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2009 R2 : SMTP Any combination of witchery to add Port Number and Secure Connection to this version?

OldNavDogOldNavDog Member Posts: 88
I have someone who needs to send SMTP Mail through Office365 in 2009 R2 Classic. I have found some information around the internet that claims that this was added as a Hotfix around January, 2011. But I can't find out if that covers both the Port Number AND the "Secure Connection" (TLS) enhancement, or not.

Edit: WIll "Option 3" (SMTP Relay) in the article below work without TLS?

https://technet.microsoft.com/en-us/library/dn554323(v=exchg.150).aspx#option3

Thanks In Advance!
Experience is what you get, when you don't get what you want. --Anon.

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