diff --git a/data/org.gnome.Loupe.gschema.xml.in b/data/org.gnome.Loupe.gschema.xml.in
index 9a9d1d5..55c4344 100644
--- a/data/org.gnome.Loupe.gschema.xml.in
+++ b/data/org.gnome.Loupe.gschema.xml.in
@@ -9,5 +9,9 @@
       <default>true</default>
       <summary>Copy the image to the clipboard after annotation changes</summary>
     </key>
+    <key name="annotation-mode" type="b">
+      <default>true</default>
+      <summary>Open images in annotation mode</summary>
+    </key>
   </schema>
 </schemalist>
diff --git a/src/widgets/image_window.rs b/src/widgets/image_window.rs
index 52ca719..c0d90cf 100644
--- a/src/widgets/image_window.rs
+++ b/src/widgets/image_window.rs
@@ -489,12 +489,17 @@ mod imp {
                     }
                 });
 
-                // Connect draw mode button (headerbar toggle)
+                // Remember annotation mode and apply it to each newly opened image.
+                let draw_mode_settings = LpApplication::default().settings();
                 imp.draw_mode_button.connect_toggled(glib::clone!(
                     #[weak]
                     obj,
                     move |btn| {
                         let active = btn.is_active();
+                        if let Err(err) = draw_mode_settings.set_boolean("annotation-mode", active)
+                        {
+                            tracing::warn!("Failed to save annotation mode setting: {err}");
+                        }
                         let imp = obj.imp();
                         imp.draw_toolbar_revealer.set_reveal_child(active);
                         if let Some(img) = imp.image_view.current_image() {
@@ -509,6 +514,11 @@ mod imp {
                         }
                     }
                 ));
+                imp.draw_mode_button.set_active(
+                    LpApplication::default()
+                        .settings()
+                        .boolean("annotation-mode"),
+                );
 
                 // Tool buttons
                 imp.draw_freeform_btn.connect_toggled(glib::clone!(
@@ -1004,6 +1014,9 @@ impl LpImageWindow {
         // Properties view
         let current_image: Option<LpImage> = current_page.as_ref().map(|x| x.image());
         imp.properties_view.set_image(current_image.as_ref());
+        if let Some(image) = current_image.as_ref() {
+            image.set_drawing_mode(imp.draw_mode_button.is_active());
+        }
 
         let has_image = current_page.is_some();