diff --git a/src/controllers/highlights/HighlightModel.cpp b/src/controllers/highlights/HighlightModel.cpp
index 676369169..329659fab 100644
--- a/src/controllers/highlights/HighlightModel.cpp
+++ b/src/controllers/highlights/HighlightModel.cpp
@@ -8,7 +8,7 @@ namespace chatterino {
 
 // commandmodel
 HighlightModel::HighlightModel(QObject *parent)
-    : SignalVectorModel<HighlightPhrase>(4, parent)
+    : SignalVectorModel<HighlightPhrase>(5, parent)
 {
 }
 
@@ -16,12 +16,13 @@ HighlightModel::HighlightModel(QObject *parent)
 HighlightPhrase HighlightModel::getItemFromRow(
     std::vector<QStandardItem *> &row, const HighlightPhrase &original)
 {
-    // key, alert, sound, regex
+    // key, alert, sound, regex, case-sensitivity
 
     return HighlightPhrase{row[0]->data(Qt::DisplayRole).toString(),
                            row[1]->data(Qt::CheckStateRole).toBool(),
                            row[2]->data(Qt::CheckStateRole).toBool(),
-                           row[3]->data(Qt::CheckStateRole).toBool()};
+                           row[3]->data(Qt::CheckStateRole).toBool(),
+                           row[4]->data(Qt::CheckStateRole).toBool()};
 }
 
 // turns a row in the model into a vector item
@@ -32,6 +33,7 @@ void HighlightModel::getRowFromItem(const HighlightPhrase &item,
     setBoolItem(row[1], item.getAlert());
     setBoolItem(row[2], item.getSound());
     setBoolItem(row[3], item.isRegex());
+    setBoolItem(row[4], item.isCaseSensitive());
 }
 
 void HighlightModel::afterInit()
diff --git a/src/controllers/highlights/HighlightPhrase.hpp b/src/controllers/highlights/HighlightPhrase.hpp
index 5db0c6999..0214fb000 100644
--- a/src/controllers/highlights/HighlightPhrase.hpp
+++ b/src/controllers/highlights/HighlightPhrase.hpp
@@ -15,21 +15,24 @@ public:
     bool operator==(const HighlightPhrase &other) const
     {
         return std::tie(this->pattern_, this->sound_, this->alert_,
-                        this->isRegex_) == std::tie(other.pattern_,
-                                                    other.sound_, other.alert_,
-                                                    other.isRegex_);
+                        this->isRegex_, this->caseSensitive_) ==
+               std::tie(other.pattern_, other.sound_, other.alert_,
+                        other.isRegex_, other.caseSensitive_);
     }
 
     HighlightPhrase(const QString &pattern, bool alert, bool sound,
-                    bool isRegex)
+                    bool isRegex, bool caseSensitive)
         : pattern_(pattern)
         , alert_(alert)
         , sound_(sound)
         , isRegex_(isRegex)
-        , regex_(isRegex_ ? pattern
-                          : "\\b" + QRegularExpression::escape(pattern) + "\\b",
-                 QRegularExpression::CaseInsensitiveOption |
-                     QRegularExpression::UseUnicodePropertiesOption)
+        , caseSensitive_(caseSensitive)
+        , regex_(
+              isRegex_ ? pattern
+                       : "\\b" + QRegularExpression::escape(pattern) + "\\b",
+              QRegularExpression::UseUnicodePropertiesOption |
+                  (caseSensitive_ ? QRegularExpression::NoPatternOption
+                                  : QRegularExpression::CaseInsensitiveOption))
     {
     }
 
@@ -60,11 +63,17 @@ public:
         return this->isValid() && this->regex_.match(subject).hasMatch();
     }
 
+    bool isCaseSensitive() const
+    {
+        return this->caseSensitive_;
+    }
+
 private:
     QString pattern_;
     bool alert_;
     bool sound_;
     bool isRegex_;
+    bool caseSensitive_;
     QRegularExpression regex_;
 };
 }  // namespace chatterino
@@ -82,6 +91,7 @@ struct Serialize<chatterino::HighlightPhrase> {
         chatterino::rj::set(ret, "alert", value.getAlert(), a);
         chatterino::rj::set(ret, "sound", value.getSound(), a);
         chatterino::rj::set(ret, "regex", value.isRegex(), a);
+        chatterino::rj::set(ret, "case", value.isCaseSensitive(), a);
 
         return ret;
     }
@@ -93,20 +103,24 @@ struct Deserialize<chatterino::HighlightPhrase> {
     {
         if (!value.IsObject())
         {
-            return chatterino::HighlightPhrase(QString(), true, false, false);
+            return chatterino::HighlightPhrase(QString(), true, false, false,
+                                               false);
         }
 
         QString _pattern;
         bool _alert = true;
         bool _sound = false;
         bool _isRegex = false;
+        bool _caseSensitive = false;
 
         chatterino::rj::getSafe(value, "pattern", _pattern);
         chatterino::rj::getSafe(value, "alert", _alert);
         chatterino::rj::getSafe(value, "sound", _sound);
         chatterino::rj::getSafe(value, "regex", _isRegex);
+        chatterino::rj::getSafe(value, "case", _caseSensitive);
 
-        return chatterino::HighlightPhrase(_pattern, _alert, _sound, _isRegex);
+            return chatterino::HighlightPhrase(_pattern, _alert, _sound,
+                                               _isRegex, _caseSensitive);
     }
 };
 
diff --git a/src/controllers/highlights/UserHighlightModel.cpp b/src/controllers/highlights/UserHighlightModel.cpp
index e04c3403e..5e3ed12c5 100644
--- a/src/controllers/highlights/UserHighlightModel.cpp
+++ b/src/controllers/highlights/UserHighlightModel.cpp
@@ -8,7 +8,7 @@ namespace chatterino {
 
 // commandmodel
 UserHighlightModel::UserHighlightModel(QObject *parent)
-    : SignalVectorModel<HighlightPhrase>(4, parent)
+    : SignalVectorModel<HighlightPhrase>(5, parent)
 {
 }
 
@@ -21,7 +21,8 @@ HighlightPhrase UserHighlightModel::getItemFromRow(
     return HighlightPhrase{row[0]->data(Qt::DisplayRole).toString(),
                            row[1]->data(Qt::CheckStateRole).toBool(),
                            row[2]->data(Qt::CheckStateRole).toBool(),
-                           row[3]->data(Qt::CheckStateRole).toBool()};
+                           row[3]->data(Qt::CheckStateRole).toBool(),
+                           row[4]->data(Qt::CheckStateRole).toBool()};
 }
 
 // row into vector item
@@ -32,6 +33,7 @@ void UserHighlightModel::getRowFromItem(const HighlightPhrase &item,
     setBoolItem(row[1], item.getAlert());
     setBoolItem(row[2], item.getSound());
     setBoolItem(row[3], item.isRegex());
+    setBoolItem(row[4], item.isCaseSensitive());
 }
 
 }  // namespace chatterino
diff --git a/src/providers/twitch/TwitchMessageBuilder.cpp b/src/providers/twitch/TwitchMessageBuilder.cpp
index 9b8d30cc2..0afcb6a68 100644
--- a/src/providers/twitch/TwitchMessageBuilder.cpp
+++ b/src/providers/twitch/TwitchMessageBuilder.cpp
@@ -952,7 +952,7 @@ void TwitchMessageBuilder::parseHighlights()
     {
         HighlightPhrase selfHighlight(
             currentUsername, getSettings()->enableSelfHighlightTaskbar,
-            getSettings()->enableSelfHighlightSound, false);
+            getSettings()->enableSelfHighlightSound, false, false);
         activeHighlights.emplace_back(std::move(selfHighlight));
     }
 
diff --git a/src/widgets/settingspages/HighlightingPage.cpp b/src/widgets/settingspages/HighlightingPage.cpp
index ec970e2dc..3fda3fd71 100644
--- a/src/widgets/settingspages/HighlightingPage.cpp
+++ b/src/widgets/settingspages/HighlightingPage.cpp
@@ -57,7 +57,7 @@ HighlightingPage::HighlightingPage()
 
                 view->addRegexHelpLink();
                 view->setTitles({"Pattern", "Flash\ntaskbar", "Play\nsound",
-                                 "Enable\nregex"});
+                                 "Enable\nregex", "Case-\nsensitive"});
                 view->getTableView()->horizontalHeader()->setSectionResizeMode(
                     QHeaderView::Fixed);
                 view->getTableView()->horizontalHeader()->setSectionResizeMode(
@@ -71,8 +71,8 @@ HighlightingPage::HighlightingPage()
                 });
 
                 view->addButtonPressed.connect([] {
-                    getApp()->highlights->phrases.appendItem(
-                        HighlightPhrase{"my phrase", true, false, false});
+                    getApp()->highlights->phrases.appendItem(HighlightPhrase{
+                        "my phrase", true, false, false, false});
                 });
             }
 
@@ -87,6 +87,9 @@ HighlightingPage::HighlightingPage()
                         .getElement();
 
                 view->addRegexHelpLink();
+
+                // Case-sensitivity doesn't make sense for user names so it is
+                // set to "false" by default & no checkbox is shown
                 view->setTitles({"Username", "Flash\ntaskbar", "Play\nsound",
                                  "Enable\nregex"});
                 view->getTableView()->horizontalHeader()->setSectionResizeMode(
@@ -103,7 +106,7 @@ HighlightingPage::HighlightingPage()
 
                 view->addButtonPressed.connect([] {
                     getApp()->highlights->highlightedUsers.appendItem(
-                        HighlightPhrase{"highlighted user", true, false,
+                        HighlightPhrase{"highlighted user", true, false, false,
                                         false});
                 });
             }