diff --git a/helix-core/src/auto_pairs.rs b/helix-core/src/auto_pairs.rs
index c037afef4..1b3de6ea0 100644
--- a/helix-core/src/auto_pairs.rs
+++ b/helix-core/src/auto_pairs.rs
@@ -1,7 +1,7 @@
 //! When typing the opening character of one of the possible pairs defined below,
 //! this module provides the functionality to insert the paired closing character.
 
-use crate::{Range, Rope, Selection, Tendril, Transaction};
+use crate::{movement::Direction, Range, Rope, Selection, Tendril, Transaction};
 use log::debug;
 use smallvec::SmallVec;
 
@@ -30,7 +30,6 @@ const CLOSE_BEFORE: &str = ")]}'\":;,> \n\r\u{000B}\u{000C}\u{0085}\u{2028}\u{20
 
 // [TODO]
 // * delete implementation where it erases the whole bracket (|) -> |
-// * do not reduce to cursors; use whole selections, and surround with pair
 // * change to multi character pairs to handle cases like placing the cursor in the
 //   middle of triple quotes, and more exotic pairs like Jinja's {% %}
 
@@ -38,20 +37,18 @@ const CLOSE_BEFORE: &str = ")]}'\":;,> \n\r\u{000B}\u{000C}\u{0085}\u{2028}\u{20
 pub fn hook(doc: &Rope, selection: &Selection, ch: char) -> Option<Transaction> {
     debug!("autopairs hook selection: {:#?}", selection);
 
-    let cursors = selection.clone().cursors(doc.slice(..));
-
     for &(open, close) in PAIRS {
         if open == ch {
             if open == close {
-                return Some(handle_same(doc, &cursors, open, CLOSE_BEFORE, OPEN_BEFORE));
+                return Some(handle_same(doc, selection, open, CLOSE_BEFORE, OPEN_BEFORE));
             } else {
-                return Some(handle_open(doc, &cursors, open, close, CLOSE_BEFORE));
+                return Some(handle_open(doc, selection, open, close, CLOSE_BEFORE));
             }
         }
 
         if close == ch {
             // && char_at pos == close
-            return Some(handle_close(doc, &cursors, open, close));
+            return Some(handle_close(doc, selection, open, close));
         }
     }
 
@@ -66,6 +63,36 @@ fn prev_char(doc: &Rope, pos: usize) -> Option<char> {
     doc.get_char(pos - 1)
 }
 
+/// calculate what the resulting range should be for an auto pair insertion
+fn get_next_range(
+    start_range: &Range,
+    offset: usize,
+    typed_char: char,
+    len_inserted: usize,
+) -> Range {
+    let end_head = start_range.head + offset + typed_char.len_utf8();
+
+    let end_anchor = match (start_range.len(), start_range.direction()) {
+        // if we have a zero width cursor, it shifts to the same number
+        (0, _) => end_head,
+
+        // if we are inserting for a regular one-width cursor, the anchor
+        // moves with the head
+        (1, Direction::Forward) => end_head - 1,
+        (1, Direction::Backward) => end_head + 1,
+
+        // if we are appending, the anchor stays where it is; only offset
+        // for multiple range insertions
+        (_, Direction::Forward) => start_range.anchor + offset,
+
+        // when we are inserting in front of a selection, we need to move
+        // the anchor over by however many characters were inserted overall
+        (_, Direction::Backward) => start_range.anchor + offset + len_inserted,
+    };
+
+    Range::new(end_anchor, end_head)
+}
+
 fn handle_open(
     doc: &Rope,
     selection: &Selection,
@@ -74,36 +101,32 @@ fn handle_open(
     close_before: &str,
 ) -> Transaction {
     let mut end_ranges = SmallVec::with_capacity(selection.len());
-
     let mut offs = 0;
 
     let transaction = Transaction::change_by_selection(doc, selection, |start_range| {
-        let start_head = start_range.head;
-
-        let next = doc.get_char(start_head);
-        let end_head = start_head + offs + open.len_utf8();
-
-        let end_anchor = if start_range.is_empty() {
-            end_head
-        } else {
-            start_range.anchor + offs
-        };
-
-        end_ranges.push(Range::new(end_anchor, end_head));
+        let cursor = start_range.cursor(doc.slice(..));
+        let next_char = doc.get_char(cursor);
+        let len_inserted;
 
-        match next {
+        let change = match next_char {
             Some(ch) if !close_before.contains(ch) => {
-                offs += open.len_utf8();
-                (start_head, start_head, Some(Tendril::from_char(open)))
+                len_inserted = open.len_utf8();
+                (cursor, cursor, Some(Tendril::from_char(open)))
             }
             // None | Some(ch) if close_before.contains(ch) => {}
             _ => {
                 // insert open & close
                 let pair = Tendril::from_iter([open, close]);
-                offs += open.len_utf8() + close.len_utf8();
-                (start_head, start_head, Some(pair))
+                len_inserted = open.len_utf8() + close.len_utf8();
+                (cursor, cursor, Some(pair))
             }
-        }
+        };
+
+        let next_range = get_next_range(start_range, offs, open, len_inserted);
+        end_ranges.push(next_range);
+        offs += len_inserted;
+
+        change
     });
 
     let t = transaction.with_selection(Selection::new(end_ranges, selection.primary_index()));
@@ -117,28 +140,28 @@ fn handle_close(doc: &Rope, selection: &Selection, _open: char, close: char) ->
     let mut offs = 0;
 
     let transaction = Transaction::change_by_selection(doc, selection, |start_range| {
-        let start_head = start_range.head;
-        let next = doc.get_char(start_head);
-        let end_head = start_head + offs + close.len_utf8();
+        let cursor = start_range.cursor(doc.slice(..));
+        let next_char = doc.get_char(cursor);
+        let mut len_inserted = 0;
 
-        let end_anchor = if start_range.is_empty() {
-            end_head
+        let change = if next_char == Some(close) {
+            // return transaction that moves past close
+            (cursor, cursor, None) // no-op
         } else {
-            start_range.anchor + offs
+            len_inserted += close.len_utf8();
+            (cursor, cursor, Some(Tendril::from_char(close)))
         };
 
-        end_ranges.push(Range::new(end_anchor, end_head));
+        let next_range = get_next_range(start_range, offs, close, len_inserted);
+        end_ranges.push(next_range);
+        offs += len_inserted;
 
-        if next == Some(close) {
-            // return transaction that moves past close
-            (start_head, start_head, None) // no-op
-        } else {
-            offs += close.len_utf8();
-            (start_head, start_head, Some(Tendril::from_char(close)))
-        }
+        change
     });
 
-    transaction.with_selection(Selection::new(end_ranges, selection.primary_index()))
+    let t = transaction.with_selection(Selection::new(end_ranges, selection.primary_index()));
+    debug!("auto pair transaction: {:#?}", t);
+    t
 }
 
 /// handle cases where open and close is the same, or in triples ("""docstring""")
@@ -154,42 +177,41 @@ fn handle_same(
     let mut offs = 0;
 
     let transaction = Transaction::change_by_selection(doc, selection, |start_range| {
-        let start_head = start_range.head;
-        let end_head = start_head + offs + token.len_utf8();
+        let cursor = start_range.cursor(doc.slice(..));
+        let mut len_inserted = 0;
 
-        // if selection, retain anchor, if cursor, move over
-        let end_anchor = if start_range.is_empty() {
-            end_head
-        } else {
-            start_range.anchor + offs
-        };
+        let next_char = doc.get_char(cursor);
+        let prev_char = prev_char(doc, cursor);
 
-        end_ranges.push(Range::new(end_anchor, end_head));
-
-        let next = doc.get_char(start_head);
-        let prev = prev_char(doc, start_head);
-
-        if next == Some(token) {
+        let change = if next_char == Some(token) {
             //  return transaction that moves past close
-            (start_head, start_head, None) // no-op
+            (cursor, cursor, None) // no-op
         } else {
             let mut pair = Tendril::with_capacity(2 * token.len_utf8() as u32);
             pair.push_char(token);
 
             // for equal pairs, don't insert both open and close if either
             // side has a non-pair char
-            if (next.is_none() || close_before.contains(next.unwrap()))
-                && (prev.is_none() || open_before.contains(prev.unwrap()))
+            if (next_char.is_none() || close_before.contains(next_char.unwrap()))
+                && (prev_char.is_none() || open_before.contains(prev_char.unwrap()))
             {
                 pair.push_char(token);
             }
 
-            offs += pair.len();
-            (start_head, start_head, Some(pair))
-        }
+            len_inserted += pair.len();
+            (cursor, cursor, Some(pair))
+        };
+
+        let next_range = get_next_range(start_range, offs, token, len_inserted);
+        end_ranges.push(next_range);
+        offs += len_inserted;
+
+        change
     });
 
-    transaction.with_selection(Selection::new(end_ranges, selection.primary_index()))
+    let t = transaction.with_selection(Selection::new(end_ranges, selection.primary_index()));
+    debug!("auto pair transaction: {:#?}", t);
+    t
 }
 
 #[cfg(test)]
@@ -252,7 +274,20 @@ mod test {
             &Selection::single(1, 0),
             PAIRS,
             |open, close| format!("{}{}", open, close),
-            &Selection::single(1, 1),
+            &Selection::single(2, 1),
+        );
+    }
+
+    /// [] -> append ( -> ([])
+    #[test]
+    fn test_append_blank() {
+        test_hooks_with_pairs(
+            // this is what happens when you have a totally blank document and then append
+            &Rope::from("\n\n"),
+            &Selection::single(0, 2),
+            PAIRS,
+            |open, close| format!("\n{}{}\n", open, close),
+            &Selection::single(0, 3),
         );
     }
 
@@ -276,26 +311,50 @@ mod test {
                 )
             },
             &Selection::new(
-                smallvec!(Range::point(1), Range::point(4), Range::point(7),),
+                smallvec!(Range::new(2, 1), Range::new(5, 4), Range::new(8, 7),),
                 0,
             ),
         );
     }
 
-    // [TODO] broken until it works with selections
     /// fo[o] -> append ( -> fo[o(])
-    #[ignore]
     #[test]
     fn test_append() {
         test_hooks_with_pairs(
-            &Rope::from("foo"),
+            &Rope::from("foo\n"),
             &Selection::single(2, 4),
-            PAIRS,
-            |open, close| format!("foo{}{}", open, close),
+            differing_pairs(),
+            |open, close| format!("foo{}{}\n", open, close),
             &Selection::single(2, 5),
         );
     }
 
+    /// fo[o]                fo[o(])
+    /// fo[o] -> append ( -> fo[o(])
+    /// fo[o]                fo[o(])
+    #[test]
+    fn test_append_multi() {
+        test_hooks_with_pairs(
+            &Rope::from("foo\nfoo\nfoo\n"),
+            &Selection::new(
+                smallvec!(Range::new(2, 4), Range::new(6, 8), Range::new(10, 12)),
+                0,
+            ),
+            differing_pairs(),
+            |open, close| {
+                format!(
+                    "foo{open}{close}\nfoo{open}{close}\nfoo{open}{close}\n",
+                    open = open,
+                    close = close
+                )
+            },
+            &Selection::new(
+                smallvec!(Range::new(2, 5), Range::new(8, 11), Range::new(14, 17)),
+                0,
+            ),
+        );
+    }
+
     /// ([]) -> insert ) -> ()[]
     #[test]
     fn test_insert_close_inside_pair() {
@@ -307,7 +366,23 @@ mod test {
                 &Selection::single(2, 1),
                 *close,
                 &doc,
-                &Selection::point(2),
+                &Selection::single(3, 2),
+            );
+        }
+    }
+
+    /// [(]) -> append ) -> [()]
+    #[test]
+    fn test_append_close_inside_pair() {
+        for (open, close) in PAIRS {
+            let doc = Rope::from(format!("{}{}\n", open, close));
+
+            test_hooks(
+                &doc,
+                &Selection::single(0, 2),
+                *close,
+                &doc,
+                &Selection::single(0, 3),
             );
         }
     }
@@ -323,8 +398,33 @@ mod test {
         );
 
         let expected_sel = Selection::new(
-            // smallvec!(Range::new(3, 2), Range::new(6, 5), Range::new(9, 8),),
-            smallvec!(Range::point(2), Range::point(5), Range::point(8),),
+            smallvec!(Range::new(3, 2), Range::new(6, 5), Range::new(9, 8),),
+            0,
+        );
+
+        for (open, close) in PAIRS {
+            let doc = Rope::from(format!(
+                "{open}{close}\n{open}{close}\n{open}{close}\n",
+                open = open,
+                close = close
+            ));
+
+            test_hooks(&doc, &sel, *close, &doc, &expected_sel);
+        }
+    }
+
+    /// [(])                [()]
+    /// [(]) -> append ) -> [()]
+    /// [(])                [()]
+    #[test]
+    fn test_append_close_inside_pair_multi_cursor() {
+        let sel = Selection::new(
+            smallvec!(Range::new(0, 2), Range::new(3, 5), Range::new(6, 8),),
+            0,
+        );
+
+        let expected_sel = Selection::new(
+            smallvec!(Range::new(0, 3), Range::new(3, 6), Range::new(6, 9),),
             0,
         );
 
@@ -343,7 +443,7 @@ mod test {
     #[test]
     fn test_insert_open_inside_pair() {
         let sel = Selection::single(2, 1);
-        let expected_sel = Selection::point(2);
+        let expected_sel = Selection::single(3, 2);
 
         for (open, close) in differing_pairs() {
             let doc = Rope::from(format!("{}{}", open, close));
@@ -357,11 +457,49 @@ mod test {
         }
     }
 
+    /// [word(]) -> append ( -> [word((]))
+    #[test]
+    fn test_append_open_inside_pair() {
+        let sel = Selection::single(0, 6);
+        let expected_sel = Selection::single(0, 7);
+
+        for (open, close) in differing_pairs() {
+            let doc = Rope::from(format!("word{}{}", open, close));
+            let expected_doc = Rope::from(format!(
+                "word{open}{open}{close}{close}",
+                open = open,
+                close = close
+            ));
+
+            test_hooks(&doc, &sel, *open, &expected_doc, &expected_sel);
+        }
+    }
+
     /// ([]) -> insert " -> ("[]")
     #[test]
     fn test_insert_nested_open_inside_pair() {
         let sel = Selection::single(2, 1);
-        let expected_sel = Selection::point(2);
+        let expected_sel = Selection::single(3, 2);
+
+        for (outer_open, outer_close) in differing_pairs() {
+            let doc = Rope::from(format!("{}{}", outer_open, outer_close,));
+
+            for (inner_open, inner_close) in matching_pairs() {
+                let expected_doc = Rope::from(format!(
+                    "{}{}{}{}",
+                    outer_open, inner_open, inner_close, outer_close
+                ));
+
+                test_hooks(&doc, &sel, *inner_open, &expected_doc, &expected_sel);
+            }
+        }
+    }
+
+    /// [(]) -> append " -> [("]")
+    #[test]
+    fn test_append_nested_open_inside_pair() {
+        let sel = Selection::single(0, 2);
+        let expected_sel = Selection::single(0, 3);
 
         for (outer_open, outer_close) in differing_pairs() {
             let doc = Rope::from(format!("{}{}", outer_open, outer_close,));
@@ -385,21 +523,44 @@ mod test {
             &Selection::single(1, 0),
             PAIRS,
             |open, _| format!("{}word", open),
-            &Selection::point(1),
+            &Selection::single(2, 1),
         )
     }
 
-    // [TODO] broken until it works with selections
     /// [wor]d -> insert ( -> ([wor]d
     #[test]
-    #[ignore]
     fn test_insert_open_with_selection() {
         test_hooks_with_pairs(
             &Rope::from("word"),
-            &Selection::single(0, 4),
+            &Selection::single(3, 0),
             PAIRS,
             |open, _| format!("{}word", open),
-            &Selection::single(1, 5),
+            &Selection::single(4, 1),
+        )
+    }
+
+    /// [wor]d -> append ) -> [wor)]d
+    #[test]
+    fn test_append_close_inside_non_pair_with_selection() {
+        let sel = Selection::single(0, 4);
+        let expected_sel = Selection::single(0, 5);
+
+        for (_, close) in PAIRS {
+            let doc = Rope::from("word");
+            let expected_doc = Rope::from(format!("wor{}d", close));
+            test_hooks(&doc, &sel, *close, &expected_doc, &expected_sel);
+        }
+    }
+
+    /// foo[ wor]d -> insert ( -> foo([) wor]d
+    #[test]
+    fn test_insert_open_trailing_word_with_selection() {
+        test_hooks_with_pairs(
+            &Rope::from("foo word"),
+            &Selection::single(7, 3),
+            differing_pairs(),
+            |open, close| format!("foo{}{} word", open, close),
+            &Selection::single(9, 4),
         )
     }
 
@@ -413,7 +574,7 @@ mod test {
     fn test_insert_open_after_non_pair() {
         let doc = Rope::from("word");
         let sel = Selection::single(5, 4);
-        let expected_sel = Selection::point(5);
+        let expected_sel = Selection::single(6, 5);
 
         test_hooks_with_pairs(
             &doc,
@@ -431,4 +592,18 @@ mod test {
             &expected_sel,
         );
     }
+
+    /// appending with only a cursor should stay a cursor
+    ///
+    /// [] -> append to end "foo -> "foo[]"
+    #[test]
+    fn test_append_single_cursor() {
+        test_hooks_with_pairs(
+            &Rope::from("\n"),
+            &Selection::single(0, 1),
+            PAIRS,
+            |open, close| format!("{}{}\n", open, close),
+            &Selection::single(1, 2),
+        );
+    }
 }
diff --git a/helix-core/src/selection.rs b/helix-core/src/selection.rs
index 116a1c7c0..884c98acf 100644
--- a/helix-core/src/selection.rs
+++ b/helix-core/src/selection.rs
@@ -7,6 +7,7 @@ use crate::{
         ensure_grapheme_boundary_next, ensure_grapheme_boundary_prev, next_grapheme_boundary,
         prev_grapheme_boundary,
     },
+    movement::Direction,
     Assoc, ChangeSet, RopeSlice,
 };
 use smallvec::{smallvec, SmallVec};
@@ -82,6 +83,13 @@ impl Range {
         std::cmp::max(self.anchor, self.head)
     }
 
+    /// Total length of the range.
+    #[inline]
+    #[must_use]
+    pub fn len(&self) -> usize {
+        self.to() - self.from()
+    }
+
     /// The (inclusive) range of lines that the range overlaps.
     #[inline]
     #[must_use]
@@ -102,6 +110,18 @@ impl Range {
         self.anchor == self.head
     }
 
+    /// `Direction::Backward` when head < anchor.
+    /// `Direction::Backward` otherwise.
+    #[inline]
+    #[must_use]
+    pub fn direction(&self) -> Direction {
+        if self.head < self.anchor {
+            Direction::Backward
+        } else {
+            Direction::Forward
+        }
+    }
+
     /// Check two ranges for overlap.
     #[must_use]
     pub fn overlaps(&self, other: &Self) -> bool {