diff --git a/devel/py-pipx/Makefile b/devel/py-pipx/Makefile
index 4d9a3ae71302..27ec6b8a4e8f 100644
--- a/devel/py-pipx/Makefile
+++ b/devel/py-pipx/Makefile
@@ -2,7 +2,7 @@
 # $FreeBSD$
 
 PORTNAME=	pipx
-PORTVERSION=	0.15.6.0
+PORTVERSION=	0.16.0.0
 CATEGORIES=	devel python
 MASTER_SITES=	CHEESESHOP
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
@@ -22,4 +22,10 @@ USE_PYTHON=	autoplist concurrent distutils
 
 NO_ARCH=	yes
 
-.include <bsd.port.mk>
+.include <bsd.port.pre.mk>
+
+.if ${PYTHON_REL} < 3800
+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 0d2e7b059df0..cf2a84e6eb52 100644
--- a/devel/py-pipx/distinfo
+++ b/devel/py-pipx/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1603038253
-SHA256 (pipx-0.15.6.0.tar.gz) = 0d20e295a236b60e5601cb4e3d0c4fad202b9027ca1b2b8c88b322e66bf42b1f
-SIZE (pipx-0.15.6.0.tar.gz) = 340737
+TIMESTAMP = 1611665431
+SHA256 (pipx-0.16.0.0.tar.gz) = ec9d63753f34eb2dde5597ecdfe23df61749104485eead42937abec4dc4f4598
+SIZE (pipx-0.16.0.0.tar.gz) = 344650