When a redstone wire is redirected towards a block by placing a block to impede the wire from going up or down (more understandable with images), a redstone repeater won't be powered by the block which should be powered by the now redirected wire.
Breaking and replacing the wire makes the repeater work as intended.
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And with the first picture, maybe you were too fast for the repeater. Repeaters always have delay no matter what.
the second picture is all right, its just for clarifying the process
in the first picture the repeater won't turn on, its not the delay
im gonna change the screenshots names

Maybe it's a duplicate of MC-3703
yeah it looks like it is, didn't known how to explain it properly so i couldn't find the pre-existent bug
The redstone is not facing into the block, so the block is not powered, so the repeater is not powered.