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Got a new filter that has a buffer option and an effects loop. I switched it to buffered bypass and noticed that if the Hoof was directly before the filter or in the effects loop it didnt just sound bad, it actually killed all the sound in the entire chain regardless of it being on or not. Works fine after the filter or with at least one pedal in between the front of the filter.

Is this to be expected or is there something extra weird going on?

That sounds weird man. When the hoof is bypassed there is nothing in the signal chain (well, as good as) - there is literally nothing for the buffer to interact with. Unless the Hoof isn't true bypass, but I'm fairly sure it is which should rule out an impedance mismatch. I'm confused.

What's the filter pedal and what are you using to power all your pedals(or those specifically).
As far as I know the hoof is true bypass and never had any issues with buffers before it.