diff --git a/graphics/py-pillow/Makefile b/graphics/py-pillow/Makefile
index ad0719438472..a42e47fdf025 100644
--- a/graphics/py-pillow/Makefile
+++ b/graphics/py-pillow/Makefile
@@ -1,81 +1,81 @@
 PORTNAME=	pillow
-PORTVERSION=	9.4.0
+PORTVERSION=	9.5.0
 CATEGORIES=	graphics python
 MASTER_SITES=	PYPI
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 DISTNAME=	Pillow-${PORTVERSION}
 
 MAINTAINER=	sunpoet@FreeBSD.org
 COMMENT=	Fork of the Python Imaging Library (PIL)
 WWW=		https://python-pillow.org/ \
 		https://github.com/python-pillow/Pillow
 
 LICENSE=	PIL
 LICENSE_NAME=	Standard PIL License
 LICENSE_FILE=	${WRKSRC}/LICENSE
 LICENSE_PERMS=	dist-mirror dist-sell pkg-mirror pkg-sell auto-accept
 
 TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}pytest>=0,1:devel/py-pytest@${PY_FLAVOR}
 
 USES=		cpe localbase python:3.7+
 USE_PYTHON=	autoplist concurrent distutils
 
 CPE_VENDOR=	python
 
 OPTIONS_DEFINE=	FREETYPE IMAGEQUANT JPEG JPEG2000 LCMS OLE PNG RAQM TIFF TKINTER WEBP XCB
 OPTIONS_DEFAULT=FREETYPE IMAGEQUANT JPEG JPEG2000 LCMS OLE PNG RAQM TIFF TKINTER WEBP XCB
 IMAGEQUANT_DESC=	Image Quantization support
 LCMS_DESC=		Little Color Management System
 OLE_DESC=		Microsoft OLE2 file format support
 RAQM_DESC=		Complex text layout support
 TKINTER_DESC=		Tkinter (Tcl/Tk) BitmapImage & PhotoImage support
 XCB_DESC=		X11 screengrab support
 
 FREETYPE_LIB_DEPENDS=	libfreetype.so:print/freetype2
 FREETYPE_VARS=		PYDISTUTILS_BUILDARGS+=--enable-freetype
 FREETYPE_VARS_OFF=	PYDISTUTILS_BUILDARGS+=--disable-freetype
 IMAGEQUANT_LIB_DEPENDS=	libimagequant.so:graphics/libimagequant
 IMAGEQUANT_VARS=	PYDISTUTILS_BUILDARGS+=--enable-imagequant
 IMAGEQUANT_VARS_OFF=	PYDISTUTILS_BUILDARGS+=--disable-imagequant
 JPEG_USES=		jpeg
 JPEG_VARS=		PYDISTUTILS_BUILDARGS+=--enable-jpeg
 JPEG_VARS_OFF=		PYDISTUTILS_BUILDARGS+=--disable-jpeg
 JPEG2000_LIB_DEPENDS=	libopenjp2.so:graphics/openjpeg
 JPEG2000_VARS=		PYDISTUTILS_BUILDARGS+=--enable-jpeg2000
 JPEG2000_VARS_OFF=	PYDISTUTILS_BUILDARGS+=--disable-jpeg2000
 LCMS_LIB_DEPENDS=	liblcms2.so:graphics/lcms2
 LCMS_VARS=		PYDISTUTILS_BUILDARGS+=--enable-lcms
 LCMS_VARS_OFF=		PYDISTUTILS_BUILDARGS+=--disable-lcms
 OLE_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}olefile>=0:devel/py-olefile@${PY_FLAVOR}
 PNG_VARS=		PYDISTUTILS_BUILDARGS+=--enable-zlib
 PNG_VARS_OFF=		PYDISTUTILS_BUILDARGS+=--disable-zlib
 RAQM_LIB_DEPENDS=	libraqm.so:print/libraqm
 RAQM_VARS=		PYDISTUTILS_BUILDARGS+=--enable-raqm
 RAQM_VARS_OFF=		PYDISTUTILS_BUILDARGS+=--disable-raqm
 TIFF_LIB_DEPENDS=	libtiff.so:graphics/tiff
 TIFF_VARS=		PYDISTUTILS_BUILDARGS+=--enable-tiff
 TIFF_VARS_OFF=		PYDISTUTILS_BUILDARGS+=--disable-tiff
 TKINTER_BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}tkinter>=0:x11-toolkits/py-tkinter@${PY_FLAVOR}
 TKINTER_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}tkinter>=0:x11-toolkits/py-tkinter@${PY_FLAVOR}
 TKINTER_USES=		tk
 TKINTER_VARS=		PYDISTUTILS_BUILDARGS+="--include-dirs=${TCL_INCLUDEDIR}:${TK_INCLUDEDIR}"
 WEBP_LIB_DEPENDS=	libwebp.so:graphics/webp
 WEBP_VARS=		PYDISTUTILS_BUILDARGS+="--enable-webp --enable-webpmux"
 WEBP_VARS_OFF=		PYDISTUTILS_BUILDARGS+="--disable-webp --disable-webpmux"
 XCB_USE=		XORG=xcb
 XCB_USES=		xorg
 XCB_VARS=		PYDISTUTILS_BUILDARGS+=--enable-xcb
 XCB_VARS_OFF=		PYDISTUTILS_BUILDARGS+=--disable-xcb
 
 .include <bsd.port.pre.mk>
 
 PYDISTUTILS_BUILD_TARGET=	build build_ext
 PYDISTUTILS_BUILDARGS+=		saveopts
 
 post-install:
 	${FIND} ${STAGEDIR}${PYTHON_SITELIBDIR} -name '*.so' -exec ${STRIP_CMD} {} +
 
 do-test:
 	cd ${WRKSRC} && ${SETENV} PYTHONPATH=${STAGEDIR}${PYTHONPREFIX_SITELIBDIR} ${PYTHON_CMD} selftest.py
 
 .include <bsd.port.post.mk>
diff --git a/graphics/py-pillow/distinfo b/graphics/py-pillow/distinfo
index e56e4a4d8a43..f37eb78fae4c 100644
--- a/graphics/py-pillow/distinfo
+++ b/graphics/py-pillow/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1674589942
-SHA256 (Pillow-9.4.0.tar.gz) = a1c2d7780448eb93fbcc3789bf3916aa5720d942e37945f4056680317f1cd23e
-SIZE (Pillow-9.4.0.tar.gz) = 50403076
+TIMESTAMP = 1680726180
+SHA256 (Pillow-9.5.0.tar.gz) = bf548479d336726d7a0eceb6e767e179fbde37833ae42794602631a070d630f1
+SIZE (Pillow-9.5.0.tar.gz) = 50488147