First, check that the affected machines are using the latest WiFi drivers. You may have to go to the WiFi chipset manufacturer to get these, as the OEM may not have made them available.
On Windows 10 computers you commonly get problems when the machines are on battery power and power-saving powers down the WiFi NIC briefly. Try disabling power saving on the WiFi NIC on a test machine and see if that solves it. This also resolves a lot of Windows 10 WiFi performance issues.
powercfg /SETDCVALUEINDEX SCHEME_CURRENT 19cbb8fa-5279-450e-9fac-8a3d5fedd0c1 12bbebe6-58d6-4636-95bb-3217ef867c1a 0
powercfg /SETACVALUEINDEX SCHEME_CURRENT 19cbb8fa-5279-450e-9fac-8a3d5fedd0c1 12bbebe6-58d6-4636-95bb-3217ef867c1a 0
Next, what does Wireless Health say?
You might be getting "association expired" expired because the client has roamed to a different AP. This may not be an actual problem.