diff --git a/www/py-cachecontrol/Makefile b/www/py-cachecontrol/Makefile
index 4f28572a1603..63fc7b2b1b52 100644
--- a/www/py-cachecontrol/Makefile
+++ b/www/py-cachecontrol/Makefile
@@ -1,33 +1,46 @@
 PORTNAME=	cachecontrol
-DISTVERSION=	0.14.0
+DISTVERSION=	0.14.4
 CATEGORIES=	www python
 MASTER_SITES=	PYPI
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
+# patch build tool from uv-build (since 0.14.4) to flit-core for FreeBSD compatability
+# https://github.com/psf/cachecontrol/pull/415
+PATCH_SITES=	https://github.com/psf/cachecontrol/commit/
+PATCHFILES=	\
+	a286f6b184227e62447410a8c0d9c084c1bbb4c0.patch:-p1 \
+	5c8a4e0ebf18e68f34b7641b54922c90d9ae9db6.patch:-p1 \
+	e0540b3a33921204f7fdd77c32d93ed267b8bad8.patch:-p1 \
+
+
 MAINTAINER=	yuri@FreeBSD.org
 COMMENT=	Caching algorithms in httplib2 for use with requests session object
 WWW=		https://github.com/psf/cachecontrol
 
 LICENSE=	APACHE20
 
-BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}flit-core>=3.2<4:devel/py-flit-core@${PY_FLAVOR}
+BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}flit-core>=3.11<5:devel/py-flit-core@${PY_FLAVOR}
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}msgpack>=0.5.2<2.0.0:devel/py-msgpack@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}requests>=2.16.0:www/py-requests@${PY_FLAVOR}
 TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}cherrypy>0:www/py-cherrypy@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}mock>0:devel/py-mock@${PY_FLAVOR}
 
 USES=		python
 USE_PYTHON=	pep517 autoplist concurrent pytest # 24 tests fail, see https://github.com/psf/cachecontrol/issues/331
 NO_ARCH=	yes
 
+# fix "ZIP does not support timestamps before 1980"
+# https://github.com/pypa/flit/issues/446
+MAKE_ENV=	SOURCE_DATE_EPOCH=347151600
+
 CONFLICTS_INSTALL=	py*-cachecontrol # bin/doesitcache
 
 OPTIONS_DEFINE=		FILECACHE REDIS
 OPTIONS_DEFAULT=	FILECACHE
 FILECACHE_DESC=		FileCache support
 REDIS_DESC=		Redis support
 
 FILECACHE_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}filelock>=3.7.1:sysutils/py-filelock@${PY_FLAVOR}
 REDIS_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}redis>=2.10.5:databases/py-redis@${PY_FLAVOR}
 
 .include <bsd.port.mk>
diff --git a/www/py-cachecontrol/distinfo b/www/py-cachecontrol/distinfo
index a166d670e722..f44f80324f6e 100644
--- a/www/py-cachecontrol/distinfo
+++ b/www/py-cachecontrol/distinfo
@@ -1,3 +1,9 @@
-TIMESTAMP = 1706945734
-SHA256 (cachecontrol-0.14.0.tar.gz) = 7db1195b41c81f8274a7bbd97c956f44e8348265a1bc7641c37dfebc39f0c938
-SIZE (cachecontrol-0.14.0.tar.gz) = 28899
+TIMESTAMP = 1784603425
+SHA256 (cachecontrol-0.14.4.tar.gz) = e6220afafa4c22a47dd0badb319f84475d79108100d04e26e8542ef7d3ab05a1
+SIZE (cachecontrol-0.14.4.tar.gz) = 16150
+SHA256 (a286f6b184227e62447410a8c0d9c084c1bbb4c0.patch) = 0778926244647632ac0080dbab559decd754bbe55fd1ef7cb455a0955d093530
+SIZE (a286f6b184227e62447410a8c0d9c084c1bbb4c0.patch) = 645
+SHA256 (5c8a4e0ebf18e68f34b7641b54922c90d9ae9db6.patch) = 8cb86cc4b08a248f9a94fb1fedee0500754620adf80f4858833eabfa9c30ac4d
+SIZE (5c8a4e0ebf18e68f34b7641b54922c90d9ae9db6.patch) = 603
+SHA256 (e0540b3a33921204f7fdd77c32d93ed267b8bad8.patch) = f8fb7f863de211da6a43d9d9a2c5393bf6fcd12089176ee6db536000eec8ac64
+SIZE (e0540b3a33921204f7fdd77c32d93ed267b8bad8.patch) = 797