diff --git a/tools/base/requirements.in b/tools/base/requirements.in
index fc63cbbde75d2..c65a504ae1242 100644
--- a/tools/base/requirements.in
+++ b/tools/base/requirements.in
@@ -34,7 +34,7 @@ ply
 # `MessageFactory class is deprecated. Please use GetMessageClass() instead of MessageFactory.GetPrototype`
 protobuf<7.35.0
 pygithub
-pyopenssl>=24.2.1
+pyopenssl>=26.1.0
 pyreadline
 pyyaml
 setuptools
diff --git a/tools/base/requirements.txt b/tools/base/requirements.txt
index ac0baa30de4a6..63e41a4e3a41c 100644
--- a/tools/base/requirements.txt
+++ b/tools/base/requirements.txt
@@ -1287,9 +1287,9 @@ pynacl==1.6.2 \
     --hash=sha256:c8a231e36ec2cab018c4ad4358c386e36eede0319a0c41fed24f840b1dac59f6 \
     --hash=sha256:c949ea47e4206af7c8f604b8278093b674f7c79ed0d4719cc836902bf4517465
     # via pygithub
-pyopenssl==26.0.0 \
-    --hash=sha256:df94d28498848b98cc1c0ffb8ef1e71e40210d3b0a8064c9d29571ed2904bf81 \
-    --hash=sha256:f293934e52936f2e3413b89c6ce36df66a0b34ae1ea3a053b8c5020ff2f513fc
+pyopenssl==26.1.0 \
+    --hash=sha256:115563879b2c8ccb207975705d3e491434d8c9d7c79667c902ecbf5f3bbd2ece \
+    --hash=sha256:737f0a2275c5bc54f3b02137687e1a765931fb3949b9a92a825e4d33b9eec08b
     # via
     #   -r requirements.in
     #   aioquic