In [18]: class Str(str):
    ...:     pass

In [19]: class Class:
    ...:     Str: str
    ...: 
    ...: 
    ...: Class.__annotations__
Out[19]: {'Str': str}

In [20]: class Class:
    ...:     Str: str = ""
    ...: 
    ...: 
    ...: Class.__annotations__
Out[20]: {'Str': str}

In [21]: class Class:
    ...:     Str: Str = ""
    ...: 
    ...: 
    ...: Class.__annotations__      # Wrong!
Out[21]: {'Str': ''}

In [22]: class Class:
    ...:     Str: Str
    ...: 
    ...: 
    ...: Class.__annotations__
Out[22]: {'Str': __main__.Str}

It reproduced all the version which support annotations as part of the core (I tested python 3.6..3.10.2)

This looks similar to https://bugs.python.org/issue36363

Yeah, it's the same behavior.  In that class, you have defined Str to be "", then you reference Str in the annotation, and its value is "".  Whatever you set Str to in the example in [21], that's the value of the annotation.

GvR closed the previous report as "not a bug", so I'm gonna do that here too.