diff --git a/security/py-pyhanko/Makefile b/security/py-pyhanko/Makefile
index 8541d75a1d02..3a8a2e5d6366 100644
--- a/security/py-pyhanko/Makefile
+++ b/security/py-pyhanko/Makefile
@@ -1,49 +1,49 @@
 PORTNAME=	pyhanko
-PORTVERSION=	0.27.1
+PORTVERSION=	0.28.0
 CATEGORIES=	security python
 MASTER_SITES=	PYPI \
 		https://github.com/MatthiasValvekens/pyHanko/releases/download/v${PORTVERSION}/
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
 MAINTAINER=	sunpoet@FreeBSD.org
 COMMENT=	Tools for stamping and signing PDF files
 WWW=		https://pyhanko.readthedocs.io/en/latest/ \
 		https://github.com/MatthiasValvekens/pyHanko
 
 LICENSE=	MIT
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
 BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}setuptools>=61:devel/py-setuptools@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}wheel>=0:devel/py-wheel@${PY_FLAVOR}
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}asn1crypto>=1.5.1:devel/py-asn1crypto@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}click>=8.1.3<8.2.0:devel/py-click@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}defusedxml>=0.7.1<0.8:devel/py-defusedxml@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}pyhanko-certvalidator>=0.26.5<0.27:security/py-pyhanko-certvalidator@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}pyhanko-certvalidator>=0.27.0<0.28:security/py-pyhanko-certvalidator@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pyyaml>=6.0:devel/py-pyyaml@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}qrcode>=7.3.1:textproc/py-qrcode@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}requests>=2.31.0:www/py-requests@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}tzlocal>=4.3:devel/py-tzlocal@${PY_FLAVOR}
 
 USES=		python
 USE_PYTHON=	autoplist concurrent cryptography pep517
 
 NO_ARCH=	yes
 
 OPTIONS_DEFINE=	ASYNC_HTTP ETSI IMAGE_SUPPORT OPENTYPE PKGCS11 XMP
 ASYNC_HTTP_DESC=Asynchronous support
 ETSI_DESC=	European Telecommunications Standards Institute (ETSI)
 IMAGE_SUPPORT_DESC=	Image handling support
 OPENTYPE_DESC=	OpenType/TrueType support
 PKGCS11_DESC=	PKGCS\#11 support
 XMP_DESC=	XMP (Extensible Metadata Platform) support
 
 ASYNC_HTTP_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}aiohttp>=3.9.0<3.12:www/py-aiohttp@${PY_FLAVOR}
 ETSI_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}xsdata>=24.4<26.0:devel/py-xsdata@${PY_FLAVOR}
 IMAGE_SUPPORT_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}pillow>=7.2.0:graphics/py-pillow@${PY_FLAVOR} \
 			${PYTHON_PKGNAMEPREFIX}python-barcode>=0.15.1<0.15.1_99:graphics/py-python-barcode@${PY_FLAVOR}
 OPENTYPE_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}fonttools>=4.33.3:print/py-fonttools@${PY_FLAVOR} \
 			${PYTHON_PKGNAMEPREFIX}uharfbuzz>=0.25.0<0.51.0:print/py-uharfbuzz@${PY_FLAVOR}
 PKGCS11_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}python-pkcs11>=0.7.0<0.8:security/py-python-pkcs11@${PY_FLAVOR}
 XMP_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}defusedxml>=0.7.1<0.8:devel/py-defusedxml@${PY_FLAVOR}
 
 .include <bsd.port.mk>
diff --git a/security/py-pyhanko/distinfo b/security/py-pyhanko/distinfo
index 4cd65e8ba54c..9f36b6fe9951 100644
--- a/security/py-pyhanko/distinfo
+++ b/security/py-pyhanko/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1747715466
-SHA256 (pyhanko-0.27.1.tar.gz) = 2378e3189591740a94d5633d772cb11d9a619dab7ed5437fa3004c95ae279de8
-SIZE (pyhanko-0.27.1.tar.gz) = 389689
+TIMESTAMP = 1748107942
+SHA256 (pyhanko-0.28.0.tar.gz) = ec9832f1347ab52b7cb4cc9ea184a2d44e168ffdf16823a667aaed391809b430
+SIZE (pyhanko-0.28.0.tar.gz) = 509521
diff --git a/security/py-pyhanko/files/patch-pyproject.toml b/security/py-pyhanko/files/patch-pyproject.toml
index eadfc8905bdf..dee4b3a1faff 100644
--- a/security/py-pyhanko/files/patch-pyproject.toml
+++ b/security/py-pyhanko/files/patch-pyproject.toml
@@ -1,17 +1,23 @@
---- pyproject.toml.orig	2024-03-07 22:13:09 UTC
+--- pyproject.toml.orig	2025-05-24 12:37:13 UTC
 +++ pyproject.toml
-@@ -1,12 +1,12 @@ requires = [
+@@ -1,17 +1,16 @@ requires = [
  [build-system]
  requires = [
 -    "setuptools>=67.4",
 +    "setuptools>=61",
      "wheel"
  ]
  build-backend = "setuptools.build_meta"
  
  [project]
 -name = "pyHanko"
 +name = "pyhanko"
  description = "Tools for stamping and signing PDF files"
  authors = [{name = "Matthias Valvekens", email = "dev@mvalvekens.be"}]
  maintainers = [{name = "Matthias Valvekens", email = "dev@mvalvekens.be"}]
+-license = "MIT"
+-license-files = ["LICENSE", "src/pyhanko/pdf_utils/LICENSE.PyPDF2"]
++license = {text = "MIT"}
+ keywords = [
+     "signature",
+     "pdf",