diff --git a/tests/src/main/java/io/openliberty/tools/eclipse/test/it/LibertyPluginSWTBotLSP4JakartaTest.java b/tests/src/main/java/io/openliberty/tools/eclipse/test/it/LibertyPluginSWTBotLSP4JakartaTest.java
index 93be2785..ad20d518 100644
--- a/tests/src/main/java/io/openliberty/tools/eclipse/test/it/LibertyPluginSWTBotLSP4JakartaTest.java
+++ b/tests/src/main/java/io/openliberty/tools/eclipse/test/it/LibertyPluginSWTBotLSP4JakartaTest.java
@@ -1,5 +1,5 @@
 /*******************************************************************************
-* Copyright (c) 2022, 2023 IBM Corporation and others.
+* Copyright (c) 2023 IBM Corporation and others.
 *
 * This program and the accompanying materials are made available under the
 * terms of the Eclipse Public License v. 2.0 which is available at
@@ -12,6 +12,8 @@
 *******************************************************************************/
 package io.openliberty.tools.eclipse.test.it;
 
+import static io.openliberty.tools.eclipse.test.it.utils.MagicWidgetFinder.goGlobal;
+import static io.openliberty.tools.eclipse.test.it.utils.SWTBotPluginOperations.launchDashboardAction;
 import static org.junit.jupiter.api.Assertions.assertTrue;
 
 import java.io.File;
@@ -29,6 +31,7 @@
 
 import io.openliberty.tools.eclipse.test.it.utils.LibertyPluginTestUtils;
 import io.openliberty.tools.eclipse.test.it.utils.SWTBotPluginOperations;
+import io.openliberty.tools.eclipse.ui.dashboard.DashboardView;
 
 /**
  * Tests LSP4Jakarta functionality within Liberty Tools for Eclipse
@@ -106,27 +109,52 @@ public static void cleanup() {
     public void testClassLevelSnippets() {
 
         try {
+            // Start dev mode.
+            launchDashboardAction(MVN_WRAPPER_APP_NAME, DashboardView.APP_MENU_ACTION_START);
+
+            goGlobal("Terminal");
+
+            // Validate application is up and running.
+            LibertyPluginTestUtils.validateApplicationOutcome(MVN_WRAPPER_APP_NAME, true,
+                    wrapperProjectPath.toAbsolutePath().toString() + "/target/liberty");
+
             // Open new class file
             SWTBotPluginOperations.createNewClass(bot, MVN_WRAPPER_APP_NAME, "MyClass", true);
 
             // Get type-ahead list
-            List<String> typeAheadOptions = SWTBotPluginOperations.getTypeAheadList(bot, "MyClass.java", "", 0, 0);
-
             boolean allFound = true;
             List<String> missingOptions = new ArrayList<String>();
-            for (String option : typeAheadOptions_classLevel) {
-                if (!typeAheadOptions.contains(option)) {
-                    allFound = false;
-                    missingOptions.add(option);
+
+            int i = 0;
+            while (i < 3) {
+                List<String> typeAheadOptions = SWTBotPluginOperations.getTypeAheadList(bot, "MyClass.java", "", 0, 0);
+                System.out.println("INFO: Type-ahead options found = " + Arrays.toString(typeAheadOptions.toArray()));
+
+                allFound = true;
+                missingOptions = new ArrayList<String>();
+                for (String option : typeAheadOptions_classLevel) {
+                    if (!typeAheadOptions.contains(option)) {
+                        allFound = false;
+                        missingOptions.add(option);
+                    }
                 }
+                i++;
             }
 
             assertTrue(allFound, "Missing type-ahead options: " + Arrays.toString(missingOptions.toArray()));
 
+        } catch (Exception e) {
+            System.out.println("Caught exception: " + e);
         } finally {
 
             // Delete new file
             LibertyPluginTestUtils.deleteFile(new File(wrapperProjectPath + "/src/main/java/test/maven/liberty/web/app/MyClass.java"));
+
+            // Stop dev mode.
+            launchDashboardAction(MVN_WRAPPER_APP_NAME, DashboardView.APP_MENU_ACTION_STOP);
+
+            // Validate application stopped.
+            LibertyPluginTestUtils.validateLibertyServerStopped(wrapperProjectPath.toAbsolutePath().toString() + "/target/liberty");
         }
     }
 
@@ -137,27 +165,52 @@ public void testClassLevelSnippets() {
     public void testInClassSnippets() {
 
         try {
+            // Start dev mode.
+            launchDashboardAction(MVN_WRAPPER_APP_NAME, DashboardView.APP_MENU_ACTION_START);
+
+            goGlobal("Terminal");
+
+            // Validate application is up and running.
+            LibertyPluginTestUtils.validateApplicationOutcome(MVN_WRAPPER_APP_NAME, true,
+                    wrapperProjectPath.toAbsolutePath().toString() + "/target/liberty");
+
             // Open new class file
             SWTBotPluginOperations.createNewClass(bot, MVN_WRAPPER_APP_NAME, "MyClass", false);
 
             // Get type-ahead list
-            List<String> typeAheadOptions = SWTBotPluginOperations.getTypeAheadList(bot, "MyClass.java", "", 3, 0);
-
             boolean allFound = true;
             List<String> missingOptions = new ArrayList<String>();
-            for (String option : typeAheadOptions_inClass) {
-                if (!typeAheadOptions.contains(option)) {
-                    allFound = false;
-                    missingOptions.add(option);
+
+            int i = 0;
+            while (i < 3) {
+                List<String> typeAheadOptions = SWTBotPluginOperations.getTypeAheadList(bot, "MyClass.java", "", 3, 0);
+                System.out.println("INFO: Type-ahead options found = " + Arrays.toString(typeAheadOptions.toArray()));
+
+                allFound = true;
+                missingOptions = new ArrayList<String>();
+                for (String option : typeAheadOptions_inClass) {
+                    if (!typeAheadOptions.contains(option)) {
+                        allFound = false;
+                        missingOptions.add(option);
+                    }
                 }
+                i++;
             }
 
             assertTrue(allFound, "Missing type-ahead options: " + Arrays.toString(missingOptions.toArray()));
 
+        } catch (Exception e) {
+            System.out.println("Caught exception: " + e);
         } finally {
 
             // Delete new file
             LibertyPluginTestUtils.deleteFile(new File(wrapperProjectPath + "/src/main/java/test/maven/liberty/web/app/MyClass.java"));
+
+            // Stop dev mode.
+            launchDashboardAction(MVN_WRAPPER_APP_NAME, DashboardView.APP_MENU_ACTION_STOP);
+
+            // Validate application stopped.
+            LibertyPluginTestUtils.validateLibertyServerStopped(wrapperProjectPath.toAbsolutePath().toString() + "/target/liberty");
         }
     }
 
@@ -193,6 +246,8 @@ public void testDiagnosticsAndQuickFixes() {
 
             assertTrue(allFound, "Missing quick-fixes: " + Arrays.toString(missingFixes.toArray()));
 
+        } catch (Exception e) {
+            System.out.println("Caught exception: " + e);
         } finally {
 
             // Delete new file
diff --git a/tests/src/main/java/io/openliberty/tools/eclipse/test/it/utils/SWTBotPluginOperations.java b/tests/src/main/java/io/openliberty/tools/eclipse/test/it/utils/SWTBotPluginOperations.java
index 3eec679b..6567f9df 100644
--- a/tests/src/main/java/io/openliberty/tools/eclipse/test/it/utils/SWTBotPluginOperations.java
+++ b/tests/src/main/java/io/openliberty/tools/eclipse/test/it/utils/SWTBotPluginOperations.java
@@ -933,6 +933,8 @@ public boolean matches(Object object) {
      */
     public static void createNewClass(SWTWorkbenchBot bot, String appName, String className, boolean clearContent) {
 
+        System.out.println("INFO: Creating new Java class: " + className);
+
         Object project = getAppInPackageExplorerTree(appName);
         context(project, "New", "Class");
 
@@ -966,7 +968,10 @@ public static void createNewClass(SWTWorkbenchBot bot, String appName, String cl
      */
     public static List<String> getTypeAheadList(SWTWorkbenchBot bot, String editorFileName, String insertText, int cursorRow,
             int cursorColumn) {
-        SWTBotPreferences.PLAYBACK_DELAY = 1000;
+
+        System.out.println("INFO: Getting type-ahead list");
+
+        SWTBotPreferences.PLAYBACK_DELAY = 10000;
 
         SWTBotEditor editor = searchForEditor(bot, editorFileName);
         SWTBotEclipseEditor e = editor.toTextEditor();
@@ -991,6 +996,9 @@ public static List<String> getTypeAheadList(SWTWorkbenchBot bot, String editorFi
      */
     public static void selectTypeAheadOption(SWTWorkbenchBot bot, String editorFileName, String option, int cursorRow,
             int cursorColumn) {
+
+        System.out.println("INFO: Selecting type-ahead option: " + option);
+
         SWTBotPreferences.PLAYBACK_DELAY = 1000;
         SWTBotEditor editor = searchForEditor(bot, editorFileName);
         SWTBotEclipseEditor e = editor.toTextEditor();
@@ -1008,6 +1016,8 @@ public static void selectTypeAheadOption(SWTWorkbenchBot bot, String editorFileN
      * @return
      */
     public static List<String> getQuickFixList(SWTWorkbenchBot bot, String editorFileName) {
+        System.out.println("INFO: Getting quick-fix list for class: " + editorFileName);
+
         SWTBotPreferences.PLAYBACK_DELAY = 1000;
 
         SWTBotEditor editor = searchForEditor(bot, editorFileName);