Not asking for pin number

I have a pin number set on my son's account so I can extend his time when needed easily.  It only asks for the pin about half of the time even if I wait for it to time out it just closes.  And when we bring it back up it starts the countdown again.  If I request more time it tells me to log in (which also only works about half the time, otherwise I get an error about either the servers being down or that the machine is on a  different account).  I have a lastpass generated password so logging in constantly means I have to copy and paste the password from lastpass which is a pain in the neck.  What is the point of a pin if it doesn't work consistently?  If anyone else has this issue or knows how to fix it that would be great.  Otherwise I'll have to try and find a time restriction solution that actually works.