diff --git a/Ghidra/Framework/Generic/src/main/java/ghidra/util/extensions/ExtensionDetails.java b/Ghidra/Framework/Generic/src/main/java/ghidra/util/extensions/ExtensionDetails.java
index 8f1ca6e9ce..703aad255d 100644
--- a/Ghidra/Framework/Generic/src/main/java/ghidra/util/extensions/ExtensionDetails.java
+++ b/Ghidra/Framework/Generic/src/main/java/ghidra/util/extensions/ExtensionDetails.java
@@ -293,10 +293,8 @@ public class ExtensionDetails implements Comparable<ExtensionDetails> {
 		// The remaining dirs are of the form: 
 		// 		<repo>/Ghidra/Extensions
 		//      <install dir>/Ghidra/Extensions
-		return extDirs.stream()
-				.skip(1)
-				.anyMatch(
-					dir -> FileUtilities.isPathContainedWithin(dir.getFile(false), installDir));
+		List<ResourceFile> remainingDirs = extDirs.subList(1, extDirs.size());
+		return FileUtilities.startsWith(remainingDirs, installDir.getAbsolutePath());
 	}
 
 	/**
diff --git a/Ghidra/Framework/Project/src/main/java/ghidra/framework/plugintool/util/PluginDescription.java b/Ghidra/Framework/Project/src/main/java/ghidra/framework/plugintool/util/PluginDescription.java
index db63e1d0f0..3962a16f75 100644
--- a/Ghidra/Framework/Project/src/main/java/ghidra/framework/plugintool/util/PluginDescription.java
+++ b/Ghidra/Framework/Project/src/main/java/ghidra/framework/plugintool/util/PluginDescription.java
@@ -168,10 +168,9 @@ public class PluginDescription implements Comparable<PluginDescription> {
 	 */
 	public boolean isInExtension() {
 		String myPath = getSourceLocation();
-		ResourceFile myLocation = new ResourceFile(myPath);
 		ApplicationLayout layout = Application.getApplicationLayout();
 		List<ResourceFile> extDirs = layout.getExtensionInstallationDirs();
-		return FileUtilities.isPathContainedWithin(extDirs, myLocation);
+		return FileUtilities.startsWith(extDirs, myPath);
 	}
 
 	/**
diff --git a/Ghidra/Framework/Utility/src/main/java/generic/jar/ResourceFile.java b/Ghidra/Framework/Utility/src/main/java/generic/jar/ResourceFile.java
index 5ccf6fc3f2..fd56ee934e 100644
--- a/Ghidra/Framework/Utility/src/main/java/generic/jar/ResourceFile.java
+++ b/Ghidra/Framework/Utility/src/main/java/generic/jar/ResourceFile.java
@@ -20,8 +20,6 @@ import java.net.*;
 import java.util.HashMap;
 import java.util.Map;
 
-import utilities.util.FileUtilities;
-
 /**
  * Class for representing file object regardless of whether they are actual files in the file system or
  * or files stored inside of a jar file.  This class provides most all the same capabilities as the
@@ -339,13 +337,4 @@ public class ResourceFile implements Comparable<ResourceFile> {
 	public URI toURI() {
 		return resource.toURI();
 	}
-
-	/**
-	 * Returns true if this file's path contains the entire path of the given file.
-	 * @param otherFile the other file to check
-	 * @return true if this file's path contains the entire path of the given file.
-	 */
-	public boolean containsPath(ResourceFile otherFile) {
-		return FileUtilities.isPathContainedWithin(getFile(false), otherFile.getFile(false));
-	}
 }
diff --git a/Ghidra/Framework/Utility/src/main/java/ghidra/GhidraApplicationLayout.java b/Ghidra/Framework/Utility/src/main/java/ghidra/GhidraApplicationLayout.java
index 619213ae65..4b1cfeabff 100644
--- a/Ghidra/Framework/Utility/src/main/java/ghidra/GhidraApplicationLayout.java
+++ b/Ghidra/Framework/Utility/src/main/java/ghidra/GhidraApplicationLayout.java
@@ -156,7 +156,7 @@ public class GhidraApplicationLayout extends ApplicationLayout {
 
 			FileUtilities.forEachFile(extensionInstallDir, extensionDir -> {
 				// Skip extensions in an application root directory... already found those.
-				if (FileUtilities.isPathContainedWithin(applicationRootDirs, extensionDir)) {
+				if (FileUtilities.startsWith(applicationRootDirs, extensionDir.getAbsolutePath())) {
 					return;
 				}
 
diff --git a/Ghidra/Framework/Utility/src/main/java/ghidra/GhidraLauncher.java b/Ghidra/Framework/Utility/src/main/java/ghidra/GhidraLauncher.java
index d3032871dc..d5f5c9ef83 100644
--- a/Ghidra/Framework/Utility/src/main/java/ghidra/GhidraLauncher.java
+++ b/Ghidra/Framework/Utility/src/main/java/ghidra/GhidraLauncher.java
@@ -286,7 +286,7 @@ public class GhidraLauncher {
 		for (GModule module : modules.values()) {
 
 			ResourceFile moduleDir = module.getModuleRoot();
-			if (!FileUtilities.isPathContainedWithin(extensionInstallationDirs, moduleDir)) {
+			if (!FileUtilities.startsWith(extensionInstallationDirs, moduleDir.getAbsolutePath())) {
 				continue; // not an extension
 			}
 
diff --git a/Ghidra/Framework/Utility/src/main/java/utilities/util/FileUtilities.java b/Ghidra/Framework/Utility/src/main/java/utilities/util/FileUtilities.java
index 43a513a0f8..96e483b8dc 100644
--- a/Ghidra/Framework/Utility/src/main/java/utilities/util/FileUtilities.java
+++ b/Ghidra/Framework/Utility/src/main/java/utilities/util/FileUtilities.java
@@ -842,12 +842,50 @@ public final class FileUtilities {
 	}
 
 	/**
-	 * Returns true if the given <code>potentialParentFile</code> is the parent path of
-	 * the given <code>otherFile</code>, or if the two file paths point to the same path.
+	 * Tests if {@code otherPath} starts with {@code potentialParentPath}. The paths are
+	 * {@link Path#normalize() normalized} before comparing.
+	 *
+	 * @param potentialParentPath The path that may be the parent
+	 * @param otherPath The path that may be the child
+	 * @return true if the normalized {@code otherPath} starts with the normalized 
+	 *   {@code potentialParentPath} and the paths are {@link Paths#get valid}; otherwise false
+	 */
+	public static boolean startsWith(String potentialParentPath, String otherPath) {
+		try {
+			return Paths.get(otherPath)
+					.normalize()
+					.startsWith(Paths.get(potentialParentPath).normalize());
+		}
+		catch (InvalidPathException e) {
+			return false;
+		}
+	}
+
+	/**
+	 * Tests if {@code otherPath} starts with any of the given {@code potentialParents}. The paths 
+	 * are {@link Path#normalize() normalized} before comparing.
+	 *
+	 * @param potentialParents The paths that may be the parent
+	 * @param otherPath The path that may be the child
+	 * @return boolean true if the normalized {@code otherPath} starts with any of the given
+	 *   normalized {@code potentialParents}s and the paths are {@link Paths#get valid}; otherwise
+	 *   false
+	 */
+	public static boolean startsWith(Collection<ResourceFile> potentialParents, String otherPath) {
+		return potentialParents.stream().anyMatch(p -> startsWith(p.getAbsolutePath(), otherPath));
+	}
+
+	/**
+	 * Returns true if the given {@code potentialParentFile} is the parent path of
+	 * the given {@code otherFile}, or if the two file paths point to the same path.
+	 * <p>
+	 * NOTE: Both files are converted to their {@link File#getCanonicalPath() canonical form} prior
+	 * to comparing their paths, which may have performance implications, particularly on Windows.
 	 *
 	 * @param potentialParentFile The file that may be the parent
 	 * @param otherFile The file that may be the child
-	 * @return boolean true if otherFile's path is within potentialParentFile's path
+	 * @return boolean true if {@code otherFile}'s canonical path is within 
+	 *   {@code potentialParentFile}'s canonical path
 	 */
 	public static boolean isPathContainedWithin(File potentialParentFile, File otherFile) {
 		try {
@@ -869,17 +907,21 @@ public final class FileUtilities {
 	}
 
 	/**
-	 * Returns true if any of the given <code>potentialParents</code> is the parent path of or has
-	 * the same path as the given <code>otherFile</code>.
+	 * Returns true if any of the given {@code potentialParents} is the parent path of or has
+	 * the same path as the given {@code otherFile}.
+	 * <p>
+	 * NOTE: All files are converted to their {@link File#getCanonicalPath() canonical form} prior
+	 * to comparing their paths, which may have performance implications, particularly on Windows.
 	 *
 	 * @param potentialParents The files that may be the parent
 	 * @param otherFile The file that may be the child
-	 * @return boolean true if otherFile's path is within any of the potentialParents' paths 
+	 * @return boolean true if {@code otherFile}'s canonical path is within any of the 
+	 *   {@code potentialParents}' canonical paths 
 	 */
 	public static boolean isPathContainedWithin(Collection<ResourceFile> potentialParents,
 			ResourceFile otherFile) {
-
-		return potentialParents.stream().anyMatch(parent -> parent.containsPath(otherFile));
+		File f = otherFile.getFile(false);
+		return potentialParents.stream().anyMatch(p -> isPathContainedWithin(p.getFile(false), f));
 	}
 
 	/**
diff --git a/Ghidra/Framework/Utility/src/main/java/utility/module/ModuleUtilities.java b/Ghidra/Framework/Utility/src/main/java/utility/module/ModuleUtilities.java
index 261175ea39..8b28d88da9 100644
--- a/Ghidra/Framework/Utility/src/main/java/utility/module/ModuleUtilities.java
+++ b/Ghidra/Framework/Utility/src/main/java/utility/module/ModuleUtilities.java
@@ -398,11 +398,11 @@ public class ModuleUtilities {
 	 *   directory
 	 */
 	public static boolean isExternalModule(GModule module, ApplicationLayout layout) {
-		File moduleRootDir = module.getModuleRoot().getFile(false);
+		String moduleRootPath = module.getModuleRoot().getFile(false).getAbsolutePath();
 		return !layout.getApplicationRootDirs()
 				.stream()
-				.map(dir -> dir.getParentFile().getFile(false))
-				.anyMatch(dir -> FileUtilities.isPathContainedWithin(dir, moduleRootDir));
+				.map(rootDir -> rootDir.getParentFile().getFile(false).getAbsolutePath())
+				.anyMatch(appPath -> FileUtilities.startsWith(appPath, moduleRootPath));
 	}
 
 	/**