diff --git a/src/CMakeLists.txt b/src/CMakeLists.txt
index 24853e752..784e5829c 100644
--- a/src/CMakeLists.txt
+++ b/src/CMakeLists.txt
@@ -568,6 +568,9 @@ set(SOURCE_FILES
         widgets/dialogs/EditHotkeyDialog.hpp
         widgets/dialogs/EmotePopup.cpp
         widgets/dialogs/EmotePopup.hpp
+        widgets/dialogs/HighlightConfigureDialog.cpp
+        widgets/dialogs/HighlightConfigureDialog.hpp
+        widgets/dialogs/HighlightConfigureDialog.ui
         widgets/dialogs/IrcConnectionEditor.cpp
         widgets/dialogs/IrcConnectionEditor.hpp
         widgets/dialogs/IrcConnectionEditor.ui
diff --git a/src/controllers/highlights/HighlightModel.cpp b/src/controllers/highlights/HighlightModel.cpp
index 974653115..fe22f52a0 100644
--- a/src/controllers/highlights/HighlightModel.cpp
+++ b/src/controllers/highlights/HighlightModel.cpp
@@ -77,7 +77,8 @@ void HighlightModel::afterInit()
     auto selfColor = ColorProvider::instance().color(ColorType::SelfHighlight);
     setColorItem(usernameRow[Column::Color], *selfColor, false);
 
-    this->insertCustomRow(usernameRow, HighlightRowIndexes::SelfHighlightRow);
+    this->insertCustomRow(
+        usernameRow, static_cast<int>(HighlightRowIndexes::SelfHighlightRow));
 
     // Highlight settings for whispers
     std::vector<QStandardItem *> whisperRow = this->createRow();
@@ -101,7 +102,8 @@ void HighlightModel::afterInit()
     auto whisperColor = ColorProvider::instance().color(ColorType::Whisper);
     setColorItem(whisperRow[Column::Color], *whisperColor, false);
 
-    this->insertCustomRow(whisperRow, HighlightRowIndexes::WhisperRow);
+    this->insertCustomRow(whisperRow,
+                          static_cast<int>(HighlightRowIndexes::WhisperRow));
 
     // Highlight settings for subscription messages
     std::vector<QStandardItem *> subRow = this->createRow();
@@ -123,7 +125,8 @@ void HighlightModel::afterInit()
     auto subColor = ColorProvider::instance().color(ColorType::Subscription);
     setColorItem(subRow[Column::Color], *subColor, false);
 
-    this->insertCustomRow(subRow, HighlightRowIndexes::SubRow);
+    this->insertCustomRow(subRow,
+                          static_cast<int>(HighlightRowIndexes::SubRow));
 
     // Highlight settings for redeemed highlight messages
     std::vector<QStandardItem *> redeemedRow = this->createRow();
@@ -148,7 +151,8 @@ void HighlightModel::afterInit()
         ColorProvider::instance().color(ColorType::RedeemedHighlight);
     setColorItem(redeemedRow[Column::Color], *RedeemedColor, false);
 
-    this->insertCustomRow(redeemedRow, HighlightRowIndexes::RedeemedRow);
+    this->insertCustomRow(redeemedRow,
+                          static_cast<int>(HighlightRowIndexes::RedeemedRow));
 
     // Highlight settings for first messages
     std::vector<QStandardItem *> firstMessageRow = this->createRow();
@@ -174,8 +178,9 @@ void HighlightModel::afterInit()
         ColorProvider::instance().color(ColorType::FirstMessageHighlight);
     setColorItem(firstMessageRow[Column::Color], *FirstMessageColor, false);
 
-    this->insertCustomRow(firstMessageRow,
-                          HighlightRowIndexes::FirstMessageRow);
+    this->insertCustomRow(
+        firstMessageRow,
+        static_cast<int>(HighlightRowIndexes::FirstMessageRow));
 
     // Highlight settings for hype chats
     std::vector<QStandardItem *> elevatedMessageRow = this->createRow();
@@ -201,8 +206,9 @@ void HighlightModel::afterInit()
     setColorItem(elevatedMessageRow[Column::Color], *elevatedMessageColor,
                  false);
 
-    this->insertCustomRow(elevatedMessageRow,
-                          HighlightRowIndexes::ElevatedMessageRow);
+    this->insertCustomRow(
+        elevatedMessageRow,
+        static_cast<int>(HighlightRowIndexes::ElevatedMessageRow));
 
     // Highlight settings for reply threads
     std::vector<QStandardItem *> threadMessageRow = this->createRow();
@@ -231,8 +237,9 @@ void HighlightModel::afterInit()
         ColorProvider::instance().color(ColorType::ThreadMessageHighlight);
     setColorItem(threadMessageRow[Column::Color], *threadMessageColor, false);
 
-    this->insertCustomRow(threadMessageRow,
-                          HighlightRowIndexes::ThreadMessageRow);
+    this->insertCustomRow(
+        threadMessageRow,
+        static_cast<int>(HighlightRowIndexes::ThreadMessageRow));
 
     // Highlight settings for automod caught messages
     const std::vector<QStandardItem *> automodRow = this->createRow();
@@ -258,52 +265,55 @@ void HighlightModel::afterInit()
         ColorProvider::instance().color(ColorType::AutomodHighlight);
     setColorItem(automodRow[Column::Color], *automodColor, false);
 
-    this->insertCustomRow(automodRow, HighlightRowIndexes::AutomodRow);
+    this->insertCustomRow(automodRow,
+                          static_cast<int>(HighlightRowIndexes::AutomodRow));
 }
 
 void HighlightModel::customRowSetData(const std::vector<QStandardItem *> &row,
                                       int column, const QVariant &value,
                                       int role, int rowIndex)
 {
-    switch (column)
+    auto rowIndex2 = static_cast<HighlightRowIndexes>(rowIndex);
+    auto column2 = static_cast<Column>(column);
+    switch (column2)
     {
         case Column::Pattern: {
             if (role == Qt::CheckStateRole)
             {
-                if (rowIndex == HighlightRowIndexes::SelfHighlightRow)
+                if (rowIndex2 == HighlightRowIndexes::SelfHighlightRow)
                 {
                     getSettings()->enableSelfHighlight.setValue(value.toBool());
                 }
-                else if (rowIndex == HighlightRowIndexes::WhisperRow)
+                else if (rowIndex2 == HighlightRowIndexes::WhisperRow)
                 {
                     getSettings()->enableWhisperHighlight.setValue(
                         value.toBool());
                 }
-                else if (rowIndex == HighlightRowIndexes::SubRow)
+                else if (rowIndex2 == HighlightRowIndexes::SubRow)
                 {
                     getSettings()->enableSubHighlight.setValue(value.toBool());
                 }
-                else if (rowIndex == HighlightRowIndexes::RedeemedRow)
+                else if (rowIndex2 == HighlightRowIndexes::RedeemedRow)
                 {
                     getSettings()->enableRedeemedHighlight.setValue(
                         value.toBool());
                 }
-                else if (rowIndex == HighlightRowIndexes::FirstMessageRow)
+                else if (rowIndex2 == HighlightRowIndexes::FirstMessageRow)
                 {
                     getSettings()->enableFirstMessageHighlight.setValue(
                         value.toBool());
                 }
-                else if (rowIndex == HighlightRowIndexes::ElevatedMessageRow)
+                else if (rowIndex2 == HighlightRowIndexes::ElevatedMessageRow)
                 {
                     getSettings()->enableElevatedMessageHighlight.setValue(
                         value.toBool());
                 }
-                else if (rowIndex == HighlightRowIndexes::ThreadMessageRow)
+                else if (rowIndex2 == HighlightRowIndexes::ThreadMessageRow)
                 {
                     getSettings()->enableThreadHighlight.setValue(
                         value.toBool());
                 }
-                else if (rowIndex == HighlightRowIndexes::AutomodRow)
+                else if (rowIndex2 == HighlightRowIndexes::AutomodRow)
                 {
                     getSettings()->enableAutomodHighlight.setValue(
                         value.toBool());
@@ -314,17 +324,17 @@ void HighlightModel::customRowSetData(const std::vector<QStandardItem *> &row,
         case Column::ShowInMentions: {
             if (role == Qt::CheckStateRole)
             {
-                if (rowIndex == HighlightRowIndexes::SelfHighlightRow)
+                if (rowIndex2 == HighlightRowIndexes::SelfHighlightRow)
                 {
                     getSettings()->showSelfHighlightInMentions.setValue(
                         value.toBool());
                 }
-                else if (rowIndex == HighlightRowIndexes::ThreadMessageRow)
+                else if (rowIndex2 == HighlightRowIndexes::ThreadMessageRow)
                 {
                     getSettings()->showThreadHighlightInMentions.setValue(
                         value.toBool());
                 }
-                else if (rowIndex == HighlightRowIndexes::AutomodRow)
+                else if (rowIndex2 == HighlightRowIndexes::AutomodRow)
                 {
                     getSettings()->showAutomodInMentions.setValue(
                         value.toBool());
@@ -335,43 +345,43 @@ void HighlightModel::customRowSetData(const std::vector<QStandardItem *> &row,
         case Column::FlashTaskbar: {
             if (role == Qt::CheckStateRole)
             {
-                if (rowIndex == HighlightRowIndexes::SelfHighlightRow)
+                if (rowIndex2 == HighlightRowIndexes::SelfHighlightRow)
                 {
                     getSettings()->enableSelfHighlightTaskbar.setValue(
                         value.toBool());
                 }
-                else if (rowIndex == HighlightRowIndexes::WhisperRow)
+                else if (rowIndex2 == HighlightRowIndexes::WhisperRow)
                 {
                     getSettings()->enableWhisperHighlightTaskbar.setValue(
                         value.toBool());
                 }
-                else if (rowIndex == HighlightRowIndexes::SubRow)
+                else if (rowIndex2 == HighlightRowIndexes::SubRow)
                 {
                     getSettings()->enableSubHighlightTaskbar.setValue(
                         value.toBool());
                 }
-                else if (rowIndex == HighlightRowIndexes::RedeemedRow)
+                else if (rowIndex2 == HighlightRowIndexes::RedeemedRow)
                 {
                     // getSettings()->enableRedeemedHighlightTaskbar.setValue(
                     //     value.toBool());
                 }
-                else if (rowIndex == HighlightRowIndexes::FirstMessageRow)
+                else if (rowIndex2 == HighlightRowIndexes::FirstMessageRow)
                 {
                     // getSettings()->enableFirstMessageHighlightTaskbar.setValue(
                     //     value.toBool());
                 }
-                else if (rowIndex == HighlightRowIndexes::ElevatedMessageRow)
+                else if (rowIndex2 == HighlightRowIndexes::ElevatedMessageRow)
                 {
                     // getSettings()
                     //     ->enableElevatedMessageHighlightTaskbar.setvalue(
                     //         value.toBool());
                 }
-                else if (rowIndex == HighlightRowIndexes::ThreadMessageRow)
+                else if (rowIndex2 == HighlightRowIndexes::ThreadMessageRow)
                 {
                     getSettings()->enableThreadHighlightTaskbar.setValue(
                         value.toBool());
                 }
-                else if (rowIndex == HighlightRowIndexes::AutomodRow)
+                else if (rowIndex2 == HighlightRowIndexes::AutomodRow)
                 {
                     getSettings()->enableAutomodHighlightTaskbar.setValue(
                         value.toBool());
@@ -382,42 +392,42 @@ void HighlightModel::customRowSetData(const std::vector<QStandardItem *> &row,
         case Column::PlaySound: {
             if (role == Qt::CheckStateRole)
             {
-                if (rowIndex == HighlightRowIndexes::SelfHighlightRow)
+                if (rowIndex2 == HighlightRowIndexes::SelfHighlightRow)
                 {
                     getSettings()->enableSelfHighlightSound.setValue(
                         value.toBool());
                 }
-                else if (rowIndex == HighlightRowIndexes::WhisperRow)
+                else if (rowIndex2 == HighlightRowIndexes::WhisperRow)
                 {
                     getSettings()->enableWhisperHighlightSound.setValue(
                         value.toBool());
                 }
-                else if (rowIndex == HighlightRowIndexes::SubRow)
+                else if (rowIndex2 == HighlightRowIndexes::SubRow)
                 {
                     getSettings()->enableSubHighlightSound.setValue(
                         value.toBool());
                 }
-                else if (rowIndex == HighlightRowIndexes::RedeemedRow)
+                else if (rowIndex2 == HighlightRowIndexes::RedeemedRow)
                 {
                     // getSettings()->enableRedeemedHighlightSound.setValue(
                     //     value.toBool());
                 }
-                else if (rowIndex == HighlightRowIndexes::FirstMessageRow)
+                else if (rowIndex2 == HighlightRowIndexes::FirstMessageRow)
                 {
                     // getSettings()->enableFirstMessageHighlightSound.setValue(
                     //     value.toBool());
                 }
-                else if (rowIndex == HighlightRowIndexes::ElevatedMessageRow)
+                else if (rowIndex2 == HighlightRowIndexes::ElevatedMessageRow)
                 {
                     // getSettings()->enableElevatedMessageHighlightSound.setValue(
                     //     value.toBool());
                 }
-                else if (rowIndex == HighlightRowIndexes::ThreadMessageRow)
+                else if (rowIndex2 == HighlightRowIndexes::ThreadMessageRow)
                 {
                     getSettings()->enableThreadHighlightSound.setValue(
                         value.toBool());
                 }
-                else if (rowIndex == HighlightRowIndexes::AutomodRow)
+                else if (rowIndex2 == HighlightRowIndexes::AutomodRow)
                 {
                     getSettings()->enableAutomodHighlightSound.setValue(
                         value.toBool());
@@ -437,27 +447,27 @@ void HighlightModel::customRowSetData(const std::vector<QStandardItem *> &row,
             // Custom sound file
             if (role == Qt::UserRole)
             {
-                if (rowIndex == HighlightRowIndexes::SelfHighlightRow)
+                if (rowIndex2 == HighlightRowIndexes::SelfHighlightRow)
                 {
                     getSettings()->selfHighlightSoundUrl.setValue(
                         value.toString());
                 }
-                else if (rowIndex == HighlightRowIndexes::WhisperRow)
+                else if (rowIndex2 == HighlightRowIndexes::WhisperRow)
                 {
                     getSettings()->whisperHighlightSoundUrl.setValue(
                         value.toString());
                 }
-                else if (rowIndex == HighlightRowIndexes::SubRow)
+                else if (rowIndex2 == HighlightRowIndexes::SubRow)
                 {
                     getSettings()->subHighlightSoundUrl.setValue(
                         value.toString());
                 }
-                else if (rowIndex == HighlightRowIndexes::ThreadMessageRow)
+                else if (rowIndex2 == HighlightRowIndexes::ThreadMessageRow)
                 {
                     getSettings()->threadHighlightSoundUrl.setValue(
                         value.toString());
                 }
-                else if (rowIndex == HighlightRowIndexes::AutomodRow)
+                else if (rowIndex2 == HighlightRowIndexes::AutomodRow)
                 {
                     getSettings()->automodHighlightSoundUrl.setValue(
                         value.toString());
@@ -474,42 +484,42 @@ void HighlightModel::customRowSetData(const std::vector<QStandardItem *> &row,
                     setting.setValue(color.name(QColor::HexArgb));
                 };
 
-                if (rowIndex == HighlightRowIndexes::SelfHighlightRow)
+                if (rowIndex2 == HighlightRowIndexes::SelfHighlightRow)
                 {
                     setColor(getSettings()->selfHighlightColor,
                              ColorType::SelfHighlight);
                 }
-                else if (rowIndex == HighlightRowIndexes::WhisperRow)
+                else if (rowIndex2 == HighlightRowIndexes::WhisperRow)
                 {
                     setColor(getSettings()->whisperHighlightColor,
                              ColorType::Whisper);
                 }
-                else if (rowIndex == HighlightRowIndexes::SubRow)
+                else if (rowIndex2 == HighlightRowIndexes::SubRow)
                 {
                     setColor(getSettings()->subHighlightColor,
                              ColorType::Subscription);
                 }
-                else if (rowIndex == HighlightRowIndexes::RedeemedRow)
+                else if (rowIndex2 == HighlightRowIndexes::RedeemedRow)
                 {
                     setColor(getSettings()->redeemedHighlightColor,
                              ColorType::RedeemedHighlight);
                 }
-                else if (rowIndex == HighlightRowIndexes::FirstMessageRow)
+                else if (rowIndex2 == HighlightRowIndexes::FirstMessageRow)
                 {
                     setColor(getSettings()->firstMessageHighlightColor,
                              ColorType::FirstMessageHighlight);
                 }
-                else if (rowIndex == HighlightRowIndexes::ElevatedMessageRow)
+                else if (rowIndex2 == HighlightRowIndexes::ElevatedMessageRow)
                 {
                     setColor(getSettings()->elevatedMessageHighlightColor,
                              ColorType::ElevatedMessageHighlight);
                 }
-                else if (rowIndex == HighlightRowIndexes::ThreadMessageRow)
+                else if (rowIndex2 == HighlightRowIndexes::ThreadMessageRow)
                 {
                     setColor(getSettings()->threadHighlightColor,
                              ColorType::ThreadMessageHighlight);
                 }
-                else if (rowIndex == HighlightRowIndexes::AutomodRow)
+                else if (rowIndex2 == HighlightRowIndexes::AutomodRow)
                 {
                     setColor(getSettings()->automodHighlightColor,
                              ColorType::AutomodHighlight);
diff --git a/src/controllers/highlights/HighlightModel.hpp b/src/controllers/highlights/HighlightModel.hpp
index be807d33e..02245076a 100644
--- a/src/controllers/highlights/HighlightModel.hpp
+++ b/src/controllers/highlights/HighlightModel.hpp
@@ -23,10 +23,11 @@ public:
         PlaySound = 5,
         SoundPath = 6,
         Color = 7,
+        Configure = 8,
         COUNT  // keep this as last member of enum
     };
 
-    enum HighlightRowIndexes {
+    enum class HighlightRowIndexes {
         SelfHighlightRow = 0,
         WhisperRow = 1,
         SubRow = 2,
@@ -35,6 +36,7 @@ public:
         ElevatedMessageRow = 5,
         ThreadMessageRow = 6,
         AutomodRow = 7,
+        COUNT,
     };
 
     enum UserHighlightRowIndexes {
diff --git a/src/widgets/dialogs/HighlightConfigureDialog.cpp b/src/widgets/dialogs/HighlightConfigureDialog.cpp
new file mode 100644
index 000000000..f368ad204
--- /dev/null
+++ b/src/widgets/dialogs/HighlightConfigureDialog.cpp
@@ -0,0 +1,23 @@
+#include "widgets/dialogs/HighlightConfigureDialog.hpp"
+
+#include "widgets/dialogs/ui_HighlightConfigureDialog.h"
+
+namespace chatterino {
+
+HighlightConfigureDialog::HighlightConfigureDialog(HighlightPhrase phrase,
+                                                   QWidget *parent)
+
+    : QDialog(parent, Qt::WindowStaysOnTopHint)
+    , ui_(new Ui::HighlightConfigureDialog)
+{
+    this->ui_->setupUi(this);
+
+    this->ui_->patternLineEdit->setText(phrase.getPattern());
+}
+
+HighlightConfigureDialog::~HighlightConfigureDialog()
+{
+    delete ui_;
+}
+
+}  // namespace chatterino
diff --git a/src/widgets/dialogs/HighlightConfigureDialog.hpp b/src/widgets/dialogs/HighlightConfigureDialog.hpp
new file mode 100644
index 000000000..08d41f65e
--- /dev/null
+++ b/src/widgets/dialogs/HighlightConfigureDialog.hpp
@@ -0,0 +1,35 @@
+#pragma once
+
+#include "controllers/highlights/HighlightPhrase.hpp"
+
+#include <QDialog>
+
+namespace Ui {
+
+class HighlightConfigureDialog;
+
+}  // namespace Ui
+
+namespace chatterino {
+
+struct IrcServerData;
+
+class HighlightConfigureDialog : public QDialog
+{
+    Q_OBJECT
+
+public:
+    explicit HighlightConfigureDialog(HighlightPhrase phrase, QWidget *parent);
+
+    HighlightConfigureDialog(const HighlightConfigureDialog &) = delete;
+    HighlightConfigureDialog(HighlightConfigureDialog &&) = delete;
+    HighlightConfigureDialog &operator=(const HighlightConfigureDialog &) =
+        delete;
+    HighlightConfigureDialog &operator=(HighlightConfigureDialog &&) = delete;
+    ~HighlightConfigureDialog() override;
+
+private:
+    Ui::HighlightConfigureDialog *ui_;
+};
+
+}  // namespace chatterino
diff --git a/src/widgets/dialogs/HighlightConfigureDialog.ui b/src/widgets/dialogs/HighlightConfigureDialog.ui
new file mode 100644
index 000000000..96531df10
--- /dev/null
+++ b/src/widgets/dialogs/HighlightConfigureDialog.ui
@@ -0,0 +1,141 @@
+<?xml version="1.0" encoding="UTF-8"?>
+<ui version="4.0">
+ <class>HighlightConfigureDialog</class>
+ <widget class="QDialog" name="HighlightConfigureDialog">
+  <property name="geometry">
+   <rect>
+    <x>0</x>
+    <y>0</y>
+    <width>400</width>
+    <height>300</height>
+   </rect>
+  </property>
+  <property name="windowTitle">
+   <string>Configure highlight</string>
+  </property>
+  <property name="modal">
+   <bool>true</bool>
+  </property>
+  <layout class="QVBoxLayout" name="verticalLayout">
+   <item>
+    <layout class="QFormLayout" name="formLayout">
+     <item row="0" column="0">
+      <widget class="QLabel" name="patternLabel">
+       <property name="text">
+        <string>Pattern</string>
+       </property>
+      </widget>
+     </item>
+     <item row="0" column="1">
+      <widget class="QLineEdit" name="patternLineEdit"/>
+     </item>
+     <item row="1" column="0">
+      <widget class="QLabel" name="showInMentionsLabel">
+       <property name="text">
+        <string>Show in Mentions</string>
+       </property>
+      </widget>
+     </item>
+     <item row="1" column="1">
+      <widget class="QCheckBox" name="showInMentionsCheckBox"/>
+     </item>
+     <item row="2" column="0">
+      <widget class="QLabel" name="flaskTaskbarLabel">
+       <property name="text">
+        <string>Flask taskbar</string>
+       </property>
+      </widget>
+     </item>
+     <item row="2" column="1">
+      <widget class="QCheckBox" name="flaskTaskbarCheckBox"/>
+     </item>
+     <item row="3" column="0">
+      <widget class="QLabel" name="enableRegexLabel">
+       <property name="text">
+        <string>Enable regex</string>
+       </property>
+      </widget>
+     </item>
+     <item row="3" column="1">
+      <widget class="QCheckBox" name="enableRegexCheckBox"/>
+     </item>
+     <item row="4" column="0">
+      <widget class="QLabel" name="playSoundLabel">
+       <property name="text">
+        <string>Play sound</string>
+       </property>
+      </widget>
+     </item>
+     <item row="4" column="1">
+      <widget class="QCheckBox" name="playSoundCheckBox"/>
+     </item>
+     <item row="5" column="0">
+      <widget class="QLabel" name="customSoundLabel">
+       <property name="text">
+        <string>Custom sound</string>
+       </property>
+      </widget>
+     </item>
+     <item row="5" column="1">
+      <widget class="QLineEdit" name="customSoundLineEdit"/>
+     </item>
+     <item row="6" column="0">
+      <widget class="QLabel" name="colorLabel">
+       <property name="text">
+        <string>Color</string>
+       </property>
+      </widget>
+     </item>
+     <item row="6" column="1">
+      <widget class="QWidget" name="colorWidget" native="true"/>
+     </item>
+    </layout>
+   </item>
+   <item>
+    <widget class="QDialogButtonBox" name="buttonBox">
+     <property name="orientation">
+      <enum>Qt::Horizontal</enum>
+     </property>
+     <property name="standardButtons">
+      <set>QDialogButtonBox::Cancel|QDialogButtonBox::Ok</set>
+     </property>
+    </widget>
+   </item>
+  </layout>
+ </widget>
+ <resources/>
+ <connections>
+  <connection>
+   <sender>buttonBox</sender>
+   <signal>accepted()</signal>
+   <receiver>HighlightConfigureDialog</receiver>
+   <slot>accept()</slot>
+   <hints>
+    <hint type="sourcelabel">
+     <x>248</x>
+     <y>254</y>
+    </hint>
+    <hint type="destinationlabel">
+     <x>157</x>
+     <y>274</y>
+    </hint>
+   </hints>
+  </connection>
+  <connection>
+   <sender>buttonBox</sender>
+   <signal>rejected()</signal>
+   <receiver>HighlightConfigureDialog</receiver>
+   <slot>reject()</slot>
+   <hints>
+    <hint type="sourcelabel">
+     <x>316</x>
+     <y>260</y>
+    </hint>
+    <hint type="destinationlabel">
+     <x>286</x>
+     <y>274</y>
+    </hint>
+   </hints>
+  </connection>
+ </connections>
+</ui>
diff --git a/src/widgets/settingspages/HighlightingPage.cpp b/src/widgets/settingspages/HighlightingPage.cpp
index 75d8ad4b5..4946dc436 100644
--- a/src/widgets/settingspages/HighlightingPage.cpp
+++ b/src/widgets/settingspages/HighlightingPage.cpp
@@ -1,4 +1,4 @@
-#include "HighlightingPage.hpp"
+#include "widgets/settingspages/HighlightingPage.hpp"
 
 #include "Application.hpp"
 #include "controllers/highlights/BadgeHighlightModel.hpp"
@@ -15,6 +15,7 @@
 #include "util/LayoutCreator.hpp"
 #include "widgets/dialogs/BadgePickerDialog.hpp"
 #include "widgets/dialogs/ColorPickerDialog.hpp"
+#include "widgets/dialogs/HighlightConfigureDialog.hpp"
 #include "widgets/helper/color/ColorItemDelegate.hpp"
 #include "widgets/helper/EditableModelView.hpp"
 
@@ -75,10 +76,17 @@ HighlightingPage::HighlightingPage()
                                     &getSettings()->highlightedMessages))
                         .getElement();
                 view->addRegexHelpLink();
-                view->setTitles({"Pattern", "Show in\nMentions",
-                                 "Flash\ntaskbar", "Enable\nregex",
-                                 "Case-\nsensitive", "Play\nsound",
-                                 "Custom\nsound", "Color"});
+                view->setTitles({
+                    "Pattern",
+                    "Show in\nMentions",
+                    "Flash\ntaskbar",
+                    "Enable\nregex",
+                    "Case-\nsensitive",
+                    "Play\nsound",
+                    "Custom\nsound",
+                    "Color",
+                    "Configure",
+                });
                 view->getTableView()->horizontalHeader()->setSectionResizeMode(
                     QHeaderView::Fixed);
                 view->getTableView()->horizontalHeader()->setSectionResizeMode(
@@ -353,6 +361,21 @@ void HighlightingPage::openColorDialog(const QModelIndex &clicked,
     dialog->show();
 }
 
+void HighlightingPage::openConfigureDialog(const QModelIndex &clicked,
+                                           EditableModelView *view,
+                                           HighlightTab tab)
+{
+    if (tab != HighlightTab::Messages)
+    {
+        return;
+    }
+
+    auto phrase =
+        getSettings()->highlightedMessages.readOnly()->at(clicked.row());
+    auto *xd = new HighlightConfigureDialog(phrase, this);
+    xd->show();
+}
+
 void HighlightingPage::tableCellClicked(const QModelIndex &clicked,
                                         EditableModelView *view,
                                         HighlightTab tab)
@@ -376,6 +399,10 @@ void HighlightingPage::tableCellClicked(const QModelIndex &clicked,
             {
                 this->openColorDialog(clicked, view, tab);
             }
+            else if (clicked.column() == Column::Configure)
+            {
+                this->openConfigureDialog(clicked, view, tab);
+            }
         }
         break;
 
diff --git a/src/widgets/settingspages/HighlightingPage.hpp b/src/widgets/settingspages/HighlightingPage.hpp
index 47a9c3e3a..6d0a6f6a5 100644
--- a/src/widgets/settingspages/HighlightingPage.hpp
+++ b/src/widgets/settingspages/HighlightingPage.hpp
@@ -28,6 +28,8 @@ private:
                          int soundColumn);
     void openColorDialog(const QModelIndex &clicked, EditableModelView *view,
                          HighlightTab tab);
+    void openConfigureDialog(const QModelIndex &clicked,
+                             EditableModelView *view, HighlightTab tab);
 };
 
 }  // namespace chatterino