diff --git a/book/src/generated/static-cmd.md b/book/src/generated/static-cmd.md
index 85f4d1d5a444..9b9b50b01981 100644
--- a/book/src/generated/static-cmd.md
+++ b/book/src/generated/static-cmd.md
@@ -65,6 +65,7 @@
 | `page_cursor_half_up` | Move page and cursor half up | normal: `` <C-u> ``, `` Z<C-u> ``, `` z<C-u> ``, `` Z<backspace> ``, `` z<backspace> ``, select: `` <C-u> ``, `` Z<C-u> ``, `` z<C-u> ``, `` Z<backspace> ``, `` z<backspace> `` |
 | `page_cursor_half_down` | Move page and cursor half down | normal: `` <C-d> ``, `` Z<C-d> ``, `` z<C-d> ``, `` Z<space> ``, `` z<space> ``, select: `` <C-d> ``, `` Z<C-d> ``, `` z<C-d> ``, `` Z<space> ``, `` z<space> `` |
 | `select_all` | Select whole document | normal: `` % ``, select: `` % `` |
+| `select_first_and_last_chars` | Select first and last characters of each selection | normal: `` <A-S> ``, select: `` <A-S> `` |
 | `select_regex` | Select all regex matches inside selections | normal: `` s ``, select: `` s `` |
 | `split_selection` | Split selections on regex matches | normal: `` S ``, select: `` S `` |
 | `split_selection_on_newline` | Split selection on newlines | normal: `` <A-s> ``, select: `` <A-s> `` |
diff --git a/book/src/keymap.md b/book/src/keymap.md
index 2797eaee2908..4de35ab09f14 100644
--- a/book/src/keymap.md
+++ b/book/src/keymap.md
@@ -117,6 +117,7 @@ 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 61d495d7c9d8..f2b07c467ede 100644
--- a/helix-term/src/commands.rs
+++ b/helix-term/src/commands.rs
@@ -349,6 +349,7 @@ impl MappableCommand {
         page_cursor_half_up, "Move page and cursor half up",
         page_cursor_half_down, "Move page and cursor half 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",
@@ -2004,6 +2005,21 @@ 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 c6cefd927574..8a7e0db29090 100644
--- a/helix-term/src/keymap/default.rs
+++ b/helix-term/src/keymap/default.rs
@@ -79,6 +79,7 @@ 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,