There isn't an intentional regression there.
In fact, I get exactly the same on both Cython 0.29.x and 3.0.0b1:
File "fused_test.pyx", line 3, in fused_test.__pyx_fused_cpdef
def add(floating a, floating b):
TypeError: No matching signature found
As far as I know, Cython doesn't handle these "fixed type" wrapper too well when calling `def` functions. The only check it really does is "isinstance(float)" since it isn't hugely easy to pick apart an arbitrary wrapper scalar. I do have a plan for how to improve this, but haven't had time yet.
If you do have an example of a regression here then please put it on the Cython bug-tracker. We've modified fused-type dispatch to make it faster, but I don't think any changes in behaviour were intended.