diff --git a/.evergreen/config.yml b/.evergreen/config.yml
index b69707402..6825aac10 100644
--- a/.evergreen/config.yml
+++ b/.evergreen/config.yml
@@ -457,6 +457,9 @@ functions:
             rm -f ./fle_creds.sh
             export LIBMONGOCRYPT_URL="${libmongocrypt_url}"
             export TEST_ENCRYPTION=1
+            if [ -n "${test_encryption_pyopenssl}" ]; then
+              export TEST_ENCRYPTION_PYOPENSSL=1
+            fi
           fi
           if [ -n "${test_crypt_shared}" ]; then
             export TEST_CRYPT_SHARED=1
@@ -2507,6 +2510,13 @@ axes:
         variables:
           test_encryption: true
         batchtime: 10080  # 7 days
+      - id: "encryption_pyopenssl"
+        display_name: "Encryption PyOpenSSL"
+        tags: ["encryption_tag"]
+        variables:
+          test_encryption: true
+          test_encryption_pyopenssl: true
+        batchtime: 10080  # 7 days
       # The path to crypt_shared is stored in the $CRYPT_SHARED_LIB_PATH expansion.
       - id: "encryption_crypt_shared"
         display_name: "Encryption shared lib"
@@ -2637,14 +2647,22 @@ buildvariants:
     ssl: "nossl"
     encryption: "*"
   display_name: "${encryption} ${platform} ${auth} ${ssl}"
-  tasks: &encryption-server-versions
-    - ".rapid"
-    - ".latest"
-    - ".6.0"
-    - ".5.0"
-    - ".4.4"
-    - ".4.2"
-    - ".4.0"
+  tasks: "test-latest-replica_set"
+  rules:
+    - if:
+        encryption: ["encryption", "encryption_crypt_shared"]
+        platform: macos-1100
+        auth: "auth"
+        ssl: "nossl"
+      then:
+        add_tasks: &encryption-server-versions
+          - ".rapid"
+          - ".latest"
+          - ".6.0"
+          - ".5.0"
+          - ".4.4"
+          - ".4.2"
+          - ".4.0"
 
 # Test one server version with zSeries, POWER8, and ARM.
 - matrix_name: "test-different-cpu-architectures"
@@ -2726,8 +2744,15 @@ buildvariants:
 #    coverage: "*"
     encryption: "*"
   display_name: "${encryption} ${python-version} ${platform} ${auth-ssl}"
-  tasks: *encryption-server-versions
-
+  tasks: "test-latest-replica_set"
+  rules:
+    - if:
+        encryption: ["encryption", "encryption_crypt_shared"]
+        platform: ubuntu-18.04
+        auth-ssl: noauth-nossl
+        python-version: "*"
+      then:
+        add_tasks: *encryption-server-versions
 
 - matrix_name: "tests-python-version-ubuntu18-without-c-extensions"
   matrix_spec:
@@ -2837,7 +2862,15 @@ buildvariants:
     auth-ssl: "*"
     encryption: "*"
   display_name: "${encryption} ${platform} ${python-version-windows} ${auth-ssl}"
-  tasks: *encryption-server-versions
+  tasks: "test-latest-replica_set"
+  rules:
+    - if:
+        encryption: ["encryption", "encryption_crypt_shared"]
+        platform: windows-64-vsMulti-small
+        python-version-windows: "*"
+        auth-ssl: "*"
+      then:
+        add_tasks: *encryption-server-versions
 
 # Storage engine tests on Ubuntu 18.04 (x86_64) with Python 3.7.
 - matrix_name: "tests-storage-engines"
diff --git a/.evergreen/run-tests.sh b/.evergreen/run-tests.sh
index 3a15163b6..556d60f07 100755
--- a/.evergreen/run-tests.sh
+++ b/.evergreen/run-tests.sh
@@ -151,8 +151,11 @@ fi
 
 if [ -n "$TEST_ENCRYPTION" ]; then
     # Need aws dependency for On-Demand KMS Credentials.
-    # Need OSCP dependency to verify OCSP TSL args.
-    python -m pip install '.[aws,ocsp]'
+    if [ -n "$TEST_ENCRYPTION_PYOPENSSL" ]; then
+        python -m pip install '.[aws,ocsp]'
+    else
+        python -m pip install '.[aws]'
+    fi
 
     # Get access to the AWS temporary credentials:
     # CSFLE_AWS_TEMP_ACCESS_KEY_ID, CSFLE_AWS_TEMP_SECRET_ACCESS_KEY, CSFLE_AWS_TEMP_SESSION_TOKEN
diff --git a/test/test_encryption.py b/test/test_encryption.py
index b7d588e74..6cdc8da3b 100644
--- a/test/test_encryption.py
+++ b/test/test_encryption.py
@@ -2159,8 +2159,11 @@ class TestKmsTLSOptions(EncryptionIntegrationTest):
         encryption = ClientEncryption(
             providers, "keyvault.datakeys", self.client, OPTS, kms_tls_options=options
         )
-        self.assertFalse(encryption._io_callbacks.opts._kms_ssl_contexts["aws"].check_ocsp_endpoint)
-        encryption.close()
+        self.addCleanup(encryption.close)
+        ctx = encryption._io_callbacks.opts._kms_ssl_contexts["aws"]
+        if not hasattr(ctx, "check_ocsp_endpoint"):
+            raise self.skipTest("OCSP not enabled")  # type:ignore
+        self.assertFalse(ctx.check_ocsp_endpoint)
 
 
 # https://github.com/mongodb/specifications/blob/50e26fe/source/client-side-encryption/tests/README.rst#unique-index-on-keyaltnames