diff --git a/Modules/Bridge/VtkGlue/itk-module-init.cmake b/Modules/Bridge/VtkGlue/itk-module-init.cmake
index 550f1dce272..acd973ccefb 100644
--- a/Modules/Bridge/VtkGlue/itk-module-init.cmake
+++ b/Modules/Bridge/VtkGlue/itk-module-init.cmake
@@ -54,4 +54,31 @@ if(NOT VTK_RENDERING_BACKEND STREQUAL "None")
   )
 endif()
 
+if(ITK_WRAP_PYTHON)
+  if(NOT VTK_WRAP_PYTHON)
+    message(
+      FATAL_ERROR
+      "ITK_WRAP_PYTHON is ON and Module_ITKVtkGlue is enabled, but the VTK at\n"
+      "  ${VTK_DIR}\n"
+      "was built with VTK_WRAP_PYTHON=OFF. Rebuild VTK with VTK_WRAP_PYTHON=ON,\n"
+      "or set Module_ITKVtkGlue=OFF."
+    )
+  endif()
+  # VTK exports no shared/static variable, so ask an imported target directly.
+  if(TARGET VTK::CommonCore)
+    get_target_property(_vtk_common_core_type VTK::CommonCore TYPE)
+    if(_vtk_common_core_type STREQUAL "STATIC_LIBRARY")
+      message(
+        FATAL_ERROR
+        "ITK_WRAP_PYTHON is ON and Module_ITKVtkGlue is enabled, but the VTK at\n"
+        "  ${VTK_DIR}\n"
+        "is a static build. Its Python wrapping collapses into a single\n"
+        "_vtkmodules_static module that ITK's wrapping cannot import. Rebuild VTK\n"
+        "with BUILD_SHARED_LIBS=ON, or set Module_ITKVtkGlue=OFF."
+      )
+    endif()
+    unset(_vtk_common_core_type)
+  endif()
+endif()
+
 set(ITKVtkGlue_VTK_LIBRARIES ${_required_vtk_libraries})
diff --git a/Modules/Bridge/VtkGlue/test/CMakeLists.txt b/Modules/Bridge/VtkGlue/test/CMakeLists.txt
index 8310ce7ff66..8856e2b5c15 100644
--- a/Modules/Bridge/VtkGlue/test/CMakeLists.txt
+++ b/Modules/Bridge/VtkGlue/test/CMakeLists.txt
@@ -110,3 +110,19 @@ if(NOT VTK_RENDERING_BACKEND STREQUAL "None")
         REQUIRES_DISPLAY
   )
 endif()
+
+# Windows has no RPATH, so VTK's DLLs must be on PATH at test time.
+if(WIN32 AND TARGET VTK::CommonCore)
+  get_property(_vtkglue_tests DIRECTORY PROPERTY TESTS)
+  if(_vtkglue_tests)
+    set_property(
+      TEST
+        ${_vtkglue_tests}
+      APPEND
+      PROPERTY
+        ENVIRONMENT_MODIFICATION
+          "PATH=path_list_prepend:$<TARGET_FILE_DIR:VTK::CommonCore>"
+    )
+  endif()
+  unset(_vtkglue_tests)
+endif()