Connecting to Win 10 computer via Remote Desktop only works after 4 tries, any fixes?

Question

This happens when I am using the latest and up-to-date Remote Desktop client on Mac OSX 10.11.3 installed via the Mac App Store. At the time of this writing the version is 8.0.26 build 26951. This does also happen with the Windows 10 built-in client as well, but slightly differently. The situation's order sometimes varies, but is usually fairly consistent along these lines:

• Open Remote Desktop client and double-click on one of the items listed under "My Desktops" (note: these are configured by IP address, all ports are open on the host machines, the credentials are saved into the configuration)

• The Windows 10 "logging in" screen appears and seems to freeze. Nothing happens for several minutes so I close the window.

• I double-click the same host again and I receive a Window from the host machine with the message "The task you are trying to do can't be completed because Remote Desktop Services is currently busy." If I close the window and double-click the host again too soon I get the same message over and over.

• I wait some arbitrary number of minutes without trying to connect and then double-click the host again, hoping not to get the above message, otherwise I start over and wait another arbitrary number of minutes. If I waited long enough when I double-click the host again instead of seeing the error message I almost instantly see my Desktop with icons galore (or apps I left open from a previous session). However, if I try to click on anything nothing responds. Mousing over the icons doesn't highlight them, I can't click them, I can't drag or close windows, and I can't type. I basically just see a screenshot of my Desktop that I cannot interact with.

• I close the window one last time and immediately double-click the host again and immediately I again see my Desktop, only this time I can interact with it and use the session as normal.

This seems to happen if I haven't connected via RDP to my host machine in a few hours or days. If I have connected recently (maybe in the last hour) it seems to work fine on the first try.

When I go from Windows 10 to Windows 10 via Remote Desktop its less of a pain. I see the Desktop immediately, but have the "can't click/interact with anything" issue as stated above. I close the window and connect again and the second time it works. The only difference between this setup and my Mac setup is that I do not have the credentials stored in the Remote Desktop app on the Windows 10 computers.

Some other facts:

• The computers involved are: a custom-built Windows 10 Pro machine with all updates, an HP Elite 8300 with Windows 10 Enterprise with all updates.

• Both windows computers have static IPs and are in completely separate networks/locations (different cities in the same state).

• The laptop is a Macbook Pro Mid 2012 with added RAM and a solid state drive.

• It make no difference whether the laptop is connected to the same network as either Win 10 machine or if its halfway across the world. Same results as the problem description.

• When connecting from one of the Win 10 machines to the other Win 10 machine I get the above problem description regardless of which machine I am on/which I am connecting to.

Has anybody ever had this issue or heard of it? Could it be a bug with Windows 10... it can't be the client because I get similar issues regardless of whether I am using the client on Windows 10 or on my Mac. I might try to take out the credentials from the client on my Mac to see if it more closely mimics the problem I get from Win 10 -> Win 10 (as the only difference is the credentials are not baked in). That would at least bring me down to only having to connect twice instead of 4 times. Any advise would be appreciated.