diff --git a/.evergreen/config.yml b/.evergreen/config.yml
index 705880be60..9083da145b 100644
--- a/.evergreen/config.yml
+++ b/.evergreen/config.yml
@@ -2305,16 +2305,6 @@ axes:
         variables:
            COVERAGE: "coverage"
 
-  # Run pyopenssl tests?
-  - id: pyopenssl
-    display_name: "PyOpenSSL"
-    values:
-      - id: "enabled"
-        display_name: "PyOpenSSL"
-        variables:
-          test_pyopenssl: true
-        batchtime: 10080  # 7 days
-
   - id: versionedApi
     display_name: "versionedApi"
     values:
@@ -3283,6 +3273,99 @@ buildvariants:
     AUTH: auth
     PYTHON_BINARY: /opt/python/pypy3.10/bin/python3
 
+# PyOpenSSL tests.
+- name: pyopenssl-macos-py3.9
+  tasks:
+    - name: .replica_set
+    - name: .7.0
+  display_name: PyOpenSSL macOS py3.9
+  run_on:
+    - macos-14
+  batchtime: 10080
+  expansions:
+    AUTH: noauth
+    test_pyopenssl: "true"
+    SSL: ssl
+    PYTHON_BINARY: /Library/Frameworks/Python.Framework/Versions/3.9/bin/python3
+- name: pyopenssl-rhel8-py3.10
+  tasks:
+    - name: .replica_set
+    - name: .7.0
+  display_name: PyOpenSSL RHEL8 py3.10
+  run_on:
+    - rhel87-small
+  batchtime: 10080
+  expansions:
+    AUTH: auth
+    test_pyopenssl: "true"
+    SSL: ssl
+    PYTHON_BINARY: /opt/python/3.10/bin/python3
+- name: pyopenssl-rhel8-py3.11
+  tasks:
+    - name: .replica_set
+    - name: .7.0
+  display_name: PyOpenSSL RHEL8 py3.11
+  run_on:
+    - rhel87-small
+  batchtime: 10080
+  expansions:
+    AUTH: auth
+    test_pyopenssl: "true"
+    SSL: ssl
+    PYTHON_BINARY: /opt/python/3.11/bin/python3
+- name: pyopenssl-rhel8-py3.12
+  tasks:
+    - name: .replica_set
+    - name: .7.0
+  display_name: PyOpenSSL RHEL8 py3.12
+  run_on:
+    - rhel87-small
+  batchtime: 10080
+  expansions:
+    AUTH: auth
+    test_pyopenssl: "true"
+    SSL: ssl
+    PYTHON_BINARY: /opt/python/3.12/bin/python3
+- name: pyopenssl-win64-py3.13
+  tasks:
+    - name: .replica_set
+    - name: .7.0
+  display_name: PyOpenSSL Win64 py3.13
+  run_on:
+    - windows-64-vsMulti-small
+  batchtime: 10080
+  expansions:
+    AUTH: auth
+    test_pyopenssl: "true"
+    SSL: ssl
+    PYTHON_BINARY: C:/python/Python313/python.exe
+- name: pyopenssl-rhel8-pypy3.9
+  tasks:
+    - name: .replica_set
+    - name: .7.0
+  display_name: PyOpenSSL RHEL8 pypy3.9
+  run_on:
+    - rhel87-small
+  batchtime: 10080
+  expansions:
+    AUTH: auth
+    test_pyopenssl: "true"
+    SSL: ssl
+    PYTHON_BINARY: /opt/python/pypy3.9/bin/python3
+- name: pyopenssl-rhel8-pypy3.10
+  tasks:
+    - name: .replica_set
+    - name: .7.0
+  display_name: PyOpenSSL RHEL8 pypy3.10
+  run_on:
+    - rhel87-small
+  batchtime: 10080
+  expansions:
+    AUTH: auth
+    test_pyopenssl: "true"
+    SSL: ssl
+    PYTHON_BINARY: /opt/python/pypy3.10/bin/python3
+
 - matrix_name: "tests-fips"
   matrix_spec:
     platform:
@@ -3305,47 +3388,6 @@ buildvariants:
   tasks:
     - ".6.0"
 
-- matrix_name: "tests-pyopenssl"
-  matrix_spec:
-    platform: rhel8
-    python-version: "*"
-    auth: "*"
-    ssl: "ssl"
-    pyopenssl: "*"
-  # Only test "noauth" with Python 3.9.
-  exclude_spec:
-    platform: rhel8
-    python-version: ["3.10", "3.11", "3.12", "3.13", "pypy3.9", "pypy3.10"]
-    auth: "noauth"
-    ssl: "ssl"
-    pyopenssl: "*"
-  display_name: "PyOpenSSL ${platform} ${python-version} ${auth}"
-  tasks:
-    - '.replica_set'
-    # Test standalone and sharded only on 7.0.
-    - '.7.0'
-
-- matrix_name: "tests-pyopenssl-macOS"
-  matrix_spec:
-    platform: macos
-    auth: "auth"
-    ssl: "ssl"
-    pyopenssl: "*"
-  display_name: "PyOpenSSL ${platform} ${auth}"
-  tasks:
-    - '.replica_set'
-
-- matrix_name: "tests-pyopenssl-windows"
-  matrix_spec:
-    platform: windows
-    python-version-windows: "*"
-    auth: "auth"
-    ssl: "ssl"
-    pyopenssl: "*"
-  display_name: "PyOpenSSL ${platform} ${python-version-windows} ${auth}"
-  tasks:
-    - '.replica_set'
-
 - matrix_name: "tests-python-version-rhel8-without-c-extensions"
   matrix_spec:
     platform: rhel8
diff --git a/.evergreen/scripts/generate_config.py b/.evergreen/scripts/generate_config.py
index a3ec798c3b..6d614a9afe 100644
--- a/.evergreen/scripts/generate_config.py
+++ b/.evergreen/scripts/generate_config.py
@@ -410,10 +410,42 @@ def create_enterprise_auth_variants():
     return variants
 
 
+def create_pyopenssl_variants():
+    base_name = "PyOpenSSL"
+    batchtime = BATCHTIME_WEEK
+    base_expansions = dict(test_pyopenssl="true", SSL="ssl")
+    variants = []
+
+    for python in ALL_PYTHONS:
+        # Only test "noauth" with min python.
+        auth = "noauth" if python == CPYTHONS[0] else "auth"
+        if python == CPYTHONS[0]:
+            host = "macos"
+        elif python == CPYTHONS[-1]:
+            host = "win64"
+        else:
+            host = "rhel8"
+        expansions = dict(AUTH=auth)
+        expansions.update(base_expansions)
+
+        display_name = get_display_name(base_name, host, python=python)
+        variant = create_variant(
+            [".replica_set", ".7.0"],
+            display_name,
+            python=python,
+            host=host,
+            expansions=expansions,
+            batchtime=batchtime,
+        )
+        variants.append(variant)
+
+    return variants
+
+
 ##################
 # Generate Config
 ##################
 
-variants = create_server_variants()
+variants = create_pyopenssl_variants()
 # print(len(variants))
 generate_yaml(variants=variants)