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 f9044602e..712b43057 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
@@ -11,7 +11,6 @@
 package org.springframework.ide.vscode.commons.boot.app.cli;
 
 import java.util.Collection;
-import java.util.Set;
 
 import org.json.JSONArray;
 import org.json.JSONObject;
@@ -26,56 +25,37 @@ public class ContextPath {
 	protected static Logger logger = LoggerFactory.getLogger(ContextPath.class);
 
 	public static final Collection<String> BOOT_1X_CONTEXTPATH = ImmutableList.of("server.context-path",
-			"server.contextPath");
+			"server.contextPath", "SERVER_CONTEXT_PATH");
 
 	public static final Collection<String> BOOT_2X_CONTEXTPATH = ImmutableList.of("server.servlet.context-path",
-			"server.servlet.contextPath");
+			"server.servlet.contextPath", "SERVER_SERVLET_CONTEXT_PATH");
 
 	public static String getContextPath(String bootVersion, String environment) {
+		String contextPath = null;
 		if (environment != null) {
 			JSONObject env = new JSONObject(environment);
 
-			Collection<String> contextPathProperties = null;
 			if ("1.x".equals(bootVersion)) {
-				contextPathProperties = BOOT_1X_CONTEXTPATH;
+				contextPath = findContextPathInBoot1x(env);
 			} 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;
-					}
-				}
+				contextPath = findContextPathInBoot2x(env);
 			}
 		}
 
-		return null;
-	}
-
-	private static String findContextPath(JSONObject env, String contextPathProp) {
-		String contextPath = null;
-		if (env != null) {
-			// Properties defined in command line args have higher priority over
-			// those defined in application configuration files (properties/yaml files)
-			contextPath = findInCommandLineArgs(env, contextPathProp);
-			if (contextPath == null) {
-				contextPath = findInApplicationConfig(env, contextPathProp);
-			}
-		}
 		return contextPath;
 	}
 
-	private static String findInApplicationConfig(JSONObject env, String contextPathProp) {
-		// boot 1.x
-		JSONObject applicationConfig = null;
+	private static String findContextPathInBoot1x(JSONObject env) {
+		// IMPORTANT: The order in which the env objects appear are assumed to be the
+		// priority order defined
+		// by boot rules in terms of which property source has higher precedence. Iterate
+		// through ALL
+		// sources in the order obtained from the env JSON
 		for (String key : env.keySet()) {
-			if (key.startsWith("applicationConfig")) {
-				applicationConfig = env.getJSONObject(key);
-				if (applicationConfig != null) {
-					String contextPathValue = applicationConfig.optString(contextPathProp);
+			JSONObject jsonObj = env.optJSONObject(key);
+			if (jsonObj != null) {
+				for (String prop : BOOT_1X_CONTEXTPATH) {
+					String contextPathValue = jsonObj.optString(prop);
 					// Warning: fetching value above may return empty string, so null check on the
 					// value is not enough
 					if (StringUtil.hasText(contextPathValue)) {
@@ -84,70 +64,27 @@ public class ContextPath {
 				}
 			}
 		}
-
-		// boot 2.x
-		if (applicationConfig == null) {
-			// Not found as direct property value... in Boot 2.0 we must look inside the
-			// 'propertySources'.
-			// Similar... but structure is more complex.
-			JSONArray propertySources = env.optJSONArray("propertySources");
-			if (propertySources != null) {
-				for (Object _source : propertySources) {
-					if (_source instanceof JSONObject) {
-						JSONObject source = (JSONObject) _source;
-						String sourceName = source.optString("name");
-						if (sourceName != null && sourceName.startsWith("applicationConfig")) {
-							JSONObject props = source.optJSONObject("properties");
-							Set<String> keySet = props.keySet();
-							// Check that the context is a key before retrieving the JSON object value.
-							// Note: attempting to fetch the JSON object value on a key that may not exist
-							// throws exception
-							// thus the reason why we are checking that the key exists first
-							if (keySet.contains(contextPathProp)) {
-								JSONObject jsonObject = props.getJSONObject(contextPathProp);
-								if (jsonObject != null) {
-									String contextPathValue = jsonObject.optString("value");
-									if (StringUtil.hasText(contextPathValue)) {
-										return contextPathValue;
-									}
-								}
-							}
-						}
-					}
-				}
-			}
-		}
 		return null;
 	}
 
-	protected static String findInCommandLineArgs(JSONObject env, String contextPathProp) {
-		// boot 1.x
-		JSONObject commandLineArgs = env.optJSONObject("commandLineArgs");
-		if (commandLineArgs != null) {
-			String contextPathValue = commandLineArgs.optString(contextPathProp);
-			// Warning: fetching value above may return empty string, so null check on the
-			// value is not enough
-			if (StringUtil.hasText(contextPathValue)) {
-				return contextPathValue;
-			}
-		}
-		// boot 2.x
-		if (commandLineArgs == null) {
-			// Not found as direct property value... in Boot 2.0 we must look inside the
-			// 'propertySources'.
-			// Similar... but structure is more complex.
-			JSONArray propertySources = env.optJSONArray("propertySources");
-			if (propertySources != null) {
-				for (Object _source : propertySources) {
-					if (_source instanceof JSONObject) {
-						JSONObject source = (JSONObject) _source;
-						String sourceName = source.optString("name");
-						if ("commandLineArgs".equals(sourceName)) {
-							JSONObject props = source.optJSONObject("properties");
-							// Find the contextPathProp in the command line args
-							JSONObject valueObject = props.optJSONObject(contextPathProp);
-							if (valueObject != null) {
-								String contextPathValue = valueObject.optString("value");
+	private static String findContextPathInBoot2x(JSONObject env) {
+		JSONArray propertySources = env.optJSONArray("propertySources");
+		if (propertySources != null) {
+
+			// IMPORTANT: The order in which the env objects appear are assumed to be the
+			// priority order defined
+			// by boot rules in terms of which property source has higher precedence. Iterate
+			// through ALL
+			// sources in the order obtained from the env JSON
+			for (Object _source : propertySources) {
+				if (_source instanceof JSONObject) {
+					JSONObject source = (JSONObject) _source;
+					JSONObject props = source.optJSONObject("properties");
+					if (props != null) {
+						for (String property : BOOT_2X_CONTEXTPATH) {
+							JSONObject propertyObj = props.optJSONObject(property);
+							if (propertyObj != null) {
+								String contextPathValue = propertyObj.optString("value");
 								if (StringUtil.hasText(contextPathValue)) {
 									return contextPathValue;
 								}