When powered by a powered block, command blocks will execute their command, but not output any resulting signal.
This setup explains the problem:
[media]The command blocks are set to "say powered by block" and "say powered by repeater", respectively. Both commands clearly execute, but there's no signal out from the one powered by the block.
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I don't think this is a bug. A command block only outputs a signal if it is a powered block itself or there's a comparator to read its SuccessCount. In the "powered by block" case, the command will trigger, but since it is the purple wool being powered and not the command block itself, it cannot output to a repeater.
that's because you're using repeaters.
replace the repeaters at the end with comparators and it should work fine π.
you used the wrong block
mods/devs mark as "work as intended"