Observers seem to block any kind of redstone signal not only passing through them, but also going down from them.
I've tried several setups with observer. They are shown on screenshots. In the background there's a furnace to show how it (possibly) should work.
(much easier to show rather than to write)
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Duplicate of MC-107671
This isn't really a bug. Observers are a "transparent" block. Try the same tests with glass or glowstone and you will have the same result.