Can I apply caulk over exterior wood filler? Leave a comment

I am re-caulking trim that is over T-111 siding over my window that faces the brunt force of winds and rain in the Pacific Northwest.
There were leaks over the window that appeared to be coming in through this joint.

The original caulking was OSI QUAD and has been hellacious to remove. It takes strands of siding with it and specks of it are still embedded in spots. Have been using dental tools to remove. If there is even a small area where the new caulk wont stick, the project is doomed.

I am worried about the gaps in the T-111 that go behind the trim and am wondering if I filled the gaps and smoothed the wood surface with Elmers carpenter wood filler (interior/exterior) or some other type of glue whether I could apply caulk (planning on using Big Stretch) once the wood filler cured.

Advice would be appreciated.

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