diff --git a/src/cli/CMakeLists.txt b/src/cli/CMakeLists.txt
index 179c35f7a0..a264c4711f 100644
--- a/src/cli/CMakeLists.txt
+++ b/src/cli/CMakeLists.txt
@@ -270,6 +270,63 @@ if(BUILD_TESTING)
     PASS_REGULAR_EXPRESSION "HI FROM ERB PYTHON PLUGIN[\r\n\t ]*HI FROM JINJA PYTHON PLUGIN"
   )
 
+  # ======================== Workflows should fail ========================
+  add_test(NAME OpenStudioCLI.Run_Validate.MissingAMeasure
+    COMMAND $<TARGET_FILE:openstudio> run --show-stdout -w missing_a_measure.osw
+    WORKING_DIRECTORY "${PROJECT_BINARY_DIR}/resources/workflow/invalid_measures/"
+  )
+  set_tests_properties(OpenStudioCLI.Run_Validate.MissingAMeasure PROPERTIES
+    WILL_FAIL TRUE
+    RESOURCE_LOCK "invalid_measures"
+  )
+
+  add_test(NAME OpenStudioCLI.Run_Validate.UnloadableMeasure
+    COMMAND $<TARGET_FILE:openstudio> run --show-stdout -w unloadable_measure.osw
+    WORKING_DIRECTORY "${PROJECT_BINARY_DIR}/resources/workflow/invalid_measures/"
+  )
+  set_tests_properties(OpenStudioCLI.Run_Validate.UnloadableMeasure PROPERTIES
+    WILL_FAIL TRUE
+    RESOURCE_LOCK "invalid_measures"
+  )
+
+  add_test(NAME OpenStudioCLI.Run_Validate.WrongMeasureTypeOrder
+    COMMAND $<TARGET_FILE:openstudio> run --show-stdout -w wrong_measure_type_order.osw
+    WORKING_DIRECTORY "${PROJECT_BINARY_DIR}/resources/workflow/invalid_measures/"
+  )
+  set_tests_properties(OpenStudioCLI.Run_Validate.WrongMeasureTypeOrder PROPERTIES
+    WILL_FAIL TRUE
+    RESOURCE_LOCK "invalid_measures"
+  )
+
+  # Classic
+  add_test(NAME OpenStudioCLI.Classic.Run_Validate.MissingAMeasure
+    COMMAND $<TARGET_FILE:openstudio> classic run --show-stdout -w missing_a_measure.osw
+    WORKING_DIRECTORY "${PROJECT_BINARY_DIR}/resources/workflow/invalid_measures/"
+  )
+  set_tests_properties(OpenStudioCLI.Classic.Run_Validate.MissingAMeasure PROPERTIES
+    WILL_FAIL TRUE
+    RESOURCE_LOCK "invalid_measures"
+  )
+
+  add_test(NAME OpenStudioCLI.Classic.Run_Validate.UnloadableMeasure
+    COMMAND $<TARGET_FILE:openstudio> run --show-stdout -w unloadable_measure.osw
+    WORKING_DIRECTORY "${PROJECT_BINARY_DIR}/resources/workflow/invalid_measures/"
+  )
+  set_tests_properties(OpenStudioCLI.Classic.Run_Validate.UnloadableMeasure PROPERTIES
+    WILL_FAIL TRUE
+    RESOURCE_LOCK "invalid_measures"
+  )
+
+  add_test(NAME OpenStudioCLI.Classic.Run_Validate.WrongMeasureTypeOrder
+    COMMAND $<TARGET_FILE:openstudio> run --show-stdout -w wrong_measure_type_order.osw
+    WORKING_DIRECTORY "${PROJECT_BINARY_DIR}/resources/workflow/invalid_measures/"
+  )
+  set_tests_properties(OpenStudioCLI.Classic.Run_Validate.WrongMeasureTypeOrder PROPERTIES
+    WILL_FAIL TRUE
+    RESOURCE_LOCK "invalid_measures"
+  )
+  # ====================== End Workflows should fail ======================
+
   if (Pytest_AVAILABLE)
     add_test(NAME OpenStudioCLI.test_loglevel
       COMMAND ${Python_EXECUTABLE} -m pytest --verbose ${Pytest_XDIST_OPTS} --os-cli-path $<TARGET_FILE:openstudio> "${CMAKE_CURRENT_SOURCE_DIR}/test/test_loglevel.py"