diff --git a/devel/py-pex/Makefile b/devel/py-pex/Makefile
index 20d7711c5a9f..08cea0553119 100644
--- a/devel/py-pex/Makefile
+++ b/devel/py-pex/Makefile
@@ -1,18 +1,22 @@
 PORTNAME=	pex
-PORTVERSION=	2.101.5
+PORTVERSION=	2.101.6
 CATEGORIES=	devel python
 MASTER_SITES=	PYPI
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
 MAINTAINER=	skreuzer@FreeBSD.org
 COMMENT=	PEX packaging toolchain
 WWW=		https://pex.readthedocs.org/en/latest/
 
 LICENSE=	APACHE20
 
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}wheel>=0.24.0:devel/py-wheel@${PY_FLAVOR}
 
-USES=		python
+USES=		python shebangfix
 USE_PYTHON=	autoplist distutils
 
+# Vendored pip/setuptools console scripts use a "#!python" placeholder.
+python_OLD_CMD+=	python
+SHEBANG_FILES=	pex/vendor/_vendored/*/.prefix/bin/*
+
 .include <bsd.port.mk>
diff --git a/devel/py-pex/distinfo b/devel/py-pex/distinfo
index b7b76833cdc3..e7b3ef46c1ef 100644
--- a/devel/py-pex/distinfo
+++ b/devel/py-pex/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1788747665
-SHA256 (pex-2.101.5.tar.gz) = 08d8900f8d57cc31b7f3e6698e96d412227183ed6afb1847676af0670a152d1b
-SIZE (pex-2.101.5.tar.gz) = 5454469
+TIMESTAMP = 1789250683
+SHA256 (pex-2.101.6.tar.gz) = e766f921c282e071ed3fc5f276c50571b407d76238ebabab76908825e0fecdec
+SIZE (pex-2.101.6.tar.gz) = 5454492