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doncaruana -> RE: 501 error trying to send external mail (24.Nov.2007 10:41:10 AM)
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Looks like I answered my own question, but I'll post what I ended up doing here for others.
I made sure all the tracing I could turn on was turned on, including the connectivity log (which needs to be done in the shell : set-transportserver -identity <server> -ConnectivityLogEnabled $true).
Looking there (C:\Program Files\Microsoft\Exchange Server\TransportRoles\Logs\Connectivity, by default), I could see that the messages were getting to my external mail server (my smarthost). Looking over at the message tracking log (C:\Program Files\Microsoft\Exchange Server\TransportRoles\Logs\MessageTracking), I saw that my smarthost was actually rejecting my e-mails because the reply-to address was set to my local domain! (me@mydomain.local, vs me@mydomain.com).
There are two ways to do this, depending on your organization.
You can go to each individual mail box and set the reply to address to your external domain name. But in order to do this, you need to uncheck "Automatically update e-mail addresses based on recipient policy". But there's an easier way to do it, but it's complicated too.
First, you have to set up an accepted domain that matches your external domain (mydomain.com). I already had one that was mydomain.local. The key here is that you have to say it's an internal relay domain (even though the option says that's for another AD in the forest). Once you've done that, go to the email address policies.
The trick in email address policies is that little dropdow arrow next to 'Add'. That allows you to create a custom address. Once you get in there you can use an 'alias'. The parameters are:
%g - Used for given name (first name); %i - Used for middle initial; %s - Used for surname (last name); %d - Used for display name; %m - Used for Exchange alias; %xs - Uses the x number of letters of the surname. For example if x=2, then the first two letters of the surname are used.; %xg - Uses the x number of letters of the given name. For example, if x=2, then the first two letters of the given name are used.
Anyway, type in the alias - in my case it's %m@mydomain.com, set that as your reply and apply the policy and voila!! Problem solved.
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