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What is the best method to remove attachments from outgoing emails using Exchange?

I need to apply the rule only to messages going to one specific email address. And I need to strip off all attachments except for one specific extension.

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How about telling us what version of Exchange you're referring to? – joeqwerty May 1 '13 at 19:33
Using Exchange 2010. – jswanson May 1 '13 at 19:49

I think you have to configure classification (which would strip the attachment) then apply the classification via transport rule. I'll have to dig up specifics but maybe this answer will jog someone else's memory

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Using the built-in capabilities of Exchange, this isn't possible. There is no transport rule action that can remove attachments.

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Are there any Exchange extensions that could possibly do this? – jswanson May 1 '13 at 19:49

You might be able to use Attachment Filtering on the server running the Edge Role:

You'd have to have at least 2 connectors setup though for outbound email. One exclusive for this external address, the other the default for everyone/everything else.

Follow the article, creating an entry for EACH extension you want blocked. Unfortunately, you can't do an "EXCEPTION" entry.

Add-AttachmentFilterEntry -Name *.EXE -Type FileName

Using the -action strip parameter in an attachment filter will strip the EXE's out and allow other non-blocked attachments through.

Set-AttachmentFilterListConfig -Action -Strip

Then set that filter on the outbound connector that is for that single email address. It has to be set on the connector so that's why 2 are needed...

Honestly though, it's clunky and 3rd party SMTP gateways/appliances/SaaS should be able to handle this better for you.

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