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This shouldn't be happening and makes no sense. It looks like the assert statement was removed at import code compilation time given the pdb trace with it from a zip file vs with it outside of a zip file:
>>> pdb.run('mod.test(False)')
> <string>(1)<module>()
(Pdb) n
False
--Return--
> <string>(1)<module>()->None
(Pdb) n
>>> pdb.run('mod.test(False)')
> <string>(1)<module>()->None
(Pdb) s
--Call--
> oss/cpython/build/mod.zip/mod.py(1)test()
-> def test(val):
(Pdb) s
> oss/cpython/build/mod.zip/mod.py(3)test()
-> print(val)
(Pdb) s
False
--Return--
> oss/cpython/build/mod.zip/mod.py(3)test()->None
-> print(val)
(Pdb) s
--Return--
> <string>(1)<module>()->None
(Pdb) s
> oss/cpython/default/Lib/bdb.py(435)run()
-> self.quitting = True
(Pdb) s
>>> 
vs no zip file:
>>> pdb.run('mod.test(False)')
> <string>(1)<module>()
(Pdb) s
--Call--
> oss/cpython/build/mod.py(1)test()
-> def test(val):
(Pdb) s
> oss/cpython/build/mod.py(2)test()
-> assert(val)
(Pdb) s
AssertionError
> oss/cpython/build/mod.py(2)test()
-> assert(val)
(Pdb) s
--Return--
> oss/cpython/build/mod.py(2)test()->None
-> assert(val)
(Pdb) s
AssertionError
> <string>(1)<module>()
(Pdb) s
--Return--
> <string>(1)<module>()->None
(Pdb) s
AssertionError
> oss/cpython/default/Lib/bdb.py(431)run()
-> exec(cmd, globals, locals)
(Pdb) s
> oss/cpython/default/Lib/bdb.py(432)run()
-> except BdbQuit:
(Pdb) s
> oss/cpython/default/Lib/bdb.py(435)run()
-> self.quitting = True
(Pdb) s
Traceback (most recent call last):
 File "<stdin>", line 1, in <module>
 File "oss/cpython/default/Lib/pdb.py", line 1568, in run
 Pdb().run(statement, globals, locals)
 File "oss/cpython/default/Lib/bdb.py", line 431, in run
 exec(cmd, globals, locals)
 File "<string>", line 1, in <module>
 File "oss/cpython/build/mod.py", line 2, in test
 assert(val)
AssertionError