I agree that your best bet for this scenario is to use OWA rather than Outlook... not only from a simplicity standpoint but from a security standpoint... no company should allow their email to be downloaded / saved to a non company computer like that. We permit OWA from anywhere in the world, and if users want to use Outlook they have to VPN in using or by connecting to a company computer. It's perfectly adequate for any remote email needs... and if they really need the added functionality of Outlook they can go through the extra steps to do so.
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