diff --git a/shared/editor/commands/toggleBlockType.ts b/shared/editor/commands/toggleBlockType.ts
index 2fd4d4b9c..50af07e5e 100644
--- a/shared/editor/commands/toggleBlockType.ts
+++ b/shared/editor/commands/toggleBlockType.ts
@@ -3,6 +3,13 @@ import { NodeType } from "prosemirror-model";
 import { Command } from "prosemirror-state";
 import isNodeActive from "../queries/isNodeActive";
 
+/**
+ * Toggles the block type of the current selection between the given type and the toggle type.
+ *
+ * @param type The node type
+ * @param toggleType The toggle node type
+ * @returns A prosemirror command.
+ */
 export default function toggleBlockType(
   type: NodeType,
   toggleType: NodeType,
diff --git a/shared/editor/commands/toggleCheckboxItem.ts b/shared/editor/commands/toggleCheckboxItem.ts
new file mode 100644
index 000000000..74ce909c1
--- /dev/null
+++ b/shared/editor/commands/toggleCheckboxItem.ts
@@ -0,0 +1,34 @@
+import { Command } from "prosemirror-state";
+import { findParentNode } from "@shared/editor/queries/findParentNode";
+
+/**
+ * A prosemirror command to toggle the checkbox item at the current selection.
+ *
+ * @returns A prosemirror command.
+ */
+export default function toggleCheckboxItem(): Command {
+  return (state, dispatch) => {
+    const { empty } = state.selection;
+
+    // if the selection has anything in it then use standard behavior
+    if (!empty) {
+      return false;
+    }
+
+    // check we're in a matching node
+    const listItem = findParentNode(
+      (node) => node.type === state.schema.nodes.checkbox_item
+    )(state.selection);
+
+    if (!listItem) {
+      return false;
+    }
+
+    dispatch?.(
+      state.tr.setNodeMarkup(listItem.pos, undefined, {
+        checked: !listItem.node.attrs.checked,
+      })
+    );
+    return true;
+  };
+}
diff --git a/shared/editor/nodes/CheckboxItem.ts b/shared/editor/nodes/CheckboxItem.ts
index 0a947ca76..bf743eeef 100644
--- a/shared/editor/nodes/CheckboxItem.ts
+++ b/shared/editor/nodes/CheckboxItem.ts
@@ -5,6 +5,7 @@ import {
   sinkListItem,
   liftListItem,
 } from "prosemirror-schema-list";
+import toggleCheckboxItem from "../commands/toggleCheckboxItem";
 import { MarkdownSerializerState } from "../lib/markdown/serializer";
 import checkboxRule from "../rules/checkboxes";
 import Node from "./Node";
@@ -93,6 +94,7 @@ export default class CheckboxItem extends Node {
         checked: false,
       }),
       Tab: sinkListItem(type),
+      "Mod-Enter": toggleCheckboxItem(),
       "Shift-Tab": liftListItem(type),
       "Mod-]": sinkListItem(type),
       "Mod-[": liftListItem(type),
diff --git a/shared/editor/nodes/index.ts b/shared/editor/nodes/index.ts
index 797c5f99b..68daefe47 100644
--- a/shared/editor/nodes/index.ts
+++ b/shared/editor/nodes/index.ts
@@ -83,7 +83,7 @@ export const basicExtensions: Nodes = [
  * editors that need advanced formatting.
  */
 export const richExtensions: Nodes = [
-  ...basicExtensions.filter((n) => n !== SimpleImage),
+  ...basicExtensions.filter((n) => n !== SimpleImage && n !== Keys),
   Image,
   HardBreak,
   CodeBlock,
@@ -109,6 +109,7 @@ export const richExtensions: Nodes = [
   Math,
   MathBlock,
   PreventTab,
+  Keys,
 ];
 
 /**
diff --git a/shared/i18n/locales/en_US/translation.json b/shared/i18n/locales/en_US/translation.json
index 07671e2e1..a3fb56f09 100644
--- a/shared/i18n/locales/en_US/translation.json
+++ b/shared/i18n/locales/en_US/translation.json
@@ -211,7 +211,6 @@
   "Choose icon": "Choose icon",
   "Loading": "Loading",
   "Select a color": "Select a color",
-  "Loading editor": "Loading editor",
   "Search": "Search",
   "Default access": "Default access",
   "View and edit": "View and edit",