I went through something similar fairly recently.  I carry a Fatboy Jumbo as an EDC.  While swimming the dogs (I'm wading), the buckle on my strap came undone and the Fatboy plopped into the water.
Then, a week or two later the exact same thing happened at the same place!  Talk about slow learner!
While my FAK is in a Pelican case, it highlighed that I hadn't been serious enough about waterproofing.  
Now, I  use a drybag as a liner for the main compartment.  
Oh, and I'm going to put a bolt through that @#~@@ quick release buckle...
-john