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Hotmail Blocking Email

4 points by missenlinx ↗ HN
I run a legitiment website & I do require that users activate their accounts via email. Now i've tried sending email to my hotmail and it doesn't go into SPAM nor the INBOX.

I have done some research and lots are stating that hotmail are dropping emails. (I read once this is illegal)

My server is in no blacklists and isn't used for spam purposes.

Any suggestions would be great.

10 comments

[ 4.5 ms ] story [ 35.7 ms ] thread
gexla
Common problem with Hotmail and a bit of a crapshoot. I assume you have done all the general SPF stuff. There is a postmaster website for Hotmail (guidelines, contact info and other tools) and also a whitelist that you can get on if you are ready to pay out the nose. Google around for it.

One thing you can do is to get an account with an external SMTP service (such as Authsmtp) and configure your email server (such as Postfix) to relay your email through that service. Many people use Gmail for this but Gmail requires unique settings that can make this kind of a pain. This allows you to piggyback on the deliverability of the other service.

If you are sending out newsletters, you might consider going with a specialized service such as Constant Contact.

If you look around, there are more blog posts and information sites that are more detailed. One of them is on hacker news as I type this. Good luck.

hhm
I had more simple problems with Hotmail. I had many cases where people sent me mails to Yahoo and Gmail accounts and if they came from Hotmail mail addresses, they just didn't reach me at all. Some Hotmail users I knew had difficulties even to subscribe to Google and Yahoo Groups too (for the same reason). Mail sent FROM Hotmail accounts many times doesn't even go to spam folders.
missenlinx
Hmm Thanks for your suggestions. I might actually just get hotmail users for now to just go via an alternate activation method.
JamesBrooks
We've had this problem a lot, even with specific in house policies for how mail should be sent from our web applications. I've found that making sure the SPF record is correct and very 'tight' helps a lot. Also make sure before you're mail server isn't running as an open relay well before you send a test e-mail to Hotmail (make sure everything is perfect before you send to hotmail).

After that, don't just start sending a large bulk of e-mail to hotmail, send a few (they'll run some tests, open port, check SPF, etc!!). After a bit then start shipping mail out to hotmail.

Even after all of this you can still be up the creak, we've gone to using AuthSMTP at work now (having Postfix directly proxy the requests on). It's fast and we can deliver to hotmail (a lot less stuffing around).

bayareaguy
Just curious, where did you read that dropping email is illegal?

It may be against the terms of service or perhaps violate a service contract but for it to be illegal there would probably need to be evidence of some other nefarious activity.

icey
It is not illegal to drop emails.

That being said, are you positive the problem is with hotmail itself and not its mail handlers?

For example, if you use the incorrect sort of line breaks [1] in an email that gets sent to a qmail server, the server will silently drop that email message. It will report an error textually but not return an actual error code. This could make it look like your email was getting dropped. This happens quite frequently with machine generated emails.

Who knows if MSN / Hotmail uses qmail, but my point is that there may be other matters afoot than Hotmail intentionally playing hardball with you.

[1] Qmail pukes when you send an email that contains carriage returns without line feeds.

tx
We had the exact same issue with these morons. Email them and explain what's up. They will add you to their "white list". Funny thing is how their SMTP server accepts messages without errors and then just silently drops them.

It's Microsoft we're dealing with here.

es
We had exactly the same problem and have tried a lot of things. But recently we have solved it. You need to set SPF and register it with hotmail. It should solve your issue.
yekmer
I had the same problem, have you got correct reverse DNS record? it may help.