I have multiple email accounts on zimbra, office 365, gmail platforms. Outlook managed to totally screw up my Gmail and zimbra accounts by moving email from one account to another. I don't know what the problem was but I lost a lot of email that day. Second problem is that synchronization between Outlook and Google was running around one email message every 10 seconds. I left the thing running for days and it never caught up.

Clients of mine who insist on using Outlook with Gmail are always complaining about it. Besides the very slow synchronization that starts running at random, The calendar is screwed up and makes messages that should be busy free instead completely transparent. Outlook can't turn off seeing calendars subscribe to under Google. All in all it's just such a cluster fark I refuse to spend your time on it. I told my clients that if they want support on Outlook, and I will hire an expensive consultant to make sure they know exactly what that tool choice was costing the company.

There is no amount compatibility Outlook could have with NaturallySpeaking that would make it worth my while to try again. The same goes for Microsoft Word and Excel. I would rather dictate into dictation box or Dragon pad and paste it into Google docs than struggle with anything from Microsoft.