diff --git a/headless-services/commons/commons-boot-app-cli/src/main/java/org/springframework/ide/vscode/commons/boot/app/cli/AbstractSpringBootApp.java b/headless-services/commons/commons-boot-app-cli/src/main/java/org/springframework/ide/vscode/commons/boot/app/cli/AbstractSpringBootApp.java
index 0d36ba88b..cd345e60f 100644
--- a/headless-services/commons/commons-boot-app-cli/src/main/java/org/springframework/ide/vscode/commons/boot/app/cli/AbstractSpringBootApp.java
+++ b/headless-services/commons/commons-boot-app-cli/src/main/java/org/springframework/ide/vscode/commons/boot/app/cli/AbstractSpringBootApp.java
@@ -397,7 +397,19 @@ public abstract class AbstractSpringBootApp implements SpringBootApp {
 	@Override
 	public String getContextPath() throws Exception {
 		String environment = getEnvironment();
-		return environment != null ? ContextPath.getContextPath(environment) : null;
+		String bootVersion = null;
+		// Boot 1.x
+		Object result = getActuatorDataFromAttribute(getObjectName("type=Endpoint,name=requestMappingEndpoint"), "Data");
+		if (result != null) {
+			bootVersion = "1.x";
+		}
+
+		// Boot 2.x
+		result = getActuatorDataFromOperation(getObjectName("type=Endpoint,name=Mappings"), "mappings");
+		if (result != null) {
+			bootVersion = "2.x";
+		}
+		return bootVersion != null && environment != null ? ContextPath.getContextPath(bootVersion, environment) : null;
 	}
 
 	/**
diff --git a/headless-services/commons/commons-boot-app-cli/src/main/java/org/springframework/ide/vscode/commons/boot/app/cli/ContextPath.java b/headless-services/commons/commons-boot-app-cli/src/main/java/org/springframework/ide/vscode/commons/boot/app/cli/ContextPath.java
index 124e9ab7b..a387df8f2 100644
--- a/headless-services/commons/commons-boot-app-cli/src/main/java/org/springframework/ide/vscode/commons/boot/app/cli/ContextPath.java
+++ b/headless-services/commons/commons-boot-app-cli/src/main/java/org/springframework/ide/vscode/commons/boot/app/cli/ContextPath.java
@@ -10,6 +10,7 @@
  *******************************************************************************/
 package org.springframework.ide.vscode.commons.boot.app.cli;
 
+import java.util.Collection;
 import java.util.Set;
 
 import org.json.JSONArray;
@@ -18,21 +19,36 @@ import org.slf4j.Logger;
 import org.slf4j.LoggerFactory;
 import org.springframework.ide.vscode.commons.util.StringUtil;
 
+import com.google.common.collect.ImmutableList;
+
 public class ContextPath {
 
 	protected static Logger logger = LoggerFactory.getLogger(ContextPath.class);
 
-	public static final String[] CONTEXTPATH = { "server.context-path", "server.contextPath", "SERVER_CONTEXT_PATH",
-			"server.servlet.context-path", "server.servlet.contextPath", "SERVER_SERVLET_CONTEXT_PATH" };
+	public static final Collection<String> BOOT_1X_CONTEXTPATH = ImmutableList.of("server.context-path",
+			"server.contextPath");
 
-	public static String getContextPath(String environment) {
+	public static final Collection<String> BOOT_2X_CONTEXTPATH = ImmutableList.of("server.servlet.context-path",
+			"server.servlet.contextPath");
+
+	public static String getContextPath(String bootVersion, String environment) {
 
 		if (environment != null) {
 			JSONObject env = new JSONObject(environment);
-			for (String prop : CONTEXTPATH) {
-				String contextPath = findContextPath(env, prop);
-				if (StringUtil.hasText(contextPath)) {
-					return contextPath;
+
+			Collection<String> contextPathProperties = null;
+			if ("1.x".equals(bootVersion)) {
+				contextPathProperties = BOOT_1X_CONTEXTPATH;
+			} else if ("2.x".equals(bootVersion)) {
+				contextPathProperties = BOOT_2X_CONTEXTPATH;
+			}
+
+			if (contextPathProperties != null) {
+				for (String prop : contextPathProperties) {
+					String contextPath = findContextPath(env, prop);
+					if (StringUtil.hasText(contextPath)) {
+						return contextPath;
+					}
 				}
 			}
 		}