diff --git a/graphics/py-moderngl-window/Makefile b/graphics/py-moderngl-window/Makefile
index 44979f73fb84..7590ac2a42f6 100644
--- a/graphics/py-moderngl-window/Makefile
+++ b/graphics/py-moderngl-window/Makefile
@@ -1,34 +1,34 @@
 PORTNAME=	moderngl-window
-DISTVERSION=	2.4.4
+DISTVERSION=	2.4.5
 CATEGORIES=	graphics
 #MASTER_SITES=	PYPI # no tests
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
 MAINTAINER=	yuri@FreeBSD.org
 COMMENT=	Library for ModernGL making window creation & resource loading simple
 WWW=		https://github.com/moderngl/moderngl-window
 
 LICENSE=	MIT
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
 BUILD_DEPENDS=	${PY_SETUPTOOLS} \
 		${PYTHON_PKGNAMEPREFIX}wheel>0:devel/py-wheel@${PY_FLAVOR}
-RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}pillow>=9:graphics/py-pillow@${PY_FLAVOR} \
+RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}pillow>=10.0.1:graphics/py-pillow@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}moderngl<6:graphics/py-moderngl@${PY_FLAVOR} \
 		${PYNUMPY} \
-		${PYTHON_PKGNAMEPREFIX}pyglet>0:graphics/py-pyglet@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}pyglet>=2.0.0:graphics/py-pyglet@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pyrr>=0.10.3,<1:math/py-pyrr@${PY_FLAVOR}
 RUN_DEPENDS+=	${PYTHON_PKGNAMEPREFIX}PyWavefront>0:misc/py-PyWavefront@${PY_FLAVOR} # optional
 #RUN_DEPENDS+=	${PYTHON_PKGNAMEPREFIX}trimesh>0:devel/py-trimesh@${PY_FLAVOR} # optional, causes conflicts due to pyglet1 vs. pyglet
 
 USES=		python
 USE_PYTHON=	pep517 autoplist pytest # some tests fail due to missing trimesh
 
 USE_GITHUB=	yes
 GH_ACCOUNT=	moderngl
 
 NO_ARCH=	yes
 
 TEST_ENV=	${MAKE_ENV} PYTHONPATH=${STAGEDIR}${PYTHONPREFIX_SITELIBDIR}
 
 .include <bsd.port.mk>
diff --git a/graphics/py-moderngl-window/distinfo b/graphics/py-moderngl-window/distinfo
index a9e174a6027c..d779647865c1 100644
--- a/graphics/py-moderngl-window/distinfo
+++ b/graphics/py-moderngl-window/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1687714148
-SHA256 (moderngl-moderngl-window-2.4.4_GH0.tar.gz) = d0b62314341a62bd344b7966b94a77a1c9f72d08e014e7180abee76004ff9a12
-SIZE (moderngl-moderngl-window-2.4.4_GH0.tar.gz) = 30989161
+TIMESTAMP = 1697346635
+SHA256 (moderngl-moderngl-window-2.4.5_GH0.tar.gz) = 9bfbb41cb29f180c40f6fcf1b26c3b3ce02c19737bb221b697f705f6d19d3c95
+SIZE (moderngl-moderngl-window-2.4.5_GH0.tar.gz) = 30982181