diff --git a/build.gradle b/build.gradle
index 75a518ea61d8..5c0329e610ec 100644
--- a/build.gradle
+++ b/build.gradle
@@ -2,6 +2,8 @@
 // For more details take a look at the Java Quickstart chapter in the Gradle
 // user guide available at http://gradle.org/docs/4.6/userguide/tutorial_java_projects.html
 
+import org.gradle.api.tasks.testing.logging.TestLogEvent
+
 plugins {
     id 'java'
     id 'jacoco'
@@ -117,12 +119,14 @@ allTests.dependsOn nonGuiTests
 test {
     systemProperty 'testfx.setup.timeout', '60000'
 
-    // Prints the currently running test's name in the CI's build log,
-    // so that we can check if tests are being silently skipped or
-    // stalling the build.
-    if (System.env.'CI') {
-        beforeTest { descriptor ->
-            logger.lifecycle("Running test: ${descriptor}")
+    testLogging {
+        events TestLogEvent.FAILED, TestLogEvent.SKIPPED
+
+        // Prints the currently running test's name in the CI's build log,
+        // so that we can check if tests are being silently skipped or
+        // stalling the build.
+        if (System.env.'CI') {
+            events << TestLogEvent.STARTED
         }
     }
 
diff --git a/src/test/java/guitests/GuiRobot.java b/src/test/java/guitests/GuiRobot.java
index d8a301aa41e7..f4e0700b22f7 100644
--- a/src/test/java/guitests/GuiRobot.java
+++ b/src/test/java/guitests/GuiRobot.java
@@ -39,6 +39,13 @@ public void pauseForHuman() {
         sleep(PAUSE_FOR_HUMAN_DELAY_MILLISECONDS);
     }
 
+    /**
+     * Returns true if tests are run in headless mode.
+     */
+    public boolean isHeadlessMode() {
+        return isHeadlessMode;
+    }
+
     /**
      * Waits for {@code event} to be true by {@code DEFAULT_WAIT_FOR_EVENT_TIMEOUT_MILLISECONDS} milliseconds.
      *
diff --git a/src/test/java/seedu/address/ui/HelpWindowTest.java b/src/test/java/seedu/address/ui/HelpWindowTest.java
index 461f5bba2eae..0dfb9842284c 100644
--- a/src/test/java/seedu/address/ui/HelpWindowTest.java
+++ b/src/test/java/seedu/address/ui/HelpWindowTest.java
@@ -3,6 +3,7 @@
 import static org.junit.Assert.assertEquals;
 import static org.junit.Assert.assertFalse;
 import static org.junit.Assert.assertTrue;
+import static org.junit.Assume.assumeFalse;
 import static seedu.address.ui.HelpWindow.USERGUIDE_FILE_PATH;
 
 import java.net.URL;
@@ -46,8 +47,12 @@ public void isShowing_helpWindowIsHiding_returnsFalse() {
     }
 
     @Test
-    public void focus_helpWindowNotFocused_focused() {
+    public void focus_helpWindowNotFocused_focused() throws Exception {
+        assumeFalse("Test skipped in headless mode: Window focus behavior is buggy.", guiRobot.isHeadlessMode());
         guiRobot.interact(helpWindow::show);
+
+        // Focus on another stage to remove focus from the helpWindow
+        FxToolkit.setupStage(Stage::requestFocus);
         assertFalse(helpWindow.getRoot().isFocused());
 
         guiRobot.interact(helpWindow::focus);