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Outlook Anywhere and SBS2008

Posted on 2015-01-26
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Last Modified: 2015-01-28
Hello,

I have a SBS server 2008 and Im being asked to set up outlook anywhere on it.  I have always relied upon the VPN, and then have people access outlook across the VPN.  Now the criteria has changes.  What are the security pitfalls if any of utilizing OutlookAnywhere?  Should I even be considering it?

Please advise.

Thank you
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Question by:John Nau
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by:Larry Struckmeyer MVP
ID: 40571854
Best thing since sliced bread.  In order I would chose Outlook Anywhere, then OWA then RWA - read mail.  The last just because it requires more clicks on the part of the user.
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Expert Comment

by:punkrawkdude99
ID: 40571855
well it uses ssl.... thats a plus....

it is pretty slow unless you have a really good dual proc system

i would get an ssl key from a trusted source.... dont self sign

make sure the users have good passwords....
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VB ITS earned 500 total points
ID: 40572045
Best thing since sliced bread.
Couldn't have said it better. Outlook Anywhere will make your users like you even more than they do now (not saying you're unlikeable or anything...)
it is pretty slow unless you have a really good dual proc system
Not sure where you got this from but that's simply not true in any of the cases that I have seen. I have several clients using low-end HP ML series servers running SBS 2008 and not one of them has complained about the speed of Outlook Anywhere.

If you already have a trusted third party SSL certificate installed on your SBS 2008 server then you'll be using the same certificate for Outlook Anywhere. Setup instructions for Outlook can be found here: https://support.office.com/en-in/article/Use-Outlook-Anywhere-to-connect-to-your-Exchange-server-without-VPN-ae01c0d6-8587-4055-9bc9-bbd5ca15e817
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Author Closing Comment

by:John Nau
ID: 40575598
I realize it was a pretty generic question as I'm not experiencing any real dilemma.  I simply have some security concerns, and now I'm more comfortable.  In truth, nothing is purely secure.  It become a balancing act of accessibility Vs. Risk.
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