diff --git a/test/functional/tools/samples_tool_conf.xml b/test/functional/tools/samples_tool_conf.xml
index 8eeb4238f5e1..d5c61cd59d13 100644
--- a/test/functional/tools/samples_tool_conf.xml
+++ b/test/functional/tools/samples_tool_conf.xml
@@ -214,6 +214,8 @@
   <tool file="interactivetool_simple.xml" />
   <tool file="interactivetool_two_entry_points.xml" />
   <tool file="converter_target_datatype.xml" />
+  
+  <tool file="tool_deleting_output.xml" />
 
   <!-- Tools interesting only for building up test workflows. -->
 
diff --git a/test/functional/tools/tool_deleting_output.xml b/test/functional/tools/tool_deleting_output.xml
new file mode 100644
index 000000000000..500bb33c2686
--- /dev/null
+++ b/test/functional/tools/tool_deleting_output.xml
@@ -0,0 +1,29 @@
+<tool id="tool_deleting_output" name="tool_deleting_output" version="0.1.0" license="AFL-3.0" profile="21.09">
+    <command><![CDATA[
+rm '$out_file1' &&
+exit $exit_code
+    ]]></command>
+    <inputs>
+        <param name="exit_code" type="integer" value="0"/>
+    </inputs>
+    <outputs>
+        <data name="out_file1" format="txt" />
+    </outputs>
+    <tests>
+        <test>
+            <param name="exit_code" value="0"/>
+            <output name="out_file1">
+                <assert_contents>
+                    <has_size value="0"/>
+                </assert_contents>
+            </output>
+        </test>
+        <test expect_exit_code="1" expect_failure="true">
+            <param name="exit_code" value="1"/>
+        </test>
+    </tests>
+    <help><![CDATA[
+        This tool tests what happens if the underlying program removes the output data set.
+        With outputs_to_working_directory this provoked https://github.com/galaxyproject/galaxy/issues/14206
+    ]]></help>
+</tool>
diff --git a/test/integration/test_job_outputs_to_working_directory.py b/test/integration/test_job_outputs_to_working_directory.py
index 7e9cbeb063e0..007b65ce73e3 100644
--- a/test/integration/test_job_outputs_to_working_directory.py
+++ b/test/integration/test_job_outputs_to_working_directory.py
@@ -15,4 +15,4 @@ def handle_galaxy_config_kwds(cls, config):
 
 instance = integration_util.integration_module_instance(JobOutputsToWorkingDirectoryIntegrationInstance)
 
-test_tools = integration_util.integration_tool_runner(["output_format", "output_empty_work_dir", "collection_creates_pair_from_work_dir"])
+test_tools = integration_util.integration_tool_runner(["output_format", "output_empty_work_dir", "collection_creates_pair_from_work_dir", "tool_deleting_output"])