diff --git a/oscrypto/_openssl/_libssl.py b/oscrypto/_openssl/_libssl.py
index 2fa2bce..56d2a25 100644
--- a/oscrypto/_openssl/_libssl.py
+++ b/oscrypto/_openssl/_libssl.py
@@ -1,7 +1,10 @@
 # coding: utf-8
 from __future__ import unicode_literals, division, absolute_import, print_function
 
-from .. import ffi
+import re
+import sys
+
+from .. import ffi, _backend_config
 
 # Initialize OpenSSL
 from ._libcrypto import libcrypto_version_info
@@ -15,6 +18,7 @@
 __all__ = [
     'libssl',
     'LibsslConst',
+    'error_code_version_info',
 ]
 
 
@@ -87,3 +91,19 @@ class LibsslConst():
 
 if libcrypto_version_info >= (1, 1, 0):
     LibsslConst.SSL_R_DH_KEY_TOO_SMALL = 394
+
+
+# The Apple version of libssl seems to have changed various codes for
+# some reason, but the rest of the API is still OpenSSL 1.0.1
+if sys.platform == 'darwin' and re.match(r'/usr/lib/libssl\.\d', _backend_config().get('libssl_path', '')):
+    LibsslConst.SSL_F_TLS_PROCESS_SERVER_CERTIFICATE = 7
+    LibsslConst.SSL_F_SSL3_GET_KEY_EXCHANGE = 9
+    LibsslConst.SSL_F_SSL3_READ_BYTES = 4
+    LibsslConst.SSL_F_SSL3_GET_RECORD = 4
+    LibsslConst.SSL_F_SSL23_GET_SERVER_HELLO = 4
+    error_code_version_info = (1, 1, 0)
+    error_code_variant = 'macos'
+
+else:
+    error_code_version_info = libcrypto_version_info
+    error_code_variant = 'openssl'
diff --git a/oscrypto/_openssl/tls.py b/oscrypto/_openssl/tls.py
index 6f180f4..4905a47 100644
--- a/oscrypto/_openssl/tls.py
+++ b/oscrypto/_openssl/tls.py
@@ -7,7 +7,7 @@
 import select
 import numbers
 
-from ._libssl import libssl, LibsslConst
+from ._libssl import error_code_version_info, error_code_variant, libssl, LibsslConst
 from ._libcrypto import libcrypto, libcrypto_version_info, handle_openssl_error, peek_openssl_error
 from .. import _backend_config
 from .._asn1 import Certificate as Asn1Certificate
@@ -554,7 +554,7 @@ def _handshake(self):
                     if info == dh_key_info_1 or info == dh_key_info_2 or info == dh_key_info_3:
                         raise_dh_params()
 
-                    if libcrypto_version_info < (1, 1):
+                    if error_code_version_info < (1, 1):
                         unknown_protocol_info = (
                             LibsslConst.ERR_LIB_SSL,
                             LibsslConst.SSL_F_SSL23_GET_SERVER_HELLO,
@@ -580,23 +580,16 @@ def _handshake(self):
                     if info == tls_version_info_error:
                         raise_protocol_version()
 
+                    # There are multiple functions that can result in a handshake failure,
+                    # but our custom handshake parsing code figures out what really happened,
+                    # and what is more, OpenSSL 3 got rid of function codes. Because of this,
+                    # we skip checking the function code.
                     handshake_error_info = (
                         LibsslConst.ERR_LIB_SSL,
-                        LibsslConst.SSL_F_SSL23_GET_SERVER_HELLO,
                         LibsslConst.SSL_R_SSLV3_ALERT_HANDSHAKE_FAILURE
                     )
-                    # OpenSSL 3.0 no longer has func codes, so this can be confused
-                    # with the following handler which needs to check for client auth
-                    if libcrypto_version_info < (3, ) and info == handshake_error_info:
-                        raise_handshake()
 
-                    handshake_failure_info = (
-                        LibsslConst.ERR_LIB_SSL,
-                        LibsslConst.SSL_F_SSL3_READ_BYTES,
-                        LibsslConst.SSL_R_SSLV3_ALERT_HANDSHAKE_FAILURE
-                    )
-                    handshake_failure_info = _homogenize_openssl3_error(handshake_failure_info)
-                    if info == handshake_failure_info:
+                    if (info[0], info[2]) == handshake_error_info:
                         saw_client_auth = False
                         for record_type, _, record_data in parse_tls_records(handshake_server_bytes):
                             if record_type != b'\x16':
@@ -609,7 +602,7 @@ def _handshake(self):
                             raise_client_auth()
                         raise_handshake()
 
-                    if libcrypto_version_info < (1, 1):
+                    if error_code_version_info < (1, 1):
                         cert_verify_failed_info = (
                             LibsslConst.ERR_LIB_SSL,
                             LibsslConst.SSL_F_SSL3_GET_SERVER_CERTIFICATE,