diff --git a/CMakeLists.txt b/CMakeLists.txt
index 61ec6150..595e5acb 100644
--- a/CMakeLists.txt
+++ b/CMakeLists.txt
@@ -29,6 +29,7 @@ set(CMAKE_INCLUDE_CURRENT_DIR ON)
 set(CMAKE_AUTOMOC ON)
 set(CMAKE_AUTOUIC ON)
 
+set(CMAKE_AUTORCC ON) # For resources.qrc
 
 # Tell websocketpp not to use system boost
 add_definitions(-DASIO_STANDALONE)
@@ -90,6 +91,7 @@ set(obs-websocket_SOURCES
     src/requesthandler/rpc/RequestResult.cpp
 	src/forms/SettingsDialog.cpp
     src/forms/ConnectInfo.cpp
+    src/forms/resources.qrc
 	src/utils/Json.cpp
     src/utils/Crypto.cpp
     src/utils/Platform.cpp
diff --git a/src/forms/SettingsDialog.cpp b/src/forms/SettingsDialog.cpp
index bb008f17..2d660082 100644
--- a/src/forms/SettingsDialog.cpp
+++ b/src/forms/SettingsDialog.cpp
@@ -11,6 +11,12 @@
 
 #include "../plugin-macros.generated.h"
 
+QString GetToolTipIcon()
+{
+	bool lightTheme = QApplication::palette().text().color().redF() < 0.5;
+	return lightTheme ? ":toolTip/images/help.svg" : ":toolTip/images/help_light.svg";
+}
+
 SettingsDialog::SettingsDialog(QWidget* parent) :
 	QDialog(parent, Qt::Dialog),
 	ui(new Ui::SettingsDialog),
@@ -18,9 +24,11 @@ SettingsDialog::SettingsDialog(QWidget* parent) :
 	sessionTableTimer(new QTimer)
 {
 	ui->setupUi(this);
-	ui->websocketSessionTable->horizontalHeader()->resizeSection(3, 100);
+	ui->websocketSessionTable->horizontalHeader()->resizeSection(3, 100); // Resize Session Table column widths
 	ui->websocketSessionTable->horizontalHeader()->resizeSection(4, 100);
 
+	ui->enableDebugLoggingToolTipLabel->setPixmap(QPixmap(GetToolTipIcon())); // Set the appropriate tooltip icon for the theme
+
 	connect(sessionTableTimer, &QTimer::timeout,
 		this, &SettingsDialog::FillSessionTable);
 	connect(ui->buttonBox, &QDialogButtonBox::clicked,
diff --git a/src/forms/SettingsDialog.ui b/src/forms/SettingsDialog.ui
index cb1431c3..9aade501 100644
--- a/src/forms/SettingsDialog.ui
+++ b/src/forms/SettingsDialog.ui
@@ -78,14 +78,44 @@
        </widget>
       </item>
       <item row="3" column="1">
-       <widget class="QCheckBox" name="enableDebugLoggingCheckBox">
-        <property name="toolTip">
-         <string>OBSWebSocket.Settings.DebugEnableHoverText</string>
+       <layout class="QHBoxLayout" name="horizontalLayout_2">
+        <property name="spacing">
+         <number>0</number>
         </property>
-        <property name="text">
-         <string>OBSWebSocket.Settings.DebugEnable</string>
-        </property>
-       </widget>
+        <item>
+         <widget class="QCheckBox" name="enableDebugLoggingCheckBox">
+          <property name="toolTip">
+           <string>OBSWebSocket.Settings.DebugEnableHoverText</string>
+          </property>
+          <property name="text">
+           <string>OBSWebSocket.Settings.DebugEnable</string>
+          </property>
+         </widget>
+        </item>
+        <item>
+         <widget class="QLabel" name="enableDebugLoggingToolTipLabel">
+          <property name="toolTip">
+           <string>OBSWebSocket.Settings.DebugEnableHoverText</string>
+          </property>
+          <property name="pixmap">
+           <pixmap resource="resources.qrc">:/toolTip/images/help.svg</pixmap>
+          </property>
+         </widget>
+        </item>
+        <item>
+         <spacer name="horizontalSpacer_3">
+          <property name="orientation">
+           <enum>Qt::Horizontal</enum>
+          </property>
+          <property name="sizeHint" stdset="0">
+           <size>
+            <width>40</width>
+            <height>20</height>
+           </size>
+          </property>
+         </spacer>
+        </item>
+       </layout>
       </item>
      </layout>
     </widget>
@@ -263,7 +293,9 @@
    </item>
   </layout>
  </widget>
- <resources/>
+ <resources>
+  <include location="resources.qrc"/>
+ </resources>
  <connections>
   <connection>
    <sender>buttonBox</sender>
diff --git a/src/forms/images/help.svg b/src/forms/images/help.svg
new file mode 100644
index 00000000..d1175742
--- /dev/null
+++ b/src/forms/images/help.svg
@@ -0,0 +1 @@
+<svg xmlns="http://www.w3.org/2000/svg" width="16" height="16" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2.5" stroke-linecap="round" stroke-linejoin="round" class="feather feather-help-circle"><circle cx="12" cy="12" r="10"></circle><path d="M9.09 9a3 3 0 0 1 5.83 1c0 2-3 3-3 3"></path><line x1="12" y1="17" x2="12.01" y2="17"></line></svg>
\ No newline at end of file
diff --git a/src/forms/images/help_light.svg b/src/forms/images/help_light.svg
new file mode 100644
index 00000000..5cd3c7df
--- /dev/null
+++ b/src/forms/images/help_light.svg
@@ -0,0 +1 @@
+<svg xmlns="http://www.w3.org/2000/svg" width="16" height="16" viewBox="0 0 24 24" fill="none" stroke="rgb(82.352941%,82.352941%,82.352941%)" stroke-width="2.5" stroke-linecap="round" stroke-linejoin="round" class="feather feather-help-circle"><circle cx="12" cy="12" r="10"></circle><path d="M9.09 9a3 3 0 0 1 5.83 1c0 2-3 3-3 3"></path><line x1="12" y1="17" x2="12.01" y2="17"></line></svg>
\ No newline at end of file
diff --git a/src/forms/resources.qrc b/src/forms/resources.qrc
new file mode 100644
index 00000000..d6add2c6
--- /dev/null
+++ b/src/forms/resources.qrc
@@ -0,0 +1,6 @@
+<RCC>
+  <qresource prefix="toolTip">
+    <file>images/help_light.svg</file>
+    <file>images/help.svg</file>
+  </qresource>
+</RCC>