diff --git a/src/app.rs b/src/app.rs
index 258b8b3..e0a4960 100644
--- a/src/app.rs
+++ b/src/app.rs
@@ -63,6 +63,7 @@ pub struct Flags {
 #[derive(Clone, Copy, Debug, Eq, PartialEq)]
 pub enum Action {
     About,
+    AddToSidebar,
     Copy,
     Cut,
     EditLocation,
@@ -104,6 +105,7 @@ impl MenuAction for Action {
     fn message(&self, entity_opt: Option<Entity>) -> Message {
         match self {
             Action::About => Message::ToggleContextPage(ContextPage::About),
+            Action::AddToSidebar => Message::AddToSidebar(entity_opt),
             Action::Copy => Message::Copy(entity_opt),
             Action::Cut => Message::Cut(entity_opt),
             Action::EditLocation => Message::EditLocation(entity_opt),
@@ -170,6 +172,7 @@ impl MenuAction for NavMenuAction {
 /// Messages that are used specifically by our [`App`].
 #[derive(Clone, Debug)]
 pub enum Message {
+    AddToSidebar(Option<Entity>),
     AppTheme(AppTheme),
     Config(Config),
     Copy(Option<Entity>),
@@ -395,18 +398,27 @@ impl App {
     fn update_nav_model(&mut self) {
         let mut nav_model = segmented_button::ModelBuilder::default();
         for (favorite_i, favorite) in self.config.favorites.iter().enumerate() {
-            if let Some(dir) = favorite.path_opt() {
+            if let Some(path) = favorite.path_opt() {
                 let name = if matches!(favorite, Favorite::Home) {
                     fl!("home")
-                } else if let Some(file_name) = dir.file_name().and_then(|x| x.to_str()) {
+                } else if let Some(file_name) = path.file_name().and_then(|x| x.to_str()) {
                     file_name.to_string()
                 } else {
                     continue;
                 };
                 nav_model = nav_model.insert(move |b| {
                     b.text(name.clone())
-                        .icon(widget::icon::icon(tab::folder_icon_symbolic(&dir, 16)).size(16))
-                        .data(Location::Path(dir.clone()))
+                        .icon(
+                            widget::icon::icon(if path.is_dir() {
+                                tab::folder_icon_symbolic(&path, 16)
+                            } else {
+                                widget::icon::from_name("text-x-generic-symbolic")
+                                    .size(16)
+                                    .handle()
+                            })
+                            .size(16),
+                        )
+                        .data(Location::Path(path.clone()))
                         .data(FavoriteIndex(favorite_i))
                 });
             }
@@ -986,6 +998,14 @@ impl Application for App {
         }
 
         match message {
+            Message::AddToSidebar(entity_opt) => {
+                let mut favorites = self.config.favorites.clone();
+                for path in self.selected_paths(entity_opt) {
+                    favorites.push(Favorite::from_path(path));
+                }
+                config_set!(favorites, favorites);
+                return self.update_config();
+            }
             Message::AppTheme(app_theme) => {
                 config_set!(app_theme, app_theme);
                 return self.update_config();
@@ -1081,6 +1101,7 @@ impl Application for App {
                 self.mounter_items.insert(mounter_key, mounter_items);
 
                 // Update nav bar
+                //TODO: this could change favorites IDs while they are in use
                 self.update_nav_model();
             }
             Message::NewItem(entity_opt, dir) => {
diff --git a/src/config.rs b/src/config.rs
index 56a1615..36c131c 100644
--- a/src/config.rs
+++ b/src/config.rs
@@ -48,6 +48,25 @@ pub enum Favorite {
 }
 
 impl Favorite {
+    pub fn from_path(path: PathBuf) -> Self {
+        // Ensure that special folders are handled properly
+        for favorite in &[
+            Self::Home,
+            Self::Documents,
+            Self::Downloads,
+            Self::Music,
+            Self::Pictures,
+            Self::Videos,
+        ] {
+            if let Some(favorite_path) = favorite.path_opt() {
+                if &favorite_path == &path {
+                    return favorite.clone();
+                }
+            }
+        }
+        Self::Path(path)
+    }
+
     pub fn path_opt(&self) -> Option<PathBuf> {
         match self {
             Self::Home => dirs::home_dir(),
diff --git a/src/menu.rs b/src/menu.rs
index b233925..e801bf3 100644
--- a/src/menu.rs
+++ b/src/menu.rs
@@ -110,7 +110,8 @@ pub fn context_menu<'a>(
                 children.push(horizontal_rule(1).into());
                 //TODO: change to Show details
                 children.push(menu_item(fl!("properties"), Action::Properties).into());
-                //TODO: Add to sidebar
+                children.push(horizontal_rule(1).into());
+                children.push(menu_item(fl!("add-to-sidebar"), Action::AddToSidebar).into());
                 children.push(horizontal_rule(1).into());
                 children.push(menu_item(fl!("move-to-trash"), Action::MoveToTrash).into());
             } else {