The "Have you installed latest updates?" question is tiresome. In Windows 10 automatic updates and with the Surface updater utility this is a meaningless question. According to my updater there was not a Surface dock update in May. Both my Surface Book and my Surface Dock are up to date.
Oddly this was not a problem for me UNTIL the May Windows 10 updates.
I have an Asus 4k monitor and Logitech wireless keyboard/mouse attached to the Surface Dock.
There are no attachments to the Surface Book except the Surface Dock.
I have power settings to sleep the monitor after 10 minutes and never sleep the computer while on power.
Within a certain period, maybe an hour or two, I can wake the external monitor with the mouse after windows has put the screen in sleep mode.
The computer never sleeps.
After long periods, maybe an hour or two and especially overnight, I can no longer wake the external monitor with the mouse. The laptop is awake.
Current (irritating) fix is to disconnect the power/dock cable, then reconnect. Of course that sometimes causes sizing issues going from QHD to 4K.
The Surface Dock is not recognizing an external monitor is attached and sending a signal after some period of sleep, but I haven't found a way to control the Surface Dock or manage attached devices. My theory is that the surface sleeps the monitor and after some period of time something in the dock stops recognizing an attached monitor so that there is not a monitor to "wake" when it resumes screen activity.
I did try setting the xHCI USB Root Hub to "Never Sleep" and there was no change.
Like I said, after the February updates everything stabilized for me, then in May Win10 updates this started happening.