Sending email to Hotmail ?

[itr]

Hi,

At my work we have a dedicated server with Rackspace - but we cannot send email to Hotmail from that server via any method! The mail log shows that Hotmail accepts the email - it just never arrives in the Inbox/Junk.

My preference is to use PHPMailer / Pear::Mail / htmlMimeMail5 classes to send mail.

On my current personal host I CAN send to Hotmail and it works every time. I'm worried that if I swap hosts I might not be able to send email to Hotmail.

I was wondering if you were aware of whether many of your clients have problems with this?
If so, is the problem isolated to Shared plans?

Thanks,

[flesso]

Have you checked to see whether the servers IP is blacklisted?

[itr]

Well - this topic isn't really about that - I'm just illustrating my concerns.

Anyway we checked and fixed EVERYTHING. It all checks out according to dnsstuff.com

I've had a Rackspace tech working on it for at least a month with zero success.

[DPS Computing]

Well at least you managed to sort yourself out in the end.

[swexpert]

Hello itr,
Such problems are not isolated to a domain, user, host or server. It can occur to anyone. Hotmail updated its anti-spam scripts some time back, around March. Since then people have been gradually trying to adapt to Hotmail's strict policies.

Most probably your Rackspace tech staff must've changed the IP or added a reverse DNS entry or added/removed mail headers to the liking of Hotmail.

Such problems occur everywhere, not just eUKhost or any other particular service provider. I have a server listed at SORBS but they wouldn't remove it without charging 50 USD, with no guarantee that it won't get listed again, since the listing program is automated. So many mailservers use SORBS's lists for filtering. In such cases, it becomes impossible to rule out such issues.

But, If there is a problem, there must always be a solution too.

Regds
IJ

[eUKhost.com]

3 most important things to make your emails reach hotmail.

1. Reverse DNS for main IP of the server.
2. Sender Email Address verification.
3. SPF Records.

You must have got Reverse DNS for your main IP address as per my knowledge but the email address which is shown as the sender must not be existing on your Server so you will need to setup that mailbox on your server. Also setup forwarders for nobody and root emails on your server.

You should also setup SPF records for your domain name which should allow only your domains to send emails using your server. We have SPF records on all our servers. I am damn sure that this 3 things will get your problem sorted.

Rackspace wont be able to sort it for you as they have Funnytical Support.

[swexpert]

Bingo! That's probably the secret of Hotmail.

Hotmail does not send anything to blackhole. It send it back or keeps it. So probably the from mail being send was xxyy@mail.server.tld and hotmail was sending it back to that very address but it was being forwarded to abuse or postmaster or mailerdaemon...kinda loop.

Regds
IJ

[eUKhost.com]

Originally Posted by swexpert

Bingo! That's probably the secret of Hotmail.

Hotmail does not send anything to blackhole. It send it back or keeps it. So probably the from mail being send was xxyy@mail.server.tld and hotmail was sending it back to that very address but it was being forwarded to abuse or postmaster or mailerdaemon...kinda loop.

Regds
IJ

its not like that. Hotmail sends "Hello!" message to the sending server for the email address which was responsible to send email to hotmail address and server needs to respond to that "Hello!" with "Ok!"

If the server fails to send "Ok!" message then the sent email is dumped. cPanel servers have this feature by default and OK! message is sent by default for nobody and root emails.

[swexpert]

That's a great piece of information. I did not know this. So hotmail generates calls back to confirm if the mail id exists. That explains inward connections from hotmail in some cases.

Regds
IJ

[eUKhost.com]

Originally Posted by swexpert

That's a great piece of information. I did not know this. So hotmail generates calls back to confirm if the mail id exists. That explains inward connections from hotmail in some cases.

Regds
IJ

not just hotmail but many mailservers including cpanel servers have this feature. If you have root access for your WHM then you will see an option in EXIM Configuration Editor in which you have an option "Verify Existence of Sender". If you enable this option then your server will have same email policy as hotmail has got.

[DPS Computing]

I also didn't know that - its a good verification technique. So does this render the "anonymous" email sending scripts on the Internet useless?

[itr]

Thanks,

eukhost, we have already setup everything you mentioned on Rackspace and it made no difference- so far!

The thing is this:

I haven't been looking after my current personal host for years - I've done nothing special with it - it has no SPF records or anything. But I CAN still send to Hotmail from it.

Now my Rackspace host originally didn't have much setup on it but now we DO have SPF, reverse DNS, PTR, postmaster + abuse mailboxes etc ... but Hotmail wont deliver our mails! The mail log shows that it accepts them but it doesn't deliver them to the Inbox. We've tried every variation of send method / email content possible.

SPF is NOT that critical as I know that it's possible to send to Hotmail without an SPF, as I do on my current personal host.

[WelshTom]

Have you made your e-mail server respond to the word "Hello" from other e-mail services. Look at the previous posts, Mark (eukhost.com) has gone into this subject more in detail.

[eUK-Martin]

It sounds like hotmail is eating the email at the top level of their spam filtering (before it gets to your junk mail). I've heard of other issues like this with hotmail.

Another test you can try is to open a shell on your server and telnet into hotmail's smtp server on port 25. Run through the SMTP commands for creating a message (just google "telnet SMTP commands") and see if the server accepts it. If it does accept it, but it doesn't find its way to your inbox, hotmail is blocking it. Only hotmail can give you more information on why they are blocking it.

[DPS Computing]

Hotmail should really send everything it considers "Junk" to the Junk folder and let you decide yourself - I thought that was what they did. Didn't know about this top level filtering.

[lorriman]

I've been affected by the same problem and in my case after a whole day spent trying to cajole an email through to my hotmail account I discovered that I had set my hotmail junk mail setting to "exclusive" (ie. only allowing emails for people in my address book) and to delete junk immediately!

aaaaaaaahhhhhhhhhh!!!!!!!!!!!!!

[DPS Computing]

Originally Posted by lorriman

I've been affected by the same problem and in my case after a whole day spent trying to cajole an email through to my hotmail account I discovered that I had set my hotmail junk mail setting to "exclusive" (ie. only allowing emails for people in my address book) and to delete junk immediately!

aaaaaaaahhhhhhhhhh!!!!!!!!!!!!!

That must have been frustrating. I would suggest that you don't delete junk straight away and that you set it so it just delivers it to the junk folder. Hotmail has made quite a few mistakes a week delivering genuine emails to my junk so I don't trust it to make the decision exclusively on its own.

[lorriman]

I would have had those sensible settings, but I never use my hotmail account, and so the radical anti-spam filtering was appropriate: except in the case of using the account for testing purposes. Hotmail retains the "junk" folder despite not being needed, so there is no visible indication of the hyper-filtering going on.

[DPS Computing]

I don't understand - how come you needed those settings just because you wern't using it?

That is bad I suppose it should give you some indication - such as removing the junk folder! Time to fill in a suggestion slip for Microsoft I think!

[lorriman]

I should say : I wasn't using it for real emails. and on the infrequent occasions that I needed to visit I preferred not to be met by a huge, steaming pile of garbage.