diff --git a/www/py-pydrive2/Makefile b/www/py-pydrive2/Makefile
index 1c20a77f48f0..f3d0204ab647 100644
--- a/www/py-pydrive2/Makefile
+++ b/www/py-pydrive2/Makefile
@@ -1,58 +1,58 @@
 PORTNAME=	PyDrive2
-PORTVERSION=	1.21.1
+DISTVERSION=	1.21.3
 CATEGORIES=	www python
 MASTER_SITES=	PYPI
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
-DISTNAME=	pydrive2-${PORTVERSION}
+DISTNAME=	pydrive2-${DISTVERSION}
 
 MAINTAINER=	matthew@wener.org
 COMMENT=	PyDrive2 is a wrapper library of google-api-python-client
 WWW=		https://github.com/iterative/PyDrive2
 
 LICENSE=	APACHE20
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
 BUILD_DEPENDS=	${PY_SETUPTOOLS} \
 		${PYTHON_PKGNAMEPREFIX}setuptools-scm>=0:devel/py-setuptools-scm@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}wheel>=0:devel/py-wheel@${PY_FLAVOR}
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}google-api-python-client>=0:www/py-google-api-python-client@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}oauth2client>=0:security/py-oauth2client@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}openssl>=0:security/py-openssl@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}openssl<=24.2.1,1:security/py-openssl@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pyyaml>=0:devel/py-pyyaml@${PY_FLAVOR}
 
 USES=		python
-USE_PYTHON=	autoplist pep517
+USE_PYTHON=	autoplist cryptography pep517
 
 NO_ARCH=	yes
 
 PORTDOCS=	*
 PORTEXAMPLES=	*
 
 OPTIONS_DEFINE=	DOCS EXAMPLES FSSPEC
 
 FSSPEC_DESC=		Filesystem interfaces for Python
 
 DOCS_BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}furo>0:textproc/py-furo@${PY_FLAVOR} \
 			${PYTHON_PKGNAMEPREFIX}sphinx>=0:textproc/py-sphinx@${PY_FLAVOR}
 FSSPEC_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}appdirs>=0:devel/py-appdirs@${PY_FLAVOR} \
-			${PYTHON_PKGNAMEPREFIX}fsspec>=0:devel/py-fsspec@${PY_FLAVOR} \
+			${PYTHON_PKGNAMEPREFIX}fsspec>=0:filesystems/py-fsspec@${PY_FLAVOR} \
 			${PYTHON_PKGNAMEPREFIX}funcy>=0:devel/py-funcy@${PY_FLAVOR} \
 			${PYTHON_PKGNAMEPREFIX}tqdm>=0:misc/py-tqdm@${PY_FLAVOR}
 
 pre-build-DOCS-on:
 	@(cd ${BUILD_WRKSRC}; \
 	${SETENVI} ${WRK_ENV} \
 	sphinx-build-${PYTHON_VER} \
 		-b html -d _build/doctress docs/ build/sphinx/html)
 
 do-install-DOCS-on:
 	@${MKDIR} ${STAGEDIR}${DOCSDIR}
 	(cd ${WRKSRC}/build/sphinx/html && \
 		${COPYTREE_SHARE} . ${STAGEDIR}${DOCSDIR} \
 		"! -name .buildinfo -and ! -name .nojekyll -and ! -name objects.inv")
 
 do-install-EXAMPLES-on:
 	${MKDIR} ${STAGEDIR}${EXAMPLESDIR}
 	(cd ${WRKSRC}/examples && ${COPYTREE_SHARE} . ${STAGEDIR}${EXAMPLESDIR})
 
 .include <bsd.port.mk>
diff --git a/www/py-pydrive2/distinfo b/www/py-pydrive2/distinfo
index 8914cf3b1aab..3e92f7d31b90 100644
--- a/www/py-pydrive2/distinfo
+++ b/www/py-pydrive2/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1731946676
-SHA256 (pydrive2-1.21.1.tar.gz) = 70da0244a29a6922e28620a32e251ac6ab018449f1bb0485e9a39114a069dde0
-SIZE (pydrive2-1.21.1.tar.gz) = 63287
+TIMESTAMP = 1739219627
+SHA256 (pydrive2-1.21.3.tar.gz) = 649b84d60c637bc7146485039535aa8f1254ad156423739f07e5d32507447c13
+SIZE (pydrive2-1.21.3.tar.gz) = 63348