I would not use silicon. Silicon is difficult to remove and does not accept reapplication very well. New silicon doesnt stick to old silicon very well.
If you have wood framing try to probe the holes to check for water damage. If the wood appears solid I would inject gorilla glue into the holes and then use a slightly larger diameter screw. Be sure to protect the surfaces around it as the glue will expand. The glue will react and make a solid repair. I would also add several more screws to really secure it.
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Paul
2018 37TS
Jeep JL
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