Crash report

What happened?

The compiler-generated __annotate__ function (PEP 649) begins with a guard if .format > VALUE_WITH_FAKE_GLOBALS: raise NotImplementedError. That comparison is emitted as a COMPARE_OP without the "convert result to bool" flag, immediately followed by POP_JUMP_IF_FALSE — which requires a boolean operand. When __annotate__ is called with a format whose > comparison returns a non-bool, the raw value reaches the jump:

python: Python/generated_cases.c.h: _PyEval_EvalFrameDefault:
    Assertion `PyStackRef_BoolCheck(cond)' failed.

Minimal reproducer (aborts on a debug build):

class NonBool:
    def __gt__(self, other):
        return None            # any non-bool result

def f(a: int):                 # any annotated function/class/module has __annotate__
    ...

f.__annotate__(NonBool())

It reproduces via a module __annotate__, a function __annotate__, and a class __annotate_func__ alike (the codegen is shared). Original find was wsgiref.types.__annotate__(obj) where obj.__gt__ returns a non-bool.

Root cause

Python/codegen.c, codegen_setup_annotations_scope():

// if .format > VALUE_WITH_FAKE_GLOBALS: raise NotImplementedError
...
ADDOP_I(c, loc, COMPARE_OP, (Py_GT << 5) | compare_masks[Py_GT]);   // no bool-cast bit (0x10)
NEW_JUMP_TARGET_LABEL(c, body);
ADDOP_JUMP(c, loc, POP_JUMP_IF_FALSE, body);

The COMPARE_OP oparg omits bit 0x10, which the eval loop checks to convert the comparison result to a bool (if (oparg & 16) in _COMPARE_OP, Python/bytecodes.c). POP_JUMP_IF_FALSE asserts its operand is a bool. Normal comparisons emit COMPARE_OP without the bit and rely on the later TO_BOOL-folding optimizer pass to set it — see the comment in codegen_addcompare():

// ... The fifth-lowest bit indicates whether the result should be converted to
// bool and is set later):
ADDOP_I(c, loc, COMPARE_OP, (cmp << 5) | compare_masks[cmp]);

But this guard emits COMPARE_OP directly followed by POP_JUMP_IF_FALSE with no intervening TO_BOOL, so the optimizer has nothing to fold and the bit is never set.

Disassembling the same > comparison two ways makes the difference concrete:

if x > 2:                     ->  COMPARE_OP  148  (bool(>))     # bit 0x10 SET
<generated __annotate__>      ->  COMPARE_OP  132  (>)           # bit 0x10 CLEAR

With a normal integer format (annotationlib.Format.VALUE, ...), int > int returns a real bool, so the assertion holds and the bug is latent. A format whose rich comparison returns a non-bool sends the raw object to the jump.

Behavior by build

• Debug build: assert(PyStackRef_BoolCheck(cond)) fails → abort.
• Release build: no assert, but POP_JUMP_IF_FALSE treats the non-Py_False value as truthy → __annotate__ spuriously raises NotImplementedError; and it consumes the operand without a decref (the jump assumes an immortal bool), leaking a heap comparison result.

More generally, the compiler is supposed to guarantee that every POP_JUMP_IF_FALSE/POP_JUMP_IF_TRUE operand is a bool; this codegen path breaks that guarantee for arbitrary format arguments.

Proposed fix

Set the bool-conversion bit on the guard's COMPARE_OP, matching what a normal if a > b: ends up with:

-    ADDOP_I(c, loc, COMPARE_OP, (Py_GT << 5) | compare_masks[Py_GT]);
+    ADDOP_I(c, loc, COMPARE_OP, (Py_GT << 5) | compare_masks[Py_GT] | 16);

(Py_GT << 5) | compare_masks[Py_GT] | 16 == 148, identical to the oparg the optimizer produces for if a > b:. (Emitting a TO_BOOL after the COMPARE_OP would also work; maintainers may prefer a named constant over the literal 16.)

Found by the fusil fuzzer (@vstinner's fuzzer, revived by @devdanzin);
investigated and drafted by Claude Code (Opus 4.8).

CPython versions tested on:

CPython main branch, 3.16, 3.15, 3.14

Operating systems tested on:

Linux

Output from running 'python -VV' on the command line:

Python 3.16.0a0 (heads/main:bcf98ddbc40, Jul 4 2026, 15:04:52) [Clang 21.1.8 (6ubuntu1)]

Linked PRs

• gh-153354: Fix bool conversion in generated __annotate__ #153360