growable_comment_array_add in parsetok.c incorrectly uses realloc, which leaks the array when allocation fails, and then causes a null pointer deref crash later when the array is freed in growable_comment_array_deallocate (the array pointer is dereferenced, passing null to free is fine). It's unlikely that this codepath is reached in normal use, since type comments need to be turned on (via the PyCF_TYPE_COMMENTS compiler flag), but I've managed to replicate the issue by injecting faults with Application Verifier. It's easiest to cause it to fail with a very large number of type comments, but presumably this could also happen with some form of heap fragmentation. The buggy code is: static int growable_comment_array_add(growable_comment_array *arr, int lineno, char *comment) { if (arr->num_items >= arr->size) { arr->size *= 2; arr->items = realloc(arr->items, arr->size * sizeof(*arr->items)); if (!arr->items) { return 0; } } arr->items[arr->num_items].lineno = lineno; arr->items[arr->num_items].comment = comment; arr->num_items++; return 1; } and the correct code would be something like: static int growable_comment_array_add(growable_comment_array *arr, int lineno, char *comment) { if (arr->num_items >= arr->size) { arr->size *= 2; void* new_items_array = realloc(arr->items, arr->size * sizeof(*arr->items)); if (!new_items_array) { return 0; } arr->items = new_items_array; } arr->items[arr->num_items].lineno = lineno; arr->items[arr->num_items].comment = comment; arr->num_items++; return 1; }

Sidenote: visual studio was misleading and made this look like a use-after-free for a little while, which was interesting.

 New changeset 51e3e450fbed46198d9be92add1a5dee6a1f7f41 by Alexander Riccio in branch 'master': bpo-40020: Fix realloc leak on failure in growable_comment_array_add (GH-19083) https://github.com/python/cpython/commit/51e3e450fbed46198d9be92add1a5dee6a1f7f41 

Alexander Riccio: Do you know want to propose a change to replace direct usage of malloc/realloc/free with PyMem_Malloc, PyMem_Realloc and PyMem_RawFree? It would add their builtin debug feature for free, and also detect most obvious buffer overflow (reject size larger than PY_SSIZE_T_MAX).

Sure, should I open a new issue?