diff --git a/book/src/keymap.md b/book/src/keymap.md
index a3e41666f3fd..f5e9f104dd7c 100644
--- a/book/src/keymap.md
+++ b/book/src/keymap.md
@@ -113,6 +113,7 @@ Normal mode is the default mode when you launch helix. You can return to it from
 | `s`                   | Select all regex matches inside selections                        | `select_regex`                       |
 | `S`                   | Split selection into sub selections on regex matches              | `split_selection`                    |
 | `Alt-s`               | Split selection on newlines                                       | `split_selection_on_newline`         |
+| `Alt-S`               | Select first and last characters of each selection                | `select_first_and_last_chars`        |
 | `Alt-minus`           | Merge selections                                                  | `merge_selections`                   |
 | `Alt-_`               | Merge consecutive selections                                      | `merge_consecutive_selections`       |
 | `&`                   | Align selection in columns                                        | `align_selections`                   |
diff --git a/helix-term/src/commands.rs b/helix-term/src/commands.rs
index 4df3278b8bba..25d4da21a848 100644
--- a/helix-term/src/commands.rs
+++ b/helix-term/src/commands.rs
@@ -278,6 +278,7 @@ impl MappableCommand {
         half_page_up, "Move half page up",
         half_page_down, "Move half page down",
         select_all, "Select whole document",
+        select_first_and_last_chars, "Select first and last characters of each selection",
         select_regex, "Select all regex matches inside selections",
         split_selection, "Split selections on regex matches",
         split_selection_on_newline, "Split selection on newlines",
@@ -1811,6 +1812,21 @@ fn select_all(cx: &mut Context) {
     doc.set_selection(view.id, Selection::single(0, end))
 }
 
+fn select_first_and_last_chars(cx: &mut Context) {
+    let (view, doc) = current!(cx.editor);
+    let text = doc.text().slice(..);
+
+    let selection = doc.selection(view.id).clone().transform_iter(|range| {
+        [
+            Range::point(range.from()),
+            Range::point(graphemes::prev_grapheme_boundary(text, range.to())),
+        ]
+        .into_iter()
+    });
+
+    doc.set_selection(view.id, selection);
+}
+
 fn select_regex(cx: &mut Context) {
     let reg = cx.register.unwrap_or('/');
     ui::regex_prompt(
diff --git a/helix-term/src/keymap/default.rs b/helix-term/src/keymap/default.rs
index 763ed4ae71ce..6a35581a774a 100644
--- a/helix-term/src/keymap/default.rs
+++ b/helix-term/src/keymap/default.rs
@@ -78,6 +78,7 @@ pub fn default() -> HashMap<Mode, KeyTrie> {
 
 
         "s" => select_regex,
+        "A-S" => select_first_and_last_chars,
         "A-s" => split_selection_on_newline,
         "A-minus" => merge_selections,
         "A-_" => merge_consecutive_selections,