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SMTP, hotmail rejecting email issue.

I am having a strange situation with hotmail rejecting emails from some of my domains.. I will provide as many details as possible.

I have 4 domains...  

I've been sending newsletters with authsmtp for years and never had any real issues.

Recently I was helping a friend send a newsletter from 2 of his domains (victorypoker.com and victorypoker.net) using authsmtp.com
Originally the .net domain would go to spam and the .com domain would not reach the account at all (completely rejected).

I added v=spf1 a mx include:authsmtp.com ~all to the .com's domain record.. I dont have access to the .net domain and the person added the record incorrectly.

Anyways.. after a month or so without do anything.. now .net gets completely rejected too..
I have another domain (playergps.com) that Ive always used authsmtp.com to send newsletters.. and now it also gets completely rejected.. so I tried another domain that use to work fine and hasnt sent any emails in over a year.. and it also gets rejected.

So I further continued to troubleshoot.. playergps.com sends email alerts (they are in HTML) with a different SMTP server automatically and regularly.. and those emails go to hotmails inbox no problem... I believe this SMTP server is local with its hosting... if that makes a difference.

I am using groupmail business edition 5.0 to send my emails.. it sends emails as HTML .. even if you just write something small like "test".. but there is a separate test function that I believe sends plain text emails.. when I do this with the playergps domain it goes to inbox.. does HTML make it more like to be considered spam?

I tried this with the other domains.. the victorypoker.net one still gets rejected.. victorypoker.com goes to spam.

So after this I tried outlook express 6.. playergps.com emails go to inbox.. victorypoker.com still goes to spam and victorypoker.net still gets rejected.

So Im curious how hotmails spam detection works.. it must give you some sort of score and things either increase or decrease the score.. and depending on the final score, it either goes to inbox, spam, or rejected?

does it make sense that HTML would make its score worse? or could it be groupmail? I just tested an email from playergps with outlook and HTML and it worked

Also I was curious if my IP had any impact on this, so i tried everything again when connected to a VPN and results were the same.

I ran a DNS report on victorypoker.com and everything came back clean..

Basically I need to get victorypoker.com to be able to send emails from my comp using a 3rd party SMTP.

I was thinking maybe it was an issue with authsmtp but it works fine with playergps domain in outlook express from my IP..

Sorry that this is a mess of random pieces of info.. I am just trying to remember all the details that could help solve the problem.

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1 Solution
Your victorypoker.com domain is blacklisted for starters. Hotmail uses RBL as its primary defense mechansm. Go to mxtoolbox.com and run your domain names. They will tell you why it has been blacklisted and then you can work on resolving the issue.

There are a number of things that get you a poor reputation. Spamming for one, Dynamic IP addresses, poorly configured dns etc.
bail3yzAuthor Commented:
very strange, I literally checked that a few hours ago and it wasnt on any lists.. now its on 2!

Thanks for pointing that out.
bail3yzAuthor Commented:
any suggestion about playergps issue?

where i can send emails fine with outlook, but not with groupmail?
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I bet you are getting flagged as a spammer. (which you may or may not be) Using 3rd party SMTP is a common trick of spammers and will be quick to get shutdown. Using Dynamic IP address will get you blacklisted quick as well. Also if your reverse DNS is wrong that will get you shut down.

The best way to send legitimate bulk email is to get a staic IP. Build your own SMTP server, then register your domain name to your static IP.

Any deviation from this will likely get you blacklisted daily.
bail3yzAuthor Commented:
Very strange..

regarding the one domain being on 2 blacklists. one isnt actually a black list it said the following when I went to details.. I believe the entire IP range is on that list

       THE PBL IS NOT A BLACKLIST. You are not blacklisted for spamming or for anything you have done. The PBL is simply a list of ALL of the world's end-user broadband IP space, i.e: IP space normally assigned to broadband/ADSL customers. It is perfectly normal for dynamic IP addresses (DSL, DHCP, cable, dialup) to be listed on the PBL. In fact all IP addresses in the world which are not designated mail server machines *should be* on the PBL.

I've used authsmtp for years without any problems until recently.. I dont send a ton of emails tho.. maybe 1 newsletter every 2-3 months.. to about 5000 customers..

Does reverse DNS matter if you use SPF records?  whats the point of spf records if reverse dns still have to match..
Spammers use a number of methods to disguise themselves as legitimate traffic. I am not sure the relationship between SPF and reverse DNS and if one over rules the other. In my experience Blacklist providers use every method available to determin the source of spam so everything you can do to make yourself legitimate the better.

As for the PBL, all dynamic IP are likely on that list. As for SMTP relays like authsmtp, well they are a haven for spammers so it is possible that they are the ones being blacklisted.

If you want to send thousands of legitimate emails then it is best to set up a legitimate looking smtp server that has staic IP, SPF, Reverse DNS, and Registered domain name etc...
bail3yzAuthor Commented:
Thanks very much, I think i have a good understanding now.. will just set up my own SMTP...  this stuff is a lot harder then it should be.. stupid spammers :)

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