diff --git a/security/libpwquality/Makefile b/security/libpwquality/Makefile
index f389a4166c5d..54eced86a0bc 100644
--- a/security/libpwquality/Makefile
+++ b/security/libpwquality/Makefile
@@ -1,35 +1,38 @@
 PORTNAME=	libpwquality
-DISTVERSION=	1.4.4
+DISTVERSION=	1.4.5
 CATEGORIES=	security
 MASTER_SITES=	https://github.com/${PORTNAME}/${PORTNAME}/releases/download/${PORTNAME}-${PORTVERSION}/
 
 MAINTAINER=	desktop@FreeBSD.org
 COMMENT=	Library for generating random passwords and quality checking
 WWW=		https://github.com/libpwquality/libpwquality
 
 LICENSE=	GPLv2+ LIBPWQUALITY
 LICENSE_COMB=	dual
 LICENSE_NAME_LIBPWQUALITY=	The libpwquality license
 LICENSE_FILE_LIBPWQUALITY=	${WRKSRC}/COPYING
 LICENSE_PERMS_LIBPWQUALITY=	dist-mirror dist-sell pkg-mirror pkg-sell auto-accept
 
 LIB_DEPENDS=	libcrack.so:security/cracklib
 
 USES=		cpe gmake libtool localbase pathfix tar:bz2
 GNU_CONFIGURE=	yes
 USE_LDCONFIG=	yes
 CPE_VENDOR=	libpwquality_project
 CONFIGURE_ARGS+=--disable-pam
 INSTALL_TARGET=	install-strip
 
 OPTIONS_DEFINE=	NLS PYTHON
 OPTIONS_DEFAULT=NLS PYTHON
 OPTIONS_SUB=	yes
 NLS_USES=	gettext gnome
 NLS_USE=	GNOME=intltool
 NLS_CONFIGURE_ENABLE=	nls
-PYTHON_USES=	python
+PYTHON_USES=	python:3.7+,build
 PYTHON_CONFIGURE_ENABLE=	python-bindings
 PYTHON_CONFIGURE_ON=	--with-python-binary=${PYTHON_CMD}
 
+post-install-PYTHON-on:
+	${STRIP_CMD} ${STAGEDIR}${PYTHON_SITELIBDIR}/pwquality*.so
+
 .include <bsd.port.mk>
diff --git a/security/libpwquality/distinfo b/security/libpwquality/distinfo
index ef9d079fe003..f11df5f2e30c 100644
--- a/security/libpwquality/distinfo
+++ b/security/libpwquality/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1602781807
-SHA256 (libpwquality-1.4.4.tar.bz2) = d43baf23dc6887fe8f8e9b75cabaabc5f4bbbaa0f9eff44278d276141752a545
-SIZE (libpwquality-1.4.4.tar.bz2) = 426923
+TIMESTAMP = 1669228314
+SHA256 (libpwquality-1.4.5.tar.bz2) = 6fcf18b75d305d99d04d2e42982ed5b787a081af2842220ed63287a2d6a10988
+SIZE (libpwquality-1.4.5.tar.bz2) = 433961
diff --git a/security/libpwquality/files/patch-python_Makefile.in b/security/libpwquality/files/patch-python_Makefile.in
new file mode 100644
index 000000000000..31e1bd4e788f
--- /dev/null
+++ b/security/libpwquality/files/patch-python_Makefile.in
@@ -0,0 +1,11 @@
+--- python/Makefile.in.orig	2022-11-18 10:22:41 UTC
++++ python/Makefile.in
+@@ -483,7 +483,7 @@ all-local:
+ 	CFLAGS="${CFLAGS} -fno-strict-aliasing" @PYTHONBINARY@ setup.py build --build-base py$(PYTHONREV)
+ 
+ install-exec-local:
+-	CFLAGS="${CFLAGS} -fno-strict-aliasing" @PYTHONBINARY@ setup.py build --build-base py$(PYTHONREV) install --prefix=${DESTDIR}${prefix}
++	CFLAGS="${CFLAGS} -fno-strict-aliasing" @PYTHONBINARY@ setup.py build --build-base py$(PYTHONREV) install --root=${DESTDIR} --single-version-externally-managed
+ 
+ clean-local:
+ 	rm -rf py$(PYTHONREV)
diff --git a/security/libpwquality/pkg-plist b/security/libpwquality/pkg-plist
index 667328b7a117..56876d7a3ab9 100644
--- a/security/libpwquality/pkg-plist
+++ b/security/libpwquality/pkg-plist
@@ -1,66 +1,70 @@
 bin/pwmake
 bin/pwscore
 etc/security/pwquality.conf
 include/pwquality.h
 lib/libpwquality.a
 lib/libpwquality.so
 lib/libpwquality.so.1
 lib/libpwquality.so.1.0.2
-%%PYTHON%%%%PYTHON_SITELIBDIR%%/pwquality-1.4.4-py%%PYTHON_VER%%.egg-info
+%%PYTHON%%%%PYTHON_SITELIBDIR%%/pwquality-1.4.5-py%%PYTHON_VER%%.egg-info/PKG-INFO
+%%PYTHON%%%%PYTHON_SITELIBDIR%%/pwquality-1.4.5-py%%PYTHON_VER%%.egg-info/SOURCES.txt
+%%PYTHON%%%%PYTHON_SITELIBDIR%%/pwquality-1.4.5-py%%PYTHON_VER%%.egg-info/dependency_links.txt
+%%PYTHON%%%%PYTHON_SITELIBDIR%%/pwquality-1.4.5-py%%PYTHON_VER%%.egg-info/top_level.txt
 %%PYTHON%%%%PYTHON_SITELIBDIR%%/pwquality%%PYTHON_EXT_SUFFIX%%.so
 libdata/pkgconfig/pwquality.pc
 man/man1/pwmake.1.gz
 man/man1/pwscore.1.gz
 man/man3/pwquality.3.gz
 man/man5/pwquality.conf.5.gz
 %%NLS%%share/locale/ar/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/as/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/az/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/bg/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/bn_IN/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/ca/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/cs/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/da/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/de/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/es/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/eu/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/fa/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/fi/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/fr/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/fur/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/gu/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/he/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/hi/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/hu/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/id/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/it/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/ja/LC_MESSAGES/libpwquality.mo
+%%NLS%%share/locale/ka/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/kk/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/km/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/kn/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/ko/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/ml/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/mr/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/nb/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/nl/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/or/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/pa/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/pl/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/pt/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/pt_BR/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/ru/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/si/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/sk/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/sq/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/sr/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/sr@latin/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/sv/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/ta/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/te/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/tr/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/uk/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/ur/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/vi/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/zh_CN/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/zh_TW/LC_MESSAGES/libpwquality.mo
 %%NLS%%share/locale/zu/LC_MESSAGES/libpwquality.mo