Pool leaking at lights

No gasket or silicon to help seal it....as u can see small leaves were inside the light fixture when I took it off.....that would tell me that water is entering the light fixture as well. Should the hole where the electrical wire comes out of the tile be better sealed to prevent water from leaving the pool?
 
I am no pool expert, but I am guessing the electrical conduit travels outside the pool deck to a junction box above water level. This way inside conduit would normally be wet. The key here is the outside surface of the conduit should have a good seal to the pool structure or tile.
 
Frankly I'm not familiar with what you have here. Is this an above ground pool? How is the pool connected? What is light model?

Depending on the type of pool that conduit may be wet or dry. I must say that is a weird way to mount the light.

Sorry it depends.
 
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