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Sending emails to Hotmail doesn't work

Posted on 2007-04-09
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Last Modified: 2010-03-06
I'm trying to get an important email across to a client who currently only has a Hotmail account until I get them on an Exchange Server installation in the next week or so. However when I send an email to their account or the test account I created a few minutes ago, nothing arrives.

My domain has no problems sending emails to other domains, and even has an SPF record. Any idea what's going on?
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Question by:DReade83
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by:Sembee
ID: 18877623
What does message tracking show?
Is the message actually being delivered to Hotmail, or are the messages sitting in the queue?

Simon.
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Author Comment

by:DReade83
ID: 18877675
The first thing I did was check the tracking info. It appears the email is being delivered to Hotmail's SMTP server, but doesn't say anything after that.
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by:Sembee
ID: 18878092
If the message is being handed off to Hotmail's server then the problem is not with Exchange. Hotmail could be flagging the message as spam. Have you checked the spam folders to see if the message is in there?

Is your server setup correctly? DNS is the main area I am thinking of. Put your domain in to dnsreport.com and see if it flags any errors in the mail server section.

Simon.
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Author Comment

by:DReade83
ID: 18878115
I've checked Hotmail's Junk Mail folder, but nothing's in there.

The results from dnsreport.com is: http://www.dnsreport.com/tools/dnsreport.ch?domain=sbhelp.co.uk
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by:Sembee
ID: 18878185
Nothing wrong there and the server isn't blacklisted either.
If you bounce the email for hotmail through your ISP using an SMTP Connector, does the message get through then?

Simon.
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Author Comment

by:DReade83
ID: 18878282
How rare - sending an email from my personal account via my ISP's SMTP server, the email hits the hotmail account, but drops into the Junk Email folder.

Another email has been sent - instead of having the Subject and Body as "This is a TEST email", I've cleared the Subject, added my company signature and sent it from the same personal account. This has NOT arrived.

This makes no sense, as "sbhelp.co.uk" has an SPF record, whereas my personal account (I own the domain) doesn't?!

I don't know what else I can do as it looks like a Hotmail problem to me. I used to be able to send from my company account to Hotmail accounts, then all of a sudden I couldn't anymore. I could try highlighting this problem with Hotmail, but their help section is absolutely useless - the keyword "fault" returns no results and "error" doesn't give me much either. My last resort in contacting Hotmail would be to email abuse@hotmail.com - it's the only address I know that's probably manned, unless you can think of anything else?
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Sembee earned 500 total points
ID: 18881693
It would appear to be a Hotmail issue.
When the message is sent via the ISPs server the score may be enough to go in to the spam filter, but when sent directly it is at the level where the message is simply dropped. I don't know how Hotmail's spam filtering works, I don't have a Hotmail account.

Simon.
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Author Comment

by:DReade83
ID: 18884854
Well unfortunately I've gone down the route of Microsoft Support. I say "unfortunately" as the responses I'm receiving are mixed and vague.

I sent a page-long email explaining in detail (more detailed than what I wrote above) the problem I was having, along with all the tests I've done. The initial response involved redirecting me to Hotmail's Postmaster website, clicking on to the SNDS info site which displays spam info about your IP range. This returned no data for over 4 weeks! Apart from that, Hotmail Support reckon it's a problem with my Exchange Server, which kinda p*ssed me off, seeing as I mentioned "no other problems with any other domains".

Microsoft PSS Support - oh, big mistake, as they simply lached on to the keyword "Exchange Server" and skipped "Hotmail" - telling me to call their Premium Rate, £199 per support ticket phone number to investigate and resolve the problem with my "Exchange Server".

Microsoft Partner Newsgroups - again, Exchange Server mentioned and lached on to. No mentions of an issue with Hotmail.

Ah well, I'll just have to keep bouncing back their questions until I get somewhere.

Thanks Simon, I appreciate your time.
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Expert Comment

by:Sembee
ID: 18885660
I call this "pin the blame on the donkey". Standard support practise - find something else to blame it on. In this particular case your Exchange server.
Most ISPs believe that their network is perfect and any problems are caused by a problem with your setup, not theirs.

Simon.
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