diff --git a/tf2_py/package.xml b/tf2_py/package.xml
index 4e6e98ff0b..e864096299 100644
--- a/tf2_py/package.xml
+++ b/tf2_py/package.xml
@@ -21,6 +21,7 @@
   <exec_depend>builtin_interfaces</exec_depend>
   <exec_depend>geometry_msgs</exec_depend>
   <exec_depend>rclpy</exec_depend>
+  <exec_depend>rpyutils</exec_depend>
 
   <test_depend>ament_lint_auto</test_depend>
   <test_depend>ament_cmake_pytest</test_depend>
diff --git a/tf2_py/test/test_buffer_core.py b/tf2_py/test/test_buffer_core.py
index 98d6ae06e7..45721dbb7c 100644
--- a/tf2_py/test/test_buffer_core.py
+++ b/tf2_py/test/test_buffer_core.py
@@ -32,9 +32,14 @@
 
 from geometry_msgs.msg import TransformStamped
 import rclpy
-
-from test_tf2_py._tf2_py import BufferCore
-from test_tf2_py._tf2_py import LookupException
+from rpyutils import add_dll_directories_from_env
+
+# Since Python 3.8, on Windows we should ensure DLL directories are explicitly added
+# to the search path.
+# See https://docs.python.org/3/whatsnew/3.8.html#bpo-36085-whatsnew
+with add_dll_directories_from_env('PATH'):
+    from test_tf2_py._tf2_py import BufferCore
+    from test_tf2_py._tf2_py import LookupException
 
 
 def build_transform(target_frame, source_frame, stamp):
diff --git a/tf2_py/tf2_py/__init__.py b/tf2_py/tf2_py/__init__.py
index b9b975159b..dea674a41f 100644
--- a/tf2_py/tf2_py/__init__.py
+++ b/tf2_py/tf2_py/__init__.py
@@ -33,4 +33,10 @@
 #
 # Author: Eitan Marder-Eppstein
 # **********************************************************
-from tf2_py._tf2_py import *  # noqa
+from rpyutils import add_dll_directories_from_env
+
+# Since Python 3.8, on Windows we should ensure DLL directories are explicitly added
+# to the search path.
+# See https://docs.python.org/3/whatsnew/3.8.html#bpo-36085-whatsnew
+with add_dll_directories_from_env('PATH'):
+    from tf2_py._tf2_py import *  # noqa