diff --git a/.evergreen/config.yml b/.evergreen/config.yml
index 3fc466a02..d759d6978 100644
--- a/.evergreen/config.yml
+++ b/.evergreen/config.yml
@@ -1335,10 +1335,13 @@ buildvariants:
   tasks:
      - ".latest"
 
-# Test CPython 2.6, 2.7, 3.5 and 3.6 against all versions on MongoDB >= 2.6
+# Test CPython 2.7, 3.5 and 3.6 against all versions on MongoDB >= 2.6
 # on Windows with the Microsoft Visual C++ Compiler for Python 2.7 or Visual Studio 2015.
-- matrix_name: "tests-windows-vs2015-python-version"
+- matrix_name: "tests-windows-vs2015-python-version-27plus"
   matrix_spec: {windows-vs2015-python-version: "*", auth-ssl: "*"}
+  exclude_spec:
+   - windows-vs2015-python-version: "2.6"
+     auth-ssl: "*"
   display_name: "Windows 64 Visual Studio 2015 ${windows-vs2015-python-version} ${auth-ssl}"
   run_on: windows-64-vs2015-test
   tasks:
@@ -1350,6 +1353,51 @@ buildvariants:
      - ".3.0"
      - ".2.6"
 
+# Test CPython 2.6 against all versions on MongoDB >= 2.6
+# on Windows with the Microsoft Visual C++ Compiler for Python 2.7.
+# Python 2.6.6 (the last 2.6 version with Windows installers) bundles
+# OpenSSL 0.9.8, which doesn't support TLS 1.1+. MongoDB 4.0+ requires
+# TLS 1.1+ by default.
+- matrix_name: "tests-windows-vs2015-python-version-26"
+  matrix_spec: {windows-vs2015-python-version: "2.6", auth: "*", ssl: "*"}
+  exclude_spec:
+   - windows-vs2015-python-version: "*"
+     auth: "noauth"
+     ssl: "ssl"
+  display_name: "Windows 64 Visual Studio 2015 ${windows-vs2015-python-version} ${auth} ${ssl}"
+  run_on: windows-64-vs2015-test
+  rules:
+    - if:
+        windows-vs2015-python-version: "*"
+        auth: "*"
+        ssl: "nossl"
+      then:
+        add_tasks:
+          - ".latest"
+          - ".4.0"
+    - if:
+        windows-vs2015-python-version: "*"
+        auth: "noauth"
+        ssl: "nossl"
+      then:
+        add_tasks:
+          - ".3.6"
+          - ".3.4"
+          - ".3.2"
+          - ".3.0"
+          - ".2.6"
+    - if:
+        windows-vs2015-python-version: "*"
+        auth: "auth"
+        ssl: "ssl"
+      then:
+        add_tasks:
+          - ".3.6"
+          - ".3.4"
+          - ".3.2"
+          - ".3.0"
+          - ".2.6"
+
 # Storage engine tests on RHEL 6.2 (x86_64) with Python 2.7.
 - matrix_name: "tests-storage-engines"
   matrix_spec: {storage-engine: "*", python-version: "2.7"}
diff --git a/test/__init__.py b/test/__init__.py
index 772b872d8..57873af11 100644
--- a/test/__init__.py
+++ b/test/__init__.py
@@ -185,7 +185,7 @@ class ClientContext(object):
         if sys.platform.startswith('java'):
             timeout_ms = 10000
         else:
-            timeout_ms = 1000
+            timeout_ms = 5000
         if COMPRESSORS:
             kwargs["compressors"] = COMPRESSORS
         client = pymongo.MongoClient(