diff --git a/devel/py-pip-run/Makefile b/devel/py-pip-run/Makefile
index 1d17d5e3ce47..aada4fe0b9db 100644
--- a/devel/py-pip-run/Makefile
+++ b/devel/py-pip-run/Makefile
@@ -1,39 +1,43 @@
 PORTNAME=	pip-run
-PORTVERSION=	12.4.0
+PORTVERSION=	12.6.1
 CATEGORIES=	devel python
 MASTER_SITES=	PYPI
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
 MAINTAINER=	sunpoet@FreeBSD.org
 COMMENT=	Install packages and run Python with them
 WWW=		https://github.com/jaraco/pip-run
 
 LICENSE=	MIT
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
 BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}setuptools>=56:devel/py-setuptools@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}setuptools_scm>=3.4.1:devel/py-setuptools_scm@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}wheel>=0:devel/py-wheel@${PY_FLAVOR}
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}autocommand>=0:devel/py-autocommand@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}jaraco.context>=0:devel/py-jaraco.context@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}jaraco.env>=0:devel/py-jaraco.env@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}jaraco.functools>=3.7:devel/py-jaraco.functools@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}jaraco.text>=0:devel/py-jaraco.text@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}more-itertools>=8.3:devel/py-more-itertools@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}packaging>=0:devel/py-packaging@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}path>=15.1:devel/py-path@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pip>=19.3:devel/py-pip@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}platformdirs>=0:devel/py-platformdirs@${PY_FLAVOR}
 
 USES=		python
 USE_PYTHON=	autoplist concurrent pep517
 
 NO_ARCH=	yes
 
 .include <bsd.port.pre.mk>
 
 .if ${PYTHON_REL} < 30900
 RUN_DEPENDS+=	${PYTHON_PKGNAMEPREFIX}importlib-resources>=0:devel/py-importlib-resources@${PY_FLAVOR}
 .endif
 
+.if ${PYTHON_REL} < 31100
+RUN_DEPENDS+=	${PYTHON_PKGNAMEPREFIX}tomli>=0:textproc/py-tomli@${PY_FLAVOR}
+.endif
+
 .include <bsd.port.post.mk>
diff --git a/devel/py-pip-run/distinfo b/devel/py-pip-run/distinfo
index 00bc07ffaae5..9d69eb50c16c 100644
--- a/devel/py-pip-run/distinfo
+++ b/devel/py-pip-run/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1696904132
-SHA256 (pip-run-12.4.0.tar.gz) = 56f4ec37562c52c4fdd1e07f3c029c2f39514ad65b7c7a34041facc58848514a
-SIZE (pip-run-12.4.0.tar.gz) = 37749
+TIMESTAMP = 1708449276
+SHA256 (pip-run-12.6.1.tar.gz) = 227914cba705e9d90ce823e7163111a8a5b614c2e37fea003d506291763dafb1
+SIZE (pip-run-12.6.1.tar.gz) = 38868