to Hotmail accounts, doesn't arrive or bounces back. It simply vanishes !

All email sent to other services arrives, even though sometimes is filtered as spam.

I've asked for support from my host and they were very helpful. I really don't see any problem from their end. My SPF records are ok and my DNS report is similar to the one from the IIS Aid (everything is ok with just a few warnings).

At this time, if i send any mail from Outlook or Webmail (Squirrelmail), it simply vanishes. But if the email sent is generated by the server (from a formmail or a maillist) it's delivered... weird...

I can also confirm what other posters said, that if you send a message from Hotmail to the mail at your domain and the reply... the message is received at Hotmail without any problems.

If you currently have commas, try removing all commas from your SPF record, especially if you have more than one domain. Then wait 3-6 hrs and then notify Hotmail of the change -
see http://postmaster.msn.com/Guidelines.aspx

Sounds strange, but it worked for me.

We've got the same problem. Mail sent from TBird to msn is dropped without any bounced message eventhough the outgoing mail server identifies the messages as queued for delivery. However if the exact same message is sent with Outlook, the outgoing mail server has the exact same "message queued for delivery" message but the mail goes through no problem.

I am an IT Admin for a financial company, I have been KILLING myself (working 24+ hours) trying to get this working... You have no idea what it means that I found out this isn't just me...

I signed the petition.

Thursday 10-18-07 Anonymous

Since yesterday pm, I have been unable tor read or send e mails from my hotmail.address. Mail extremely important to me is presently unavailable to me. Whenever I go to hotmail.com from msn.com and click on mail, I get dropped off line instant! I have other e mail services so can get other mail at my other address. However, I have tried to correct the problem by checking for malware etc or viruses and found my system clear so far. I tried setting the restore setting to two days ago but still can't access my hotmail inbox. Has anyone got any suggestions? I can't seem to contact hotmail itself to ask for help. Would someone explain to me what being whitelisted means? I am politically active and have great concern over the state of our country. Am I being tracked and blocked?

I would very much appreciate help ....

Thank you.

Sounds like your issue is to do with hotmail usage rather than trying to send email to hotmail from an external account, so unfortunately I won't be able to help you with this. I would personally be surprised if it was anything to do with your computer if hotmail is the only website it is happening on. Whitelisting is a method where a mail server administrator is able to add a list of IP addresses of other mail servers that are considered safe/trusted, and therefore are not subject to any of the anti-spam technologies that might be in place. Think of it like being on a guest list to a popular club where if you are on it you get to bypass the queue and go straight in. I very much doubt you are being tracked or blocked due to your political aspirations, and would instead just notch this down to being a hotmail thing. I personally would never ever be using hotmail for any important correspondence.

----------------
Dominic Ryan
3 x Microsoft IIS MVP, MCSE, MCSA
IIS Aid owner/webmaster

I just stumbled across this problem, have contacted Microsoft.... ticket has been passed onto the filtering team. We'll see when they respond, but I am feeling like it's either Sender Score Certification, use an ESP, or ban hotmail accounts? What worries me is sympatico, and potentially other ISPs using SmartScreen.... seems like outsourcing to an ESP is the only realistic solution.

Now, if it were truly the case that Outlook only is being whitelisted, and someone can gather enough evidence of that, maybe we should contact the DOJ and various state AGs regarding antitrust issues. Start w/the AGs who were involved in the last go-around with Microsoft....

BTW, I had the same problem with AOL, but after a call to their postmaster toll free number, they whitelisted the IP (pending evidence of bad behavior I guess) w/in 48 hrs. That's good but also scary in that who knows how many other medium ISPs may be using technology that automatically blacklists certain IP blocks. Again suggesting the ESP route to let someone else manage relationships with various postmasters. Only catch is that most ESPs have a limit of usu betw 100 and 500 recipients max before you are require to subscribe to email marketing services.... The cost isn't high money wise (some are quite reasonable) but the pain of rewriting your software to send msgs to above the threshold recipients to use their mailing list mechanism as opposed to standard SMTP.

I am surprised this problem has not struck more people and there isn't a bigger outcry. Another angle is we should try to get "email neutrality" into the net neutrality discussion.

I feel your pain, and good luck with hotmail support. Seriously. I came to the same point as you some time ago, but as the volume of emails I send is quite low the Sender Score Certified or ESP routes where not viable. Besides that it is the principle of the situation. I have a secure and standards compliant email server, so I shouldn't have to pay for these extra services just to be able to send to email servers using Hotmail's SmartScreen filter. It was because of all these reasons I decided to block Hotmail accounts. I've also been quite surprised as there have been quite a few

As for Outlook I don't think it is as black and white that using it will guarantee delivery, however it definitely looks as if Outlook is given a lower spam score in the SmartScreen filter compared to the likes of Thunderbird. A lot more testing/probing is needed to see what email gets through and what doesn't before anti trust cases are looked at. My testing proves Hotmail are non standards compliant causing the loss of email communication with support that is near non existent, but that is about it. I just really feel for the uninformed people who are actually paying for their Hotmail/Smartscreen based service.
----------------
Dominic Ryan
3 x Microsoft IIS MVP, MCSE, MCSA
IIS Aid owner/webmaster

I am unable to send messages from my windows live hotmail. Keep getting the same message unable to send message, server may be down, try later. Have been trying for 5 hours now

We host several sites, all send email from the same server, I have added SPF to all these domains. Here is what I get

-- result 1
Domain A, email 1 - hotmail into junk,, gmail ok
Domain A, email 2 - hotmail ok, gmail ok
-- result 2
Domain B, email 1 - hotmail into junk, gmail ok
Domain B, email 2 - hotmail into junk, gmail ok

as I said, all emails send from the same server, both domain A and B has SPF, sure they have the same SPF points to our IP range.

from result 1, we can tell hotmail may check subject/body to decide the spam, since 2 email from the same place, but one is marked as spam, maybe it contains some spam word like "congratulation"?

from result 2, we can tell hotmail may not just check SPF (I don;t see any sender id reminder neither), but the sender email (not the real ip since they are the same) ?

The real problem is I can not find out why hotmail marks them as spam, someone from MS says they for sure don;t want spammer know how hotmail filter spam email. But what about people like us, we are not spammer , and just trying to get client's emails go through, and they are not spam emails!

After several days of tests i came to the same conclusion, that emails sent to hotmail customers vanish.
Iam in contact now (just the initail contact) with a support guy, but hope is slim after reading here.....
It is just so strange that not more people are affected. ! My domain is in a shared hosting environment (reseller account) with an Aussie company, but you should think that other people on the same server (email server) whould have the same problem.... or not???

Peter

I'd say it depends on what layer for their antispam defense catches your email. From my understanding SmartScreen blocks at an IP level, which would mean all email using the MTA on that IP would be blocked regardless of domain, owner or anything like that. However if your mail is being caught further up the tree based on your email content rather than who is sending it, it might be possible that others can use the same MTA without any issues. All guesses though....
----------------
Dominic Ryan
3 x Microsoft IIS MVP, MCSE, MCSA
IIS Aid owner/webmaster

I have also wasted days on this problem. I have now banned sign up with emails including passport.com, live.com, hotmail.com and microsoft.com.

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 http://download.microsoft.com/download/e/3/3/e3397e7c-17a6-497d-9693-78f80be272fb/enhance_deliver.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!

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 hotmail.com-domain 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:"

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.

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

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)

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