diff --git a/requirements/ocsp.txt b/requirements/ocsp.txt
index a507b03d22..b83341f7b3 100644
--- a/requirements/ocsp.txt
+++ b/requirements/ocsp.txt
@@ -7,7 +7,7 @@
 # pyopenssl, cryptography, and service_identity must be set in tandem.
 # https://www.pyopenssl.org/en/stable/api/ssl.html#OpenSSL.SSL.Context.set_default_verify_paths
 certifi>=2023.7.22;os.name=='nt' or sys_platform=='darwin'
-pyopenssl>=23.2.0
+pyopenssl>=26.0.0
 requests>=2.23.0,<3.0
 cryptography>=42.0.0
 service_identity>=23.1.0
diff --git a/uv.lock b/uv.lock
index 78d0cc213f..2896f6575d 100644
--- a/uv.lock
+++ b/uv.lock
@@ -1595,7 +1595,7 @@ requires-dist = [
     { name = "pymongo-auth-aws", marker = "extra == 'aws'", specifier = ">=1.1.0,<2.0.0" },
     { name = "pymongo-auth-aws", marker = "extra == 'encryption'", specifier = ">=1.1.0,<2.0.0" },
     { name = "pymongocrypt", marker = "extra == 'encryption'", specifier = ">=1.13.0,<2.0.0" },
-    { name = "pyopenssl", marker = "extra == 'ocsp'", specifier = ">=23.2.0" },
+    { name = "pyopenssl", marker = "extra == 'ocsp'", specifier = ">=26.0.0" },
     { name = "pytest", marker = "extra == 'test'", specifier = ">=8.2" },
     { name = "pytest-asyncio", marker = "extra == 'test'", specifier = ">=0.24.0" },
     { name = "python-snappy", marker = "extra == 'snappy'", specifier = ">=0.6.0" },
@@ -1657,15 +1657,15 @@ wheels = [
 
 [[package]]
 name = "pyopenssl"
-version = "25.3.0"
+version = "26.2.0"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
     { name = "cryptography" },
     { name = "typing-extensions", marker = "python_full_version < '3.13'" },
 ]
-sdist = { url = "https://files.pythonhosted.org/packages/80/be/97b83a464498a79103036bc74d1038df4a7ef0e402cfaf4d5e113fb14759/pyopenssl-25.3.0.tar.gz", hash = "sha256:c981cb0a3fd84e8602d7afc209522773b94c1c2446a3c710a75b06fe1beae329", size = 184073, upload-time = "2025-09-17T00:32:21.037Z" }
+sdist = { url = "https://files.pythonhosted.org/packages/1a/51/27a5ad5f939d08f690a326ef9582cda7140555180db71695f6fb747d6a36/pyopenssl-26.2.0.tar.gz", hash = "sha256:8c6fcecd1183a7fc897548dfe388b0cdb7f37e018200d8409cf33959dbe35387", size = 182195, upload-time = "2026-05-04T23:06:09.72Z" }
 wheels = [
-    { url = "https://files.pythonhosted.org/packages/d1/81/ef2b1dfd1862567d573a4fdbc9f969067621764fbb74338496840a1d2977/pyopenssl-25.3.0-py3-none-any.whl", hash = "sha256:1fda6fc034d5e3d179d39e59c1895c9faeaf40a79de5fc4cbbfbe0d36f4a77b6", size = 57268, upload-time = "2025-09-17T00:32:19.474Z" },
+    { url = "https://files.pythonhosted.org/packages/73/b8/a0e2790ae249d6f38c9f66de7a211621a7ab2650217bcd04e1262f578a56/pyopenssl-26.2.0-py3-none-any.whl", hash = "sha256:4f9d971bc5298b8bc1fab282803da04bf000c755d4ad9d99b52de2569ca19a70", size = 55823, upload-time = "2026-05-04T23:06:08.395Z" },
 ]
 
 [[package]]