diff --git a/Misc/NEWS.d/next/Core and Builtins/2023-12-01-19-02-21.gh-issue-105967.Puq5Cn.rst b/Misc/NEWS.d/next/Core and Builtins/2023-12-01-19-02-21.gh-issue-105967.Puq5Cn.rst
new file mode 100644
index 00000000000000..c69511218e3e16
--- /dev/null
+++ b/Misc/NEWS.d/next/Core and Builtins/2023-12-01-19-02-21.gh-issue-105967.Puq5Cn.rst	
@@ -0,0 +1,4 @@
+Workaround a bug in Apple's macOS platform zlib library where
+:func:`zlib.crc32` and :func:`binascii.crc32` could produce incorrect results
+on multi-gigabyte inputs. Including when using :mod:`zipfile` on zips
+containing large data.
diff --git a/Modules/binascii.c b/Modules/binascii.c
index 4ecff4793be9a0..0614edf4bc03aa 100644
--- a/Modules/binascii.c
+++ b/Modules/binascii.c
@@ -780,12 +780,20 @@ binascii_crc32_impl(PyObject *module, Py_buffer *data, unsigned int crc)
 
         Py_BEGIN_ALLOW_THREADS
         /* Avoid truncation of length for very large buffers. crc32() takes
-           length as an unsigned int, which may be narrower than Py_ssize_t. */
-        while ((size_t)len > UINT_MAX) {
-            crc = crc32(crc, buf, UINT_MAX);
-            buf += (size_t) UINT_MAX;
-            len -= (size_t) UINT_MAX;
+           length as an unsigned int, which may be narrower than Py_ssize_t.
+           We further limit size due to bugs in Apple's macOS zlib.
+           See https://github.com/python/cpython/issues/105967
+         */
+#define ZLIB_CRC_CHUNK_SIZE 0x40000000
+#if ZLIB_CRC_CHUNK_SIZE > INT_MAX
+# error "unsupported less than 32-bit platform?"
+#endif
+        while ((size_t)len > ZLIB_CRC_CHUNK_SIZE) {
+            crc = crc32(crc, buf, ZLIB_CRC_CHUNK_SIZE);
+            buf += (size_t) ZLIB_CRC_CHUNK_SIZE;
+            len -= (size_t) ZLIB_CRC_CHUNK_SIZE;
         }
+#undef ZLIB_CRC_CHUNK_SIZE
         crc = crc32(crc, buf, (unsigned int)len);
         Py_END_ALLOW_THREADS
     } else {
diff --git a/Modules/zlibmodule.c b/Modules/zlibmodule.c
index b67844a67c315c..f94c57e4c89c4f 100644
--- a/Modules/zlibmodule.c
+++ b/Modules/zlibmodule.c
@@ -1890,12 +1890,20 @@ zlib_crc32_impl(PyObject *module, Py_buffer *data, unsigned int value)
 
         Py_BEGIN_ALLOW_THREADS
         /* Avoid truncation of length for very large buffers. crc32() takes
-           length as an unsigned int, which may be narrower than Py_ssize_t. */
-        while ((size_t)len > UINT_MAX) {
-            value = crc32(value, buf, UINT_MAX);
-            buf += (size_t) UINT_MAX;
-            len -= (size_t) UINT_MAX;
+           length as an unsigned int, which may be narrower than Py_ssize_t.
+           We further limit size due to bugs in Apple's macOS zlib.
+           See https://github.com/python/cpython/issues/105967.
+         */
+#define ZLIB_CRC_CHUNK_SIZE 0x40000000
+#if ZLIB_CRC_CHUNK_SIZE > INT_MAX
+# error "unsupported less than 32-bit platform?"
+#endif
+        while ((size_t)len > ZLIB_CRC_CHUNK_SIZE) {
+            value = crc32(value, buf, ZLIB_CRC_CHUNK_SIZE);
+            buf += (size_t) ZLIB_CRC_CHUNK_SIZE;
+            len -= (size_t) ZLIB_CRC_CHUNK_SIZE;
         }
+#undef ZLIB_CRC_CHUNK_SIZE
         value = crc32(value, buf, (unsigned int)len);
         Py_END_ALLOW_THREADS
     } else {