I ran Process Monitor when it didn’t work and it’s pulling back some random domain so I’ll leave it using forwarders for now. I did this a number of times and sure enough if I’m using Root Hints Outlook Anywhere does not work. I then changed the DNS to use a forwarder (8.8.8.8) instead of root hints, re-ran the test and it worked!!!!! I changed it back to Root Hints, cleared the cache, it failed. Running the same test on any of the machines at the site failed, I then tried running the same test on a PC at our office and it worked, pauses to scratch head, pauses some more….potential light-bulb moment… When we plumbed the details in and ran the test the result showed a failure This installs an application that allows you to test from a client Then I tried something new…The Remote Connectivity Analyzer Client…
Running Exchange Remote Connectivity Analyzer for Outlook Anywhere.Logging in to the portal and ensuring that worked fine.And you’ll take wing as you learn best practices for connecting the people and resources you need, and orchestrating the results you want.We had a client on Office 365 where Outlook kept prompting for a password, anyone who’s used Exchange Online or Office 365 has probably come across this at some point. Below are the few requirements to configure Outlook Anywhere: Presence of account on Microsoft Exchange Server 2016. Requirements to configure Outlook Anywhere. However, Outlook Anywhere provides a connection outside the organization even without VPN to work remotely. If your mailbox has been migrated from on-premises Exchange to Office 365 or you have two mailboxes connected in Outlook (one from the on-premises Exchange, the second from Office 365) and you use an RPC connection, in this case Outlook doesn’t use Modern Authentication (also used for MFA). A VPN allows working in Outlook within the organization’s firewall only. Guided by business productivity expert Katherine Murray, you’ll get a running start with Office 365 cloud-based business services. Change Office 365 User Authentication Method. Now you can connect, collaborate, and get things done-virtually anywhere-using Microsoft Office 365. I used a workaround I found in the forums to do an Advanced setup and get Email and Calendar working for Office 365.
I install with my account and everything seems to work great with that. I cannot add my Office 365 account to the device. Microsoft Office 365: Connect and Collaborate Virtually Anywhere, Anytime I have seen reference to this issue in other posts, but the resolution didn't suffice for me.
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