We recently implement DUO 2FA on our firms Remote Desktop Server (Windows2016). We setup DUO so that my home's IP Address is the second factor to allow me to work from home without being asked for the one-time number from the DUO App. After we did this the following always occurs.
I am asked twice for my password (noting around 40 times to date - thus "I know" I am not typing my password wrongly the first time everytime!).
* The first time, Remote Desktop software (password entry dialog) says incorrect password
* the second time it works. - logs me in cleanly.
I have also tried this with two test accounts on our system - same issue occurs - it is 100% reproduceable. Duo logs (according to my techs) say there was only ever one connection logged - almost like Remote Desktop didn't send the first one!
I am organising for a test Mac and a bunch of other options to test with moving forward.
But before I start that - has anyone else seen this problem?