Hi,
I'm having water leak from my tiled shower floor. The water is damaging my ceiling wall downstairs. I've plugged the drain and filled my shower to about 1/4" (without splashing the walls). Sure enough, water starts to leak (slowly) within a min.

This is what my drain looks like... I'm wondering if this drain even has weeping holes. Can someone confirm?

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Drains do have weep holes but I cant open your attachment,can you try again. Either way you have to tear open that ceiling to dry and repair it so do it now and you may see your problem better. Shower pan can leak but far less often than the drain line connections.