Squared Up may behave erratically if installed on a Windows 2012 server where the Microsoft hotfix KB3052480 is not installed.
To confirm this is the issue check the Squared Up log files in
C:\inetpub\wwwroot\SquaredUpv4\Transient\Log for the following message:
Other symptoms may include:
Squared Up application pool recycling many times, which results in users being unexpectedly logged off or unable to log in
Many different Squared Up log files created very quickly (rolling-20160913, rolling-201609131, rolling-201609132 etc.)
Make sure that your Squared Up server(s) are up to date with all the available Microsoft updates.
If the Squared Up log files show the message below, please configure the anti-virus exclusions as described in Users are unexpectedly logged out