diff --git a/net/py-urllib3/Makefile b/net/py-urllib3/Makefile
index 67c0e9ca18f4..7640cbbdda4c 100644
--- a/net/py-urllib3/Makefile
+++ b/net/py-urllib3/Makefile
@@ -1,48 +1,47 @@
 PORTNAME=	urllib3
-PORTVERSION=	1.26.18
-PORTREVISION=	1
+PORTVERSION=	1.26.19
 PORTEPOCH=	1
 CATEGORIES=	net python
 MASTER_SITES=	PYPI \
 		https://github.com/urllib3/urllib3/releases/download/${PORTVERSION}/
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
 MAINTAINER=	python@FreeBSD.org
 COMMENT=	HTTP library with thread-safe connection pooling, file post, and more
 WWW=		https://github.com/urllib3/urllib3
 
 LICENSE=	MIT
 LICENSE_FILE=	${WRKSRC}/LICENSE.txt
 
 TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}flaky>=3.6.1:devel/py-flaky@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}mock>=0:devel/py-mock@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pysocks>=1.5.6:net/py-pysocks@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pytest-timeout>=0:devel/py-pytest-timeout@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}python-dateutil>=2.8.1:devel/py-python-dateutil@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}tornado>=0:www/py-tornado@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}trustme>=0.6.0:security/py-trustme@${PY_FLAVOR}
 
 USES=		cpe python
 USE_PYTHON=	autoplist concurrent cryptography_test distutils pytest
 
 CPE_VENDOR=	python
 
 NO_ARCH=	yes
 TEST_ENV=	LC_ALL=en_US.UTF-8 PYTHONPATH=${WRKSRC}/src
 
 # Test 'test_ssl_read_timeout' fails with FreeBSD >= 12.0. That was already the case with earlier versions of net/py-urllib3.
 PYTEST_IGNORED_TESTS=	test_ssl_read_timeout
 
 SUB_FILES=	pkg-message
 
 OPTIONS_DEFINE=	BROTLI SOCKS SSL
 OPTIONS_DEFAULT=SOCKS
 
 BROTLI_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}brotli>=1.0.9:archivers/py-brotli@${PY_FLAVOR}
 SOCKS_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}pysocks>=1.5.6<2.0:net/py-pysocks@${PY_FLAVOR}
 SSL_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}certifi>=0:security/py-certifi@${PY_FLAVOR} \
 			${PYTHON_PKGNAMEPREFIX}idna>=2.0.0:dns/py-idna@${PY_FLAVOR} \
 			${PYTHON_PKGNAMEPREFIX}openssl>=0.14:security/py-openssl@${PY_FLAVOR}
 SSL_USE=		PYTHON=cryptography
 
 .include <bsd.port.mk>
diff --git a/net/py-urllib3/distinfo b/net/py-urllib3/distinfo
index af88c63f947b..a465608539d9 100644
--- a/net/py-urllib3/distinfo
+++ b/net/py-urllib3/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1698341317
-SHA256 (urllib3-1.26.18.tar.gz) = f8ecc1bba5667413457c529ab955bf8c67b45db799d159066261719e328580a0
-SIZE (urllib3-1.26.18.tar.gz) = 305687
+TIMESTAMP = 1718690552
+SHA256 (urllib3-1.26.19.tar.gz) = 3e3d753a8618b86d7de333b4223005f68720bcd6a7d2bcb9fbd2229ec7c1e429
+SIZE (urllib3-1.26.19.tar.gz) = 306068