diff --git a/src/org/labkey/test/tests/assay/AssayTransformMissingParentDirTest.java b/src/org/labkey/test/tests/assay/AssayTransformMissingParentDirTest.java
index d0979ba985..5cd0267904 100644
--- a/src/org/labkey/test/tests/assay/AssayTransformMissingParentDirTest.java
+++ b/src/org/labkey/test/tests/assay/AssayTransformMissingParentDirTest.java
@@ -1,9 +1,11 @@
 package org.labkey.test.tests.assay;
 
 import org.apache.commons.io.FileUtils;
+import org.apache.commons.lang3.SystemUtils;
 import org.junit.Test;
 import org.junit.experimental.categories.Category;
 import org.labkey.api.util.FileUtil;
+import org.labkey.api.util.StringUtilsLabKey;
 import org.labkey.test.Locator;
 import org.labkey.test.TestFileUtils;
 import org.labkey.test.categories.Assays;
@@ -13,12 +15,14 @@
 import org.labkey.test.pages.assay.AssayImportPage;
 import org.labkey.test.pages.assay.AssayRunsPage;
 import org.labkey.test.params.assay.GeneralAssayDesign;
+import org.labkey.test.util.search.SearchAdminAPIHelper;
 
 import java.io.File;
 import java.io.IOException;
 import java.nio.file.AccessDeniedException;
 import java.nio.file.Files;
 import java.nio.file.Path;
+import java.util.stream.Stream;
 
 /**
  * Issue 54156: Regression test to ensure a reasonable error message is shown when an assay design references
@@ -48,11 +52,19 @@ public void testMissingParentDirectoryRegression() throws Exception
         assayDesignerPage.addTransformScript(transformFile);
         assayDesignerPage.clickSave();
 
-        // Now delete the parent dir to ensure we handle it reasonably. On Windows something locks the directory, maybe
-        // an external process. If that happens sleep for a second and try again.
+        // Now delete the parent dir to ensure we handle it reasonably.
+        // Sometimes on Windows the directory could be locked, maybe by an external process, or the child directory is
+        // readonly. Use a retry mechanism to set the writeable flag and then try to delete the parent directory.
         for (int attempt = 1; attempt <= 10; attempt++) {
             try
             {
+                parentDir.toFile().setWritable(true, false);
+
+                // Wrap in a try to close the stream.
+                try (Stream<Path> files = Files.walk(parentDir)) {
+                    files.forEach(p -> p.toFile().setWritable(true, false));
+                }
+
                 FileUtils.deleteDirectory(parentDir.toFile());
                 log(String.format("Deletion of directory %s was successful.", parentDir));
                 break;
@@ -67,7 +79,25 @@ public void testMissingParentDirectoryRegression() throws Exception
             catch (IOException ioException) {
                 log(String.format("IOException trying to delete directory %s. Error: %s. Waiting 10s and retrying. Attempt %d of 10.",
                         parentDir, ioException.getMessage(), attempt));
-                if (attempt == 10) throw ioException;
+                if (attempt == 10)
+                {
+                    log("Dump the heap.");
+                    dumpHeap();
+
+                    if (SystemUtils.IS_OS_WINDOWS) {
+                        try {
+                            log("Lock diagnostic...");
+                            ProcessBuilder pb = new ProcessBuilder("tasklist");
+                            pb.redirectErrorStream(true);
+                            Process p = pb.start();
+                            String output = new String(p.getInputStream().readAllBytes(), StringUtilsLabKey.DEFAULT_CHARSET);
+                            log("Running processes:\n" + output);
+                        } catch (IOException diagnosticException) {
+                            log("Failed to run lock diagnostic: " + diagnosticException.getMessage());
+                        }
+                    }
+                    throw ioException;
+                }
                 sleep(10_000);
             }
         }