diff --git a/UNRELEASED.md b/UNRELEASED.md
index c5395159e5d..4fc29749097 100644
--- a/UNRELEASED.md
+++ b/UNRELEASED.md
@@ -28,4 +28,6 @@ Use [the changelog guidelines](https://git.io/polaris-changelog-guidelines) to f
 
 ### Code quality
 
+- Simplified logic in Checkbox component ([#1453](https://github.com/Shopify/polaris-react/pull/1453))
+
 ### Deprecations
diff --git a/src/components/Checkbox/Checkbox.tsx b/src/components/Checkbox/Checkbox.tsx
index 8eb68c05e29..2db1aa6d3c1 100644
--- a/src/components/Checkbox/Checkbox.tsx
+++ b/src/components/Checkbox/Checkbox.tsx
@@ -53,8 +53,8 @@ class Checkbox extends React.PureComponent<CombinedProps, never> {
 
   componentDidUpdate({disabled: prevDisabled}: Props) {
     if (
+      prevDisabled === true &&
       this.props.disabled &&
-      !prevDisabled !== true &&
       this.inputNode.current &&
       this.inputNode.current.checked
     ) {