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If you have the Edge Transport Role installed on an Exchange 2010, mail may be rejected with the following error:

My.User@domain.com mail.domain.com #<mail.domain.com #5.7.1 smtp; 550 5.7.1 Message rejected as spam by Content Filtering.> #SMTP#

Don’t ask me why Microsoft has buried this feature! From what I can tell, the only way to whitelist in Exchange 2010 is through the Powershell – not the GUI.  Thanks to Chris Caldwell for the fix.

Specific Address

$list = (Get-ContentFilterConfig).BypassedSenders
$list.add("new.mail@address.com")
Set-ContentFilterConfig -BypassedSenders $list

Entire Domain

$list = (Get-ContentFilterConfig).BypassedSenderDomains
$list.add("domain.com")
Set-ContentFilterConfig -BypassedSenderDomains ...