diff --git a/crates/editor/src/selection.rs b/crates/editor/src/selection.rs
index c8b56d1682..a4373b1de1 100644
--- a/crates/editor/src/selection.rs
+++ b/crates/editor/src/selection.rs
@@ -87,6 +87,25 @@ impl Editor {
         result
     }
 
+    /// Re-resolves selection anchors so they reference live buffer fragments.
+    ///
+    /// Deleted CRDT fragments remain as tombstones. An anchor associated with a
+    /// tombstone can resolve to the correct visible offset while causing later
+    /// insertions to be ordered on the wrong side of the cursor. Round-tripping
+    /// selections through their offsets creates fresh anchors associated with
+    /// live fragments.
+    ///
+    /// This does not emit selection effects, but it replaces pending selection
+    /// state with the resolved selections.
+    pub fn refresh_selection_anchors(&mut self, cx: &mut Context<Self>) {
+        let snapshot = self.display_snapshot(cx);
+        let selections = self.selections.all::<MultiBufferOffset>(&snapshot);
+        self.selections
+            .change_with(&snapshot, |selection_collection| {
+                selection_collection.select(selections);
+            });
+    }
+
     /// Defers the effects of selection change, so that the effects of multiple calls to
     /// `change_selections` are applied at the end. This way these intermediate states aren't added
     /// to selection history and the state of popovers based on selection position aren't
diff --git a/crates/vim/src/helix.rs b/crates/vim/src/helix.rs
index df1cd9606d..fb6e8cc423 100644
--- a/crates/vim/src/helix.rs
+++ b/crates/vim/src/helix.rs
@@ -1882,7 +1882,7 @@ mod test {
 
     use super::{HELIX_JUMP_LABEL_LIMIT, HelixJumpToWord};
     use crate::{
-        HELIX_JUMP_OVERLAY_KEY, Vim, VimAddon,
+        HELIX_JUMP_OVERLAY_KEY, SwitchToHelixNormalMode, Vim, VimAddon,
         state::{Mode, Operator},
         test::VimTestContext,
     };
@@ -4671,4 +4671,24 @@ mod test {
         cx.simulate_keystrokes("x");
         cx.assert_state("«  aa  \nˇ»bbb\nccc\n", Mode::HelixNormal);
     }
+
+    #[gpui::test]
+    async fn test_insert_line_with_multi_keybinding_to_helix_normal(cx: &mut gpui::TestAppContext) {
+        let mut cx = VimTestContext::new(cx, true).await;
+        cx.enable_helix();
+
+        cx.update(|_, cx| {
+            cx.bind_keys([KeyBinding::new(
+                "j j",
+                SwitchToHelixNormalMode,
+                Some("vim_mode == insert"),
+            )]);
+        });
+
+        cx.set_state("hello worldˇ\n", Mode::Insert);
+        cx.simulate_keystrokes("j j");
+        cx.assert_state("hello worldˇ\n", Mode::HelixNormal);
+        cx.simulate_keystrokes("o");
+        cx.assert_state("hello world\nˇ\n", Mode::Insert);
+    }
 }
diff --git a/crates/vim/src/test.rs b/crates/vim/src/test.rs
index b4cac5772c..0fa0439379 100644
--- a/crates/vim/src/test.rs
+++ b/crates/vim/src/test.rs
@@ -35,7 +35,10 @@ use serde_json::json;
 use workspace::notifications::{NotificationId, simple_message_notification::MessageNotification};
 use workspace::{DeploySearch, MultiWorkspace};
 
-use crate::{PushSneak, PushSneakBackward, VimAddon, insert::NormalBefore, motion, state::Mode};
+use crate::{
+    PushSneak, PushSneakBackward, SwitchToNormalMode, VimAddon, insert::NormalBefore, motion,
+    state::Mode,
+};
 
 use util_macros::perf;
 
@@ -387,6 +390,25 @@ async fn test_escape_cancels(cx: &mut gpui::TestAppContext) {
     cx.assert_state("aˇbc", Mode::Normal);
 }
 
+#[gpui::test]
+async fn test_insert_line_with_multi_keybinding_to_normal(cx: &mut gpui::TestAppContext) {
+    let mut cx = VimTestContext::new(cx, true).await;
+
+    cx.update(|_, cx| {
+        cx.bind_keys([KeyBinding::new(
+            "j j",
+            SwitchToNormalMode,
+            Some("vim_mode == insert"),
+        )]);
+    });
+
+    cx.set_state("hello worldˇ\n", Mode::Insert);
+    cx.simulate_keystrokes("j j");
+    cx.assert_state("hello worldˇ\n", Mode::Normal);
+    cx.simulate_keystrokes("o");
+    cx.assert_state("hello world\nˇ\n", Mode::Insert);
+}
+
 #[cfg(target_os = "windows")]
 #[gpui::test]
 async fn test_escape_dismisses_workspace_notification_in_normal_modes(
diff --git a/crates/vim/src/vim.rs b/crates/vim/src/vim.rs
index 0c6c59f36e..b9bbb1ee44 100644
--- a/crates/vim/src/vim.rs
+++ b/crates/vim/src/vim.rs
@@ -1266,6 +1266,17 @@ impl Vim {
             }
         }
 
+        // Multi-key bindings in Insert mode temporarily insert their pending keys
+        // and remove them only after the action runs. Refresh the selection anchors
+        // afterward so they re-attach to the remaining text.
+        if last_mode == Mode::Insert && matches!(self.mode, Mode::Normal | Mode::HelixNormal) {
+            cx.defer_in(window, |vim, _window, cx| {
+                vim.update_editor(cx, |_, editor, cx| {
+                    editor.refresh_selection_anchors(cx);
+                });
+            })
+        }
+
         if leave_selections {
             return;
         }