diff --git a/src/actions/actions.ts b/src/actions/actions.ts
index 5cb6cefd..baa0a179 100644
--- a/src/actions/actions.ts
+++ b/src/actions/actions.ts
@@ -131,12 +131,7 @@ export const actions: Action[] = [
   }),
 
   parseKeysExact(['a'], [Mode.Normal], (vimState, editor) => {
-    editor.selections = editor.selections.map((selection) => {
-      const newPosition = positionUtils.right(editor.document, selection.active);
-      return new vscode.Selection(newPosition, newPosition);
-    });
-
-    enterInsertMode(vimState);
+    enterInsertMode(vimState, false);
     setModeCursorStyle(vimState.mode, editor);
     removeTypeSubscription(vimState);
   }),
diff --git a/src/modes.ts b/src/modes.ts
index f0610dbc..4b10bf9d 100644
--- a/src/modes.ts
+++ b/src/modes.ts
@@ -4,12 +4,14 @@ import { HelixState } from './helix_state_types';
 import { Mode } from './modes_types';
 import { removeTypeSubscription } from './type_subscription';
 
-export function enterInsertMode(helixState: HelixState): void {
+export function enterInsertMode(helixState: HelixState, before = true): void {
   // To fix https://github.com/jasonwilliams/vscode-helix/issues/14 we should clear selections on entering insert mode
   // Helix doesn't clear selections on insert but doesn't overwrite the selection either, so our best option is to just clear them
   const editor = helixState.editorState.activeEditor!;
-  const activeSelection = editor.selection.active;
-  editor.selections = [new vscode.Selection(activeSelection, activeSelection)];
+  editor.selections = editor.selections.map((selection) => {
+    const position = before ? selection.anchor : selection.active;
+    return new vscode.Selection(position, position);
+  });
 
   helixState.mode = Mode.Insert;
   setModeContext('extension.helixKeymap.insertMode');