diff --git a/data/jorts.gschema.xml.in b/data/jorts.gschema.xml.in
index 08409008..7026d1f0 100644
--- a/data/jorts.gschema.xml.in
+++ b/data/jorts.gschema.xml.in
@@ -12,9 +12,9 @@
 			<description>Whether to hide the actionbar and its buttons</description>
 		</key>
 		<key name="list-item-start" type="s">
-			<default>" • "</default>
-			<summary>Hide actionbar</summary>
-			<description>Whether to hide the actionbar and its buttons</description>
+			<default>"• "</default>
+			<summary>List item start</summary>
+			<description>The string to use at the start of a list item</description>
 		</key>
 	</schema>
 </schemalist>
diff --git a/src/Services/ZoomController.vala b/src/Services/ZoomController.vala
index 753b2ff9..78c9c3b1 100644
--- a/src/Services/ZoomController.vala
+++ b/src/Services/ZoomController.vala
@@ -105,6 +105,7 @@ public class Jorts.ZoomController : Object {
         window.remove_css_class (Jorts.Zoom.from_int ( _old_zoom).to_css_class ());
         _old_zoom = new_zoom;
         window.add_css_class (Jorts.Zoom.from_int ( new_zoom).to_css_class ());
+        window.textview.refresh_list_item_indentation ();
 
         // Adapt headerbar size to avoid weird flickering
         window.view.headerbar.height_request = Jorts.Zoom.from_int (new_zoom).to_ui_size ();
diff --git a/src/Views/PreferencesView.vala b/src/Views/PreferencesView.vala
index 1bd2a638..466e7763 100644
--- a/src/Views/PreferencesView.vala
+++ b/src/Views/PreferencesView.vala
@@ -10,6 +10,16 @@
     private Granite.Toast toast;
     public Gtk.Button close_button;
 
+    private void commit_list_prefix (Gtk.Entry entry) {
+        var current_prefix = Application.gsettings.get_string (KEY_LIST);
+
+        if (entry.text == current_prefix) {
+            return;
+        }
+
+        Application.gsettings.set_string (KEY_LIST, entry.text);
+    }
+
     construct {
         var overlay = new Gtk.Overlay ();
         child = overlay;
@@ -50,6 +60,15 @@
                 list_entry.secondary_icon_name = "view-refresh-symbolic";
                 list_entry.secondary_icon_tooltip_text = _("Reset to default");
                 list_entry.icon_press.connect (on_reset_prefix);
+                list_entry.activate.connect (() => {
+                    commit_list_prefix (list_entry);
+                });
+
+                var list_entry_focus = new Gtk.EventControllerFocus ();
+                list_entry_focus.leave.connect (() => {
+                    commit_list_prefix (list_entry);
+                });
+                list_entry.add_controller (list_entry_focus);
 
                 var list_label = new Granite.HeaderLabel (_("List item prefix")) {
                     mnemonic_widget = list_entry,
@@ -63,7 +82,7 @@
 
                 Application.gsettings.bind (KEY_LIST,
                     list_entry, "text",
-                    SettingsBindFlags.DEFAULT);
+                    SettingsBindFlags.GET);
 
                 settingsbox.append (lists_box);
 
diff --git a/src/Widgets/TextView.vala b/src/Widgets/TextView.vala
index 06a9bcf5..3a12e49c 100644
--- a/src/Widgets/TextView.vala
+++ b/src/Widgets/TextView.vala
@@ -12,7 +12,22 @@
 public class Jorts.TextView : Granite.HyperTextView {
 
     private Gtk.EventControllerKey keyboard;
-    public string list_item_start {get; set;}
+    private Gtk.TextBuffer? observed_buffer;
+    private ulong buffer_changed_handler_id = 0;
+    private bool list_item_restore_queued = false;
+    private string _list_item_start = "";
+    public string list_item_start {
+        get { return _list_item_start; }
+        set {
+            if (_list_item_start == value) {
+                return;
+            }
+
+            var old_prefix = _list_item_start;
+            _list_item_start = value;
+            migrate_list_prefixes (old_prefix, value);
+        }
+    }
     public bool on_list_item {public get; private set;}
 
     public string text {
@@ -75,12 +90,118 @@ public class Jorts.TextView : Granite.HyperTextView {
         /*              CONNECTS AND BINDS                 */
         /***************************************************/
 
+        notify["buffer"].connect (() => {
+            attach_buffer_observers ();
+            queue_restore_list_item_indentation ();
+        });
+        attach_buffer_observers ();
+
         Application.gsettings.bind (KEY_LIST,
             this, "list-item-start",
             GLib.SettingsBindFlags.DEFAULT);
     }
 
+    private void attach_buffer_observers () {
+        if (observed_buffer == buffer) {
+            return;
+        }
+
+        detach_buffer_observers ();
+        observed_buffer = buffer;
+
+        buffer_changed_handler_id = observed_buffer.changed.connect_after (queue_restore_list_item_indentation);
+    }
+
+    private void detach_buffer_observers () {
+        if (observed_buffer == null) {
+            return;
+        }
+
+        if (buffer_changed_handler_id != 0) {
+            SignalHandler.disconnect (observed_buffer, buffer_changed_handler_id);
+            buffer_changed_handler_id = 0;
+        }
+
+        observed_buffer = null;
+    }
+
+    private void queue_restore_list_item_indentation () {
+        if (list_item_restore_queued) {
+            return;
+        }
+
+        list_item_restore_queued = true;
+
+        Idle.add (() => {
+            list_item_restore_queued = false;
+            restore_list_item_indentation ();
+            return false;
+        });
+    }
+
+    private void ensure_tags () {
+        if (list_item_start == "") {
+            return;
+        }
+
+        var measured_prefix = list_item_start.strip ();
+
+        if (measured_prefix == "") {
+            measured_prefix = list_item_start;
+        }
+
+        var layout = this.create_pango_layout (measured_prefix);
+        int width, height;
+        layout.get_pixel_size (out width, out height);
+
+        var indent_width = int.max (width + 4, 8);
+
+        var list_item_tag = buffer.tag_table.lookup ("list_item");
+
+        if (list_item_tag == null) {
+            buffer.create_tag ("list_item",
+                "indent", -indent_width,
+                "left-margin", SPACING_DOUBLE + indent_width
+            );
+            return;
+        }
+
+        list_item_tag.indent = -indent_width;
+        list_item_tag.left_margin = SPACING_DOUBLE + indent_width;
+    }
+
+    public void refresh_list_item_indentation () {
+        ensure_tags ();
+    }
+
+    public void restore_list_item_indentation () {
+        Gtk.TextIter start, end;
+        buffer.get_bounds (out start, out end);
+        buffer.remove_tag_by_name ("list_item", start, end);
+
+        if (list_item_start == "") {
+            return;
+        }
+
+        ensure_tags ();
+
+        var line_count = buffer.get_line_count ();
+
+        for (int line_number = 0; line_number < line_count; line_number++) {
+            if (!this.has_prefix (line_number)) {
+                continue;
+            }
+
+            Gtk.TextIter line_start, line_end;
+            buffer.get_iter_at_line_offset (out line_start, line_number, 0);
+            line_end = line_start.copy ();
+            line_end.forward_to_line_end ();
+            buffer.apply_tag_by_name ("list_item", line_start, line_end);
+        }
+    }
+
     public void toggle_list () {
+        ensure_tags ();
         Gtk.TextIter start, end;
         buffer.get_selection_bounds (out start, out end);
 
@@ -105,8 +226,8 @@ public class Jorts.TextView : Granite.HyperTextView {
     /**
      * Add the list prefix only to lines who hasnt it already
      */
-    private bool has_prefix (int line_number) {
-        if (list_item_start == "") {return false;}
+    private bool has_specific_prefix (int line_number, string prefix) {
+        if (prefix == "") {return false;}
 
         Gtk.TextIter start, end;
         buffer.get_iter_at_line_offset (out start, line_number, 0);
@@ -116,7 +237,54 @@ public class Jorts.TextView : Granite.HyperTextView {
 
         var text_in_line = buffer.get_slice (start, end, false);
 
-        return text_in_line.has_prefix (list_item_start);
+        return text_in_line.has_prefix (prefix);
+    }
+
+    private bool has_prefix (int line_number) {
+        return has_specific_prefix (line_number, list_item_start);
+    }
+
+    private void replace_prefix (int line_number, string old_prefix, string new_prefix) {
+        Gtk.TextIter line_start, prefix_end;
+
+        buffer.get_iter_at_line_offset (out line_start, line_number, 0);
+        buffer.get_iter_at_line_offset (out prefix_end, line_number, old_prefix.char_count ());
+        buffer.delete (ref line_start, ref prefix_end);
+
+        buffer.get_iter_at_line_offset (out line_start, line_number, 0);
+        buffer.insert (ref line_start, new_prefix, -1);
+    }
+
+    private void migrate_list_prefixes (string old_prefix, string new_prefix) {
+        if (old_prefix == "") {
+            if (new_prefix == "") {
+                Gtk.TextIter start, end;
+                buffer.get_bounds (out start, out end);
+                buffer.remove_tag_by_name ("list_item", start, end);
+            }
+
+            return;
+        }
+
+        var line_count = buffer.get_line_count ();
+        var did_change = false;
+
+        buffer.begin_user_action ();
+
+        for (int line_number = 0; line_number < line_count; line_number++) {
+            if (!has_specific_prefix (line_number, old_prefix)) {
+                continue;
+            }
+
+            replace_prefix (line_number, old_prefix, new_prefix);
+            did_change = true;
+        }
+
+        buffer.end_user_action ();
+
+        if (did_change || new_prefix == "") {
+            restore_list_item_indentation ();
+        }
     }
 
     /**
@@ -147,6 +315,13 @@ public class Jorts.TextView : Granite.HyperTextView {
                 buffer.get_iter_at_line_offset (out line_start, line_number, 0);
                 buffer.insert (ref line_start, list_item_start, -1);
             }
+
+            // Apply hanging indent tag to the line
+            Gtk.TextIter ls, le;
+            buffer.get_iter_at_line_offset (out ls, line_number, 0);
+            le = ls.copy ();
+            le.forward_to_line_end ();
+            buffer.apply_tag_by_name ("list_item", ls, le);
         }
     }
 
@@ -163,13 +338,19 @@ public class Jorts.TextView : Granite.HyperTextView {
      * Remove list prefix from line x to line y. Presuppose it is there
      */
     private void remove_prefix (int line_number) {
-        Gtk.TextIter line_start, prefix_end;
+        Gtk.TextIter line_start, prefix_end, line_end;
         var remove_range = list_item_start.char_count ();
 
         debug ("doing line " + line_number.to_string ());
         buffer.get_iter_at_line_offset (out line_start, line_number, 0);
         buffer.get_iter_at_line_offset (out prefix_end, line_number, remove_range);
         buffer.delete (ref line_start, ref prefix_end);
+
+        // Remove hanging indent tag from the line
+        buffer.get_iter_at_line_offset (out line_start, line_number, 0);
+        line_end = line_start.copy ();
+        line_end.forward_to_line_end ();
+        buffer.remove_tag_by_name ("list_item", line_start, line_end);
     }
 
     /**
@@ -177,10 +358,10 @@ public class Jorts.TextView : Granite.HyperTextView {
      * Some local stuff is deduplicated in the Ifs, because i do not like the idea of getting computation done not needed 98% of the time
      */
     private bool on_key_pressed (uint keyval, uint keycode, Gdk.ModifierType state) {
+        ensure_tags ();
 
         // If backspace on a prefix: Delete the prefix.
         if (keyval == Gdk.Key.BackSpace) {
-            print ("backspace");
 
             Gtk.TextIter start, end;
             buffer.get_selection_bounds (out start, out end);
@@ -197,6 +378,13 @@ public class Jorts.TextView : Granite.HyperTextView {
                     buffer.begin_user_action ();
                     buffer.delete (ref start, ref end);
                     buffer.insert_at_cursor ("\n", -1);
+
+                    // The line is now an empty normal line, so remove the hanging indent
+                    buffer.get_iter_at_line_offset (out start, line_number, 0);
+                    end = start.copy ();
+                    end.forward_to_line_end ();
+                    buffer.remove_tag_by_name ("list_item", start, end);
+
                     buffer.end_user_action ();
                 }
             }
@@ -212,6 +400,13 @@ public class Jorts.TextView : Granite.HyperTextView {
 
                 buffer.begin_user_action ();
                 buffer.insert_at_cursor ("\n" + list_item_start, -1);
+
+                // Ensure new line has tag applied since it was just inserted
+                buffer.get_iter_at_line_offset (out start, line_number + 1, 0);
+                end = start.copy ();
+                end.forward_to_line_end ();
+                buffer.apply_tag_by_name ("list_item", start, end);
+
                 buffer.end_user_action ();
 
                 return true;
diff --git a/src/Windows/StickyNoteWindow.vala b/src/Windows/StickyNoteWindow.vala
index 27305c02..441bd37c 100644
--- a/src/Windows/StickyNoteWindow.vala
+++ b/src/Windows/StickyNoteWindow.vala
@@ -199,6 +199,7 @@ public class Jorts.StickyNoteWindow : Gtk.ApplicationWindow {
         color_controller.theme = data.theme;
         zoom_controller.zoom = data.zoom;
         view.monospace = data.monospace;
+        textview.restore_list_item_indentation ();
     }
 
     public void has_changed () {