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AOL is pretty much the bane of IT Pros existence.  Like garlic to a vampire, even the name AOL invokes a guttural response.  People devote blogs, websites and write songs about hating AOL (some songs as bad as AOL itself).  But, like Kmart, somehow AOL keeps plugging along.

So what do you do when SBS users complain that they can’t email their contacts / friends / mom / etc. on AOL anymore?  Cheer?  Well, I had an interesting AOL email situation today, and I’d like to share the experience with everyone.  Maybe this will save you some AOL pain down the road.

SBS Network in question:
One SBS 2003 Premium box, about 2 years old, ISA 2004 installed, completely patched, the only major change was switching ISPs about a month ago.  No major hiccups reported in the migration to the new iSP.

Reported Issue:
The SBS network users complains that any email sent to AOL users is not being received on the other end.  Users can get email FROM AOL, but can’t send it TO AOL.  Frustrations are high, people are fussy, yada yada yada.

It’s gotta be you:
I send a test email to a normal AOL user.  It bounces with the following error:

“There was a SMTP communication problem with the recipient’s email server. Please contact your system administrator. <domainxyz.com #3.3.0 smtp;554-: (RLY:CH)   http://postmaster.info.aol.com/errors/554rlych.html>”

Gut reaction:
In plain English, that error message means that some time in the past one or more AOL user clicked the “Um, I think this is spam” button and now this SBS box is probably on the spam list.  You’ve gotta love AOL users! 

1) Contacting AOL
On the  AOL Postmaster Contact Information page is a link to the Before you call page that wants you to have 3 things before you call:
 1) your IP address (Checked)
 2) make sure your reverse DNS is working (Ignored)
 3) your AOL error message (Checked)

I ignore #2 because I think “Hey, the dumb AOL user clicked the spam button – not me.  This is an AOL problem, not something on my end, right?”

So I call the AOL postmaster (888-212-5537) to resolve the issue.  They get my error # and IP address.  Then check my Reverse DNS and say that it isn’t setup for this IP address.  DOH!  Now I have to get that fixed first and then call them back.  I get my case number and hang up.

2) Checking Your Reverse DNS
First, I go to http://www.dnsstuff.com.  I enter the server IP address in the “Reverse DNS Lookup” box, and click RevDNS button.  Sure enough, there is no PTR record setup.  The test results says:

“No PTR records exist for xxx.xxx.xx.xxx.  (Neg TTL=3600 seconds)”

Thinking to self – “Oh yeah… this SBS box is on a different ISP now.  They probably didn’t setup the PTR” (smacks forehead).

M’kay.  So I double-check the AOL Reverse DNS Lookup tool at http://postmaster.info.aol.com/tools/rdns.html.  Same deal: 

“RDNS Results
——————————
DNS Server Response:
NXDOMAIN

Failure! Unfortunately we were unable to resolve Reverse DNS for the IP address you entered. Contact your ISP or e-mail administrator to modify these settings. Also please note the following points:

• AOL does require that all connecting Mail Transfer Agents have established reverse DNS, regardless of whether it matches the domain.
• Reverse DNS must be in the form of a fully-qualified domain name. Reverse DNSes containing in-addr-arpa are not acceptable, as these are merely placeholders for a valid PTR record. Reverse DNSes consisting only of IP addresses are also not acceptable, as they do not correctly establish the relationship between domain and IP address.”

Okey doke – so we need a PTR record setup for this box.  No problemo.

3) Contacting the ISP (for a PTR)
I call the ISP (Time-Warner in this case), give my info and hang up.  I wait a while and a Tier 2 tech calls me back.  He sets up the PTR record on his end and now it’s just a waiting game.  Since the TTL is 3600 seconds I wait an hour and then check the Reverse DNS Lookup on DNSStuff.com: 

“Answer:
xxx.xxx.xx.xxx PTR record:  mail.domain.com.  [TTL 7200s]  [A=xxx.xxx.xx.xxx]“

Bingo!  I double-check the AOL page next – Success!

4) Setup a Feedback Loop Request (FBL)
The Postmaster at AOL mentioned that I should setup a Feedback Loop Request (FBL) after I get the Reverse DNS working.  In a nutshell, a Feedback Loop will forward any mail reported as spam back to a specific email address (more info on the AOL FBL click here). 

Example.  When Employee A forwards an internet hoax virus warning to AOL User B, and the AOL User B flags it as spam, the SBS administrator is going to know that people at AOL are manually kicking out some email.  Due to member privacy restrictions, AOL won’t tell you WHO complained, but the email from SCOMP@aol.net will let you know that you’re being reported as sending spam so you can take appropriate action on your part.

Note:  The best practice when setting up a FBL is to create a separate email alias, like feedback@domain.com or some other clever method (maybe a mail-enabled public folder).  Totally up to you.  Anyway, I setup the email alias on the Exchange server and I fill out the AOL Feedback Loop Request Form to setup the FBL.  Moving on…

5) Contacting AOL Again
I pickup the phone again and give the AOL Postmaster a ring.  They take the case number from Step 1 and check the reverse DNS.  It’s all good.  I give them the original email error number (554 RLY:CH) and they manually approve the server IP address.  Easy stuff.

The tech says it’ll take 24-48 hours before it bakes completely, so don’t expect any immediate action on the email front.  Think of it like domain name propagation.  Just hang tight for a day or so before telling everyone “The AOL email issue is fixed”. 

And your done.  You should be ready to email those AOL soccer moms and home-based businesses at will now. 🙂

6) Optional Final Step – Apply for the AOL Whitelist
If you email a LOT of customers that are on AOL, it may be a good idea to apply for the AOL Whitelist.  To be on the Whitelist you have to have Reverse DNS setup (duh), you have to send a minimum of 100 emails to AOL per month, and you have to meet some other conditions.  Like I said, it’s totally optional and not for everyone, but if you send a ton of email to AOL you may want to check it out. 

Footnote:  I do have to give some props by saying that the techs at the AOL Postmaster helpdesk were very professional and my wait time was minimal (under 2 minutes).  They called me sir more times than the kid at the video store.  And Time-Warner tech support wasn’t too bad today either (also under 2 minutes).  Nuf said.