Can you paint over Layered caulk?
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can you re-state what your question is?
I agree with Sharon. What kind of answer are you seeking? What problem are you trying to solve?
Don't paint over any surface that is not clean and sound. Don't try to paint over silicone caulk. Those conditions satisfied, get the brush out and give it a try. Worst that will happen is the paint will peel off.