diff --git a/graphics/py-pillow/Makefile b/graphics/py-pillow/Makefile
index bdcff341147e..a2d86f859daa 100644
--- a/graphics/py-pillow/Makefile
+++ b/graphics/py-pillow/Makefile
@@ -1,77 +1,77 @@
 PORTNAME=	pillow
-PORTVERSION=	11.3.0
-PORTREVISION=	2
+PORTVERSION=	12.3.0
 CATEGORIES=	graphics python
 MASTER_SITES=	PYPI
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
 MAINTAINER=	sunpoet@FreeBSD.org
-COMMENT=	Fork of the Python Imaging Library (PIL)
+COMMENT=	Python Imaging Library (fork)
 WWW=		https://python-pillow.github.io/ \
 		https://pillow.readthedocs.io/en/stable/ \
 		https://github.com/python-pillow/Pillow
 
 LICENSE=	MIT-CMU
 LICENSE_NAME=	CMU License
 LICENSE_FILE=	${WRKSRC}/LICENSE
 LICENSE_PERMS=	auto-accept dist-mirror dist-sell pkg-mirror pkg-sell
 
-BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}setuptools>=61:devel/py-setuptools@${PY_FLAVOR} \
+BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}pybind11>=0:devel/py-pybind11@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}setuptools>=61:devel/py-setuptools@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}wheel>=0:devel/py-wheel@${PY_FLAVOR}
 TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}pytest>=0,1:devel/py-pytest@${PY_FLAVOR}
 
 USES=		cpe jpeg localbase python
 USE_PYTHON=	autoplist concurrent pep517 pytest
 
 PEP517_BUILD_CONFIG_SETTING=	\
 		--config-setting jpeg=enable \
 		--config-setting zlib=enable
 TEST_ENV=	PYTHONPATH=${STAGEDIR}${PYTHON_SITELIBDIR}
 
 CPE_VENDOR=	python
 
 OPTIONS_DEFINE=	AVIF FREETYPE IMAGEQUANT JPEG2000 LCMS OLE RAQM TIFF TKINTER WEBP XCB
 OPTIONS_DEFAULT=AVIF FREETYPE IMAGEQUANT JPEG2000 LCMS OLE 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
 
 AVIF_LIB_DEPENDS=	libavif.so:graphics/libavif
 AVIF_VARS=		PEP517_BUILD_CONFIG_SETTING+="--config-setting avif=enable"
 AVIF_VARS_OFF=		PEP517_BUILD_CONFIG_SETTING+="--config-setting avif=disable"
 FREETYPE_LIB_DEPENDS=	libfreetype.so:print/freetype2
 FREETYPE_VARS=		PEP517_BUILD_CONFIG_SETTING+="--config-setting freetype=enable"
 FREETYPE_VARS_OFF=	PEP517_BUILD_CONFIG_SETTING+="--config-setting freetype=disable"
 IMAGEQUANT_LIB_DEPENDS=	libimagequant.so:graphics/libimagequant
 IMAGEQUANT_VARS=	PEP517_BUILD_CONFIG_SETTING+="--config-setting imagequant=enable"
 IMAGEQUANT_VARS_OFF=	PEP517_BUILD_CONFIG_SETTING+="--config-setting imagequant=disable"
 JPEG2000_LIB_DEPENDS=	libopenjp2.so:graphics/openjpeg
 JPEG2000_VARS=		PEP517_BUILD_CONFIG_SETTING+="--config-setting jpeg2000=enable"
 JPEG2000_VARS_OFF=	PEP517_BUILD_CONFIG_SETTING+="--config-setting jpeg2000=disable"
 LCMS_LIB_DEPENDS=	liblcms2.so:graphics/lcms2
 LCMS_VARS=		PEP517_BUILD_CONFIG_SETTING+="--config-setting lcms=enable"
 LCMS_VARS_OFF=		PEP517_BUILD_CONFIG_SETTING+="--config-setting lcms=disable"
 OLE_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}olefile>=0:devel/py-olefile@${PY_FLAVOR}
 RAQM_LIB_DEPENDS=	libraqm.so:print/libraqm
 RAQM_VARS=		PEP517_BUILD_CONFIG_SETTING+="--config-setting raqm=enable"
 RAQM_VARS_OFF=		PEP517_BUILD_CONFIG_SETTING+="--config-setting raqm=disable"
 TIFF_LIB_DEPENDS=	libtiff.so:graphics/tiff
 TIFF_VARS=		PEP517_BUILD_CONFIG_SETTING+="--config-setting tiff=enable"
 TIFF_VARS_OFF=		PEP517_BUILD_CONFIG_SETTING+="--config-setting tiff=disable"
 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}
 WEBP_LIB_DEPENDS=	libwebp.so:graphics/webp
 WEBP_VARS=		PEP517_BUILD_CONFIG_SETTING+="--config-setting webp=enable"
 WEBP_VARS_OFF=		PEP517_BUILD_CONFIG_SETTING+="--config-setting webp=disable"
 XCB_USE=		XORG=xcb
 XCB_USES=		xorg
 XCB_VARS=		PEP517_BUILD_CONFIG_SETTING+="--config-setting xcb=enable"
 XCB_VARS_OFF=		PEP517_BUILD_CONFIG_SETTING+="--config-setting xcb=disable"
 
 post-install:
 	${FIND} ${STAGEDIR}${PYTHON_SITELIBDIR} -name '*.so' -exec ${STRIP_CMD} {} +
 
 .include <bsd.port.mk>
diff --git a/graphics/py-pillow/distinfo b/graphics/py-pillow/distinfo
index 612f07901e64..980d76e8d7f7 100644
--- a/graphics/py-pillow/distinfo
+++ b/graphics/py-pillow/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1751622375
-SHA256 (pillow-11.3.0.tar.gz) = 3828ee7586cd0b2091b6209e5ad53e20d0649bbe87164a459d0676e035e8f523
-SIZE (pillow-11.3.0.tar.gz) = 47113069
+TIMESTAMP = 1788500236
+SHA256 (pillow-12.3.0.tar.gz) = 3b8182a766685eaa002637e28b4ec8d6b18819a0c71f579bf0dbaa5830297cce
+SIZE (pillow-12.3.0.tar.gz) = 47025035
diff --git a/graphics/py-pillow/files/patch-pyproject.toml b/graphics/py-pillow/files/patch-pyproject.toml
index b9adef928b09..0ee5a6e66fe3 100644
--- a/graphics/py-pillow/files/patch-pyproject.toml
+++ b/graphics/py-pillow/files/patch-pyproject.toml
@@ -1,21 +1,21 @@
---- pyproject.toml.orig	2025-04-12 17:02:40 UTC
+--- pyproject.toml.orig	2026-07-01 09:47:15 UTC
 +++ pyproject.toml
-@@ -1,7 +1,7 @@ requires = [
- [build-system]
+@@ -2,7 +2,7 @@ requires = [
  build-backend = "backend"
  requires = [
+   "pybind11",
 -  "setuptools>=77",
 +  "setuptools>=61",
  ]
  backend-path = [
    "_custom_build",
-@@ -14,8 +14,7 @@ keywords = [
+@@ -15,8 +15,7 @@ keywords = [
  keywords = [
    "Imaging",
  ]
 -license = "MIT-CMU"
 -license-files = [ "LICENSE" ]
 +license = { text = "MIT-CMU" }
  authors = [
-   { name = "Jeffrey A. Clark", email = "aclark@aclark.net" },
+   { name = "Jeffrey 'Alex' Clark", email = "aclark@aclark.net" },
  ]