diff --git a/security/py-keyrings.alt/Makefile b/security/py-keyrings.alt/Makefile
index ae367d6b6ec3..a864a42c133a 100644
--- a/security/py-keyrings.alt/Makefile
+++ b/security/py-keyrings.alt/Makefile
@@ -1,39 +1,37 @@
 PORTNAME=	keyrings.alt
-PORTVERSION=	3.1.1
+PORTVERSION=	4.2.0
 CATEGORIES=	security python
 MASTER_SITES=	CHEESESHOP
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
 MAINTAINER=	douglas@douglasthrift.net
 COMMENT=	Alternate Python keyring implementations
 WWW=		https://pypi.org/project/keyrings.alt/
 
 LICENSE=	MIT
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
-DEPRECATED=	Depends on expired security/py-pycrypto
-EXPIRATION_DATE=2022-09-30
-
 BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}setuptools_scm>=1.15.0:devel/py-setuptools_scm@${PY_FLAVOR}
-RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}six>0:devel/py-six@${PY_FLAVOR}
+RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}jaraco.classes>0:devel/py-jaraco.classes@${PY_FLAVOR}
 TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}mock>0:devel/py-mock@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}keyring>=10.3.1:security/py-keyring@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}pycrypto>0:security/py-pycrypto@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}pycryptodome>0:security/py-pycryptodome@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}pycryptodomex>0:security/py-pycryptodomex@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}fs>=0.5:devel/py-fs@${PY_FLAVOR}
 
 USES=		python:3.6+ pytest
 USE_PYTHON=	autoplist distutils
 
 NO_ARCH=	yes
 
 OPTIONS_DEFINE=		ENCRYPTED_FILE GNOME_KEYRING PYFS
 ENCRYPTED_FILE_DESC=	Install pycrypto to support the Encrypted File backend
 GNOME_KEYRING_DESC=	Install GNOME Keyring to support the Gnome backend
 PYFS_DESC=		Install pyfilesystem to support the pyfs backend
 
 ENCRYPTED_FILE_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}pycrypto>=2.5:security/py-pycrypto@${PY_FLAVOR}
 GNOME_KEYRING_USES=		gnome
 GNOME_KEYRING_USE=		GNOME=pygobject3
 PYFS_RUN_DEPENDS=		${PYTHON_PKGNAMEPREFIX}fs>=0.5:devel/py-fs@${PY_FLAVOR}
 
 .include <bsd.port.mk>
diff --git a/security/py-keyrings.alt/distinfo b/security/py-keyrings.alt/distinfo
index fc308241f164..9cb90d65c9b6 100644
--- a/security/py-keyrings.alt/distinfo
+++ b/security/py-keyrings.alt/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1547319605
-SHA256 (keyrings.alt-3.1.1.tar.gz) = 0bc7b75c7e710a3dd7bc4c3841c71467b24ccbce1b85efb2586bdf0c4713f751
-SIZE (keyrings.alt-3.1.1.tar.gz) = 28193
+TIMESTAMP = 1666637575
+SHA256 (keyrings.alt-4.2.0.tar.gz) = 2ba3d56441ba0637f5f9c096068f67010ac0453f9d0b626de2aa3019353b6431
+SIZE (keyrings.alt-4.2.0.tar.gz) = 29855
diff --git a/security/py-keyrings.alt/files/patch-setup.py b/security/py-keyrings.alt/files/patch-setup.py
new file mode 100644
index 000000000000..4c888842fa8b
--- /dev/null
+++ b/security/py-keyrings.alt/files/patch-setup.py
@@ -0,0 +1,9 @@
+--- setup.py.orig	2022-10-24 19:25:10 UTC
++++ setup.py
+@@ -0,0 +1,6 @@
++#!/usr/bin/env python
++
++import setuptools
++
++if __name__ == "__main__":
++    setuptools.setup()
diff --git a/security/py-keyrings.alt/files/patch-tests_test__crypto.py b/security/py-keyrings.alt/files/patch-tests_test__crypto.py
index c990d71647b7..c40de57ea426 100644
--- a/security/py-keyrings.alt/files/patch-tests_test__crypto.py
+++ b/security/py-keyrings.alt/files/patch-tests_test__crypto.py
@@ -1,13 +1,13 @@
 # mock dependency set in TEST_DEPENDS is actually backports.unittest_mock
 # but this package doesn't exist in the ports tree yet, so adjust the import
 # here to import 'mock' proper. TODO
 
---- tests/test_crypto.py.orig	2019-01-04 05:26:47 UTC
+--- tests/test_crypto.py.orig	2022-10-24 18:56:47 UTC
 +++ tests/test_crypto.py
 @@ -1,5 +1,5 @@
- import unittest
+ import getpass
 -from unittest import mock
 +import mock
  
- from .test_file import FileKeyringTests
+ import pytest
  
diff --git a/security/py-keyrings.alt/files/patch-tests_test__file.py b/security/py-keyrings.alt/files/patch-tests_test__file.py
index 01a402ea0cd0..09e1fb8089ab 100644
--- a/security/py-keyrings.alt/files/patch-tests_test__file.py
+++ b/security/py-keyrings.alt/files/patch-tests_test__file.py
@@ -1,15 +1,15 @@
 # mock dependency set in TEST_DEPENDS is actually backports.unittest_mock
 # but this package doesn't exist in the ports tree yet, so adjust the import
 # here to import 'mock' proper. TODO
 
---- tests/test_file.py.orig	2019-01-04 05:24:38 UTC
+--- tests/test_file.py.orig	2022-09-05 01:38:48 UTC
 +++ tests/test_file.py
-@@ -7,7 +7,7 @@ import unittest
- from six.moves import configparser
+@@ -6,7 +6,7 @@ import getpass
+ import configparser
  
  import pytest
 -from unittest import mock
 +import mock
  
- from keyring.tests.test_backend import BackendBasicTests
- from keyring.tests.util import random_string
+ from keyring.testing.backend import BackendBasicTests
+ from keyring.testing.util import random_string