RustPython · youknowone · Aug 22, 2026 · Aug 21, 2026
diff --git a/crates/stdlib/src/bisect.rs b/crates/stdlib/src/bisect.rs
@@ -106,15 +106,15 @@ mod _bisect {
 
     #[pyfunction]
     fn insort_left(BisectArgs { a, x, lo, hi, key }: BisectArgs, vm: &VirtualMachine) -> PyResult {
-        let x = if let Some(ref key) = key {
-            key.call((x,), vm)?
-        } else {
-            x
+        // The search runs on the key, the insert has to put back the item itself.
+        let needle = match key {
+            Some(ref key) => key.call((x.clone(),), vm)?,
+            None => x.clone(),
         };
         let index = bisect_left(
             BisectArgs {
                 a: a.clone(),
-                x: x.clone(),
+                x: needle,
                 lo,
                 hi,
                 key,
@@ -126,15 +126,15 @@ mod _bisect {
 
     #[pyfunction]
     fn insort_right(BisectArgs { a, x, lo, hi, key }: BisectArgs, vm: &VirtualMachine) -> PyResult {
-        let x = if let Some(ref key) = key {
-            key.call((x,), vm)?
-        } else {
-            x
+        // The search runs on the key, the insert has to put back the item itself.
+        let needle = match key {
+            Some(ref key) => key.call((x.clone(),), vm)?,
+            None => x.clone(),
         };
         let index = bisect_right(
             BisectArgs {
                 a: a.clone(),
-                x: x.clone(),
+                x: needle,
                 lo,
                 hi,
                 key,

diff --git a/extra_tests/snippets/stdlib_bisect.py b/extra_tests/snippets/stdlib_bisect.py
@@ -0,0 +1,73 @@
+from bisect import bisect_left, bisect_right, insort, insort_left, insort_right
+
+# A key decides where the item goes, but the item is what gets stored.
+for insort_fn in (insort, insort_left, insort_right):
+    words = ["a", "ccc"]
+    insort_fn(words, "bb", key=len)
+    assert words == ["a", "bb", "ccc"], (insort_fn.__name__, words)
+
+    numbers = [1, 3]
+    insort_fn(numbers, -2, key=abs)
+    assert numbers == [1, -2, 3], (insort_fn.__name__, numbers)
+
+    pairs = [(1, "a"), (3, "b")]
+    insort_fn(pairs, (2, "x"), key=lambda pair: pair[0])
+    assert pairs == [(1, "a"), (2, "x"), (3, "b")], (insort_fn.__name__, pairs)
+
+
+descending = [3, 1]
+insort(descending, 2, key=lambda value: -value)
+assert descending == [3, 2, 1], descending
+
+
+class Tagged:
+    def __init__(self, size, tag):
+        self.size = size
+        self.tag = tag
+
+
+def sizes_and_tags(items):
+    return [(item.size, item.tag) for item in items]
+
+
+by_size = [Tagged(1, "old"), Tagged(2, "old")]
+
+# On a tie, left goes before the equal element and right goes after it.
+left = list(by_size)
+insort_left(left, Tagged(2, "new"), key=lambda item: item.size)
+assert sizes_and_tags(left) == [(1, "old"), (2, "new"), (2, "old")]
+
+right = list(by_size)
+insort_right(right, Tagged(2, "new"), key=lambda item: item.size)
+assert sizes_and_tags(right) == [(1, "old"), (2, "old"), (2, "new")]
+
+
+# The key runs once on the new item, whatever the search does afterwards.
+seen = []
+
+
+def counting_key(value):
+    seen.append(value)
+    return value
+
+
+data = [1, 3, 5, 7]
+insort(data, 4, key=counting_key)
+assert data == [1, 3, 4, 5, 7], data
+assert seen.count(4) == 1, seen
+
+
+# lo and hi bound the search and leave the inserted item alone.
+bounded = [3, 1]
+insort(bounded, 2, 0, 1, key=lambda value: -value)
+assert bounded == [3, 2, 1], bounded
+
+
+plain = [1, 3]
+insort(plain, 2)
+assert plain == [1, 2, 3], plain
+
+# The search takes the key value itself, so these two stay where they were.
+sizes = ["a", "bb", "ccc"]
+assert bisect_left(sizes, 2, key=len) == 1
+assert bisect_right(sizes, 2, key=len) == 2