diff --git a/packages/web/src/javascripts/Components/SuperEditor/Lexical/Theme/lists.scss b/packages/web/src/javascripts/Components/SuperEditor/Lexical/Theme/lists.scss
index 813d881b5..1df4b7775 100644
--- a/packages/web/src/javascripts/Components/SuperEditor/Lexical/Theme/lists.scss
+++ b/packages/web/src/javascripts/Components/SuperEditor/Lexical/Theme/lists.scss
@@ -1,5 +1,10 @@
 :root {
   --lexical-ordered-list-left-margin: 16px;
+
+  --checkbox-size: 18px;
+  @media screen and (max-width: 450px) {
+    --checkbox-size: 26px;
+  }
 }
 .monospace-font {
   --lexical-ordered-list-left-margin: 42px;
@@ -52,11 +57,19 @@
 .Lexical__listItemChecked,
 .Lexical__listItemUnchecked {
   position: relative;
-  padding-left: calc(var(--font-size) + 0.5rem);
-  padding-right: calc(var(--font-size) + 0.5rem);
+  padding-left: calc(var(--checkbox-size) + 0.5rem);
+  padding-right: calc(var(--checkbox-size) + 0.5rem);
   list-style-type: none;
   outline: none;
   vertical-align: middle;
+  --line-height: calc(var(--checkbox-size) + 0.375rem);
+  line-height: var(--line-height);
+
+  @media screen and (max-width: 450px) {
+    &:not(:last-child) {
+      margin-bottom: 0.15rem;
+    }
+  }
 
   &:focus,
   &:focus-within {
@@ -70,12 +83,12 @@
 }
 .Lexical__listItemUnchecked:before,
 .Lexical__listItemChecked:before {
+  /* checkbox */
   content: '';
-  --size: 16px;
-  width: var(--size);
-  height: var(--size);
+  width: var(--checkbox-size);
+  height: var(--checkbox-size);
   left: 0;
-  top: calc(var(--line-height, 1) * var(--font-size) / 2);
+  top: calc(var(--line-height) / 2);
   transform: translateY(-50%);
   cursor: pointer;
   background-size: cover;
@@ -97,19 +110,19 @@
   background-repeat: no-repeat;
 }
 .Lexical__listItemChecked:after {
+  /* checkmark */
   content: '';
   cursor: pointer;
-  border-color: var(--sn-stylekit-info-contrast-color);
-  border-style: solid;
+  background-image: url('data:image/svg+xml,%3Csvg%20viewBox%3D%220%200%2020%2020%22%20fill%3D%22white%22%20xmlns%3D%22http%3A%2F%2Fwww.w3.org%2F2000%2Fsvg%22%3E%3Cpath%20d%3D%22M17.5001%205.83345L7.50008%2015.8334L2.91675%2011.2501L4.09175%2010.0751L7.50008%2013.4751L16.3251%204.65845L17.5001%205.83345Z%22%2F%3E%3C%2Fsvg%3E%0A');
+  background-repeat: no-repeat;
   position: absolute;
+  left: 0;
+  --top: calc(var(--line-height) / 2);
+  top: var(--top);
+  transform: translateY(-50%);
   display: block;
-  width: 5px;
-  height: 11px;
-  --top: calc(var(--line-height, 1) * var(--font-size) / 2);
-  top: calc(var(--top) - 1px);
-  left: 5px;
-  transform: translateY(-50%) rotate(45deg);
-  border-width: 0 2px 2px 0;
+  width: var(--checkbox-size);
+  height: var(--checkbox-size);
 }
 .Lexical__nestedListItem {
   list-style-type: none;
diff --git a/packages/web/src/javascripts/Components/SuperEditor/Plugins/CheckListPlugin.tsx b/packages/web/src/javascripts/Components/SuperEditor/Plugins/CheckListPlugin.tsx
index 7809d3fef..f40bf1684 100644
--- a/packages/web/src/javascripts/Components/SuperEditor/Plugins/CheckListPlugin.tsx
+++ b/packages/web/src/javascripts/Components/SuperEditor/Plugins/CheckListPlugin.tsx
@@ -7,6 +7,7 @@ import {
   $isRangeSelection,
   COMMAND_PRIORITY_LOW,
   KEY_ENTER_COMMAND,
+  SKIP_DOM_SELECTION_TAG,
 } from 'lexical'
 import { useEffect } from 'react'
 import { useApplication } from '../../ApplicationProvider'
@@ -53,8 +54,6 @@ export function CheckListPlugin(): null {
             return
           }
 
-          editor.getRootElement()?.focus()
-
           const rect = target.getBoundingClientRect()
 
           const listItemElementStyles = getComputedStyle(target)
@@ -81,25 +80,40 @@ export function CheckListPlugin(): null {
 
         function handleClick(event: Event) {
           handleCheckItemEvent(event as PointerEvent, () => {
+            const isTouchEvent = (event as PointerEvent).pointerType === 'touch'
             if (!editor.isEditable()) {
               return
             }
 
-            editor.update(() => {
-              const domNode = event.target as HTMLElement
+            editor.update(
+              () => {
+                const domNode = event.target
+                if (!(domNode instanceof HTMLElement)) {
+                  return
+                }
 
-              if (!event.target) {
-                return
-              }
+                const node = $getNearestNodeFromDOMNode(domNode)
 
-              const node = $getNearestNodeFromDOMNode(domNode)
+                if (!$isListItemNode(node)) {
+                  return
+                }
 
-              if (!$isListItemNode(node)) {
-                return
-              }
+                const isFocusWithinEditor = editor.getRootElement()?.contains(document.activeElement)
+                if (!isTouchEvent && !isFocusWithinEditor) {
+                  // on desktop, we want to focus & select the list item so that if you then press the up or down arrow keys,
+                  // the caret moves in the editor instead of triggering the note navigation shortcuts.
+                  // however on mobile, focusing the editor brings up the keyboard even if you just want to quickly toggle
+                  // an item. the keyboard also causes a layout shift which might end up leading to an incorrect toggle.
+                  node.selectStart()
+                }
 
-              node.toggleChecked()
-            })
+                node.toggleChecked()
+              },
+              {
+                // without this lexical will reconcile the new selection to the dom and focus the editor causing the keyboard to show up
+                tag: isTouchEvent ? SKIP_DOM_SELECTION_TAG : undefined,
+              },
+            )
           })
         }