Amusingly enough...or more like how things always go in technology...I think I figured it out. It looks like (at least in this case), if you have the "Count" option for the monitor set to 0 (ie. permanent connection), it gets itself confused when SQL is bounced (reboot or service restart). It doesn't seem to reopen the connection, but tries to re-use the old one despite SQL having cut all connections on the restart. Not sure why I didn't think of this before, but I tried setting it to 1 and after ~10 instances of a restart or reboot, I'm not seeing the problem anymore. Sorry for the needless question. Though I am interested if this is by design or a bug.