diff --git a/devel/py-pipx/Makefile b/devel/py-pipx/Makefile
index bb3e1cb4bd4ac..cd86a3757dfce 100644
--- a/devel/py-pipx/Makefile
+++ b/devel/py-pipx/Makefile
@@ -1,7 +1,7 @@
 # Created by: Po-Chuan Hsieh <sunpoet@FreeBSD.org>
 
 PORTNAME=	pipx
-PORTVERSION=	0.16.3
+PORTVERSION=	0.16.4
 CATEGORIES=	devel python
 MASTER_SITES=	CHEESESHOP
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
@@ -14,7 +14,7 @@ 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} \
-		${PYTHON_PKGNAMEPREFIX}userpath>=1.5.0:devel/py-userpath@${PY_FLAVOR}
+		${PYTHON_PKGNAMEPREFIX}userpath>=1.6.0:devel/py-userpath@${PY_FLAVOR}
 
 USES=		python:3.6+
 USE_PYTHON=	autoplist concurrent distutils
diff --git a/devel/py-pipx/distinfo b/devel/py-pipx/distinfo
index d21eb0afddeeb..e0807e8b34035 100644
--- a/devel/py-pipx/distinfo
+++ b/devel/py-pipx/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1624189733
-SHA256 (pipx-0.16.3.tar.gz) = 51fa41281383212db3b2a6906713871edc1a7d597ae387873026402e281a0b25
-SIZE (pipx-0.16.3.tar.gz) = 348094
+TIMESTAMP = 1628439050
+SHA256 (pipx-0.16.4.tar.gz) = 992e78082c0b33c7bc708176ce9e0df9bac9ae3b08bf111c368571bc32e723d6
+SIZE (pipx-0.16.4.tar.gz) = 348116