diff --git a/src/util/root.rs b/src/util/root.rs
index 0c5a0be..a389830 100644
--- a/src/util/root.rs
+++ b/src/util/root.rs
@@ -1,4 +1,4 @@
-// Copyright (c) 2024 Sophie Herold
+// Copyright (c) 2024-2025 Sophie Herold
 //
 // This program is free software: you can redistribute it and/or modify
 // it under the terms of the GNU General Public License as published by
@@ -17,7 +17,7 @@
 
 use gtk::prelude::*;
 
-use crate::widgets::LpWindow;
+use crate::widgets::{LpEditWindow, LpWindow};
 
 pub trait ParentWindow: WidgetExt {
     fn window(&self) -> LpWindow {
@@ -29,6 +29,15 @@ pub trait ParentWindow: WidgetExt {
 
         result.unwrap()
     }
+
+    fn edit_window(&self) -> LpEditWindow {
+        let parent = self.parent().unwrap();
+
+        parent
+            .clone()
+            .downcast()
+            .unwrap_or_else(|_| parent.edit_window())
+    }
 }
 
 impl<T: WidgetExt> ParentWindow for T {}
diff --git a/src/widgets/edit/crop.rs b/src/widgets/edit/crop.rs
index 8dbd38b..4d50ab0 100644
--- a/src/widgets/edit/crop.rs
+++ b/src/widgets/edit/crop.rs
@@ -18,6 +18,7 @@
 //! Shows an resizable cropping selection
 
 use std::cell::{Cell, OnceCell};
+use std::marker::PhantomData;
 
 use adw::prelude::*;
 use adw::subclass::prelude::*;
@@ -29,7 +30,7 @@ use crate::util::gettext::*;
 use crate::util::root::ParentWindow;
 use crate::util::ErrorType;
 use crate::widgets::edit::LpEditCropSelection;
-use crate::widgets::{LpEditWindow, LpImage};
+use crate::widgets::LpImage;
 
 /// Aspect ratio modes that can be selected
 #[derive(Debug, Clone, Copy, Default, glib::Enum, glib::Variant)]
@@ -59,6 +60,7 @@ pub enum LpOrientation {
 }
 
 mod imp {
+
     use super::*;
 
     #[derive(Debug, Default, gtk::CompositeTemplate, glib::Properties)]
@@ -79,8 +81,8 @@ mod imp {
 
         #[property(get, construct_only)]
         original_image: OnceCell<LpImage>,
-        #[property(get, construct_only)]
-        edit_window: OnceCell<LpEditWindow>,
+        #[property(get=Self::cropped)]
+        cropped: PhantomData<bool>,
 
         #[property(get, set)]
         child: OnceCell<gtk::Widget>,
@@ -173,8 +175,6 @@ mod imp {
                     obj.imp().selection_changed();
                 }
             ));
-
-            let _ = self.apply_reset();
         }
 
         fn dispose(&self) {
@@ -183,6 +183,12 @@ mod imp {
     }
 
     impl WidgetImpl for LpEditCrop {
+        fn root(&self) {
+            self.parent_root();
+
+            let _ = self.apply_reset();
+        }
+
         fn size_allocate(&self, width: i32, height: i32, baseline: i32) {
             let obj = self.obj();
 
@@ -223,12 +229,14 @@ mod imp {
                 self.crop_area_image_coord.replace(crop_area_image_coord);
             }
 
-            let apply_sensitive = self.selection.is_cropped();
+            let apply_sensitive = self.cropped();
             self.apply_crop.set_visible(apply_sensitive);
+
+            self.obj().notify_cropped();
         }
 
         fn crop_area_image_coord(&self) -> Option<(u32, u32, u32, u32)> {
-            if !self.selection.is_cropped() {
+            if !self.cropped() {
                 return None;
             }
 
@@ -265,6 +273,10 @@ mod imp {
             (x.round(), y.round(), w.round(), h.round())
         }
 
+        fn cropped(&self) -> bool {
+            self.selection.is_cropped()
+        }
+
         fn reset_selection(&self) {
             let image = &self.image;
 
@@ -277,7 +289,7 @@ mod imp {
             self.selection.reset(x, y, width, height);
         }
 
-        fn apply_crop(&self) {
+        pub(super) fn apply_crop(&self) {
             if let Some(crop) = self.crop_area_image_coord.get() {
                 self.add_operation(Operation::Clip(crop));
 
@@ -372,11 +384,12 @@ glib::wrapper! {
 }
 
 impl LpEditCrop {
-    pub fn new(edit_window: LpEditWindow) -> Self {
-        glib::Object::builder()
-            .property("original_image", edit_window.original_image())
-            .property("edit_window", edit_window)
-            .build()
+    pub fn new(original_image: LpImage) -> Self {
+        let obj: Self = glib::Object::builder()
+            .property("original_image", original_image)
+            .build();
+
+        obj
     }
 
     pub fn selection(&self) -> LpEditCropSelection {
@@ -385,11 +398,15 @@ impl LpEditCrop {
 
     fn handle_error(&self, res: Result<(), EditingError>) {
         if let Err(err) = res {
-            self.edit_window().window().show_error(
+            self.window().show_error(
                 &gettext("Failed to Edit Image"),
                 &format!("Failed to edit image: {err}"),
                 ErrorType::General,
             );
         }
     }
+
+    pub fn apply_crop(&self) {
+        self.imp().apply_crop();
+    }
 }
diff --git a/src/widgets/edit_window.rs b/src/widgets/edit_window.rs
index 9c0f5c0..e21e1f1 100644
--- a/src/widgets/edit_window.rs
+++ b/src/widgets/edit_window.rs
@@ -45,6 +45,8 @@ mod imp {
 
         #[property(get, construct_only)]
         original_image: OnceCell<LpImage>,
+        #[property(get, construct_only)]
+        pub edit_crop: OnceCell<LpEditCrop>,
 
         pub(super) operations: RefCell<Option<Arc<Operations>>>,
     }
@@ -87,9 +89,6 @@ mod imp {
 
             let obj = self.obj();
 
-            self.toolbar_view
-                .set_content(Some(&LpEditCrop::new(obj.to_owned())));
-
             self.cancel.connect_clicked(glib::clone!(
                 #[weak]
                 obj,
@@ -109,7 +108,19 @@ mod imp {
         }
     }
 
-    impl WidgetImpl for LpEditWindow {}
+    impl WidgetImpl for LpEditWindow {
+        fn root(&self) {
+            self.parent_root();
+
+            let obj = self.obj();
+
+            obj.edit_crop().connect_cropped_notify(glib::clone!(
+                #[weak]
+                obj,
+                move |_| obj.imp().done.set_sensitive(obj.is_done_sensitive())
+            ));
+        }
+    }
     impl BinImpl for LpEditWindow {}
 
     impl LpEditWindow {
@@ -194,6 +205,9 @@ mod imp {
         /// Returns `true` if editing and saving was successful
         async fn save(&self, current_file: gio::File, new_file: gio::File) -> bool {
             let obj = self.obj();
+
+            obj.edit_crop().apply_crop();
+
             let editor = glycin::Editor::new(current_file);
             if let Some(operations) = obj.operations() {
                 log::debug!("Computing edited image.");
@@ -260,7 +274,8 @@ impl LpEditWindow {
 
     pub fn new(image: LpImage) -> Self {
         glib::Object::builder()
-            .property("original_image", image)
+            .property("original_image", image.clone())
+            .property("edit_crop", LpEditCrop::new(image))
             .build()
     }
 
@@ -270,13 +285,17 @@ impl LpEditWindow {
 
     pub fn set_operations(&self, operations: Option<Arc<glycin::Operations>>) {
         let imp = self.imp();
-
-        let done_sensitive = operations
-            .as_ref()
-            .is_some_and(|x| !x.operations().is_empty());
-        imp.done.set_sensitive(done_sensitive);
-
         imp.operations.replace(operations);
+        imp.done.set_sensitive(self.is_done_sensitive());
+    }
+
+    pub fn is_done_sensitive(&self) -> bool {
+        self.imp()
+            .operations
+            .borrow()
+            .as_ref()
+            .is_some_and(|x| !x.operations().is_empty())
+            || self.edit_crop().cropped()
     }
 
     pub fn add_operation(&self, operation: glycin::Operation) {
diff --git a/src/widgets/edit_window.ui b/src/widgets/edit_window.ui
index 3c3422a..bb6ac1b 100644
--- a/src/widgets/edit_window.ui
+++ b/src/widgets/edit_window.ui
@@ -4,6 +4,7 @@
     <property name="child">
       <object class="AdwToolbarView" id="toolbar_view">
         <property name="top-bar-style">raised</property>
+        <property name="content" bind-source="LpEditWindow" bind-property="edit_crop" />
         <child type="top">
           <object class="AdwHeaderBar">
             <property name="show-start-title-buttons">false</property>
diff --git a/src/widgets/image_view.rs b/src/widgets/image_view.rs
index ea1c9c0..3c72a62 100644
--- a/src/widgets/image_view.rs
+++ b/src/widgets/image_view.rs
@@ -529,7 +529,10 @@ impl LpImageView {
         }
 
         let Some(new_index) = self.model().index_of(new_file) else {
-            log::warn!("Could not navigate to file {}", new_file.uri());
+            log::warn!(
+                "Could not navigate to file '{}': Not in model",
+                new_file.uri()
+            );
             return;
         };
 
diff --git a/src/widgets/window.rs b/src/widgets/window.rs
index 4d79537..ce78b56 100644
--- a/src/widgets/window.rs
+++ b/src/widgets/window.rs
@@ -248,6 +248,7 @@ impl LpWindow {
     }
 
     pub fn show_specific_image(&self, file: gio::File) {
+        log::debug!("Showting specific image: {}", file.uri());
         self.image_view().set_images_from_files(vec![file]);
         self.show_image();
     }