diff --git a/Ghidra/Framework/Docking/src/main/java/docking/options/editor/IconPropertyEditor.java b/Ghidra/Framework/Docking/src/main/java/docking/options/editor/IconPropertyEditor.java
index 9ccfd99661..95c07b84ec 100644
--- a/Ghidra/Framework/Docking/src/main/java/docking/options/editor/IconPropertyEditor.java
+++ b/Ghidra/Framework/Docking/src/main/java/docking/options/editor/IconPropertyEditor.java
@@ -176,7 +176,7 @@ public class IconPropertyEditor extends PropertyEditorSupport {
 			chooser.setApproveButtonToolTipText("Import Icon");
 			chooser.setFileSelectionMode(GhidraFileChooserMode.FILES_ONLY);
 			chooser.setSelectedFileFilter(
-				ExtensionFileFilter.forExtensions("Icon Files", ".png", "gif"));
+				ExtensionFileFilter.forExtensions("Icon Files", "png", "gif"));
 			String lastDir = Preferences.getProperty(LAST_ICON_DIR_PREFERENCE_KEY);
 			if (lastDir != null) {
 				chooser.setCurrentDirectory(new File(lastDir));
diff --git a/Ghidra/Framework/Docking/src/test.slow/java/docking/widgets/filechooser/GhidraFileChooserTest.java b/Ghidra/Framework/Docking/src/test.slow/java/docking/widgets/filechooser/GhidraFileChooserTest.java
index bc835d9fa3..62bbf7186f 100644
--- a/Ghidra/Framework/Docking/src/test.slow/java/docking/widgets/filechooser/GhidraFileChooserTest.java
+++ b/Ghidra/Framework/Docking/src/test.slow/java/docking/widgets/filechooser/GhidraFileChooserTest.java
@@ -1541,7 +1541,8 @@ public class GhidraFileChooserTest extends AbstractDockingTest {
 					file1.getName().toLowerCase().endsWith("exe"));
 		}
 
-		runSwing(() -> chooser.setFileFilter(new ExtensionFileFilter("exe", "dll")));
+		runSwing(() -> chooser.setFileFilter(
+			new ExtensionFileFilter(new String[] { "exe", "dll" }, "Executables")));
 		setDir(file);
 
 		waitForNewDirLoad(file);
diff --git a/Ghidra/Framework/Gui/src/main/java/ghidra/util/filechooser/ExtensionFileFilter.java b/Ghidra/Framework/Gui/src/main/java/ghidra/util/filechooser/ExtensionFileFilter.java
index fe026f04c1..d9aa279f10 100644
--- a/Ghidra/Framework/Gui/src/main/java/ghidra/util/filechooser/ExtensionFileFilter.java
+++ b/Ghidra/Framework/Gui/src/main/java/ghidra/util/filechooser/ExtensionFileFilter.java
@@ -4,9 +4,9 @@
  * Licensed under the Apache License, Version 2.0 (the "License");
  * you may not use this file except in compliance with the License.
  * You may obtain a copy of the License at
- * 
+ *
  *      http://www.apache.org/licenses/LICENSE-2.0
- * 
+ *
  * Unless required by applicable law or agreed to in writing, software
  * distributed under the License is distributed on an "AS IS" BASIS,
  * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
@@ -15,11 +15,13 @@
  */
 package ghidra.util.filechooser;
 
+import java.io.File;
+import java.io.FileFilter;
 import java.util.*;
 import java.util.stream.Collectors;
 
-import java.io.File;
-import java.io.FileFilter;
+import ghidra.util.Msg;
+import utilities.util.reflection.ReflectionUtilities;
 
 /**
  * A convenience implementation of FileFilter that filters out
@@ -73,11 +75,21 @@ public class ExtensionFileFilter implements GhidraFileFilter {
 	public ExtensionFileFilter(String[] filters, String description) {
 		this.extensions = Arrays.asList(filters)
 				.stream()
-				.map(String::toLowerCase)
+				.map(ExtensionFileFilter::clean)
 				.collect(Collectors.toList());
 		this.description = description;
 	}
 
+	private static String clean(String ext) {
+		String lc = ext.toLowerCase();
+		if (lc.startsWith(".")) {
+			Msg.error(ExtensionFileFilter.class, "Extensions cannot start with '.': " + ext,
+				ReflectionUtilities.createJavaFilteredThrowable());
+			return lc.substring(1);
+		}
+		return lc;
+	}
+
 	/**
 	 * Return true if this file should be shown in the directory pane,
 	 * false if it shouldn't.
@@ -97,19 +109,23 @@ public class ExtensionFileFilter implements GhidraFileFilter {
 		if (extensions.isEmpty()) {
 			return true;
 		}
+
 		String filename = f.getName().toLowerCase();
 		if (filename.startsWith(".")) {
-			return false;
+			return false; // assuming we don't want to allow hidden files?
 		}
-		int fnLen = filename.length();
+
+		int n = filename.length();
 		for (String ext : extensions) {
-			int extLen = ext.length();
-			int extStart = fnLen - extLen;
-			if (extStart > 0 && filename.substring(extStart).equals(ext) &&
-				filename.charAt(extStart - 1) == '.') {
+			if (ext.length() >= n) {
+				continue; // >= since we will add the '.'
+			}
+
+			if (filename.endsWith('.' + ext)) {
 				return true;
 			}
 		}
+
 		return false;
 	}