diff --git a/src/widgets/header_row.py b/src/widgets/header_row.py
index a789a75..39cf0fe 100644
--- a/src/widgets/header_row.py
+++ b/src/widgets/header_row.py
@@ -30,14 +30,23 @@ class HeaderRow(Gtk.Box):
     value_entry = Gtk.Template.Child()
     remove_button = Gtk.Template.Child()
 
-    # Signal emitted when remove button clicked
+    # Signals
     __gsignals__ = {
-        'remove-requested': (GObject.SIGNAL_RUN_FIRST, None, ())
+        'remove-requested': (GObject.SIGNAL_RUN_FIRST, None, ()),
+        'changed': (GObject.SIGNAL_RUN_FIRST, None, ())
     }
 
     def __init__(self):
         super().__init__()
 
+        # Connect to entry changes to emit our own changed signal
+        self.key_entry.connect('changed', self._on_entry_changed)
+        self.value_entry.connect('changed', self._on_entry_changed)
+
+    def _on_entry_changed(self, entry):
+        """Handle changes to key or value entries."""
+        self.emit('changed')
+
     @Gtk.Template.Callback()
     def on_remove_clicked(self, button):
         """Handle remove button click."""
diff --git a/src/window.py b/src/window.py
index e93bc08..bfcd043 100644
--- a/src/window.py
+++ b/src/window.py
@@ -837,6 +837,7 @@ class RosterWindow(Adw.ApplicationWindow):
         row = HeaderRow()
         row.set_header(key, value)
         row.connect('remove-requested', self._on_header_remove)
+        row.connect('changed', self._on_request_changed)
         self.headers_listbox.append(row)
 
         # Mark as changed if we're adding a non-empty header