diff --git a/code/src/java/pcgen/gui2/PCGenFrame.java b/code/src/java/pcgen/gui2/PCGenFrame.java
index fd5c17e9e41..fbe8dd2aa7d 100644
--- a/code/src/java/pcgen/gui2/PCGenFrame.java
+++ b/code/src/java/pcgen/gui2/PCGenFrame.java
@@ -100,6 +100,7 @@
 import pcgen.system.PCGenPropBundle;
 import pcgen.system.PCGenSettings;
 import pcgen.system.PropertyContext;
+import pcgen.system.PropertyContextFactory;
 import pcgen.util.Logging;
 import pcgen.util.chooser.ChooserFactory;
 import pcgen.util.chooser.RandomChooser;
@@ -823,11 +824,7 @@ boolean saveAllCharacters()
 	boolean showSaveCharacterChooser(CharacterFacade character)
 	{
 		PCGenSettings context = PCGenSettings.getInstance();
-		String parentPath = lastCharacterPath;
-		if (parentPath == null)
-		{
-			parentPath = context.getProperty(PCGenSettings.PCG_SAVE_PATH);
-		}
+		String parentPath = resolveCharacterChooserDir(lastCharacterPath, context);
 
 		FileChooser fileChooser = new FileChooser();
 		fileChooser.setTitle("Save PCGen Character File");
@@ -881,6 +878,7 @@ boolean showSaveCharacterChooser(CharacterFacade character)
 				}
 
 				lastCharacterPath = file.getParent();
+				rememberCharacterChooserDir(lastCharacterPath);
 				return true;
 			}
 			catch (Exception e)
@@ -926,12 +924,8 @@ public void revertCharacter(CharacterFacade character)
 	public void showOpenCharacterChooser()
 	{
 		GuiAssertions.assertIsNotJavaFXThread();
-		PropertyContext context = PCGenSettings.getInstance();
-		String path = lastCharacterPath;
-		if (path == null)
-		{
-			path = context.getProperty(PCGenSettings.PCG_SAVE_PATH);
-		}
+		PCGenSettings context = PCGenSettings.getInstance();
+		String path = resolveCharacterChooserDir(lastCharacterPath, context);
 
 		FileChooser fileChooser = new FileChooser();
 		fileChooser.setTitle("Open PCGen Character");
@@ -948,10 +942,44 @@ public void showOpenCharacterChooser()
 		if (file != null)
 		{
 			lastCharacterPath = file.getAbsoluteFile().getParent();
+			rememberCharacterChooserDir(lastCharacterPath);
 			loadCharacterFromFile(file);
 		}
 	}
 
+	/**
+	 * Persists the last-used character folder to {@code options.ini} so it
+	 * survives a clean shutdown — and immediately flushes it so it also
+	 * survives an abrupt exit (window close from a desktop manager, crash).
+	 * Note: a forced kill (Ctrl-C, SIGKILL) before this point cannot be
+	 * caught, so the most recent folder may still be lost in that case.
+	 */
+	private static void rememberCharacterChooserDir(String dir)
+	{
+		PCGenSettings.getInstance().setProperty(PCGenSettings.LAST_CHARACTER_PATH, dir);
+		PropertyContextFactory.getDefaultFactory().savePropertyContexts();
+	}
+
+	/**
+	 * Resolve the initial folder for the character Open/Save chooser, in order:
+	 * the in-session {@code lastInSessionPath}; the persisted
+	 * {@link PCGenSettings#LAST_CHARACTER_PATH} from prior runs; the user's
+	 * configured {@link PCGenSettings#PCG_SAVE_PATH} default.
+	 */
+	static String resolveCharacterChooserDir(String lastInSessionPath, PropertyContext context)
+	{
+		String path = lastInSessionPath;
+		if (path == null || path.isEmpty())
+		{
+			path = context.getProperty(PCGenSettings.LAST_CHARACTER_PATH);
+		}
+		if (path == null || path.isEmpty())
+		{
+			path = context.getProperty(PCGenSettings.PCG_SAVE_PATH);
+		}
+		return path;
+	}
+
 	void showOpenPartyChooser()
 	{
 		PropertyContext context = PCGenSettings.getInstance();
diff --git a/code/src/java/pcgen/system/PCGenSettings.java b/code/src/java/pcgen/system/PCGenSettings.java
index 3badedbb3c9..97f9a990067 100644
--- a/code/src/java/pcgen/system/PCGenSettings.java
+++ b/code/src/java/pcgen/system/PCGenSettings.java
@@ -61,6 +61,8 @@ public final class PCGenSettings extends PropertyContext
 	public static final String PCP_SAVE_PATH = "pcgen.files.parties";
 	public static final String CHAR_PORTRAITS_PATH = "pcgen.files.portaits";
 	public static final String BACKUP_PCG_PATH = "pcgen.files.characters.backup";
+	/** Last folder used in the character Open/Save chooser; remembers across launches. */
+	public static final String LAST_CHARACTER_PATH = "pcgen.files.characters.lastUsed";
 	public static final String SELECTED_SPELL_SHEET_PATH = "pcgen.files.selectedSpellOutputSheet";
 	public static final String RECENT_CHARACTERS = "recentCharacters";
 	public static final String RECENT_PARTIES = "recentParties";
@@ -84,20 +86,39 @@ public final class PCGenSettings extends PropertyContext
 	private PCGenSettings()
 	{
 		super("options.ini");
-		setProperty(PCG_SAVE_PATH,
-			(ConfigurationSettings.getUserDir() + "/characters").replace('/', File.separatorChar));
-		setProperty(PCP_SAVE_PATH,
-			(ConfigurationSettings.getUserDir() + "/characters").replace('/', File.separatorChar));
-		setProperty(CHAR_PORTRAITS_PATH,
-			(ConfigurationSettings.getUserDir() + "/characters").replace('/', File.separatorChar));
-		setProperty(BACKUP_PCG_PATH,
-			(ConfigurationSettings.getUserDir() + "/characters").replace('/', File.separatorChar));
+		String defaultCharsDir = defaultCharactersDir();
+		setProperty(PCG_SAVE_PATH, defaultCharsDir);
+		setProperty(PCP_SAVE_PATH, defaultCharsDir);
+		setProperty(CHAR_PORTRAITS_PATH, defaultCharsDir);
+		setProperty(BACKUP_PCG_PATH, defaultCharsDir);
 		setProperty(VENDOR_DATA_DIR, "@vendordata");
 		setProperty(HOMEBREW_DATA_DIR, "@homebrewdata");
 		setProperty(CUSTOM_DATA_DIR, "@data/customsources".replace('/', File.separatorChar));
 		OutputDB.registerBooleanPreference(OPTION_SHOW_OUTPUT_NAME_FOR_OTHER_ITEMS, false);
 	}
 
+	/**
+	 * Default characters/portraits/backups dir, rooted in the user's home so it
+	 * stays writable when PCGen is installed under Program Files.
+	 */
+	static String defaultCharactersDir()
+	{
+		String root = SystemUtils.USER_HOME;
+		if (SystemUtils.IS_OS_WINDOWS)
+		{
+			String userProfile = System.getenv("USERPROFILE");
+			if (userProfile != null && !userProfile.isEmpty())
+			{
+				File documents = new File(userProfile, "Documents");
+				if (documents.isDirectory())
+				{
+					root = documents.getAbsolutePath();
+				}
+			}
+		}
+		return root + File.separator + "PCGen" + File.separator + "characters";
+	}
+
 	@Override
 	protected void beforePropertiesSaved()
 	{
diff --git a/code/src/test/pcgen/gui2/PCGenFrameResolveCharacterChooserDirTest.java b/code/src/test/pcgen/gui2/PCGenFrameResolveCharacterChooserDirTest.java
new file mode 100644
index 00000000000..b8b0b37af9f
--- /dev/null
+++ b/code/src/test/pcgen/gui2/PCGenFrameResolveCharacterChooserDirTest.java
@@ -0,0 +1,80 @@
+/*
+ * Copyright 2026 Vest <Vest@users.noreply.github.com>
+ *
+ * This library is free software; you can redistribute it and/or
+ * modify it under the terms of the GNU Lesser General Public
+ * License as published by the Free Software Foundation; either
+ * version 2.1 of the License, or (at your option) any later version.
+ *
+ * This library is distributed in the hope that it will be useful,
+ * but WITHOUT ANY WARRANTY; without even the implied warranty of
+ * MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the GNU
+ * Lesser General Public License for more details.
+ */
+package pcgen.gui2;
+
+import static org.junit.jupiter.api.Assertions.assertEquals;
+
+import pcgen.system.PCGenSettings;
+import pcgen.system.PropertyContext;
+
+import org.junit.jupiter.api.Test;
+
+/**
+ * Verifies the fallback order of {@link PCGenFrame#resolveCharacterChooserDir}:
+ * in-session path → persisted LAST_CHARACTER_PATH → configured PCG_SAVE_PATH.
+ */
+class PCGenFrameResolveCharacterChooserDirTest
+{
+	private static final String IN_SESSION = "/session/path";
+	private static final String LAST_USED = "/persisted/path";
+	private static final String DEFAULT_PCG = "/default/path";
+
+	@Test
+	void inSessionPathWinsWhenSet()
+	{
+		PropertyContext ctx = new TestContext();
+		ctx.setProperty(PCGenSettings.LAST_CHARACTER_PATH, LAST_USED);
+		ctx.setProperty(PCGenSettings.PCG_SAVE_PATH, DEFAULT_PCG);
+
+		assertEquals(IN_SESSION, PCGenFrame.resolveCharacterChooserDir(IN_SESSION, ctx));
+	}
+
+	@Test
+	void persistedPathWinsWhenInSessionIsNull()
+	{
+		PropertyContext ctx = new TestContext();
+		ctx.setProperty(PCGenSettings.LAST_CHARACTER_PATH, LAST_USED);
+		ctx.setProperty(PCGenSettings.PCG_SAVE_PATH, DEFAULT_PCG);
+
+		assertEquals(LAST_USED, PCGenFrame.resolveCharacterChooserDir(null, ctx));
+	}
+
+	@Test
+	void persistedPathWinsWhenInSessionIsEmpty()
+	{
+		PropertyContext ctx = new TestContext();
+		ctx.setProperty(PCGenSettings.LAST_CHARACTER_PATH, LAST_USED);
+		ctx.setProperty(PCGenSettings.PCG_SAVE_PATH, DEFAULT_PCG);
+
+		assertEquals(LAST_USED, PCGenFrame.resolveCharacterChooserDir("", ctx));
+	}
+
+	@Test
+	void defaultPathIsUsedWhenNothingElseSet()
+	{
+		PropertyContext ctx = new TestContext();
+		ctx.setProperty(PCGenSettings.PCG_SAVE_PATH, DEFAULT_PCG);
+
+		assertEquals(DEFAULT_PCG, PCGenFrame.resolveCharacterChooserDir(null, ctx));
+	}
+
+	/** Plain {@link PropertyContext} so the test doesn't touch the singleton. */
+	private static final class TestContext extends PropertyContext
+	{
+		TestContext()
+		{
+			super("test-options.ini");
+		}
+	}
+}
diff --git a/code/src/test/pcgen/system/PCGenSettingsTest.java b/code/src/test/pcgen/system/PCGenSettingsTest.java
new file mode 100644
index 00000000000..19d862909b1
--- /dev/null
+++ b/code/src/test/pcgen/system/PCGenSettingsTest.java
@@ -0,0 +1,89 @@
+/*
+ * Copyright 2026 Vest <Vest@users.noreply.github.com>
+ *
+ * This library is free software; you can redistribute it and/or
+ * modify it under the terms of the GNU Lesser General Public
+ * License as published by the Free Software Foundation; either
+ * version 2.1 of the License, or (at your option) any later version.
+ *
+ * This library is distributed in the hope that it will be useful,
+ * but WITHOUT ANY WARRANTY; without even the implied warranty of
+ * MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the GNU
+ * Lesser General Public License for more details.
+ */
+package pcgen.system;
+
+import static org.junit.jupiter.api.Assertions.assertEquals;
+import static org.junit.jupiter.api.Assertions.assertNotEquals;
+import static org.junit.jupiter.api.Assertions.assertTrue;
+
+import java.io.File;
+import java.nio.file.Path;
+
+import org.apache.commons.lang3.SystemUtils;
+import org.junit.jupiter.api.Test;
+import org.junit.jupiter.api.io.TempDir;
+
+/**
+ * Tests the writable default and the round-trip persistence of
+ * {@link PCGenSettings#LAST_CHARACTER_PATH}.
+ */
+class PCGenSettingsTest
+{
+	@Test
+	void defaultCharactersDirIsRootedInUserHome()
+	{
+		String dir = PCGenSettings.defaultCharactersDir();
+
+		assertTrue(dir.startsWith(SystemUtils.USER_HOME),
+				"Expected default characters dir to live under USER_HOME but was: " + dir);
+		assertTrue(dir.endsWith(File.separator + "PCGen" + File.separator + "characters"),
+				"Expected default characters dir to end with PCGen/characters but was: " + dir);
+	}
+
+	@Test
+	void defaultCharactersDirIsNotInsideInstallDir()
+	{
+		// USER_DIR is the JVM working directory; under Program Files installs it is the
+		// install root, which is not user-writable. The fix decouples the default from it.
+		String dir = PCGenSettings.defaultCharactersDir();
+		String installRootedDefault = SystemUtils.USER_DIR + File.separator + "characters";
+
+		assertNotEquals(installRootedDefault, dir,
+				"Default characters dir must not equal user.dir/characters");
+	}
+
+	/**
+	 * Locks the durability claim: {@code LAST_CHARACTER_PATH} written in one
+	 * "session" is read back in the next via {@code options.ini}.
+	 */
+	@Test
+	void lastCharacterPathRoundTripsViaOptionsIni(@TempDir Path settingsDir)
+	{
+		String chosenFolder = "/some/folder/the/user/picked";
+
+		// Session 1: write the property and flush options.ini to the temp dir.
+		PropertyContextFactory factory1 = new PropertyContextFactory(settingsDir.toString());
+		TestableSettings session1 = new TestableSettings();
+		factory1.registerAndLoadPropertyContext(session1);
+		session1.setProperty(PCGenSettings.LAST_CHARACTER_PATH, chosenFolder);
+		factory1.savePropertyContexts();
+
+		// Session 2: a fresh factory + context reads the same file back.
+		PropertyContextFactory factory2 = new PropertyContextFactory(settingsDir.toString());
+		TestableSettings session2 = new TestableSettings();
+		factory2.registerAndLoadPropertyContext(session2);
+
+		assertEquals(chosenFolder, session2.getProperty(PCGenSettings.LAST_CHARACTER_PATH),
+				"Persisted folder must survive a save+load cycle through options.ini");
+	}
+
+	/** Plain {@link PropertyContext} so we don't touch the {@code PCGenSettings} singleton. */
+	private static final class TestableSettings extends PropertyContext
+	{
+		TestableSettings()
+		{
+			super("options.ini");
+		}
+	}
+}