diff --git a/www/py-requests/Makefile b/www/py-requests/Makefile
index f75e303ab9d2..9d9e69c6ec01 100644
--- a/www/py-requests/Makefile
+++ b/www/py-requests/Makefile
@@ -1,43 +1,44 @@
 PORTNAME=	requests
-PORTVERSION=	2.32.5
+PORTVERSION=	2.33.1
 CATEGORIES=	www python
 MASTER_SITES=	PYPI \
 		https://github.com/psf/requests/releases/download/v${PORTVERSION}/
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
 MAINTAINER=	sunpoet@FreeBSD.org
 COMMENT=	Python HTTP for Humans
 WWW=		https://docs.python-requests.org/en/latest/ \
 		https://requests.readthedocs.io/en/latest/ \
 		https://github.com/psf/requests
 
 LICENSE=	APACHE20
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
-BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}setuptools>=0:devel/py-setuptools@${PY_FLAVOR} \
+BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}setuptools>=61.0:devel/py-setuptools@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}wheel>=0:devel/py-wheel@${PY_FLAVOR}
-RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}certifi>=2017.4.17:security/py-certifi@${PY_FLAVOR} \
+RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}certifi>=2023.5.7:security/py-certifi@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}charset-normalizer>=2<4:textproc/py-charset-normalizer@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}idna>=2.5<4:dns/py-idna@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}urllib3>=1.21.1,1<3,1:net/py-urllib3@${PY_FLAVOR}
-TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}pysocks>=1.5.6:net/py-pysocks@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}urllib3>=1.26,1<3,1:net/py-urllib3@${PY_FLAVOR}
+TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}httpbin>=0.10.0<0.11:www/py-httpbin@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}pysocks>=1.5.6:net/py-pysocks@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pytest-cov>=0:devel/py-pytest-cov@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}pytest-httpbin>=0.0.7:devel/py-pytest-httpbin@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}pytest-httpbin>=2.1.0<2.1.0_99:devel/py-pytest-httpbin@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pytest-mock>=0:devel/py-pytest-mock@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pytest-xdist>=0,1:devel/py-pytest-xdist@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}trustme>=0:security/py-trustme@${PY_FLAVOR}
 
 USES=		cpe python
 USE_PYTHON=	autoplist concurrent pep517 pytest
 
 NO_ARCH=	yes
 
 CPE_VENDOR=	python
 
 OPTIONS_DEFINE=	SOCKS
 OPTIONS_DEFAULT=SOCKS
 SOCKS_DESC=	Extra socks functionalities
 
 SOCKS_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}pysocks>=1.5.6:net/py-pysocks@${PY_FLAVOR}
 
 .include <bsd.port.mk>
diff --git a/www/py-requests/distinfo b/www/py-requests/distinfo
index 9d0fc3943ec4..bdc02a85f9ea 100644
--- a/www/py-requests/distinfo
+++ b/www/py-requests/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1757120874
-SHA256 (requests-2.32.5.tar.gz) = dbba0bac56e100853db0ea71b82b4dfd5fe2bf6d3754a8893c3af500cec7d7cf
-SIZE (requests-2.32.5.tar.gz) = 134517
+TIMESTAMP = 1775587708
+SHA256 (requests-2.33.1.tar.gz) = 18817f8c57c6263968bc123d237e3b8b08ac046f5456bd1e307ee8f4250d3517
+SIZE (requests-2.33.1.tar.gz) = 134120