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Regarding TLS SMTP communications: there is an issue with downgrade attacks. Basically, you can't trust email transactions to be 100% encrypted. You also need to consider Microsoft's own infrastructure (not just the SMTP traffic for sending mail from one O365 domain to another) given Edward Snowden's 2013 revelation of PRISM, a US government program to ...


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Email was never designed to verify an email actually came from the person it says it came from. The model is largely one of snail mail, where it's trivial to print an address of President Of The United States as the origin. The most likely scenario is the header address appeared as employee B, but the reply to: address was set to someone else like ...


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You read this part, which I emphasized a few keywords: Office 365 sends mail using TLS encryption, provided that the destination server also supports TLS. If your partner organization supports TLS, you only need to create a connector if you want to enforce certain security restrictions Then the answer to your question is: not systematically or… ...


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As luck would have it, Microsoft has documented this. The answer to your question is yes. They use TLS 1.2 between any Office 365 groups, and they also use it opportunistically for external destinations, so as long as the recipient's server supports it, that message path will also be encrypted. https://technet.microsoft.com/en-us/library/mt163898.aspx and ...



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