1980s Shower Handle Escutcheon Plate Reinstall

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I have a Delta two-handle shower/tub from the 1980s. The plumber removed the 3.25 inch x 3.25 inch square escutcheon plates (green arrow) to repair a leak and did a poor job replacing them. The hot-sided escutcheon plate isn't even flush against the tile (it was before). I want to remove the escutcheon plates, clean any buildup behind them, reinstall, reapply silicone caulk around the border.

1. I don't see any screws. How do I get the escutcheon plates to stick to the tile when I reinstall them?

2. How do I make sure water doesn't get into the wall where the middle hole in the escutcheon plate meets the trim sleeve? (red arrow) Do I need to apply plumber's putty?

Thanks for your help!

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