diff --git a/Ghidra/Framework/Docking/src/main/java/docking/widgets/filechooser/GhidraFileChooser.java b/Ghidra/Framework/Docking/src/main/java/docking/widgets/filechooser/GhidraFileChooser.java
index f4220d8d51..ecd77cd33b 100644
--- a/Ghidra/Framework/Docking/src/main/java/docking/widgets/filechooser/GhidraFileChooser.java
+++ b/Ghidra/Framework/Docking/src/main/java/docking/widgets/filechooser/GhidraFileChooser.java
@@ -1702,8 +1702,13 @@ public class GhidraFileChooser extends DialogComponentProvider
 	void userSelectedFiles(List<File> files) {
 		selectedFiles.setFiles(files);
 
-		// Update the display when we are in single selection mode
-		if (!isMultiSelectionEnabled()) {
+		// Update the display to...
+		if (isMultiSelectionEnabled() && selectedFiles.size() > 1) {
+			// clear the filename text field when multiple files are selected
+			filenameTextField.setText("");
+		}
+		else {
+			// set the filename text on single selection, regardless of mode
 			updateTextFieldForFile(selectedFiles.getFile());
 		}
 	}
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 05fd71f780..928490e2a5 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
@@ -20,6 +20,7 @@ package docking.widgets.filechooser;
 
 import static docking.widgets.filechooser.GhidraFileChooserMode.*;
 import static org.hamcrest.Matchers.*;
+import static org.hamcrest.text.IsEmptyString.isEmptyOrNullString;
 import static org.junit.Assert.*;
 
 import java.awt.*;
@@ -1875,6 +1876,57 @@ public class GhidraFileChooserTest extends AbstractDockingTest {
 		assertChosen(results, CollectionUtils.asIterable(files.files, files.dirs)); // dirs are dropped
 	}
 
+	@Test
+	public void testSelectingFileUpdatesTheTextField_SingleSelection() throws Exception {
+
+		TestFiles files = createMixedDirectory();
+		showSingleSelectionChooser(files.parent, GhidraFileChooserMode.FILES_ONLY);
+
+		File file = files.files.get(0);
+		selectFiles(file);
+
+		waitForChooser();
+		String filenameFieldText = getFilenameFieldText();
+		assertEquals("Filename text field not updated upon file selection", file.getName(),
+			filenameFieldText);
+	}
+
+	@Test
+	public void testSelectingFileUpdatesTheTextField_MultiSelection() throws Exception {
+
+		TestFiles files = createMixedDirectory();
+		showMultiSelectionChooser(files.parent, GhidraFileChooserMode.FILES_ONLY);
+
+		File file = files.files.get(0);
+		selectFiles(file);
+
+		//		
+		// A single file selection will set the text field text
+		// 
+		waitForChooser();
+		String filenameFieldText = getFilenameFieldText();
+		assertEquals("Filename text field not updated upon file selection", file.getName(),
+			filenameFieldText);
+
+		//
+		// A multi-selection will clear the text field text
+		// 
+		selectFiles(files.files);
+		waitForChooser();
+		filenameFieldText = getFilenameFieldText();
+		assertThat("Filename text field not cleared upon multi-file selection", filenameFieldText,
+			isEmptyOrNullString());
+
+		//
+		// Clear the multi-selection; a single file selection will set the text field text
+		// 
+		selectFiles(file);
+		waitForChooser();
+		filenameFieldText = getFilenameFieldText();
+		assertEquals("Filename text field not updated upon file selection", file.getName(),
+			filenameFieldText);
+	}
+
 //==================================================================================================
 // Private Methods
 //==================================================================================================
@@ -1976,8 +2028,11 @@ public class GhidraFileChooserTest extends AbstractDockingTest {
 		}
 	}
 
-	private void selectFiles(Iterable<File> files) {
+	private void selectFiles(File file) {
+		selectFiles(CollectionUtils.asIterable(file));
+	}
 
+	private void selectFiles(Iterable<File> files) {
 		DirectoryList dirlist = getListView();
 		runSwing(() -> dirlist.setSelectedFiles(files));
 	}
@@ -2284,6 +2339,28 @@ public class GhidraFileChooserTest extends AbstractDockingTest {
 		show(null, useDefaults);
 	}
 
+	private CompletableFuture<List<File>> showSingleSelectionChooser(File dir,
+			GhidraFileChooserMode mode) throws Exception {
+
+		close();
+
+		CompletableFuture<List<File>> theFuture = new CompletableFuture<>();
+
+		chooser = new GhidraFileChooser(null);
+		chooser.setFileSelectionMode(mode);
+
+		runSwing(() -> {
+			chooser.setCurrentDirectory(dir);
+			chooser.setMultiSelectionEnabled(false);
+			List<File> choice = chooser.getSelectedFiles();
+			theFuture.complete(choice);
+		}, false);
+
+		initialize(chooser, dir, true);
+
+		return theFuture;
+	}
+
 	private CompletableFuture<List<File>> showMultiSelectionChooser(File dir,
 			GhidraFileChooserMode mode) throws Exception {
 		close();