diff --git a/Libraries/LibWeb/Page/EventHandler.cpp b/Libraries/LibWeb/Page/EventHandler.cpp
index d25f436e09c..e64658b93c9 100644
--- a/Libraries/LibWeb/Page/EventHandler.cpp
+++ b/Libraries/LibWeb/Page/EventHandler.cpp
@@ -1068,6 +1068,18 @@ static bool produces_character_value(u32 code_point)
         || Unicode::code_point_has_symbol_general_category(code_point);
 }
 
+// https://github.com/w3c/uievents/issues/183#issuecomment-448091687
+static bool is_enter_key_or_interoperable_enter_key_combo(UIEvents::KeyCode key, u32 modifiers)
+{
+    if (key != UIEvents::KeyCode::Key_Return)
+        return false;
+    if (!modifiers)
+        return true;
+    if (modifiers & (UIEvents::KeyModifier::Mod_Shift | UIEvents::KeyModifier::Mod_Ctrl))
+        return true;
+    return false;
+}
+
 EventResult EventHandler::input_event(FlyString const& event_name, FlyString const& input_type, HTML::Navigable& navigable, u32 code_point)
 {
     auto document = navigable.active_document();
@@ -1115,7 +1127,10 @@ EventResult EventHandler::handle_keydown(UIEvents::KeyCode key, u32 modifiers, u
     // https://w3c.github.io/uievents/#event-type-keypress
     // If supported by a user agent, this event MUST be dispatched when a key is pressed down, if and only if that key
     // normally produces a character value.
-    if (produces_character_value(code_point)) {
+    // AD-HOC: For web compat and for interop with other engines, we make an exception here for the Enter key. See:
+    //         https://github.com/w3c/uievents/issues/183#issuecomment-448091687 and
+    //         https://github.com/w3c/uievents/issues/266#issuecomment-1887917756
+    if (produces_character_value(code_point) || is_enter_key_or_interoperable_enter_key_combo(key, modifiers)) {
         dispatch_result = fire_keyboard_event(UIEvents::EventNames::keypress, m_navigable, key, modifiers, code_point, repeat);
         if (dispatch_result != EventResult::Accepted)
             return dispatch_result;
diff --git a/Tests/LibWeb/Text/expected/UIEvents/KeyEvent-keypress.txt b/Tests/LibWeb/Text/expected/UIEvents/KeyEvent-keypress.txt
index 4d4617ea838..5c74fa59aeb 100644
--- a/Tests/LibWeb/Text/expected/UIEvents/KeyEvent-keypress.txt
+++ b/Tests/LibWeb/Text/expected/UIEvents/KeyEvent-keypress.txt
@@ -3,3 +3,12 @@ keypress key=A charCode=65
 keydown key=Shift charCode=0
 keydown key=B charCode=0
 keypress key=B charCode=66
+keydown key=Enter charCode=0
+keypress key=Enter charCode=0
+keydown key=Enter charCode=0 modifiers=Alt
+keydown key=Enter charCode=0 modifiers=Control
+keypress key=Enter charCode=0 modifiers=Control
+keydown key=Enter charCode=0 modifiers=Shift
+keypress key=Enter charCode=0 modifiers=Shift
+keydown key=Enter charCode=0
+keydown key=Enter charCode=0
diff --git a/Tests/LibWeb/Text/input/UIEvents/KeyEvent-keypress.html b/Tests/LibWeb/Text/input/UIEvents/KeyEvent-keypress.html
index 459f2cf66b0..4653c2259e7 100644
--- a/Tests/LibWeb/Text/input/UIEvents/KeyEvent-keypress.html
+++ b/Tests/LibWeb/Text/input/UIEvents/KeyEvent-keypress.html
@@ -4,15 +4,39 @@
     test(() => {
         let input = document.getElementById("input");
 
+        const modifierKeys = ['Alt', 'Control', 'Shift', 'Super', 'NumLock'];
         input.addEventListener("keydown", e => {
-            println(`keydown key=${e.key} charCode=${e.charCode}`);
+            const activeModifiers = modifierKeys.filter(modifier => e.getModifierState(modifier));
+            if (activeModifiers.length > 0) {
+                  println(`keydown key=${e.key} charCode=${e.charCode} modifiers=${activeModifiers.join(', ')}`);
+            } else {
+                  println(`keydown key=${e.key} charCode=${e.charCode}`);
+            }
         });
         input.addEventListener("keypress", e => {
-            println(`keypress key=${e.key} charCode=${e.charCode}`);
+            const activeModifiers = modifierKeys.filter(modifier => e.getModifierState(modifier));
+            if (activeModifiers.length > 0) {
+                println(`keypress key=${e.key} charCode=${e.charCode} modifiers=${activeModifiers.join(', ')}`);
+            } else {
+                println(`keypress key=${e.key} charCode=${e.charCode}`);
+            }
         });
 
         internals.sendText(input, "A");
         internals.sendKey(input, "LeftShift");
         internals.sendText(input, "B");
+
+        internals.sendKey(input, "Return");
+
+        let modifiers = 1 << 0; // Mod_Alt
+        internals.sendKey(input, "Return", modifiers);
+        modifiers = 1 << 1; // Mod_Ctrl
+        internals.sendKey(input, "Return", modifiers);
+        modifiers = 1 << 2; // Mod_Shift
+        internals.sendKey(input, "Return", modifiers);
+        modifiers = 1 << 3; // Mod_Super
+        internals.sendKey(input, "Return", modifiers);
+        modifiers = 1 << 4; // Mod_Keypad
+        internals.sendKey(input, "Return", modifiers);
     });
 </script>