diff --git a/settings/setting.h b/settings/setting.h
index 08217003a..98f95d185 100644
--- a/settings/setting.h
+++ b/settings/setting.h
@@ -11,18 +11,34 @@ namespace settings {
 class BaseSetting
 {
 public:
+    BaseSetting(const QString &_name)
+        : name(_name)
+    {
+    }
+
     virtual void save(QSettings &settings) = 0;
     virtual void load(const QSettings &settings) = 0;
+
+    const QString &
+    getName() const
+    {
+        return this->name;
+    }
+
+private:
+    QString name;
 };
 
 template <typename T>
 class Setting : public BaseSetting
 {
 public:
-    Setting(const QString &_name, const T &defaultValue)
-        : name(_name)
+    Setting(std::vector<std::reference_wrapper<BaseSetting>> &settingItems,
+            const QString &_name, const T &defaultValue)
+        : BaseSetting(_name)
         , value(defaultValue)
     {
+        settingItems.push_back(*this);
     }
 
     const T &
@@ -53,21 +69,13 @@ public:
         QVariant newValue = settings.value(this->getName(), QVariant());
         if (newValue.isValid()) {
             assert(newValue.canConvert<T>());
-            this->value = newValue.value<T>();
+            this->set(newValue.value<T>());
         }
     }
 
     boost::signals2::signal<void(const T &newValue)> valueChanged;
 
-protected:
-    const QString &
-    getName() const
-    {
-        return name;
-    }
-
 private:
-    QString name;
     T value;
 };
 
diff --git a/settings/settings.cpp b/settings/settings.cpp
index 3a5f7c8d7..2bf638ff4 100644
--- a/settings/settings.cpp
+++ b/settings/settings.cpp
@@ -1,5 +1,6 @@
 #include "settings/settings.h"
 
+#include <QDebug>
 #include <QDir>
 #include <QStandardPaths>
 
@@ -14,62 +15,38 @@ Settings::Settings()
           QSettings::IniFormat)
     , portable(false)
     , wordTypeMask(messages::Word::Default)
-    , theme("", "dark")
-    , user("", "")
-    , emoteScale("", 1.0)
-    , scaleEmotesByLineHeight("", false)
-    , showTimestamps("", true)
-    , showTimestampSeconds("", false)
-    , showLastMessageIndicator("", false)
-    , allowDouplicateMessages("", true)
-    , linksDoubleClickOnly("", false)
-    , hideEmptyInput("", false)
-    , showMessageLength("", false)
-    , seperateMessages("", false)
-    , mentionUsersWithAt("", false)
-    , allowCommandsAtEnd("", false)
-    , enableHighlights("", true)
-    , enableHighlightSound("", true)
-    , enableHighlightTaskbar("", true)
-    , customHighlightSound("", false)
-    , enableTwitchEmotes("", true)
-    , enableBttvEmotes("", true)
-    , enableFfzEmotes("", true)
-    , enableEmojis("", true)
-    , enableGifAnimations("", true)
-    , enableGifs("", true)
-    , inlineWhispers("", true)
-    , windowTopMost("", true)
-    , hideTabX("", false)
+    , theme(this->settingsItems, "theme", "dark")
+    , user(this->settingsItems, "userNotSureWhatThisMaybeOAuthOrSomething", "")
+    , emoteScale(this->settingsItems, "emoteScale", 1.0)
+    , scaleEmotesByLineHeight(this->settingsItems, "scaleEmotesByLineHeight",
+                              false)
+    , showTimestamps(this->settingsItems, "showTimestamps", true)
+    , showTimestampSeconds(this->settingsItems, "showTimestampSeconds", false)
+    , showLastMessageIndicator(this->settingsItems, "showLastMessageIndicator",
+                               false)
+    , allowDouplicateMessages(this->settingsItems, "allowDouplicateMessages",
+                              true)
+    , linksDoubleClickOnly(this->settingsItems, "linksDoubleClickOnly", false)
+    , hideEmptyInput(this->settingsItems, "hideEmptyInput", false)
+    , showMessageLength(this->settingsItems, "showMessageLength", false)
+    , seperateMessages(this->settingsItems, "seperateMessages", false)
+    , mentionUsersWithAt(this->settingsItems, "mentionUsersWithAt", false)
+    , allowCommandsAtEnd(this->settingsItems, "allowCommandsAtEnd", false)
+    , enableHighlights(this->settingsItems, "enableHighlights", true)
+    , enableHighlightSound(this->settingsItems, "enableHighlightSound", true)
+    , enableHighlightTaskbar(this->settingsItems, "enableHighlightTaskbar",
+                             true)
+    , customHighlightSound(this->settingsItems, "customHighlightSound", false)
+    , enableTwitchEmotes(this->settingsItems, "enableTwitchEmotes", true)
+    , enableBttvEmotes(this->settingsItems, "enableBttvEmotes", true)
+    , enableFfzEmotes(this->settingsItems, "enableFfzEmotes", true)
+    , enableEmojis(this->settingsItems, "enableEmojis", true)
+    , enableGifAnimations(this->settingsItems, "enableGifAnimations", true)
+    , enableGifs(this->settingsItems, "enableGifs", true)
+    , inlineWhispers(this->settingsItems, "inlineWhispers", true)
+    , windowTopMost(this->settingsItems, "windowTopMost", true)
+    , hideTabX(this->settingsItems, "hideTabX", false)
 {
-    settingsItems.push_back(theme);
-    settingsItems.push_back(user);
-    settingsItems.push_back(emoteScale);
-    settingsItems.push_back(scaleEmotesByLineHeight);
-    settingsItems.push_back(showTimestamps);
-    settingsItems.push_back(showTimestampSeconds);
-    settingsItems.push_back(showLastMessageIndicator);
-    settingsItems.push_back(allowDouplicateMessages);
-    settingsItems.push_back(linksDoubleClickOnly);
-    settingsItems.push_back(hideEmptyInput);
-    settingsItems.push_back(showMessageLength);
-    settingsItems.push_back(seperateMessages);
-    settingsItems.push_back(mentionUsersWithAt);
-    settingsItems.push_back(allowCommandsAtEnd);
-    settingsItems.push_back(enableHighlights);
-    settingsItems.push_back(enableHighlightSound);
-    settingsItems.push_back(enableHighlightTaskbar);
-    settingsItems.push_back(customHighlightSound);
-    settingsItems.push_back(enableTwitchEmotes);
-    settingsItems.push_back(enableBttvEmotes);
-    settingsItems.push_back(enableFfzEmotes);
-    settingsItems.push_back(enableEmojis);
-    settingsItems.push_back(enableGifAnimations);
-    settingsItems.push_back(enableGifs);
-    settingsItems.push_back(inlineWhispers);
-    settingsItems.push_back(windowTopMost);
-    settingsItems.push_back(hideTabX);
-
     this->showTimestamps.valueChanged.connect(
         [this](const auto &) { this->updateWordTypeMask(); });
     this->showTimestampSeconds.valueChanged.connect(
@@ -96,6 +73,7 @@ void
 Settings::load()
 {
     for (auto &item : settingsItems) {
+        qDebug() << "Loading settings for " << item.get().getName();
         item.get().load(settings);
     }
 }
diff --git a/widgets/settingsdialog.cpp b/widgets/settingsdialog.cpp
index 410dcbb1b..3f20dda3f 100644
--- a/widgets/settingsdialog.cpp
+++ b/widgets/settingsdialog.cpp
@@ -231,6 +231,9 @@ SettingsDialog::createCheckbox(const QString &title,
 {
     auto checkbox = new QCheckBox(title);
 
+    // Set checkbox initial state
+    checkbox->setChecked(setting.get());
+
     QObject::connect(checkbox, &QCheckBox::toggled, this,
                      [&setting, this](bool state) { setting.set(state); });