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See Vapor-proof A luminary filled with water, socket submerged.
A) Perhaps more than a Vapor-proof gasket issue?

[Linked Image from electrical-photos.com]

[Linked Image from electrical-photos.com]

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See Vapor-proof B partially filled by condensation with burnt lamp.
B) Perhaps a typical Vapor-proof gasket leak?

[Linked Image from electrical-photos.com]

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Installer sandwiched 2x4's, between two J-boxes, hoping clear Silicon provides extra barrier as shown.

I'd prefer weather-tight UF connectors, wrapped directly to ceiling-mount box, since EMT with extra box could be removed.

But, vine trimming on truss may require EMT, and five identically-installed luminaries have no water penetration.

A diamond bit on glass jar bottom could also arrange jars to drain.

What say you is the best repair?

Ramsy