diff --git a/CodeEdit/Features/CEWorkspace/Models/CEWorkspaceFile.swift b/CodeEdit/Features/CEWorkspace/Models/CEWorkspaceFile.swift
index ac6acc55f..3e116900a 100644
--- a/CodeEdit/Features/CEWorkspace/Models/CEWorkspaceFile.swift
+++ b/CodeEdit/Features/CEWorkspace/Models/CEWorkspaceFile.swift
@@ -55,16 +55,16 @@ final class CEWorkspaceFile: Codable, Comparable, Hashable, Identifiable, Editor
     /// If the item already is the top-level ``CEWorkspaceFile`` this returns `nil`.
     var parent: CEWorkspaceFile?
 
-    private let fileDocumentSubject = PassthroughSubject<Void, Never>()
+    private let fileDocumentSubject = PassthroughSubject<CodeFileDocument?, Never>()
 
     var fileDocument: CodeFileDocument? {
         didSet {
-            fileDocumentSubject.send()
+            fileDocumentSubject.send(fileDocument)
         }
     }
 
     /// Publisher for fileDocument property
-    var fileDocumentPublisher: AnyPublisher<Void, Never> {
+    var fileDocumentPublisher: AnyPublisher<CodeFileDocument?, Never> {
         fileDocumentSubject.eraseToAnyPublisher()
     }
 
diff --git a/CodeEdit/Features/Documents/Controllers/CodeEditWindowController.swift b/CodeEdit/Features/Documents/Controllers/CodeEditWindowController.swift
index 41aab954d..56c9f7dab 100644
--- a/CodeEdit/Features/Documents/Controllers/CodeEditWindowController.swift
+++ b/CodeEdit/Features/Documents/Controllers/CodeEditWindowController.swift
@@ -7,6 +7,7 @@
 
 import Cocoa
 import SwiftUI
+import Combine
 
 final class CodeEditWindowController: NSWindowController, NSToolbarDelegate, ObservableObject {
     static let minSidebarWidth: CGFloat = 242
@@ -23,6 +24,8 @@ final class CodeEditWindowController: NSWindowController, NSToolbarDelegate, Obs
 
     var splitViewController: NSSplitViewController!
 
+    internal var cancellables = [AnyCancellable]()
+
     init(window: NSWindow, workspace: WorkspaceDocument) {
         super.init(window: window)
         self.workspace = workspace
@@ -47,6 +50,10 @@ final class CodeEditWindowController: NSWindowController, NSToolbarDelegate, Obs
         registerCommands()
     }
 
+    deinit {
+        cancellables.forEach({ $0.cancel() })
+    }
+
     @available(*, unavailable)
     required init?(coder: NSCoder) {
         fatalError("init(coder:) has not been implemented")
@@ -106,6 +113,7 @@ final class CodeEditWindowController: NSWindowController, NSToolbarDelegate, Obs
         splitVC.addSplitViewItem(inspector)
 
         self.splitViewController = splitVC
+        self.listenToDocumentEdited(workspace: workspace)
     }
 
     private func setupToolbar() {
diff --git a/CodeEdit/Features/Documents/Controllers/CodeEditWindowControllerExtensions.swift b/CodeEdit/Features/Documents/Controllers/CodeEditWindowControllerExtensions.swift
index f5899054c..0bec375d5 100644
--- a/CodeEdit/Features/Documents/Controllers/CodeEditWindowControllerExtensions.swift
+++ b/CodeEdit/Features/Documents/Controllers/CodeEditWindowControllerExtensions.swift
@@ -6,6 +6,7 @@
 //
 
 import SwiftUI
+import Combine
 
 extension CodeEditWindowController {
     @objc
@@ -63,6 +64,53 @@ extension CodeEditWindowController {
             command: CommandClosureWrapper(closure: { self.toggleLastPanel() })
         )
     }
+
+    // Listen to changes in all tabs/files
+    internal func listenToDocumentEdited(workspace: WorkspaceDocument) {
+        workspace.editorManager.$activeEditor
+            .flatMap({ editor in
+                editor.$tabs
+            })
+            .compactMap({ tab in
+                Publishers.MergeMany(tab.elements.compactMap({ $0.fileDocumentPublisher }))
+            })
+            .switchToLatest()
+            .compactMap({ fileDocument in
+                fileDocument?.isDocumentEditedPublisher
+            })
+            .flatMap({ $0 })
+            .sink { isDocumentEdited in
+                if isDocumentEdited {
+                    self.setDocumentEdited(true)
+                    return
+                }
+
+                self.updateDocumentEdited(workspace: workspace)
+            }
+            .store(in: &cancellables)
+
+        // Listen to change of tabs, if closed tab without saving content,
+        // we also need to recalculate isDocumentEdited
+        workspace.editorManager.$activeEditor
+            .flatMap({ editor in
+                editor.$tabs
+            })
+            .sink { _ in
+                self.updateDocumentEdited(workspace: workspace)
+            }
+            .store(in: &cancellables)
+    }
+
+    // Recalculate documentEdited by checking if any tab/file is edited
+    private func updateDocumentEdited(workspace: WorkspaceDocument) {
+        let hasEditedDocuments = !workspace
+            .editorManager
+            .editorLayout
+            .gatherOpenFiles()
+            .filter({ $0.fileDocument?.isDocumentEdited == true })
+            .isEmpty
+        self.setDocumentEdited(hasEditedDocuments)
+    }
 }
 
 extension NSToolbarItem.Identifier {