diff --git a/Ladybird/AppKit/UI/Event.mm b/Ladybird/AppKit/UI/Event.mm
index f119f587a5f..de029ca5367 100644
--- a/Ladybird/AppKit/UI/Event.mm
+++ b/Ladybird/AppKit/UI/Event.mm
@@ -298,11 +298,15 @@ Web::KeyEvent ns_event_to_key_event(Web::KeyEvent::Type type, NSEvent* event)
     auto modifiers = ns_modifiers_to_key_modifiers(event.modifierFlags);
     auto key_code = ns_key_code_to_key_code(event.keyCode, modifiers);
 
-    auto const* utf8 = [event.characters UTF8String];
-    Utf8View utf8_view { StringView { utf8, strlen(utf8) } };
-
     // FIXME: WebContent should really support multi-code point key events.
-    auto code_point = utf8_view.is_empty() ? 0u : *utf8_view.begin();
+    u32 code_point = 0;
+
+    if (event.type == NSEventTypeKeyDown || event.type == NSEventTypeKeyUp) {
+        auto const* utf8 = [event.characters UTF8String];
+        Utf8View utf8_view { StringView { utf8, strlen(utf8) } };
+
+        code_point = utf8_view.is_empty() ? 0u : *utf8_view.begin();
+    }
 
     // NSEvent assigns PUA code points to to functional keys, e.g. arrow keys. Do not propagate them.
     if (code_point >= 0xE000 && code_point <= 0xF8FF)
diff --git a/Ladybird/AppKit/UI/LadybirdWebView.mm b/Ladybird/AppKit/UI/LadybirdWebView.mm
index 4b0504ebf6e..5905f4e5a3a 100644
--- a/Ladybird/AppKit/UI/LadybirdWebView.mm
+++ b/Ladybird/AppKit/UI/LadybirdWebView.mm
@@ -58,6 +58,11 @@ struct HideCursor {
     Optional<String> m_context_menu_search_text;
 
     Optional<HideCursor> m_hidden_cursor;
+
+    // We have to send key events for modifer keys, but AppKit does not generate key down/up events when only a modifier
+    // key is pressed. Instead, we only receive an event that the modifier flags have changed, and we must determine for
+    // ourselves whether the modifier key was pressed or released.
+    NSEventModifierFlags m_modifier_flags;
 }
 
 @property (nonatomic, weak) id<LadybirdWebViewObserver> observer;
@@ -135,6 +140,8 @@ struct HideCursor {
         [self addTrackingArea:area];
 
         [self registerForDraggedTypes:[NSArray arrayWithObjects:NSPasteboardTypeFileURL, nil]];
+
+        m_modifier_flags = 0;
     }
 
     return self;
@@ -1676,6 +1683,36 @@ static void copy_data_to_clipboard(StringView data, NSPasteboardType pasteboard_
     m_web_view_bridge->enqueue_input_event(move(key_event));
 }
 
+- (void)flagsChanged:(NSEvent*)event
+{
+    if (self.event_being_redispatched == event) {
+        return;
+    }
+
+    auto enqueue_event_if_needed = [&](auto flag) {
+        auto is_flag_set = [&](auto flags) { return (flags & flag) != 0; };
+        Web::KeyEvent::Type type;
+
+        if (is_flag_set(event.modifierFlags) && !is_flag_set(m_modifier_flags)) {
+            type = Web::KeyEvent::Type::KeyDown;
+        } else if (!is_flag_set(event.modifierFlags) && is_flag_set(m_modifier_flags)) {
+            type = Web::KeyEvent::Type::KeyUp;
+        } else {
+            return;
+        }
+
+        auto key_event = Ladybird::ns_event_to_key_event(type, event);
+        m_web_view_bridge->enqueue_input_event(move(key_event));
+    };
+
+    enqueue_event_if_needed(NSEventModifierFlagShift);
+    enqueue_event_if_needed(NSEventModifierFlagControl);
+    enqueue_event_if_needed(NSEventModifierFlagOption);
+    enqueue_event_if_needed(NSEventModifierFlagCommand);
+
+    m_modifier_flags = event.modifierFlags;
+}
+
 #pragma mark - NSDraggingDestination
 
 - (NSDragOperation)draggingEntered:(id<NSDraggingInfo>)event