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Theory: Stubborn ISP, Smarthost, Exchange and Terms of Use

Posted on 2007-11-14
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Last Modified: 2013-12-25
SCENARIO: We have an exchange server (2007) in place and working properly. Inbound e-mail, destined to us, is first sent to our ISP's MTA, which we then forward (after they spam check via Postini) to the aforementioned (internal) Exchange server. To send out, our internal Exchange server uses our ISP's MTA as a smarthost.

According to our ISP, this (using them as a smarthost) violates their terms of use. If we use avoid the smarthost setup by using a dedicated public IP address for our exchange server (making it "external" if you will) certain e-mails will be blocked by AOL, Hotmail, Gmail, etc. (I know this from experience, which is why we use our ISP for e-mail now), due to other IP addresses in that block (public class C) being black listed for "bad behavior." Thus our public IP address is marked as suspect (despite our well-behaved server), and certain e-mails do not arrive or send properly.

Our ISP will not assign us an alternate IP address in an alternate block.

REQUIREMENT: Properly working Exchange server and reliable inbound / outbound e-mail.

QUESTION: Should I investigate another ISP? Or should I take the ISP's advice and include, in Outlook, another "account" (POP3/SMTP with a higher priority than Exchange to make it the default sender) that sends through our ISP in accordance with the ISP's terms of use? Am I overlooking something?
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Question by:light-blue
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wingatesl earned 1000 total points
ID: 20286339
Have you run a reverse DNS lookup on your public IP to verify the existence of a PTR record? I have not seen an entire Class C block from an ISP in a while. If yours truly is then I would look into moving ISPs. IMO any ISP that would allow an entire range of their IP addresses to get blocked for abuse and complain about your server using them as a smarthost is replaceable. The idea of putting another account in outlook to send email (through them no less) is bogus. I am sure you are using NAT or PAT to get to the internet so it makes no difference usage wise whether you send from outlook or exchange. They probably want you to by email boxes from them. Sorry for my rant, but I have dealt with a similar situation too much recently.
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by:Sembee
Sembee earned 1000 total points
ID: 20287825
This sounds like usual ISP support line garbage. If you haven't realised, ISP support only has one goal - to find something to blame your problems on so they can say "we don't support that" and hang up.
If the ISP claims use of their server is against the terms of service, ask them to show where (as I presume you have a copy and have read it). If they are providing you with a business class connection then you should get that kind of service. Sounds like the ISP is more concerned with the volume of email getting their server blacklisted.

Have you actually checked to see if your IP address is blacklisted? There are many tools that will do that.

Otherwise it is the usual suspects of reverse DNS (lack of), SMTP banner invalid etc. Put your domain in to dnsreport.com and see whether it flags errors in the mail server section.

However I would echo what has been said above - ISPs should be disposable. If they cannot do what you need and you have a choice, then change ISP. I have done that in a number of cases, including one where I removed about UK£20k of annual business and had an account manager crying down the phone.

Simon.
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by:light-blue
ID: 31409265
Thank you both!
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