diff --git a/checkbox/internal/checkbox.ts b/checkbox/internal/checkbox.ts
index 21a8ee03b5..653fae554d 100644
--- a/checkbox/internal/checkbox.ts
+++ b/checkbox/internal/checkbox.ts
@@ -23,6 +23,11 @@ import {
   getValidityAnchor,
   mixinConstraintValidation,
 } from '../../labs/behaviors/constraint-validation.js';
+import {
+  hasState,
+  mixinCustomStateSet,
+  toggleState,
+} from '../../labs/behaviors/custom-state-set.js';
 import {mixinElementInternals} from '../../labs/behaviors/element-internals.js';
 import {
   getFormState,
@@ -34,7 +39,7 @@ import {CheckboxValidator} from '../../labs/behaviors/validators/checkbox-valida
 // Separate variable needed for closure.
 const checkboxBaseClass = mixinDelegatesAria(
   mixinConstraintValidation(
-    mixinFormAssociated(mixinElementInternals(LitElement)),
+    mixinFormAssociated(mixinCustomStateSet(mixinElementInternals(LitElement))),
   ),
 );
 
@@ -59,14 +64,26 @@ export class Checkbox extends checkboxBaseClass {
   /**
    * Whether or not the checkbox is selected.
    */
-  @property({type: Boolean}) checked = false;
+  @property({type: Boolean})
+  get checked(): boolean {
+    return this[hasState]('checked');
+  }
+  set checked(checked: boolean) {
+    this[toggleState]('checked', checked);
+  }
 
   /**
    * Whether or not the checkbox is indeterminate.
    *
    * https://developer.mozilla.org/en-US/docs/Web/HTML/Element/input/checkbox#indeterminate_state_checkboxes
    */
-  @property({type: Boolean}) indeterminate = false;
+  @property({type: Boolean})
+  get indeterminate(): boolean {
+    return this[hasState]('indeterminate');
+  }
+  set indeterminate(indeterminate: boolean) {
+    this[toggleState]('indeterminate', indeterminate);
+  }
 
   /**
    * When true, require the checkbox to be selected when participating in
diff --git a/checkbox/internal/checkbox_test.ts b/checkbox/internal/checkbox_test.ts
index 61f368a332..a086a6c15c 100644
--- a/checkbox/internal/checkbox_test.ts
+++ b/checkbox/internal/checkbox_test.ts
@@ -152,6 +152,31 @@ describe('checkbox', () => {
       expect(input.checked).toEqual(true);
       expect(harness.element.checked).toEqual(true);
     });
+
+    it('matches :state(checked) when true', async () => {
+      // Arrange
+      const {harness} = await setupTest();
+
+      // Act
+      harness.element.checked = true;
+      await env.waitForStability();
+
+      // Assert
+      expect(harness.element.matches(':state(checked)'))
+        .withContext("element.matches(':state(checked)')")
+        .toBeTrue();
+    });
+
+    it('does not match :state(checked) when false', async () => {
+      // Arrange
+      // Act
+      const {harness} = await setupTest();
+
+      // Assert
+      expect(harness.element.matches(':state(checked)'))
+        .withContext("element.matches(':state(checked)')")
+        .toBeFalse();
+    });
   });
 
   describe('indeterminate', () => {
@@ -169,6 +194,31 @@ describe('checkbox', () => {
       expect(input.indeterminate).toEqual(false);
       expect(input.getAttribute('aria-checked')).not.toEqual('mixed');
     });
+
+    it('matches :state(indeterminate) when true', async () => {
+      // Arrange
+      const {harness} = await setupTest();
+
+      // Act
+      harness.element.indeterminate = true;
+      await env.waitForStability();
+
+      // Assert
+      expect(harness.element.matches(':state(indeterminate)'))
+        .withContext("element.matches(':state(indeterminate)')")
+        .toBeTrue();
+    });
+
+    it('does not match :state(indeterminate) when false', async () => {
+      // Arrange
+      // Act
+      const {harness} = await setupTest();
+
+      // Assert
+      expect(harness.element.matches(':state(indeterminate)'))
+        .withContext("element.matches(':state(indeterminate)')")
+        .toBeFalse();
+    });
   });
 
   describe('disabled', () => {
@@ -186,13 +236,15 @@ describe('checkbox', () => {
 
   describe('form submission', () => {
     async function setupFormTest(propsInit: Partial<Checkbox> = {}) {
-      return await setupTest(html` <form>
-        <md-test-checkbox
-          .checked=${propsInit.checked === true}
-          .disabled=${propsInit.disabled === true}
-          .name=${propsInit.name ?? ''}
-          .value=${propsInit.value ?? ''}></md-test-checkbox>
-      </form>`);
+      return await setupTest(
+        html`<form>
+          <md-test-checkbox
+            .checked=${propsInit.checked === true}
+            .disabled=${propsInit.disabled === true}
+            .name=${propsInit.name ?? ''}
+            .value=${propsInit.value ?? ''}></md-test-checkbox>
+        </form>`,
+      );
     }
 
     it('does not submit if not checked', async () => {
diff --git a/docs/components/checkbox.md b/docs/components/checkbox.md
index 2ae0332224..9ccf73eb2d 100644
--- a/docs/components/checkbox.md
+++ b/docs/components/checkbox.md
@@ -209,3 +209,10 @@ Token                                    | Default value
 <!-- mdformat on(autogenerated might break rendering in catalog) -->
 
 <!-- auto-generated API docs end -->
+
+#### States
+
+| State | Description |
+| --- | --- |
+| `:state(checked)` | Matches when the checkbox is checked. |
+| `:state(indeterminate)` | Matches when the checkbox is indeterminate. |