diff --git a/Ghidra/Configurations/Public_Release/src/global/docs/WhatsNew.md b/Ghidra/Configurations/Public_Release/src/global/docs/WhatsNew.md
index 63d889a12f..d8eae8d5a2 100644
--- a/Ghidra/Configurations/Public_Release/src/global/docs/WhatsNew.md
+++ b/Ghidra/Configurations/Public_Release/src/global/docs/WhatsNew.md
@@ -100,59 +100,20 @@ can also be used in headless mode with the new `-mirror` command line option.
 ## PyGhidra
 PyGhidra 3.0.0 (compatible with Ghidra 12.0 and later) introduces many new Python-specific API 
 methods with the goal of making the most common Ghidra tasks quick and easy, such as opening a 
-project, getting a program, and running a GhidraScript. Legacy API fuctions such as 
+project, getting a program, and running a GhidraScript. Legacy API functions such as 
 `pyghidra.open_program()` and `pyghidra_run_script()` have been deprecated in favor of the new 
-methods. Below is an example program that showcases some of the new API functionality. See the 
-PyGhidra library README for more information.
-```python
-import os, jpype, pyghidra
-pyghidra.start()
+methods, which are outlined at https://pypi.org/project/pyghidra.
 
-# Open/create a project
-with pyghidra.open_project(os.environ["GHIDRA_PROJECT_DIR"], "ExampleProject", create=True) as project:
-
-    # Walk a Ghidra release zip file, load every decompiler binary, and save them to the project
-    with pyghidra.open_filesystem(f"{os.environ['DOWNLOADS_DIR']}/ghidra_11.4_PUBLIC_20250620.zip") as fs:
-        loader = pyghidra.program_loader().project(project)
-        for f in fs.files(lambda f: "os/" in f.path and f.name.startswith("decompile")):
-            loader = loader.source(f.getFSRL()).projectFolderPath("/" + f.parentFile.name)
-            with loader.load() as load_results:
-                load_results.save(pyghidra.monitor())
-
-    # Analyze the windows decompiler program for a maximum of 10 seconds
-    with pyghidra.program_context(project, "/win_x86_64/decompile.exe") as program:
-        analysis_props = pyghidra.analysis_properties(program)
-        with pyghidra.transaction(program):
-            analysis_props.setBoolean("Non-Returning Functions - Discovered", False)
-        analysis_log = pyghidra.analyze(program, pyghidra.monitor(10))
-        program.save("Analyzed", pyghidra.monitor())
-    
-    # Walk the project and set a property in each decompiler program
-    def set_property(domain_file, program):
-        with pyghidra.transaction(program):
-            program_info = pyghidra.program_info(program)
-            program_info.setString("PyGhidra Property", "Set by PyGhidra!")
-        program.save("Setting property", pyghidra.monitor())
-    pyghidra.walk_programs(project, set_property, program_filter=lambda f, p: p.name.startswith("decompile"))
-
-    # Load some bytes as a new program
-    ByteArrayCls = jpype.JArray(jpype.JByte)
-    my_bytes = ByteArrayCls(b"\xaa\xbb\xcc\xdd\xee\xff")
-    loader = pyghidra.program_loader().project(project).source(my_bytes).name("my_bytes")
-    loader = loader.loaders("BinaryLoader").language("DATA:LE:64:default")
-    with loader.load() as load_results:
-        load_results.save(pyghidra.monitor())
-
-    # Run a GhidraScript
-    pyghidra.ghidra_script(f"{os.environ['GHIDRA_SCRIPTS_DIR']}/HelloWorldScript.java", project)
-```
+The default Python scripting engine has been changed in Ghidra 12.0 from Jython to PyGhidra.
+Existing Jython scripts will need to include the `# @runtime Jython` script header in order to
+continue running within the Jython environment.
 
 ## Z3 Concolic Emulation and Symbolic Summary
-We've added an experimental Z3-based symbolic emulator, which runs as an "auxilliary" domain to the 
+We've added an experimental Z3-based symbolic emulator, which runs as an "auxiliary" domain to the 
 concrete emulator, effectively constructing what is commonly called a "concolic" emulator. The 
 symbolic emulator creates Z3 expressions and branching constraints, but it only follows the path 
 determined by concrete emulation. This is most easily accessed by installing the "SymbolicSummaryZ3"
-extension (**File** → **Install Extensions**) and then enabling the `Z3SummaryPlugin` in the 
+extension (**File** -> **Install Extensions**) and then enabling the `Z3SummaryPlugin` in the 
 Debugger or Emulator tool, which includes a GUI for viewing and sorting through the results. The Z3
 emulator requires z3-4.13.0, available from https://github.com/Z3Prover/z3. Other versions may work,
 but our current test configuration uses 4.13.0. Depending on the release and your platform, the
diff --git a/Ghidra/Features/Base/src/main/java/ghidra/app/plugin/core/symtable/NewSymbolFilter.java b/Ghidra/Features/Base/src/main/java/ghidra/app/plugin/core/symtable/NewSymbolFilter.java
index 2cda64dea8..955b1fe30b 100644
--- a/Ghidra/Features/Base/src/main/java/ghidra/app/plugin/core/symtable/NewSymbolFilter.java
+++ b/Ghidra/Features/Base/src/main/java/ghidra/app/plugin/core/symtable/NewSymbolFilter.java
@@ -270,7 +270,9 @@ public class NewSymbolFilter implements SymbolFilter {
 		for (Element child : children) {
 			String childName = child.getAttributeValue(Filter.NAME_ATTRIBUTE);
 			Filter f = filterMap.get(childName);
-			f.restoreFromXml(child);
+			if (f != null) { // NOTE: filter definition may have been dropped and not found
+				f.restoreFromXml(child);
+			}
 		}
 
 		rebuildActiveFilters();
diff --git a/Ghidra/Features/Base/src/test.slow/java/ghidra/framework/options/ToolPluginOptionsTest.java b/Ghidra/Features/Base/src/test.slow/java/ghidra/framework/options/ToolPluginOptionsTest.java
index ac45a400c7..8e2da468fb 100644
--- a/Ghidra/Features/Base/src/test.slow/java/ghidra/framework/options/ToolPluginOptionsTest.java
+++ b/Ghidra/Features/Base/src/test.slow/java/ghidra/framework/options/ToolPluginOptionsTest.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.
@@ -129,30 +129,6 @@ public class ToolPluginOptionsTest extends AbstractGhidraHeadedIntegrationTest {
 		}
 	}
 
-	@Test
-	public void testOptionsWithoutRegisteredOwnerGoAway() {
-		//
-		// Test that an option value that is not set or read will disappear after saving the 
-		// owning tool.
-		//
-
-		Options options = loadSearchOptions();
-
-		Pair<String, String> changedOption = changeStringTestOption(options);
-
-		//
-		// See if the options are there again after saving and reloading.  They should be there, 
-		// since the previous operation set the value.  We are careful here to simply check
-		// for the options existence, but not to retrieve it, as doing so would trigger the 
-		// option to be stored again.
-		//
-		options = saveAndLoadOptions();
-		verifyStringOptionStillChanged_WithoutUsingOptionsAPI(options, changedOption.first);
-
-		options = saveAndLoadOptions();
-		verifyUnusedOptionNoLongerHasEntry(options, changedOption.first);
-	}
-
 	@Test
 	public void testSaveOnlyNonDefaultOptions() {
 		ToolOptions options = loadSearchOptions();
@@ -177,6 +153,8 @@ public class ToolPluginOptionsTest extends AbstractGhidraHeadedIntegrationTest {
 		// Repeatedly save/load options, accessing them each time, and make sure that they 
 		// re-appear each load.
 		//
+		// Note: options removal is now controlled through use of an age-off mechanism
+		//
 
 		Options options = loadSearchOptions();
 
@@ -194,11 +172,11 @@ public class ToolPluginOptionsTest extends AbstractGhidraHeadedIntegrationTest {
 		verifyStringOptionsStillChanged_UsingTheOptionsAPI(options, changedOption);
 
 		//
-		// now save twice in a row without accessing and the untouched option should be gone
+		// now save twice in a row without accessing and the untouched option should *not* be gone
 		// 
 		options = saveAndLoadOptions();
 		options = saveAndLoadOptions();
-		verifyUnusedOptionNoLongerHasEntry(options, changedOption.first);
+		verifyStringOptionsStillChanged_UsingTheOptionsAPI(options, changedOption);
 	}
 
 	@Test
diff --git a/Ghidra/Features/Base/src/test/java/ghidra/framework/options/OptionsTest.java b/Ghidra/Features/Base/src/test/java/ghidra/framework/options/OptionsTest.java
index 75b9f4eb7a..50eb9ad547 100644
--- a/Ghidra/Features/Base/src/test/java/ghidra/framework/options/OptionsTest.java
+++ b/Ghidra/Features/Base/src/test/java/ghidra/framework/options/OptionsTest.java
@@ -24,6 +24,8 @@ import java.awt.event.KeyEvent;
 import java.beans.PropertyChangeListener;
 import java.beans.PropertyEditorSupport;
 import java.io.File;
+import java.text.SimpleDateFormat;
+import java.time.LocalDate;
 import java.util.*;
 
 import javax.swing.JComponent;
@@ -34,7 +36,7 @@ import org.junit.*;
 
 import generic.test.AbstractGuiTest;
 import generic.theme.GThemeDefaults.Colors.Palette;
-import ghidra.util.HelpLocation;
+import ghidra.util.*;
 import ghidra.util.bean.opteditor.OptionsVetoException;
 import ghidra.util.exception.InvalidInputException;
 import gui.event.MouseBinding;
@@ -454,12 +456,133 @@ public class OptionsTest extends AbstractGuiTest {
 		assertTrue(options.contains("Foo"));
 		assertTrue(options.contains("Bar"));
 
-		options.registerOption("Bar", 0, null, "foo");
-
+		options.registerOption("Bar", 0, null, "Bar description");
 		options.removeUnusedOptions();
 
-		assertFalse(options.contains("Foo"));
+		// registered; should stay around
 		assertTrue(options.contains("Bar"));
+		// not registered, but not aged-off; should stay around
+		assertTrue(options.contains("Foo"));
+
+		// Save, edit the date of the options to be older than 1 year, which is our age cutoff. 
+		// Make sure any unregistered option is then removed.
+		Element savedRoot = options.getXmlRoot(false);
+		LocalDate twoYearsAgo = LocalDate.now().minusYears(2);
+		Set<String> optionNames = Set.of("Bar", "Foo");
+		setLastUsedDate(savedRoot, twoYearsAgo, optionNames);
+
+		options = new ToolOptions(savedRoot);
+		assertTrue(options.contains("Foo"));
+		assertTrue(options.contains("Bar"));
+
+		options.registerOption("Bar", 0, null, "Bar description");
+		options.removeUnusedOptions();
+
+		// registered; should stay around
+		assertTrue(options.contains("Bar"));
+		// not registered, and older than 1 year; should be removed
+		assertFalse(options.contains("Foo"));
+	}
+
+	@Test
+	public void testRemoveUnusedOption_WrappedOption() throws Exception {
+
+		Date date = new Date();
+		options.setDate("Foo", date);
+		options.setDate("Bar", date);
+		saveAndRestoreOptions();
+		assertEquals(date, options.getDate("Foo", null));
+		assertEquals(date, options.getDate("Bar", null));
+
+		Date defaultDate = new SimpleDateFormat("yyyy-MM-dd").parse("2025-09-12");
+
+		options.registerOption("Bar", defaultDate, null, "Bar description");
+		options.removeUnusedOptions();
+
+		// registered; should stay around
+		assertTrue(options.contains("Bar"));
+		// not registered, but not aged-off; should stay around
+		assertTrue(options.contains("Foo"));
+
+		// Save, edit the date of the options to be older than 1 year, which is our age cutoff. 
+		// Make sure any unregistered option is then removed.
+		Element savedRoot = options.getXmlRoot(false);
+		LocalDate twoYearsAgo = LocalDate.now().minusYears(2);
+		Set<String> optionNames = Set.of("Bar", "Foo");
+		setLastUsedDate(savedRoot, twoYearsAgo, optionNames);
+
+		options = new ToolOptions(savedRoot);
+		assertTrue(options.contains("Foo"));
+		assertTrue(options.contains("Bar"));
+
+		options.registerOption("Bar", defaultDate, null, "Bar description");
+		options.removeUnusedOptions();
+
+		// registered; should stay around
+		assertTrue(options.contains("Bar"));
+		// not registered, and older than 1 year; should be removed
+		assertFalse(options.contains("Foo"));
+	}
+
+	@Test
+	public void testUnregisteredWarningMessage() {
+
+		/*
+		 	Test that options access, but not registered, will trigger a warning message.   
+		 */
+
+		SpyErrorLogger spyLogger = new SpyErrorLogger();
+		Msg.setErrorLogger(spyLogger);
+
+		options.getInt("Foo", 1);
+		assertTrue(spyLogger.isEmtpy());
+
+		options.validateOptions();
+		spyLogger.assertLogMessage("Unregistered", "property", "Foo");
+
+		spyLogger.reset();
+		options.registerOption("Foo", 0, null, "Description");
+		options.getInt("Foo", 2);
+		options.validateOptions();
+		assertTrue(spyLogger.isEmtpy());
+	}
+
+	private void setLastUsedDate(Element savedRoot, LocalDate lastRegisteredDate,
+			Set<String> names) {
+
+		/*
+		 
+		 Msg.debug(this, XmlUtilities.toString(savedRoot));
+		
+			<CATEGORY NAME="Test">
+			    <SAVE_STATE NAME="Bar" TYPE="int" VALUE="3" LAST_REGISTERED="2025-09-17" />
+				<SAVE_STATE NAME="Bar" TYPE="boolean" VALUE="false" LAST_REGISTERED="2025-09-17" />
+			</CATEGORY> 
+		
+		 */
+
+		String dateString = lastRegisteredDate.format(ToolOptions.LAST_REGISTERED_DATE_FORMATTER);
+
+		List<Element> elements = getElementsByName(savedRoot, names);
+		for (Element element : elements) { // <SAVE_STATE NAME="Foo" ...>
+			element.setAttribute(ToolOptions.LAST_REGISTERED_DATE_ATTIBUTE, dateString);
+		}
+
+	}
+
+	@SuppressWarnings("unchecked")
+	private List<Element> getElementsByName(Element savedRoot, Set<String> names) {
+
+		List<Element> matches = new ArrayList<>();
+		List<Element> children = savedRoot.getChildren();
+		for (Element saveState : children) {
+			String name = saveState.getAttributeValue("NAME");
+			if (names.contains(name)) {
+				matches.add(saveState);
+			}
+		}
+
+		return matches;
 	}
 
 	@Test
diff --git a/Ghidra/Features/Decompiler/src/main/java/ghidra/app/decompiler/DecompileOptions.java b/Ghidra/Features/Decompiler/src/main/java/ghidra/app/decompiler/DecompileOptions.java
index ffd97c4953..55453956c7 100644
--- a/Ghidra/Features/Decompiler/src/main/java/ghidra/app/decompiler/DecompileOptions.java
+++ b/Ghidra/Features/Decompiler/src/main/java/ghidra/app/decompiler/DecompileOptions.java
@@ -538,7 +538,7 @@ public class DecompileOptions {
 
 		grabFromProgram(program);
 
-		// assuming if one is not registered, then none area
+		// assuming if one is not registered, then none are
 		if (!opt.isRegistered(PREDICATE_OPTIONSTRING)) {
 			return;
 		}
diff --git a/Ghidra/Framework/Generic/src/main/java/ghidra/framework/options/AttributedSaveState.java b/Ghidra/Framework/Generic/src/main/java/ghidra/framework/options/AttributedSaveState.java
new file mode 100644
index 0000000000..97a1ad097a
--- /dev/null
+++ b/Ghidra/Framework/Generic/src/main/java/ghidra/framework/options/AttributedSaveState.java
@@ -0,0 +1,154 @@
+/* ###
+ * IP: GHIDRA
+ *
+ * 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.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+package ghidra.framework.options;
+
+import java.util.*;
+import java.util.Map.Entry;
+
+import org.jdom.Attribute;
+import org.jdom.Element;
+
+/**
+ * A version of {@link SaveState} that allows clients to add attributes to properties in this save
+ * state.  The following code shows how to use this class:
+ * <pre>
+ * AttributedSaveState ss = new AttributedSaveState();
+ * ss.putBoolean("Happy", true);
+ * 
+ * Map<String, String> attrs = Map.of("MyAttribute", "AttributeValue");
+ * ss.addAttrbibutes("Happy", attrs);
+ * </pre>
+ * 
+ * <p>In this example, the property "Happy" will be given the attribute "MyAttribute" with the value
+ * of "AttributeValue".  This is useful for clients that wish to add attributes to individual 
+ * properties, such as a date for tracking usage.
+ * 
+ * <p><u>Usage Note:</u> The given attributes are only supported when writing and reading xml. Json
+ * is not supported.
+ */
+public class AttributedSaveState extends SaveState {
+
+	private Map<String, Map<String, String>> propertyAttributes;
+
+	public AttributedSaveState() {
+		super();
+	}
+
+	public AttributedSaveState(String name) {
+		super(name);
+	}
+
+	public AttributedSaveState(Element root) {
+		super(root);
+	}
+
+	/**
+	 * Adds the given map of attribute name/value pairs to this save state.
+	 * @param propertyName the property name within this save state that will be attributed
+	 * @param attributes the attributes
+	 */
+	public void addAttributes(String propertyName, Map<String, String> attributes) {
+		getPropertyAttributes().put(propertyName, attributes);
+	}
+
+	/**
+	 * Removes all attributes associated with the given property name.
+	 * @param propertyName the property name within this save state that has the given attributes
+	 */
+	public void removeAttributes(String propertyName) {
+		getPropertyAttributes().remove(propertyName);
+	}
+
+	/**
+	 * Gets the attributes currently associated with the given property name
+	 * @param propertyName the property name for which to get attributes
+	 * @return the attributes or null
+	 */
+	public Map<String, String> getAttributes(String propertyName) {
+		return getPropertyAttributes().get(propertyName);
+	}
+
+	private Map<String, Map<String, String>> getPropertyAttributes() {
+		if (propertyAttributes == null) {
+			propertyAttributes = new HashMap<>();
+		}
+		return propertyAttributes;
+	}
+
+	@Override
+	protected SaveState createSaveState() {
+		return new AttributedSaveState();
+	}
+
+	@Override
+	protected void initializeElement(Element e) {
+
+		String name = e.getAttributeValue(NAME);
+		if (name == null) {
+			return; // sub-element; properties not supported
+		}
+
+		// 
+		// Overridden to add our attributes to the newly created element, used to create xml
+		// 
+		Map<String, String> attrs = getPropertyAttributes().get(name);
+		if (attrs != null) {
+			Set<Entry<String, String>> entries = attrs.entrySet();
+			for (Entry<String, String> entry : entries) {
+				String key = entry.getKey();
+				String value = entry.getValue();
+				e.setAttribute(key, value);
+			}
+		}
+	}
+
+	@Override
+	protected void processElement(Element element) {
+		super.processElement(element);
+
+		String name = element.getAttributeValue(NAME);
+		if (name == null) {
+			return; // sub-element; properties not supported
+		}
+
+		//
+		// Overridden to extract non-standard attributes from the given element.  The element was 
+		// created after restoring from xml.   We extract the attributes that we added above in
+		// initializeElement().
+		// 
+		Map<String, String> newAttrs = new HashMap<>();
+
+		@SuppressWarnings("unchecked")
+		List<Attribute> attrs = element.getAttributes();
+		for (Attribute attr : attrs) {
+
+			String attrName = attr.getName();
+			String attrValue = switch (attrName) {
+				// ignore standard attributes, as they are managed by the parent class
+				case NAME, TYPE, VALUE -> null;
+				default -> attr.getValue();
+			};
+
+			if (attrValue != null) {
+				newAttrs.put(attrName, attrValue);
+			}
+		}
+
+		if (!newAttrs.isEmpty()) {
+			getPropertyAttributes().put(name, newAttrs);
+		}
+	}
+}
diff --git a/Ghidra/Framework/Generic/src/main/java/ghidra/framework/options/GProperties.java b/Ghidra/Framework/Generic/src/main/java/ghidra/framework/options/GProperties.java
index 7cd4fa87ac..081a9bb19a 100644
--- a/Ghidra/Framework/Generic/src/main/java/ghidra/framework/options/GProperties.java
+++ b/Ghidra/Framework/Generic/src/main/java/ghidra/framework/options/GProperties.java
@@ -78,7 +78,7 @@ public class GProperties {
 	private static final String STATE = "STATE";
 	protected static final String TYPE = "TYPE";
 	protected static final String NAME = "NAME";
-	private static final String VALUE = "VALUE";
+	protected static final String VALUE = "VALUE";
 	public static DateFormat DATE_FORMAT = new SimpleDateFormat("yyyy-MM-dd'T'HH:mm:ssZ");
 	private static final String ARRAY_ELEMENT_NAME = "A";
 	protected TreeMap<String, Object> map; // use ordered map for deterministic serialization
@@ -505,35 +505,34 @@ public class GProperties {
 		return root;
 	}
 
-	protected Element createElement(String key, Object value) {
+	protected Element createElement(String propertyName, Object value) {
 		Element elem = null;
 		if (value instanceof Element) {
-			elem = createElementFromElement(key, (Element) value);
+			elem = createElementFromElement(propertyName, (Element) value);
 		}
 		else if (value instanceof Byte) {
-			elem = setAttributes(key, "byte", ((Byte) value).toString());
+			elem = setAttributes(propertyName, "byte", ((Byte) value).toString());
 		}
 		else if (value instanceof Short) {
-			elem = setAttributes(key, "short", ((Short) value).toString());
+			elem = setAttributes(propertyName, "short", ((Short) value).toString());
 		}
 		else if (value instanceof Integer) {
-			elem = setAttributes(key, "int", ((Integer) value).toString());
+			elem = setAttributes(propertyName, "int", ((Integer) value).toString());
 		}
 		else if (value instanceof Long) {
-			elem = setAttributes(key, "long", ((Long) value).toString());
+			elem = setAttributes(propertyName, "long", ((Long) value).toString());
 		}
 		else if (value instanceof Float) {
-			elem = setAttributes(key, "float", ((Float) value).toString());
+			elem = setAttributes(propertyName, "float", ((Float) value).toString());
 		}
 		else if (value instanceof Double) {
-			elem = setAttributes(key, "double", ((Double) value).toString());
+			elem = setAttributes(propertyName, "double", ((Double) value).toString());
 		}
 		else if (value instanceof Boolean) {
-			elem = setAttributes(key, "boolean", ((Boolean) value).toString());
+			elem = setAttributes(propertyName, "boolean", ((Boolean) value).toString());
 		}
 		else if (value instanceof String) {
-			elem = new Element(STATE);
-			elem.setAttribute(NAME, key);
+			elem = createElement(STATE, propertyName);
 			elem.setAttribute(TYPE, "string");
 			if (XmlUtilities.hasInvalidXMLCharacters((String) value)) {
 				elem.setAttribute("ENCODED_VALUE", NumericUtilities
@@ -544,71 +543,66 @@ public class GProperties {
 			}
 		}
 		else if (value instanceof Color) {
-			elem = setAttributes(key, "Color", Integer.toString(((Color) value).getRGB()));
+			elem = setAttributes(propertyName, "Color", Integer.toString(((Color) value).getRGB()));
 		}
 		else if (value instanceof Date) {
-			elem = setAttributes(key, "Date", DATE_FORMAT.format((Date) value));
+			elem = setAttributes(propertyName, "Date", DATE_FORMAT.format((Date) value));
 		}
 		else if (value instanceof File) {
-			elem = setAttributes(key, "File", ((File) value).getAbsolutePath());
+			elem = setAttributes(propertyName, "File", ((File) value).getAbsolutePath());
 		}
 		else if (value instanceof KeyStroke) {
-			elem = setAttributes(key, "KeyStroke", value.toString());
+			elem = setAttributes(propertyName, "KeyStroke", value.toString());
 		}
 		else if (value instanceof Font font) {
-			elem = setAttributes(key, "Font", toFontString(font));
+			elem = setAttributes(propertyName, "Font", toFontString(font));
 		}
 		else if (value instanceof byte[]) {
-			elem = new Element("BYTES");
-			elem.setAttribute(NAME, key);
+			elem = createElement("BYTES", propertyName);
 			elem.setAttribute(VALUE, NumericUtilities.convertBytesToString((byte[]) value));
 		}
 		else if (value instanceof short[]) {
-			elem = setArrayAttributes(key, "short", value);
+			elem = setArrayAttributes(propertyName, "short", value);
 		}
 		else if (value instanceof int[]) {
-			elem = setArrayAttributes(key, "int", value);
+			elem = setArrayAttributes(propertyName, "int", value);
 		}
 		else if (value instanceof long[]) {
-			elem = setArrayAttributes(key, "long", value);
+			elem = setArrayAttributes(propertyName, "long", value);
 		}
 		else if (value instanceof float[]) {
-			elem = setArrayAttributes(key, "float", value);
+			elem = setArrayAttributes(propertyName, "float", value);
 		}
 		else if (value instanceof double[]) {
-			elem = setArrayAttributes(key, "double", value);
+			elem = setArrayAttributes(propertyName, "double", value);
 		}
 		else if (value instanceof boolean[]) {
-			elem = setArrayAttributes(key, "boolean", value);
+			elem = setArrayAttributes(propertyName, "boolean", value);
 		}
 		else if (value instanceof String[]) {
-			elem = setArrayAttributes(key, "string", value);
+			elem = setArrayAttributes(propertyName, "string", value);
 		}
 		else if (value instanceof Enum) {
 			Enum<?> e = (Enum<?>) value;
-			elem = new Element("ENUM");
-			elem.setAttribute(NAME, key);
+			elem = createElement("ENUM", propertyName);
 			elem.setAttribute(TYPE, "enum");
 			elem.setAttribute("CLASS", e.getClass().getName());
 			elem.setAttribute(VALUE, e.name());
 		}
 		else if (value instanceof GProperties) {
 			Element savedElement = ((GProperties) value).saveToXml();
-			elem = new Element(GPROPERTIES_TAG);
-			elem.setAttribute(NAME, key);
+			elem = createElement(GPROPERTIES_TAG, propertyName);
 			elem.setAttribute(TYPE, G_PROPERTIES_TYPE);
 			elem.addContent(savedElement);
 		}
 		else {
-			elem = new Element("NULL");
-			elem.setAttribute(NAME, key);
+			elem = createElement("NULL", propertyName);
 		}
 		return elem;
 	}
 
-	private <T> Element setArrayAttributes(String key, String type, Object values) {
-		Element elem = new Element("ARRAY");
-		elem.setAttribute(NAME, key);
+	private <T> Element setArrayAttributes(String propertyName, String type, Object values) {
+		Element elem = createElement("ARRAY", propertyName);
 		elem.setAttribute(TYPE, type);
 		for (int i = 0; i < Array.getLength(values); i++) {
 			Object value = Array.get(values, i);
@@ -621,10 +615,19 @@ public class GProperties {
 		return elem;
 	}
 
-	private Element setAttributes(String key, String type, String value) {
-		Element elem;
-		elem = new Element(STATE);
-		elem.setAttribute(NAME, key);
+	protected Element createElement(String tag, String name) {
+		Element e = new Element(tag);
+		e.setAttribute(NAME, name);
+		initializeElement(e);
+		return e;
+	}
+
+	protected void initializeElement(Element e) {
+		// subclasses may override
+	}
+
+	private Element setAttributes(String propertyName, String type, String value) {
+		Element elem = createElement(STATE, propertyName);
 		elem.setAttribute(TYPE, type);
 		elem.setAttribute(VALUE, value);
 		return elem;
@@ -792,8 +795,7 @@ public class GProperties {
 	}
 
 	protected Element createElementFromElement(String internalKey, Element internalElement) {
-		Element newElement = new Element("XML");
-		newElement.setAttribute(NAME, internalKey);
+		Element newElement = createElement("XML", internalKey);
 
 		Element internalElementClone = (Element) internalElement.clone();
 		newElement.addContent(internalElementClone);
@@ -1420,11 +1422,11 @@ public class GProperties {
 		return true;
 	}
 
-	private String toFontString(Font font) {
+	private static String toFontString(Font font) {
 		return String.format("%s-%s-%s", font.getName(), getStyleString(font), font.getSize());
 	}
 
-	private String getStyleString(Font font) {
+	private static String getStyleString(Font font) {
 		boolean bold = font.isBold();
 		boolean italic = font.isItalic();
 		if (bold && italic) {
diff --git a/Ghidra/Framework/Generic/src/main/java/ghidra/framework/options/SaveState.java b/Ghidra/Framework/Generic/src/main/java/ghidra/framework/options/SaveState.java
index e90e3c28b6..af93e7413a 100644
--- a/Ghidra/Framework/Generic/src/main/java/ghidra/framework/options/SaveState.java
+++ b/Ghidra/Framework/Generic/src/main/java/ghidra/framework/options/SaveState.java
@@ -17,6 +17,7 @@ package ghidra.framework.options;
 
 import java.io.File;
 import java.io.IOException;
+import java.util.List;
 
 import org.jdom.Element;
 
@@ -114,31 +115,86 @@ public class SaveState extends XmlProperties {
 		return getAsType(name, null, SaveState.class);
 	}
 
+	@SuppressWarnings("unchecked")
 	@Override
 	protected void processElement(Element element) {
 		String tag = element.getName();
-
-		if (tag.equals("SAVE_STATE")) {
-			Element child = (Element) element.getChildren().get(0);
-			if (child != null) {
-				String name = element.getAttributeValue(NAME);
-				map.put(name, new SaveState(child));
-				return;
-			}
+		if (!tag.equals("SAVE_STATE")) {
+			super.processElement(element);
+			return;
 		}
-		super.processElement(element);
+
+		/*
+		 	When using a SaveState inside of a SaveState, we produce xml that looks like this: 
+		 	
+		 	<SAVE_STATE NAME="Bar" TYPE="SaveState">
+		        <STATE NAME="Bar" TYPE="int" VALUE="3" />
+		    </SAVE_STATE>
+		 */
+
+		SaveState saveState = createSaveState();
+
+		List<Element> children = element.getChildren();
+		if (children.isEmpty()) {
+			return;
+		}
+
+		Element child = (Element) element.getChildren().get(0);
+		String childTag = child.getName();
+		if (childTag.equals("SAVE_STATE")) {
+			/*
+			 	Old style tag, with one level of extra nesting
+			 	
+			 	<SAVE_STATE NAME="Bar" TYPE="SaveState">
+			        <SAVE_STATE>
+			            <STATE NAME="DATED_OPTION" TYPE="int" VALUE="3" />
+			        </SAVE_STATE>
+			    </SAVE_STATE>
+			 	
+			 */
+			children = child.getChildren();
+		}
+
+		for (Element e : children) {
+			saveState.processElement(e);
+		}
+
+		String parentName = element.getAttributeValue(NAME);
+		map.put(parentName, saveState);
 	}
 
+	@SuppressWarnings("unchecked")
 	@Override
 	protected Element createElement(String key, Object value) {
-		if (value instanceof SaveState saveState) {
-			Element savedElement = saveState.saveToXml();
-			Element element = new Element("SAVE_STATE");
-			element.setAttribute(NAME, key);
-			element.setAttribute(TYPE, "SaveState");
-			element.addContent(savedElement);
-			return element;
+		if (!(value instanceof SaveState saveState)) {
+			return super.createElement(key, value);
 		}
-		return super.createElement(key, value);
+
+		/*
+		 	When using a SaveState inside of a SaveState, we produce xml that looks like this: 
+		 	
+		 	<SAVE_STATE NAME="Bar" TYPE="SaveState">
+		        <STATE NAME="Bar" TYPE="int" VALUE="3" />
+		    </SAVE_STATE>
+		 */
+
+		Element savedElement = saveState.saveToXml();
+		Element element = new Element("SAVE_STATE");
+		element.setAttribute(NAME, key);
+		element.setAttribute(TYPE, "SaveState");
+
+		// do not write an extra <SAVE_STATE> intermediate node
+		List<Element> children = savedElement.getChildren();
+		for (Element e : children) {
+			Element newElement = (Element) e.clone();
+			element.addContent(newElement);
+		}
+
+		return element;
+	}
+
+	// allows subclasses to override how sub-save states are created
+	protected SaveState createSaveState() {
+		return new SaveState();
 	}
 }
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 3042a7be4c..c6e477782d 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
@@ -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.
@@ -268,10 +268,8 @@ public class ExtensionDetails implements Comparable<ExtensionDetails> {
 	}
 
 	/**
-	 * Returns true if this extension is installed under an installation folder or inside of a 
-	 * source control repository folder.
-	 * @return true if this extension is installed under an installation folder or inside of a 
-	 * source control repository folder.
+	 * {@return true if this extension is installed under an installation folder or inside of a 
+	 * source control repository folder}
 	 */
 	public boolean isInstalledInInstallationFolder() {
 		if (installDir == null) {
@@ -287,11 +285,10 @@ public class ExtensionDetails implements Comparable<ExtensionDetails> {
 		}
 
 		// extDirs.get(0) is the user extension dir
-		ResourceFile appExtDir = extDirs.get(1);
-		if (FileUtilities.isPathContainedWithin(appExtDir.getFile(false), installDir)) {
-			return true;
-		}
-		return false;
+		return extDirs.stream()
+				.skip(1)
+				.anyMatch(
+					dir -> FileUtilities.isPathContainedWithin(dir.getFile(false), installDir));
 	}
 
 	/**
diff --git a/Ghidra/Framework/Generic/src/test/java/ghidra/util/SpyErrorLogger.java b/Ghidra/Framework/Generic/src/test/java/ghidra/util/SpyErrorLogger.java
index e98b648da4..5c3fb54606 100644
--- a/Ghidra/Framework/Generic/src/test/java/ghidra/util/SpyErrorLogger.java
+++ b/Ghidra/Framework/Generic/src/test/java/ghidra/util/SpyErrorLogger.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.
@@ -15,7 +15,7 @@
  */
 package ghidra.util;
 
-import static org.junit.Assert.fail;
+import static org.junit.Assert.*;
 
 import java.util.Arrays;
 import java.util.Iterator;
@@ -88,6 +88,10 @@ public class SpyErrorLogger implements ErrorLogger, Iterable<String> {
 		messages.clear();
 	}
 
+	public boolean isEmtpy() {
+		return messages.isEmpty();
+	}
+
 	public void assertLogMessage(String... words) {
 		for (String message : this) {
 			if (StringUtilities.containsAllIgnoreCase(message, words)) {
diff --git a/Ghidra/Framework/Gui/src/main/java/ghidra/framework/options/AbstractOptions.java b/Ghidra/Framework/Gui/src/main/java/ghidra/framework/options/AbstractOptions.java
index 93a99f05b4..adb2d50894 100644
--- a/Ghidra/Framework/Gui/src/main/java/ghidra/framework/options/AbstractOptions.java
+++ b/Ghidra/Framework/Gui/src/main/java/ghidra/framework/options/AbstractOptions.java
@@ -260,8 +260,11 @@ public abstract class AbstractOptions implements Options {
 		if (option == null) {
 			return null;
 		}
-		if (option.getOptionType() != type) {
-			Msg.error(this, "Registered option incompatible with existing option: " + optionName,
+		OptionType existingType = option.getOptionType();
+		if (existingType != type) {
+			Msg.error(this, "Registered option incompatible with existing option: '%s'. " +
+				"Existing type '%s'; registered type '%s'.".formatted(optionName, existingType,
+					type),
 				new AssertException());
 			return null;
 		}
diff --git a/Ghidra/Framework/Gui/src/main/java/ghidra/framework/options/Option.java b/Ghidra/Framework/Gui/src/main/java/ghidra/framework/options/Option.java
index 580ee354c2..d51d878fa7 100644
--- a/Ghidra/Framework/Gui/src/main/java/ghidra/framework/options/Option.java
+++ b/Ghidra/Framework/Gui/src/main/java/ghidra/framework/options/Option.java
@@ -16,6 +16,7 @@
 package ghidra.framework.options;
 
 import java.beans.PropertyEditor;
+import java.time.LocalDate;
 import java.util.Objects;
 
 import ghidra.util.HelpLocation;
@@ -23,11 +24,15 @@ import ghidra.util.SystemUtilities;
 import utilities.util.reflection.ReflectionUtilities;
 
 public abstract class Option {
+
 	public static final String UNREGISTERED_OPTION = "Unregistered Option";
 
+	private static final LocalDate ONE_YEAR_AGO = LocalDate.now().minusYears(1);
+
 	private final String name;
 	private Object defaultValue;
 	private boolean isRegistered;
+	private LocalDate lastRegisteredDate;
 	private String description;
 	private HelpLocation helpLocation;
 	private OptionType optionType;
@@ -45,7 +50,10 @@ public abstract class Option {
 		this.defaultValue = defaultValue;
 		this.isRegistered = isRegistered;
 		this.propertyEditor = editor;
-		if (!isRegistered) {
+		if (isRegistered) {
+			lastRegisteredDate = LocalDate.now();
+		}
+		else {
 			recordInception();
 		}
 	}
@@ -67,6 +75,7 @@ public abstract class Option {
 		defaultValue = defaultValue != null ? defaultValue : updatedDefaultValue;
 		propertyEditor = propertyEditor != null ? propertyEditor : updatedEditor;
 		isRegistered = true;
+		lastRegisteredDate = LocalDate.now();
 	}
 
 	public abstract Object getCurrentValue();
@@ -74,7 +83,8 @@ public abstract class Option {
 	public abstract void doSetCurrentValue(Object value);
 
 	public void setCurrentValue(Object value) {
-		this.isRegistered = true;
+		isRegistered = true;
+		lastRegisteredDate = LocalDate.now();
 		doSetCurrentValue(value);
 	}
 
@@ -109,10 +119,44 @@ public abstract class Option {
 		return value;
 	}
 
+	public boolean wasRegisteredInPreviousSession() {
+		return lastRegisteredDate != null;
+	}
+
 	public boolean isRegistered() {
 		return isRegistered;
 	}
 
+	public void setLastRegisteredDate(LocalDate date) {
+		lastRegisteredDate = date;
+	}
+
+	public LocalDate getLastRegisteredDate() {
+		LocalDate date = lastRegisteredDate;
+		if (date == null) {
+			// This implies a new option that has not been registered and was not in a saved tool.
+			// Pick an old date so the option will not linger.
+			date = ONE_YEAR_AGO;
+		}
+		return date;
+	}
+
+	/**
+	 * Returns true if the last registered date for this option is older than 1 year ago.  That 
+	 * means that the option has not been registered and is likely no longer valid. This may not be
+	 * true, if the given option still exists, but is only active on-demand by the user.   If the
+	 * option has expired, it will be removed.  If it is still an existing on-demand option, it can
+	 * again be saved when the user loads the owning provider and changes the option.  In this case, 
+	 * it will remain in the tool for at least another year.
+	 * @return true if expired
+	 */
+	public boolean hasExpired() {
+		if (lastRegisteredDate == null) {
+			return false;
+		}
+		return lastRegisteredDate.isBefore(ONE_YEAR_AGO);
+	}
+
 	public void restoreDefault() {
 		setCurrentValue(defaultValue);
 	}
@@ -151,4 +195,5 @@ public abstract class Option {
 	public OptionType getOptionType() {
 		return optionType;
 	}
+
 }
diff --git a/Ghidra/Framework/Gui/src/main/java/ghidra/framework/options/ToolOptions.java b/Ghidra/Framework/Gui/src/main/java/ghidra/framework/options/ToolOptions.java
index 6cd8ea33b9..b4714e90d0 100644
--- a/Ghidra/Framework/Gui/src/main/java/ghidra/framework/options/ToolOptions.java
+++ b/Ghidra/Framework/Gui/src/main/java/ghidra/framework/options/ToolOptions.java
@@ -20,6 +20,8 @@ import java.awt.Font;
 import java.beans.PropertyEditor;
 import java.io.File;
 import java.lang.reflect.Constructor;
+import java.time.LocalDate;
+import java.time.format.DateTimeFormatter;
 import java.util.*;
 
 import javax.swing.KeyStroke;
@@ -45,10 +47,16 @@ import ghidra.util.exception.AssertException;
  * <p>The Options Dialog shows the delimited hierarchy in tree format.
  */
 public class ToolOptions extends AbstractOptions {
+
 	private static final String CLASS_ATTRIBUTE = "CLASS";
 	private static final String NAME_ATTRIBUTE = "NAME";
 	private static final String WRAPPED_OPTION_NAME = "WRAPPED_OPTION";
 	private static final String CLEARED_VALUE_ELEMENT_NAME = "CLEARED_VALUE";
+
+	public static final String LAST_REGISTERED_DATE_ATTIBUTE = "LAST_REGISTERED";
+	public static final DateTimeFormatter LAST_REGISTERED_DATE_FORMATTER =
+		DateTimeFormatter.ISO_LOCAL_DATE;
+
 	public static final Set<Class<?>> PRIMITIVE_CLASSES = buildPrimitiveClassSet();
 	public static final Set<Class<?>> WRAPPABLE_CLASSES = buildWrappableClassSet();
 
@@ -91,7 +99,7 @@ public class ToolOptions extends AbstractOptions {
 	public ToolOptions(Element root) {
 		this(root.getAttributeValue(NAME_ATTRIBUTE));
 
-		SaveState saveState = new SaveState(root);
+		AttributedSaveState saveState = new AttributedSaveState(root);
 
 		readNonWrappedOptions(saveState);
 
@@ -103,16 +111,35 @@ public class ToolOptions extends AbstractOptions {
 		}
 	}
 
-	private void readNonWrappedOptions(SaveState saveState) {
+	private void readNonWrappedOptions(AttributedSaveState saveState) {
 		for (String optionName : saveState.getNames()) {
 			Object object = saveState.getObject(optionName);
-			Option option =
-				createUnregisteredOption(optionName, OptionType.getOptionType(object), null);
+			OptionType type = OptionType.getOptionType(object);
+			Option option = createUnregisteredOption(optionName, type, null);
 			option.doSetCurrentValue(object);  // use doSet versus set so that it is not registered
+
+			LocalDate date = getLastRegisteredDateString(saveState, optionName);
+			option.setLastRegisteredDate(date);
+
 			valueMap.put(optionName, option);
 		}
 	}
 
+	private LocalDate getLastRegisteredDateString(AttributedSaveState saveState,
+			String optionName) {
+
+		// Get the last registered date.  No date implies an old xml format.
+		Map<String, String> attrs = saveState.getAttributes(optionName);
+		if (attrs != null) {
+			String dateString = attrs.get(LAST_REGISTERED_DATE_ATTIBUTE);
+			if (dateString != null) {
+				return LocalDate.parse(dateString, LAST_REGISTERED_DATE_FORMATTER);
+			}
+		}
+
+		return LocalDate.now();
+	}
+
 	private void readWrappedOptions(Element root) throws ReflectiveOperationException {
 
 		Iterator<?> it = root.getChildren(WRAPPED_OPTION_NAME).iterator();
@@ -124,19 +151,19 @@ public class ToolOptions extends AbstractOptions {
 				continue; // shouldn't happen
 			}
 
-			String optionName = element.getAttributeValue(NAME_ATTRIBUTE);
 			Class<?> c = Class.forName(element.getAttributeValue(CLASS_ATTRIBUTE));
 			Constructor<?> constructor = c.getDeclaredConstructor();
 			WrappedOption wo = (WrappedOption) constructor.newInstance();
 			wo.readState(new SaveState(element));
-
 			if (wo instanceof WrappedCustomOption wrappedCustom && !wrappedCustom.isValid()) {
 				continue;
 			}
+
 			if (wo instanceof WrappedKeyStroke wrappedKs) {
 				wo = wrappedKs.toWrappedActionTrigger();
 			}
 
+			String optionName = element.getAttributeValue(NAME_ATTRIBUTE);
 			Option option = createUnregisteredOption(optionName, wo.getOptionType(), null);
 			valueMap.put(optionName, option);
 
@@ -149,6 +176,15 @@ public class ToolOptions extends AbstractOptions {
 			else {
 				option.doSetCurrentValue(wo.getObject()); // use doSet so that it is not registered
 			}
+
+			// Get the last registered date.  No date implies an old xml format.
+			LocalDate date = LocalDate.now();
+			String dateString = element.getAttributeValue(LAST_REGISTERED_DATE_ATTIBUTE);
+			if (dateString != null) {
+				date = LocalDate.parse(dateString, LAST_REGISTERED_DATE_FORMATTER);
+			}
+
+			option.setLastRegisteredDate(date);
 		}
 	}
 
@@ -162,7 +198,7 @@ public class ToolOptions extends AbstractOptions {
 	 */
 	public Element getXmlRoot(boolean includeDefaultBindings) {
 
-		SaveState saveState = new SaveState(XML_ELEMENT_NAME);
+		AttributedSaveState saveState = new AttributedSaveState(XML_ELEMENT_NAME);
 
 		writeNonWrappedOptions(includeDefaultBindings, saveState);
 
@@ -174,18 +210,31 @@ public class ToolOptions extends AbstractOptions {
 		return root;
 	}
 
-	private void writeNonWrappedOptions(boolean includeDefaultBindings, SaveState saveState) {
+	private void writeNonWrappedOptions(boolean includeDefaultBindings,
+			AttributedSaveState saveState) {
 		for (String optionName : valueMap.keySet()) {
-			Option optionValue = valueMap.get(optionName);
-			if (includeDefaultBindings || !optionValue.isDefault()) {
-				Object value = optionValue.getValue(null);
-				if (isSupportedBySaveState(value)) {
-					saveState.putObject(optionName, value);
-				}
+			Option option = valueMap.get(optionName);
+			if (includeDefaultBindings || !option.isDefault()) {
+				writeNonWrappedOption(saveState, optionName, option);
 			}
 		}
 	}
 
+	private void writeNonWrappedOption(AttributedSaveState saveState, String optionName,
+			Option option) {
+		Object value = option.getValue(null);
+		if (!isSupportedBySaveState(value)) {
+			return;
+		}
+
+		saveState.putObject(optionName, value);
+
+		LocalDate date = option.getLastRegisteredDate();
+		String dateString = date.format(LAST_REGISTERED_DATE_FORMATTER);
+		Map<String, String> attrs = Map.of(LAST_REGISTERED_DATE_ATTIBUTE, dateString);
+		saveState.addAttributes(optionName, attrs);
+	}
+
 	private void writeWrappedOptions(boolean includeDefaultBindings, Element root) {
 		for (String optionName : valueMap.keySet()) {
 			Option option = valueMap.get(optionName);
@@ -195,36 +244,47 @@ public class ToolOptions extends AbstractOptions {
 			}
 
 			if (includeDefaultBindings || !option.isDefault()) {
-				Object value = option.getCurrentValue();
-				if (isSupportedBySaveState(value)) {
-					continue; // handled above
-				}
-
-				WrappedOption wrappedOption = wrapOption(option);
-				if (wrappedOption == null) {
-					continue; // cannot write an option without a value to determine its type
-				}
-
-				SaveState ss = new SaveState(WRAPPED_OPTION_NAME);
-				Element elem = null;
-				if (value == null) {
-					// Handle the null case ourselves, not using the wrapped option (and when
-					// reading from xml) so the logic does not need to be in each wrapped option
-					elem = ss.saveToXml();
-					elem.addContent(new Element(CLEARED_VALUE_ELEMENT_NAME));
-				}
-				else {
-					wrappedOption.writeState(ss);
-					elem = ss.saveToXml();
-				}
-
-				elem.setAttribute(NAME_ATTRIBUTE, optionName);
-				elem.setAttribute(CLASS_ATTRIBUTE, wrappedOption.getClass().getName());
-				root.addContent(elem);
+				writeWrappedOption(root, optionName, option);
 			}
 		}
 	}
 
+	private void writeWrappedOption(Element root, String optionName, Option option) {
+		Object value = option.getCurrentValue();
+		if (isSupportedBySaveState(value)) {
+			return; // handled above
+		}
+
+		WrappedOption wrappedOption = wrapOption(option);
+		if (wrappedOption == null) {
+			return; // cannot write an option without a value to determine its type
+		}
+
+		SaveState ss = new SaveState(WRAPPED_OPTION_NAME);
+		Element element = null;
+		if (value == null) {
+			// Handle the null case ourselves, not using the wrapped option (and when
+			// reading from xml) so the logic does not need to be in each wrapped option
+			element = ss.saveToXml();
+			element.addContent(new Element(CLEARED_VALUE_ELEMENT_NAME));
+		}
+		else {
+			wrappedOption.writeState(ss);
+			element = ss.saveToXml();
+		}
+
+		element.setAttribute(NAME_ATTRIBUTE, optionName);
+
+		String className = wrappedOption.getClass().getName();
+		element.setAttribute(CLASS_ATTRIBUTE, className);
+
+		LocalDate date = option.getLastRegisteredDate();
+		String dateString = date.format(LAST_REGISTERED_DATE_FORMATTER);
+		element.setAttribute(LAST_REGISTERED_DATE_ATTIBUTE, dateString);
+
+		root.addContent(element);
+	}
+
 	private boolean isSupportedBySaveState(Object obj) {
 		if (obj == null) {
 			return false;
@@ -310,7 +370,7 @@ public class ToolOptions extends AbstractOptions {
 		List<String> optionNames = new ArrayList<>(valueMap.keySet());
 		for (String optionName : optionNames) {
 			Option optionState = valueMap.get(optionName);
-			if (!optionState.isRegistered()) {
+			if (optionState.hasExpired()) {
 				removeOption(optionName);
 			}
 		}
@@ -377,11 +437,15 @@ public class ToolOptions extends AbstractOptions {
 		Set<String> keySet = valueMap.keySet();
 		for (String propertyName : keySet) {
 			Option optionState = valueMap.get(propertyName);
-			if (optionState.isRegistered()) {
+			if (optionState.isRegistered() || optionState.wasRegisteredInPreviousSession()) {
 				continue;
 			}
-			Msg.warn(this, "Unregistered property \"" + propertyName + "\" in Options \"" + name +
-				"\"\n     " + optionState.getInceptionInformation());
+
+			// getting here means that this option was used in the current tool session, but was not
+			// registered this session or in a previous session
+			Msg.warn(this,
+				"Unregistered property \"" + propertyName + "\" in Options \"" + name +
+					"\"\n     " + optionState.getInceptionInformation());
 		}
 	}
 
diff --git a/Ghidra/Framework/Gui/src/main/java/ghidra/framework/options/WrappedOption.java b/Ghidra/Framework/Gui/src/main/java/ghidra/framework/options/WrappedOption.java
index 71bae742b6..8a438afd14 100644
--- a/Ghidra/Framework/Gui/src/main/java/ghidra/framework/options/WrappedOption.java
+++ b/Ghidra/Framework/Gui/src/main/java/ghidra/framework/options/WrappedOption.java
@@ -1,13 +1,12 @@
 /* ###
  * IP: GHIDRA
- * REVIEWED: YES
  *
  * 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.
@@ -17,30 +16,29 @@
 package ghidra.framework.options;
 
 /**
- * Wrapper class for an object that represents a property value and is
- * saved as a set of primitives.
+ * Wrapper class for an object that represents a property value and is saved as a set of primitives.
  */
 public interface WrappedOption {
 
 	/**
-	 * Get the object that is the property value.
+	 * {@return Get the object that is the property value}
 	 */
 	public abstract Object getObject();
 
 	/**
-	 * Concrete subclass of WrappedOption should read all of its
-	 * state from the given saveState object.
+	 * Subclasses of WrappedOption should read all state from the given save state object.
 	 * @param saveState container of state information
 	 */
 	public abstract void readState(SaveState saveState);
 
 	/**
-	 * Concrete subclass of WrappedOption should write all of its
-	 * state to the given saveState object.
+	 * Subclasses of WrappedOption should write all state to the given save state object.
 	 * @param saveState container of state information
 	 */
 	public abstract void writeState(SaveState saveState);
 
+	/**
+	 * {@return the option type}
+	 */
 	public abstract OptionType getOptionType();
-
 }
diff --git a/Ghidra/Framework/Utility/src/main/java/ghidra/GhidraApplicationLayout.java b/Ghidra/Framework/Utility/src/main/java/ghidra/GhidraApplicationLayout.java
index e0a9336ad3..619213ae65 100644
--- a/Ghidra/Framework/Utility/src/main/java/ghidra/GhidraApplicationLayout.java
+++ b/Ghidra/Framework/Utility/src/main/java/ghidra/GhidraApplicationLayout.java
@@ -227,9 +227,8 @@ public class GhidraApplicationLayout extends ApplicationLayout {
 	 * Returns a prioritized list of directories where Ghidra extensions are installed. These
 	 * should be at the following locations:<br>
 	 * <ul>
-	 * <li><code>[user settings dir]/Extensions</code></li>
-	 * <li><code>[application install dir]/Ghidra/Extensions</code> (Release Mode)</li>
-	 * <li><code>ghidra/Ghidra/Extensions</code> (Development Mode)</li>
+	 * <li>{@code [user settings dir]/Extensions}</li>
+	 * <li>{@code [application root dirs]/Extensions}</li>
 	 * </ul>
 	 *
 	 * @return the install folder, or null if can't be determined
diff --git a/Ghidra/Framework/Utility/src/main/java/utility/application/ApplicationLayout.java b/Ghidra/Framework/Utility/src/main/java/utility/application/ApplicationLayout.java
index a7fd7b0653..e7967d3051 100644
--- a/Ghidra/Framework/Utility/src/main/java/utility/application/ApplicationLayout.java
+++ b/Ghidra/Framework/Utility/src/main/java/utility/application/ApplicationLayout.java
@@ -129,9 +129,8 @@ public abstract class ApplicationLayout {
 	 * Returns a prioritized {@link List ordered list} of the application Extensions installation 
 	 * directories.   Typically, the values may be any of the following locations:<br>
 	 * <ul>
-	 * <li><code>[user settings dir]/Extensions</code></li>
-	 * <li><code>[application install dir]/Ghidra/Extensions</code> (Release Mode)</li>
-	 * <li><code>ghidra/Ghidra/Extensions</code> (Development Mode)</li>
+	 * <li>{@code [user settings dir]/Extensions}</li>
+	 * <li>{@code [application root dirs]/Extensions}</li>
 	 * </ul>
 	 *
 	 * @return an {@link List ordered list} of the application Extensions installation directories.
diff --git a/GhidraBuild/MarkdownSupport/src/main/java/ghidra/markdown/MarkdownToHtml.java b/GhidraBuild/MarkdownSupport/src/main/java/ghidra/markdown/MarkdownToHtml.java
index 2d73ccf79e..d1821def11 100644
--- a/GhidraBuild/MarkdownSupport/src/main/java/ghidra/markdown/MarkdownToHtml.java
+++ b/GhidraBuild/MarkdownSupport/src/main/java/ghidra/markdown/MarkdownToHtml.java
@@ -127,9 +127,31 @@ public class MarkdownToHtml {
 
 		@Override
 		public void setAttributes(Node node, String tagName, Map<String, String> attributes) {
-			if (node instanceof Code || node instanceof IndentedCodeBlock ||
-				node instanceof FencedCodeBlock) {
-				attributes.put("style", "background-color: #eef;");
+			// NOTE: This method will get called on both the <pre> and <code> tags, so be careful
+			// not to apply things twice
+
+			if (node instanceof FencedCodeBlock && tagName.equals("pre")) {
+				StringBuilder sb = new StringBuilder();
+				sb.append("background: #f4f4f4;");
+				sb.append("border: 1px solid #ddd;");
+				sb.append("border-left: 3px solid #f36d33;");
+				sb.append("color: #666;");
+				sb.append("display: block;");
+				sb.append("font-family: monospace;");
+				sb.append("line-height: 1.6;");
+				sb.append("margin-bottom: 1.6em;");
+				sb.append("max-width: 100%;");
+				sb.append("overflow: auto;");
+				sb.append("padding: 1em 1.5em;");
+				sb.append("page-break-inside: avoid;");
+				sb.append("word-wrap: break-word;");
+				attributes.put("style", sb.toString());
+			}
+			else if (node instanceof Code || node instanceof IndentedCodeBlock) {
+				StringBuilder sb = new StringBuilder();
+				sb.append("background: #f4f4f4;");
+				sb.append("font-family: monospace;");
+				attributes.put("style", sb.toString());
 			}
 		}
 	}