diff --git a/newrelic/packages/urllib3/contrib/_securetransport/bindings.py b/newrelic/packages/urllib3/contrib/_securetransport/bindings.py
index 11524d400..264d564db 100644
--- a/newrelic/packages/urllib3/contrib/_securetransport/bindings.py
+++ b/newrelic/packages/urllib3/contrib/_securetransport/bindings.py
@@ -48,7 +48,7 @@
 )
 from ctypes.util import find_library
 
-from urllib3.packages.six import raise_from
+from ...packages.six import raise_from
 
 if platform.system() != "Darwin":
     raise ImportError("Only macOS is supported")
diff --git a/newrelic/packages/urllib3/util/ssltransport.py b/newrelic/packages/urllib3/util/ssltransport.py
index c2186bced..4a7105d17 100644
--- a/newrelic/packages/urllib3/util/ssltransport.py
+++ b/newrelic/packages/urllib3/util/ssltransport.py
@@ -2,8 +2,8 @@
 import socket
 import ssl
 
-from urllib3.exceptions import ProxySchemeUnsupported
-from urllib3.packages import six
+from ..exceptions import ProxySchemeUnsupported
+from ..packages import six
 
 SSL_BLOCKSIZE = 16384
 
diff --git a/tests/adapter_gevent/test_patch_thread.py b/tests/adapter_gevent/test_patching.py
similarity index 60%
rename from tests/adapter_gevent/test_patch_thread.py
rename to tests/adapter_gevent/test_patching.py
index 41fdab2cc..4451d9823 100644
--- a/tests/adapter_gevent/test_patch_thread.py
+++ b/tests/adapter_gevent/test_patching.py
@@ -12,8 +12,22 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 
-import gevent.monkey
-
 
 def test_patch_thread():
+    import gevent.monkey
+
     gevent.monkey.patch_thread()
+
+
+def test_patch_ssl_recursion():
+    import gevent.monkey
+
+    gevent.monkey.patch_all()
+
+    # Delay imports and test creation of contexts from both bundled and installed urllib3
+    import urllib3.util.ssl_
+
+    import newrelic.packages.urllib3.util.ssl_
+
+    context1 = urllib3.util.ssl_.create_urllib3_context()
+    context2 = newrelic.packages.urllib3.util.ssl_.create_urllib3_context()
diff --git a/tox.ini b/tox.ini
index 60ac0ee35..53a41f19d 100644
--- a/tox.ini
+++ b/tox.ini
@@ -157,6 +157,7 @@ deps =
     adapter_cheroot: cheroot
     adapter_gevent: WSGIProxy2
     adapter_gevent: gevent
+    adapter_gevent: urllib3
     adapter_gunicorn-aiohttp1: aiohttp<2.0
     adapter_gunicorn-aiohttp3: aiohttp<4.0
     adapter_gunicorn-gunicorn19: gunicorn<20