This has been a nagging issue for a long time. I have not been able to send mail to 
certain groups - messages would just get stuck in the Retry Queue "Awaiting Directory 
Lookup". This was also coincidental with IIS memory leak. I can't believe how simple 
the cause of the problem is!

The groups that experience problems are mail-enabled global security groups AND some 
members of the group are not mail-enabled. That's all.

I have been looking at all other things trying to solve the problem. I thought that 
for some reason there was a duplication of an SMTP address somewhere (actually that 
used to be another bug in earlier version of Exchange 2000) or maybe the 
LegacyExchangeDN was screwed up... I can't believe it did not occur to me to check all 
the group's members to see if any of them were somehow different.

Now we do have a reason for having such mixed groups for customer provisioning methods.

Andrey Fyodorov
Senior Exchange Administrator
iNNERHOST
http://www.innerhost.com

P.S. please consider this bug officially claimed by Andrey Fyodorov, the founder of 
the Scientific Jiggle Method and the Scientific Poking Around method. :)

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