Are Hotmail cutting their own throat

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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.

Conclusion

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?

Comments

Anonymous's picture

Geez

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.

Anonymous's picture

When I click on hotmail.com in box, I get kicked off line ...

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.

Brashquido's picture

Sounds like your issue is to

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.

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

Anonymous's picture

I guess there's no "solution" to this?

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.

Brashquido's picture

I feel your pain, and good

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

Anonymous's picture

Can no longer send messages

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

Anonymous's picture

I am having the similar problem too.

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!

Anonymous's picture

Same Same here.......

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

Brashquido's picture

I'd say it depends on what

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

Anonymous's picture

This is ridiculous

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.