I "overstayed" once although it was more of a paperwork error. My work permit exemption was valid for an additional year but my passport expired. They tell you to come in with the new passport and pay a small fee to change over the stamp... When I did that they informed me I had "technically" overstayed by a few months (despite having travelled in and out with the old stamp and new passport a few months prior).
I had to pay the $50,000 fee plus the $5,000 to move my stamp to the new passport. It was definitly a money grab but that's how things work, and it was my fault for failing to remember that PICA eats technicalities for breakfast.
the 50k is a civil fine paid to PICA. If they reffer you for criminally overstaying or you get caught by police for some reason it's punishable by a fine of up to $10,000 JMD or 30 days in Jail, as well as deportation & a 5 year ban from entry. My situation was much less severe because I was already a legal resident who just hit a paperwork technicality - but even then stay on top of it and don't wind up with the headache. Having the citizenship now is such a burden lifted off my shoulders - I only have to worry about renewing a passport every 10 years instead of various immigration documetns every 1-3 years