Microsoft Exchange server-side transport rule question

I'm trying to create a successful rule that says when an e-mail is sent to John Smith and the From address matches 'domain.com', copy the message to 'Jane Smith'.

I tested this scenario with my personal and work e-mails and had the message copied to a dummy account and changed the parameters to match the circumstances involved.  However, 'Jane Smith' said she's not getting the e-mails.

The Transport Rule logic reads like this:

Apply rule to messages
sent to 'johnsmith@mycompany.com'
   and when the From address matches 'domain.com'
copy the message to 'janesmith@mycompany.com'

Is there anything else that would prevent this from functioning properly?
LVL 3
djhathAsked:
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MHMAdminsConnect With a Mentor Commented:
No lies, I've asked a few other exchange guys and they said to try and run the powershell command from elevated mode and then see if it works as sometimes the GUI is a little fickle.
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MHMAdminsCommented:
try to set it as a BCC to janesmith, but I would check if she has any aliases and verify the correct SMTP address being sent to that users mailbox.
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djhathAuthor Commented:
Thank you for your response.  The idea of the transport rule is to catch anything that is domain-specific (i.e. "domain.com").  Does that change anything?
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David CarrCommented:
Have you investigated where the messages are going that do not get  delivered to Jane Smith?
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MHMAdminsCommented:
It would be if her correct SMTP address is Janesmith1@mydomain.com and an alias is not set for Janesmith@mydomain.com.
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djhathAuthor Commented:
I deleted and re-created the rule and wanted to provide the output of what it looks like as an EMS command.

Exchange Management Shell command completed:
New-TransportRule -Name 'Rule' -Comments '' -Priority '0' -Enabled $true -SentTo 'johnsmith@mycompany.com' -FromAddressMatchesPatterns 'domain.com' -CopyTo 'janesmith@mycompany.com'

Looking at the rule logic through the EMC New Transport Rule wizard:

Apply rule to messages
sent to 'johnsmith@mycompany.com'
   and when the From address matches 'domain.com'
copy the message to 'janesmith@mycompany.com

When choosing the 'sentto' and 'copyto' addresses, I'm choosing straight from a list of all mailboxes in Exchange, so I can't imagine the smtp address is being transposed incorrectly by the system.

I did check the aliases and both johnsmith and janesmith have no other aliases.
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MHMAdminsCommented:
When you specify and when the From Address Matches try adding asterisk so it should look like '*.domain.com' and see if that works.
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djhathAuthor Commented:
The period between the asterisk and 'domain.com' would suggest that there are subdomains, no?
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MHMAdminsCommented:
just using the wildard would specify ANY address with the domain name attached.
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djhathAuthor Commented:
It wouldn't take the asterisk as a wildcard in front of domain.com:

*domain.com

or

*.domain.com

"The regular expression you entered contains the following error: There's a problem with your use of the wildcard ( * ) character. In a regular expression, you need at least one character before the wildcard character.
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MHMAdminsCommented:
If you have a character infront of the * it would filter J*.domain.com it would then only use the rule if anyone with an email address that starts with J@domain.com. The *.domain would allow any username followed by domain.com to run the rule.
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djhathAuthor Commented:
As mentioned, I tried "*.domain.com" and it generated the same error and would not accept that as a wildcard expression.

I suppose I could do something like

a*@domain.com
b*@domain.com
c*@domain.com
d*@domain.com
e*@domain.com
f*@domain.com
g*@domain.com
h*@domain.com
i*@domain.com
j*@domain.com
k*@domain.com
l*@domain.com
m*@domain.com
n*@domain.com
o*@domain.com
p*@domain.com
q*@domain.com
r*@domain.com
s*@domain.com
t*@domain.com
u*@domain.com
v*@domain.com
w*@domain.com
x*@domain.com
y*@domain.com
z*@domain.com

It seems like a bastardized way of something that should be a lot simpler.
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djhathAuthor Commented:
That's a good point.  I actually went ahead and did the bastardized version I wrote in my last post.  However, if that doesn't work, I'm going to re-do it, capture the EMS command expression and syntax, then re-create the rule again using EMS in elevated mode.  I will advise as things progress.
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