Jake, I saw you tightening your drain plugs with pliers .... I thought this strange as I didn't think there was much pressure on the plugs that hand tightening wouldn't solve.
Was this before, or after, your ... errr ... "casual sail"?
After - and the wrench was used so nobody would ever remove them again. The ONLY two times I have ever needed drain plugs was when I forgot to put them in the hull in the first place. I rarely ever remove drain plugs but I either did it for the long haul or someone else did it as I had some people helping me de-rig the boat last time.