diff --git a/eclipse-extensions/org.springframework.ide.eclipse.boot/plugin.xml b/eclipse-extensions/org.springframework.ide.eclipse.boot/plugin.xml
index cbc4b5e3d..0996cf6f2 100644
--- a/eclipse-extensions/org.springframework.ide.eclipse.boot/plugin.xml
+++ b/eclipse-extensions/org.springframework.ide.eclipse.boot/plugin.xml
@@ -11,7 +11,7 @@
           class="org.springframework.ide.eclipse.boot.core.BootPropertyTester"
           id="org.springsource.ide.eclipse.boot.BootPropertyTester"
           namespace="org.springsource.ide.eclipse.boot"
-          properties="isBootProject,isBootResource,hasBootDevTools"
+          properties="isBootProject,isBootResource,hasBootDevTools,isBoot2Project,isBoot2Resource"
           type="org.eclipse.core.resources.IResource">
     <!--       type="java.lang.Object" -->
     </propertyTester>
@@ -19,7 +19,7 @@
           class="org.springframework.ide.eclipse.boot.core.BootJavaElementPropertyTester"
           id="org.springframework.ide.eclipse.boot.core.BootJavaElementPropertyTester"
           namespace="org.springsource.ide.eclipse.boot.javaelement"
-          properties="isInBootProject,isInBootProjectWithDevTools"
+          properties="isInBootProject,isInBootProjectWithDevTools,isInBoot2Project"
           type="org.eclipse.jdt.core.IJavaElement">
     <!--       type="java.lang.Object" -->
     </propertyTester>
diff --git a/eclipse-extensions/org.springframework.ide.eclipse.boot/src/org/springframework/ide/eclipse/boot/core/BootJavaElementPropertyTester.java b/eclipse-extensions/org.springframework.ide.eclipse.boot/src/org/springframework/ide/eclipse/boot/core/BootJavaElementPropertyTester.java
index 4f525da81..6a0cbcc80 100644
--- a/eclipse-extensions/org.springframework.ide.eclipse.boot/src/org/springframework/ide/eclipse/boot/core/BootJavaElementPropertyTester.java
+++ b/eclipse-extensions/org.springframework.ide.eclipse.boot/src/org/springframework/ide/eclipse/boot/core/BootJavaElementPropertyTester.java
@@ -31,6 +31,19 @@ public class BootJavaElementPropertyTester extends PropertyTester {
 		if (je instanceof IJavaElement && "isInBootProjectWithDevTools".equals(property)) {
 			return hasBootDevTools((IJavaElement) je);
 		}
+		if (je instanceof IJavaElement && "isInBoot2Project".equals(property)) {
+			return isInBoot2Project((IJavaElement) je);
+		}
+		return false;
+	}
+
+	private boolean isInBoot2Project(IJavaElement je) {
+		if (je!=null) {
+			IJavaProject jp = je.getJavaProject();
+			if (jp!=null) {
+				return BootPropertyTester.isBoot2Project(jp.getProject());
+			}
+		}
 		return false;
 	}
 
diff --git a/eclipse-extensions/org.springframework.ide.eclipse.boot/src/org/springframework/ide/eclipse/boot/core/BootPropertyTester.java b/eclipse-extensions/org.springframework.ide.eclipse.boot/src/org/springframework/ide/eclipse/boot/core/BootPropertyTester.java
index 260da08ee..371597e15 100644
--- a/eclipse-extensions/org.springframework.ide.eclipse.boot/src/org/springframework/ide/eclipse/boot/core/BootPropertyTester.java
+++ b/eclipse-extensions/org.springframework.ide.eclipse.boot/src/org/springframework/ide/eclipse/boot/core/BootPropertyTester.java
@@ -70,6 +70,12 @@ public class BootPropertyTester extends PropertyTester {
 		if (rsrc instanceof IResource && "hasBootDevTools".equals(property)) {
 			return hasBootDevTools(((IResource) rsrc).getProject());
 		}
+		if (rsrc instanceof IProject && "isBoot2Project".equals(property)) {
+			return expectedValue.equals(isBoot2Project((IProject)rsrc));
+		}
+		if (rsrc instanceof IResource && "isBoot2Resource".equals(property)) {
+			return expectedValue.equals(isBoot2Resource((IResource) rsrc));
+		}
 		return false;
 	}
 
@@ -128,6 +134,30 @@ public class BootPropertyTester extends PropertyTester {
 		return false;
 	}
 
+	public static boolean isBoot2Project(IProject project) {
+		if (project==null || ! project.isAccessible()) {
+			return false;
+		}
+		try {
+			if (project.hasNature(JavaCore.NATURE_ID)) {
+				if (!isExcludedProject(project)) {
+					IJavaProject jp = JavaCore.create(project);
+					IClasspathEntry[] classpath = jp.getResolvedClasspath(true);
+					//Look for a 'spring-boot' jar or project entry
+
+					for (IClasspathEntry e : classpath) {
+						if ((isBootJar(e) || isBootProject(e)) && isVersion(e, "2.")) {
+							return true;
+						}
+					}
+				}
+			}
+		} catch (Exception e) {
+			CorePlugin.log(e);
+		}
+		return false;
+	}
+
 	public static boolean hasBootDevTools(IProject project) {
 		try {
 			ISpringBootProject bootProject = SpringBootCore.getDefault().project(project);
@@ -231,6 +261,14 @@ public class BootPropertyTester extends PropertyTester {
 		return result;
 	}
 
+	private Object isBoot2Resource(IResource rsrc) {
+		if (rsrc==null || ! rsrc.isAccessible()) {
+			return false;
+		}
+		boolean result = isBoot2Project(rsrc.getProject());
+		return result;
+	}
+
 	public static boolean isBootProject(IClasspathEntry e) {
 		if (e.getEntryKind()==IClasspathEntry.CPE_PROJECT) {
 			IPath path = e.getPath();
@@ -240,6 +278,16 @@ public class BootPropertyTester extends PropertyTester {
 		return false;
 	}
 
+	public static boolean isVersion(IClasspathEntry e, String v) {
+		if (e.getEntryKind() == IClasspathEntry.CPE_LIBRARY) {
+			IPath path = e.getPath();
+			String name = path.lastSegment();
+			String version = getVersionFromJarName(name);
+			return version.startsWith(v);
+		}
+		return false;
+	}
+
 	public static boolean isBootJar(IClasspathEntry e) {
 		if (e.getEntryKind()==IClasspathEntry.CPE_LIBRARY) {
 			IPath path = e.getPath();
diff --git a/eclipse-language-servers/org.springframework.tooling.boot.ls/plugin.xml b/eclipse-language-servers/org.springframework.tooling.boot.ls/plugin.xml
index 504c33d20..44d3069bc 100644
--- a/eclipse-language-servers/org.springframework.tooling.boot.ls/plugin.xml
+++ b/eclipse-language-servers/org.springframework.tooling.boot.ls/plugin.xml
@@ -173,6 +173,10 @@
               </with>
             </activeWhen>
       </handler>
+      <handler
+            class="org.springframework.tooling.boot.ls.commands.UpgradeToBoot3Handler"
+            commandId="org.springframework.tooling.boot.ls.UpgradeToBoot3">
+      </handler>
    </extension>
    <extension
          point="org.eclipse.ui.commands">
@@ -187,6 +191,12 @@
             categoryId="org.springframework.ide.eclipse.commands"
             name="Toggle Comment">
       </command>
+      <command
+            categoryId="org.springframework.ide.eclipse.commands"
+            description="Upgrade Spring Boot 2.x prohect to Spring Boot 3.x"
+            id="org.springframework.tooling.boot.ls.UpgradeToBoot3"
+            name="Upgrade to Boot 3">
+      </command>
    </extension>
 
 	<extension
@@ -355,6 +365,70 @@
             class="org.springframework.tooling.boot.ls.prefs.RemoteAppsFromPrefsDataContributor">
       </injection>
    </extension>
+   <extension
+         point="org.eclipse.ui.menus">
+      <menuContribution
+            allPopups="false"
+            locationURI="popup:org.springframework.ide.eclipse.ui.tools?after=boot">
+         <command
+               commandId="org.springframework.tooling.boot.ls.UpgradeToBoot3"
+               id="org.springframework.tooling.boot.ls.UpgradeToBoot3"
+               label="Upgrade to Boot 3"
+               style="push">
+            <visibleWhen
+                  checkEnabled="false">
+               <and>
+                  <count
+                        value="1">
+                  </count>
+                  <iterate>
+                     <or>
+                        <adapt
+                              type="org.eclipse.core.resources.IResource">
+                           <and>
+                              <test
+                                    forcePluginActivation="true"
+                                    property="org.springsource.ide.eclipse.boot.isBoot2Resource">
+                              </test>
+                              <or>
+                                 <test
+                                       property="org.eclipse.core.resources.name"
+                                       value="pom.xml">
+                                 </test>
+                                 <adapt
+                                       type="org.eclipse.core.resources.IProject">
+                                    <test
+                                          property="org.eclipse.core.resources.projectNature"
+                                          value="org.eclipse.m2e.core.maven2Nature">
+                                    </test>
+                                 </adapt>
+                              </or>
+                           </and>
+                        </adapt>
+                        <and>
+                           <instanceof
+                                 value="org.eclipse.jdt.core.IJavaProject">
+                           </instanceof>
+                           <test
+                                 property="org.springsource.ide.eclipse.commons.java.projectNature"
+                                 value="org.eclipse.m2e.core.maven2Nature">
+                           </test>
+                           <test
+                                 forcePluginActivation="true"
+                                 property="org.springsource.ide.eclipse.boot.javaelement.isInBoot2Project">
+                           </test>
+                        </and>
+                     </or>
+                  </iterate>
+                  <systemTest
+                        property="sts.rewrite.recipes"
+                        value="true">
+                  </systemTest>
+               </and>
+            </visibleWhen>
+         </command>
+      </menuContribution>
+   </extension>
 <!--
    <extension
          point="org.eclipse.wildwebdeveloper.xml.lemminxExtension">
diff --git a/eclipse-language-servers/org.springframework.tooling.boot.ls/src/org/springframework/tooling/boot/ls/commands/UpgradeToBoot3Handler.java b/eclipse-language-servers/org.springframework.tooling.boot.ls/src/org/springframework/tooling/boot/ls/commands/UpgradeToBoot3Handler.java
new file mode 100644
index 000000000..572771b9f
--- /dev/null
+++ b/eclipse-language-servers/org.springframework.tooling.boot.ls/src/org/springframework/tooling/boot/ls/commands/UpgradeToBoot3Handler.java
@@ -0,0 +1,62 @@
+/*******************************************************************************
+ * Copyright (c) 2022 VMware, Inc.
+ * All rights reserved. This program and the accompanying materials
+ * are made available under the terms of the Eclipse Public License v1.0
+ * which accompanies this distribution, and is available at
+ * https://www.eclipse.org/legal/epl-v10.html
+ *
+ * Contributors:
+ *     VMware, Inc. - initial API and implementation
+ *******************************************************************************/
+package org.springframework.tooling.boot.ls.commands;
+
+import java.util.List;
+import java.util.concurrent.CompletableFuture;
+
+import org.eclipse.core.commands.AbstractHandler;
+import org.eclipse.core.commands.ExecutionEvent;
+import org.eclipse.core.commands.ExecutionException;
+import org.eclipse.core.resources.IProject;
+import org.eclipse.core.resources.IResource;
+import org.eclipse.jdt.annotation.NonNull;
+import org.eclipse.jface.viewers.IStructuredSelection;
+import org.eclipse.lsp4e.LanguageServiceAccessor;
+import org.eclipse.lsp4j.ExecuteCommandParams;
+import org.eclipse.lsp4j.services.LanguageServer;
+import org.eclipse.ui.handlers.HandlerUtil;
+import org.springsource.ide.eclipse.commons.livexp.util.Log;
+
+public class UpgradeToBoot3Handler extends AbstractHandler {
+	
+	private static final String UPGRADE_TO_BOOT_3_COMMAND_ID = "sts/rewrite/recipe/org.openrewrite.java.spring.boot3.UpgradeSpringBoot_3_0";
+	
+	@Override
+	public Object execute(ExecutionEvent event) throws ExecutionException {
+		
+		IStructuredSelection selection = HandlerUtil.getCurrentStructuredSelection(event);
+		Object o = selection.getFirstElement();
+		if (o instanceof IResource) {
+			IProject project = ((IResource) o).getProject();
+			if (project != null) {
+				List<@NonNull LanguageServer> usedLanguageServers = LanguageServiceAccessor.getActiveLanguageServers(serverCapabilities -> true);
+
+				if (!usedLanguageServers.isEmpty()) {
+					ExecuteCommandParams commandParams = new ExecuteCommandParams();
+					commandParams.setCommand(UPGRADE_TO_BOOT_3_COMMAND_ID);					
+					commandParams.setArguments(List.of(project.getLocationURI().toString()));
+
+					try {
+						CompletableFuture.allOf(usedLanguageServers.stream().map(ls ->
+							ls.getWorkspaceService().executeCommand(commandParams)).toArray(CompletableFuture[]::new));
+					}
+					catch (Exception e) {
+						Log.log(e);
+					}
+				}
+				
+			}
+		}
+		return null;
+	}
+
+}
diff --git a/headless-services/commons/commons-java/src/main/java/org/springframework/ide/vscode/commons/jandex/BasicJandexIndex.java b/headless-services/commons/commons-java/src/main/java/org/springframework/ide/vscode/commons/jandex/BasicJandexIndex.java
index cb3c26486..dcbe182e2 100644
--- a/headless-services/commons/commons-java/src/main/java/org/springframework/ide/vscode/commons/jandex/BasicJandexIndex.java
+++ b/headless-services/commons/commons-java/src/main/java/org/springframework/ide/vscode/commons/jandex/BasicJandexIndex.java
@@ -45,7 +45,7 @@ public class BasicJandexIndex {
 
 	private static final Logger log = LoggerFactory.getLogger(BasicJandexIndex.class);
 
-	private static final String JAVA_IO_TMPDIR = "java.io.tmpdir";
+	private static final String USER_HOME = "user.home";
 
 	@FunctionalInterface
 	public static interface IndexFileFinder {
@@ -53,7 +53,7 @@ public class BasicJandexIndex {
 	}
 
 	public static File getIndexFolder() {
-		File folder = new File(System.getProperty(JAVA_IO_TMPDIR), "jandex");
+		File folder = new File(System.getProperty(USER_HOME), ".sts-jandex");
 		if (!folder.isDirectory()) {
 			folder.mkdirs();
 		}