diff --git a/Userland/DevTools/HackStudio/LanguageServers/FileDB.cpp b/Userland/DevTools/HackStudio/LanguageServers/FileDB.cpp
index 13f14959fe..6b3e7c25a8 100644
--- a/Userland/DevTools/HackStudio/LanguageServers/FileDB.cpp
+++ b/Userland/DevTools/HackStudio/LanguageServers/FileDB.cpp
@@ -102,6 +102,7 @@ public:
     virtual void document_did_change() override {};
     virtual void document_did_set_text() override {};
     virtual void document_did_set_cursor(const GUI::TextPosition&) override {};
+    virtual void document_did_update_undo_stack() override { }
 
     virtual bool is_automatic_indentation_enabled() const override { return false; }
     virtual int soft_tab_width() const override { return 4; }
diff --git a/Userland/Libraries/LibGUI/TextDocument.cpp b/Userland/Libraries/LibGUI/TextDocument.cpp
index e007ce65cc..7686e67a0b 100644
--- a/Userland/Libraries/LibGUI/TextDocument.cpp
+++ b/Userland/Libraries/LibGUI/TextDocument.cpp
@@ -28,6 +28,13 @@ TextDocument::TextDocument(Client* client)
     append_line(make<TextDocumentLine>(*this));
     set_unmodified();
 
+    m_undo_stack.on_state_change = [this] {
+        if (m_client_notifications_enabled) {
+            for (auto* client : m_clients)
+                client->document_did_update_undo_stack();
+        }
+    };
+
     m_undo_timer = Core::Timer::create_single_shot(
         2000, [this] {
             update_undo();
@@ -694,6 +701,7 @@ void TextDocument::redo()
 void TextDocument::add_to_undo_stack(NonnullOwnPtr<TextDocumentUndoCommand> undo_command)
 {
     m_undo_stack.push(move(undo_command));
+    notify_did_change();
 }
 
 TextDocumentUndoCommand::TextDocumentUndoCommand(TextDocument& document)
diff --git a/Userland/Libraries/LibGUI/TextDocument.h b/Userland/Libraries/LibGUI/TextDocument.h
index fa1b7beeef..aac61254fb 100644
--- a/Userland/Libraries/LibGUI/TextDocument.h
+++ b/Userland/Libraries/LibGUI/TextDocument.h
@@ -47,6 +47,7 @@ public:
         virtual void document_did_change() = 0;
         virtual void document_did_set_text() = 0;
         virtual void document_did_set_cursor(const TextPosition&) = 0;
+        virtual void document_did_update_undo_stack() = 0;
 
         virtual bool is_automatic_indentation_enabled() const = 0;
         virtual int soft_tab_width() const = 0;
diff --git a/Userland/Libraries/LibGUI/TextEditor.cpp b/Userland/Libraries/LibGUI/TextEditor.cpp
index fcb9bfe542..bd9b9754e9 100644
--- a/Userland/Libraries/LibGUI/TextEditor.cpp
+++ b/Userland/Libraries/LibGUI/TextEditor.cpp
@@ -1324,8 +1324,6 @@ void TextEditor::did_change()
 {
     update_content_size();
     recompute_all_visual_lines();
-    m_undo_action->set_enabled(can_undo());
-    m_redo_action->set_enabled(can_redo());
     if (m_autocomplete_box && !m_should_keep_autocomplete_box) {
         m_autocomplete_box->close();
         if (m_autocomplete_timer)
@@ -1636,6 +1634,12 @@ void TextEditor::document_did_change()
     update();
 }
 
+void TextEditor::document_did_update_undo_stack()
+{
+    m_undo_action->set_enabled(can_undo());
+    m_redo_action->set_enabled(can_redo());
+}
+
 void TextEditor::document_did_set_text()
 {
     m_line_visual_data.clear();
diff --git a/Userland/Libraries/LibGUI/TextEditor.h b/Userland/Libraries/LibGUI/TextEditor.h
index 44de99cbc9..d99929718b 100644
--- a/Userland/Libraries/LibGUI/TextEditor.h
+++ b/Userland/Libraries/LibGUI/TextEditor.h
@@ -223,6 +223,7 @@ private:
     virtual void document_did_change() override;
     virtual void document_did_set_text() override;
     virtual void document_did_set_cursor(const TextPosition&) override;
+    virtual void document_did_update_undo_stack() override;
 
     // ^Syntax::HighlighterClient
     virtual Vector<TextDocumentSpan>& spans() final { return document().spans(); }