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Outlook / SBS 2011 / Exchange 2010: Can we protect users from themselves sending confidential info?

A client is concerned about sending confidential info to the wrong people (friendly competitors, etc.)

They asked about being able to get a warning pop up in outlook when an email they are working on has an external email address in the to, cc or bcc lines. They are thinking that will urge the user to doublecheck the names selected.

This is what they sent me:

I would want a temporary notice on Outlook to pop up on the top of the mail screen that notifies our employee sender during the DRAFT stage of an email that they have included an external sender in the address lines. I would like the external sender function to only show up during the draft stage of sending an email, not in the final version sent to the recipient.
 

a) is this notice possible? Either in outlook or some other method to catch emails elsewhere on the network - The SBS 2011 server they have? in the UTM?  On phones maybe not using outlook? If we insist on outlook on phones would that help? On OWA?

b) does anyone have a client with this?

I personally think that it's pointless. People will still click through the warning - they will get this on almost every email they send and will quickly tune it out. I'd envision they'd want to be able to clear the message once they check that email and it would re-occur if they added someone else to the list?

And they do have friendly competitors that they email. So then it becomes a question that each employee has to answer: I am writing to a competitor. Is this information that's ok to send them.  

Thoughts on implementing a solution and the viability of that solution?
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Amit Kumar
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thanks.  That's a neat way to do it. But realistically, doesn't seem viable? That administrator will be loaded down with checking many emails. They want to put the onus on not sending out the wrong stuff on the employees themselves. Yeah, certainly not foolproof!  But what they want (just short of scrapping the idea completely :<g>
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Cliff Galiher
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I could see the client saying they want to keep employee from forwarding an email that might have confidential info. Not just attached docs.  With that in mind, that rules out the microsoft solution?

ever hear of:  https://www.safesendsoftware.com/videos/ ?

waiting to hear from them for costs.
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I see 'very expensive' and shy away. Any idea what type of order of magnitude of cost for 20 users?
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too small for an enterprise solution : (

I also got that answer for https://www.safesendsoftware.com/videos/

I understand the business reasons for that from the vendors... but it's frustrating - small businesses have the same needs to protect their data too.
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