diff --git a/src/extensions/yfm/Checkbox/actions.ts b/src/extensions/yfm/Checkbox/actions.ts
index d564476c..e32f67ce 100644
--- a/src/extensions/yfm/Checkbox/actions.ts
+++ b/src/extensions/yfm/Checkbox/actions.ts
@@ -1,8 +1,8 @@
 import {Fragment, Node, Schema} from 'prosemirror-model';
-import {Command, TextSelection} from 'prosemirror-state';
-import {findChildrenByType, findParentNodeOfType} from 'prosemirror-utils';
+import {Command, TextSelection, Transaction} from 'prosemirror-state';
 
 import type {ActionSpec} from '../../../core';
+import {get$Cursor, isNodeSelection} from '../../../utils/selection';
 import {pType} from '../../base/BaseSchema';
 
 import {checkboxInputType, checkboxLabelType, checkboxType} from './utils';
@@ -14,42 +14,48 @@ const createCheckbox = (schema: Schema, content?: Fragment | Node | Node[]) =>
     ]);
 
 export const addCheckboxCmd: Command = (state, dispatch) => {
-    const paragraph = findParentNodeOfType(pType(state.schema))(state.selection);
-    const checkboxParent = findParentNodeOfType(checkboxType(state.schema))(state.selection);
-    const parent = paragraph || checkboxParent;
-
-    if (!parent) return false;
-
-    const checkboxChild = findChildrenByType(parent.node, checkboxLabelType(state.schema));
-
-    if (checkboxChild.length) {
-        if (dispatch) {
-            const {tr} = state;
-
-            tr.insert(parent.pos + parent.node.nodeSize, createCheckbox(state.schema, undefined));
+    function insertCheckbox(tr: Transaction, pos: number, content?: Fragment): Transaction {
+        tr.insert(pos, createCheckbox(state.schema, content));
+        return tr.setSelection(TextSelection.create(tr.doc, pos + 3)); // move cursor inside checkbox
+    }
 
-            tr.setSelection(new TextSelection(tr.doc.resolve(tr.selection.$from.after() + 4)));
+    if (isNodeSelection(state.selection) && rootOrNonComplex(state.selection.node)) {
+        const pos = state.selection.to;
+        dispatch?.(insertCheckbox(state.tr, pos).scrollIntoView());
+        return true;
+    }
 
-            dispatch(tr);
-        }
+    const $cursor = get$Cursor(state.selection);
+    if (!$cursor) return false;
 
+    const inCheckbox =
+        $cursor.parent.type === checkboxLabelType(state.schema) &&
+        $cursor.node($cursor.depth - 1).type === checkboxType(state.schema);
+    if (inCheckbox) {
+        const pos = $cursor.after($cursor.depth - 1);
+        dispatch?.(insertCheckbox(state.tr, pos).scrollIntoView());
         return true;
     }
 
-    const {tr} = state;
-
-    if (dispatch) {
-        tr.replaceWith(
-            parent.pos,
-            parent.pos + parent.node.nodeSize,
-            createCheckbox(state.schema, parent.node.content),
-        );
+    if (!rootOrNonComplex($cursor.parent)) return false;
 
-        tr.setSelection(new TextSelection(tr.doc.resolve(tr.selection.$from.after() - 1)));
+    if (!dispatch) return true;
 
-        dispatch?.(tr);
+    const {tr} = state;
+    const inParagraph = $cursor.parent.type === pType(state.schema);
+
+    if (inParagraph) {
+        const from = $cursor.before(),
+            to = $cursor.after();
+        // replace para with checkbox with same content
+        tr.replaceWith(from, to, createCheckbox(state.schema, $cursor.parent.content));
+        tr.setSelection(TextSelection.create(tr.doc, $cursor.pos + 2)); // save cursor position in text
+    } else {
+        const pos = $cursor.after();
+        insertCheckbox(tr, pos);
     }
 
+    dispatch(tr.scrollIntoView());
     return true;
 };
 
@@ -59,3 +65,8 @@ export const addCheckbox = (): ActionSpec => {
         run: addCheckboxCmd,
     };
 };
+
+function rootOrNonComplex(node: Node): boolean {
+    const {complex} = node.type.spec;
+    return !complex || complex === 'root';
+}
diff --git a/src/utils/inputrules.ts b/src/utils/inputrules.ts
index 682538f2..9f1bf62e 100644
--- a/src/utils/inputrules.ts
+++ b/src/utils/inputrules.ts
@@ -2,7 +2,7 @@ import {InputRule} from 'prosemirror-inputrules';
 import {Fragment, Mark, MarkType, Node} from 'prosemirror-model';
 import {EditorState, TextSelection} from 'prosemirror-state';
 
-import {codeType} from '../extensions';
+import {codeType} from '../extensions/markdown/specs';
 import {isFunction} from '../lodash';
 import {isMarkActive} from '../utils/marks';
 // TODO: remove explicit import from code extension