diff --git a/devel/py-pipx/Makefile b/devel/py-pipx/Makefile
index cd86a3757dfc..f6e5bdabbff7 100644
--- a/devel/py-pipx/Makefile
+++ b/devel/py-pipx/Makefile
@@ -1,30 +1,30 @@
 # Created by: Po-Chuan Hsieh <sunpoet@FreeBSD.org>
 
 PORTNAME=	pipx
-PORTVERSION=	0.16.4
+PORTVERSION=	0.16.5
 CATEGORIES=	devel python
 MASTER_SITES=	CHEESESHOP
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
 MAINTAINER=	sunpoet@FreeBSD.org
 COMMENT=	Install and Run Python Applications in Isolated Environments
 
 LICENSE=	MIT
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}argcomplete>=1.9.4<2.0:devel/py-argcomplete@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}packaging>=20.0:devel/py-packaging@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}userpath>=1.6.0:devel/py-userpath@${PY_FLAVOR}
 
 USES=		python:3.6+
 USE_PYTHON=	autoplist concurrent distutils
 
 NO_ARCH=	yes
 
 .include <bsd.port.pre.mk>
 
 .if ${PYTHON_REL} < 30800
 RUN_DEPENDS+=	${PYTHON_PKGNAMEPREFIX}importlib-metadata>=3.3.0:devel/py-importlib-metadata@${PY_FLAVOR}
 .endif
 
 .include <bsd.port.post.mk>
diff --git a/devel/py-pipx/distinfo b/devel/py-pipx/distinfo
index e0807e8b3403..88ccd2a28ac9 100644
--- a/devel/py-pipx/distinfo
+++ b/devel/py-pipx/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1628439050
-SHA256 (pipx-0.16.4.tar.gz) = 992e78082c0b33c7bc708176ce9e0df9bac9ae3b08bf111c368571bc32e723d6
-SIZE (pipx-0.16.4.tar.gz) = 348116
+TIMESTAMP = 1641045958
+SHA256 (pipx-0.16.5.tar.gz) = 2a12ee8911d36c0fc08ad3dba78c7d002797810e562739a34e1a2ce6acd85019
+SIZE (pipx-0.16.5.tar.gz) = 349346