diff --git a/rosbag2_transport/package.xml b/rosbag2_transport/package.xml
index 039dc587e..1fc5258a4 100644
--- a/rosbag2_transport/package.xml
+++ b/rosbag2_transport/package.xml
@@ -15,6 +15,7 @@
   <depend>rosbag2_compression</depend>
   <depend>rosbag2_cpp</depend>
   <depend>rmw</depend>
+  <depend>rpyutils</depend>
   <depend>shared_queues_vendor</depend>
   <depend>yaml_cpp_vendor</depend>
 
diff --git a/rosbag2_transport/rosbag2_transport/__init__.py b/rosbag2_transport/rosbag2_transport/__init__.py
index f8087f749..fd206f59a 100644
--- a/rosbag2_transport/rosbag2_transport/__init__.py
+++ b/rosbag2_transport/rosbag2_transport/__init__.py
@@ -15,10 +15,16 @@
 import importlib
 import os
 
+from rpyutils import add_dll_directories_from_env
+
 
 def _import(name):
     try:
-        return importlib.import_module(name, package='rosbag2_transport')
+        # 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'):
+            return importlib.import_module(name, package='rosbag2_transport')
     except ImportError as e:
         if e.path is not None and os.path.isfile(e.path):
             e.msg += \