diff --git a/devel/py-pip/Makefile b/devel/py-pip/Makefile
index 4ec009d8ebad..0408950c182b 100644
--- a/devel/py-pip/Makefile
+++ b/devel/py-pip/Makefile
@@ -1,75 +1,75 @@
 # Created by: Nicola Vitale <nivit@FreeBSD.org>
 
 PORTNAME=	pip
-PORTVERSION=	22.0.4
+PORTVERSION=	22.1
 CATEGORIES=	devel python
 MASTER_SITES=	https://files.pythonhosted.org/packages/fb/58/9efbfe68482dab9557c49d433a60fff9efd7ed8835f829eba8297c2c124a/:test_setuptools \
 		https://files.pythonhosted.org/packages/27/d6/003e593296a85fd6ed616ed962795b2f87709c3eee2bca4f6d0fe55c6d00/:test_wheel
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 DISTFILES=	setuptools-62.1.0-py3-none-any.whl:test_setuptools \
 		wheel-0.37.1-py2.py3-none-any.whl:test_wheel
 DIST_SUBDIR=	${PORTNAME}
 EXTRACT_ONLY=	${DISTNAME}${EXTRACT_SUFX}
 
 MAINTAINER=	python@FreeBSD.org
 COMMENT=	Tool for installing and managing Python packages
 
 LICENSE=	MIT
 LICENSE_FILE=	${WRKSRC}/LICENSE.txt
 
 # Tests also need bzr, git, otherwise they fail
 TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}cryptography>=0:security/py-cryptography@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}freezegun>=0:devel/py-freezegun@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pytest>=0,1:devel/py-pytest@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pytest-cov>=0:devel/py-pytest-cov@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pytest-rerunfailures>=0:devel/py-pytest-rerunfailures@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pytest-xdist>=0:devel/py-pytest-xdist@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}scripttest>=0:devel/py-scripttest@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}sqlite3>=0:databases/py-sqlite3@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}tomli-w>=0:textproc/py-tomli-w@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}virtualenv>=0:devel/py-virtualenv@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}werkzeug>=0:www/py-werkzeug@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}wheel>=0:devel/py-wheel@${PY_FLAVOR} \
 		hg:devel/mercurial \
 		git:devel/git \
 		svn:devel/subversion
 
 USES=		cpe python:3.7+ shebangfix
 CPE_VENDOR=	pypa
 USE_PYTHON=	autoplist concurrent distutils
 
 MAKE_ENV=	PYTHONPATH=${WRKSRC}/src/
 NO_ARCH=	yes
 
 USE_GITHUB=	yes
 GH_ACCOUNT=	pypa
 
 SHEBANG_FILES=	src/pip/__init__.py
 
 OPTIONS_DEFINE=	DOCS
 
 DOCS_BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}furo>=0:textproc/py-furo@${PY_FLAVOR} \
 			${PYTHON_PKGNAMEPREFIX}myst-parser>=0:textproc/py-myst-parser@${PY_FLAVOR} \
 			${PYTHON_PKGNAMEPREFIX}sphinx>=4.2,1<5,1:textproc/py-sphinx@${PY_FLAVOR} \
 			${PYTHON_PKGNAMEPREFIX}sphinx-copybutton>=0:textproc/py-sphinx-copybutton@${PY_FLAVOR} \
 			${PYTHON_PKGNAMEPREFIX}sphinx-inline-tabs>=0:textproc/py-sphinx-inline-tabs@${PY_FLAVOR} \
 			${PYTHON_PKGNAMEPREFIX}sphinxcontrib-towncrier>=0.2.0a0:textproc/py-sphinxcontrib-towncrier@${PY_FLAVOR} \
 			${PYTHON_PKGNAMEPREFIX}towncrier>=0:textproc/py-towncrier@${PY_FLAVOR}
 DOCS_PORTDOCS=		*
 DOCS_VARS=		PYDISTUTILS_BUILD_TARGET=build_sphinx \
 			PYDISTUTILS_BUILDARGS="-n --all-files --fresh-env"
 
 post-install-DOCS-on:
 	@${MKDIR} ${STAGEDIR}${DOCSDIR}
 	(cd ${WRKSRC}/build/sphinx/html && \
 	${COPYTREE_SHARE} . ${STAGEDIR}${DOCSDIR} "! -name .buildinfo -and ! -name objects.inv")
 
 do-test:
 	${MKDIR} ${WRKSRC}/tests/data/common_wheels
 	# the tests check for these wheel files, so fetch them and copy them in
-	${CP} ${DISTDIR}/${DIST_SUBDIR}/setuptools-44.0.0-py2.py3-none-any.whl ${WRKSRC}/tests/data/common_wheels
-	${CP} ${DISTDIR}/${DIST_SUBDIR}/wheel-0.35.1-py2.py3-none-any.whl ${WRKSRC}/tests/data/common_wheels
+	${CP} ${DISTDIR}/${DIST_SUBDIR}/setuptools-62.1.0-py3-none-any.whl ${WRKSRC}/tests/data/common_wheels
+	${CP} ${DISTDIR}/${DIST_SUBDIR}/wheel-0.37.1-py2.py3-none-any.whl ${WRKSRC}/tests/data/common_wheels
 	${LN} -sf ${LOCALBASE}/bin/pip ${LOCALBASE}/bin/pip3
-	cd ${WRKSRC} && ${PYTHON_CMD} -m pytest -v -rs
+	cd ${WRKSRC} && ${SETENV} PYTHONPATH=${STAGEDIR}${PYTHON_SITELIBDIR} ${PYTHON_CMD} -m pytest -rs -v
 
 .include <bsd.port.mk>
diff --git a/devel/py-pip/distinfo b/devel/py-pip/distinfo
index 52a95d1e9e0b..b262fc364d63 100644
--- a/devel/py-pip/distinfo
+++ b/devel/py-pip/distinfo
@@ -1,7 +1,7 @@
-TIMESTAMP = 1652122933
+TIMESTAMP = 1652446350
 SHA256 (pip/setuptools-62.1.0-py3-none-any.whl) = 26ead7d1f93efc0f8c804d9fafafbe4a44b179580a7105754b245155f9af05a8
 SIZE (pip/setuptools-62.1.0-py3-none-any.whl) = 1144059
 SHA256 (pip/wheel-0.37.1-py2.py3-none-any.whl) = 4bdcd7d840138086126cd09254dc6195fb4fc6f01c050a1d7236f2630db1d22a
 SIZE (pip/wheel-0.37.1-py2.py3-none-any.whl) = 35301
-SHA256 (pip/pypa-pip-22.0.4_GH0.tar.gz) = a9828528aa21cf87093e9332f94ea65931a51c443216f5d3a8f14451ef4f2bbf
-SIZE (pip/pypa-pip-22.0.4_GH0.tar.gz) = 9325766
+SHA256 (pip/pypa-pip-22.1_GH0.tar.gz) = 6012bf6a28761df91edefb7dc5f271631e37026d0535fca14e2c00f43d19417f
+SIZE (pip/pypa-pip-22.1_GH0.tar.gz) = 9345819