diff --git a/src/cdk/menu/menu-item-checkbox.spec.ts b/src/cdk/menu/menu-item-checkbox.spec.ts
index e0a1f249e055..d9a69536bee4 100644
--- a/src/cdk/menu/menu-item-checkbox.spec.ts
+++ b/src/cdk/menu/menu-item-checkbox.spec.ts
@@ -3,6 +3,21 @@ import {ComponentFixture, TestBed} from '@angular/core/testing';
 import {By} from '@angular/platform-browser';
 import {CdkMenuModule} from './menu-module';
 import {CdkMenuItemCheckbox} from './menu-item-checkbox';
+import {MENU_STACK, MenuStack} from './menu-stack';
+import {ENTER, SPACE} from '../keycodes';
+
+/**
+ * Simulates what the browser does when a native button is activated from the keyboard: a trusted
+ * keydown that the item lets through, followed by a click with a `detail` of 0.
+ */
+function pressKeyOnNativeButton(item: CdkMenuItemCheckbox, element: HTMLElement, keyCode: number) {
+  item._onKeydown({
+    keyCode,
+    isTrusted: true,
+    preventDefault: () => {},
+  } as unknown as KeyboardEvent);
+  element.dispatchEvent(new MouseEvent('click', {bubbles: true, detail: 0}));
+}
 
 describe('MenuItemCheckbox', () => {
   let fixture: ComponentFixture<SingleCheckboxButton>;
@@ -72,6 +87,42 @@ describe('MenuItemCheckbox', () => {
     expect(spy).toHaveBeenCalledTimes(1);
   });
 
+  describe('keyboard activation of a native button', () => {
+    let menuStack: MenuStack;
+
+    beforeEach(() => {
+      menuStack = fixture.debugElement
+        .query(By.directive(CdkMenuItemCheckbox))
+        .injector.get(MENU_STACK);
+      spyOn(menuStack, 'closeAll');
+    });
+
+    it('should keep the menu open when toggled with space', () => {
+      pressKeyOnNativeButton(checkbox, checkboxElement, SPACE);
+
+      expect(checkbox.checked).toBeTrue();
+      expect(menuStack.closeAll).not.toHaveBeenCalled();
+    });
+
+    it('should close the menu when toggled with enter', () => {
+      pressKeyOnNativeButton(checkbox, checkboxElement, ENTER);
+
+      expect(checkbox.checked).toBeTrue();
+      expect(menuStack.closeAll).toHaveBeenCalled();
+    });
+
+    it('should close the menu on a mouse click after the space key was pressed', () => {
+      checkbox._onKeydown({
+        keyCode: SPACE,
+        isTrusted: true,
+        preventDefault: () => {},
+      } as unknown as KeyboardEvent);
+      checkboxElement.dispatchEvent(new MouseEvent('click', {bubbles: true, detail: 1}));
+
+      expect(menuStack.closeAll).toHaveBeenCalled();
+    });
+  });
+
   it('should not emit on clicked emitter when disabled', () => {
     const spy = jasmine.createSpy('cdkMenuItemCheckbox clicked spy');
     checkbox.triggered.subscribe(spy);
diff --git a/src/cdk/menu/menu-item-radio.spec.ts b/src/cdk/menu/menu-item-radio.spec.ts
index fed614abe45a..d4fc2a774051 100644
--- a/src/cdk/menu/menu-item-radio.spec.ts
+++ b/src/cdk/menu/menu-item-radio.spec.ts
@@ -3,6 +3,8 @@ import {ComponentFixture, TestBed} from '@angular/core/testing';
 import {By} from '@angular/platform-browser';
 import {CdkMenuModule} from './menu-module';
 import {CdkMenuItemRadio} from './menu-item-radio';
+import {MENU_STACK} from './menu-stack';
+import {SPACE} from '../keycodes';
 
 describe('MenuItemRadio', () => {
   let fixture: ComponentFixture<SimpleRadioButton>;
@@ -62,6 +64,24 @@ describe('MenuItemRadio', () => {
     expect(spy).toHaveBeenCalledTimes(1);
   });
 
+  it('should keep the menu open when a native button is checked with space', () => {
+    const menuStack = fixture.debugElement
+      .query(By.directive(CdkMenuItemRadio))
+      .injector.get(MENU_STACK);
+    spyOn(menuStack, 'closeAll');
+
+    // The browser turns a trusted space keydown on a button into a click with a `detail` of 0.
+    radioButton._onKeydown({
+      keyCode: SPACE,
+      isTrusted: true,
+      preventDefault: () => {},
+    } as unknown as KeyboardEvent);
+    radioElement.dispatchEvent(new MouseEvent('click', {bubbles: true, detail: 0}));
+
+    expect(radioButton.checked).toBeTrue();
+    expect(menuStack.closeAll).not.toHaveBeenCalled();
+  });
+
   it('should not emit on clicked emitter when disabled', () => {
     const spy = jasmine.createSpy('cdkMenuItemRadio clicked spy');
     radioButton.triggered.subscribe(spy);
diff --git a/src/cdk/menu/menu-item.ts b/src/cdk/menu/menu-item.ts
index b4be5f390d51..6e9ff8505360 100644
--- a/src/cdk/menu/menu-item.ts
+++ b/src/cdk/menu/menu-item.ts
@@ -98,6 +98,12 @@ export class CdkMenuItem implements FocusableOption, FocusableElement, Toggler,
   /** Whether the item should close the menu if triggered by the spacebar. */
   protected closeOnSpacebarTrigger = true;
 
+  /**
+   * Whether the click that the browser dispatches for the last keydown should keep the menu open.
+   * Native buttons turn space and enter into a click, so the keydown handler can't trigger them.
+   */
+  private _keepOpenOnKeyboardClick = false;
+
   /** Emits when the menu item is destroyed. */
   protected readonly destroyed = new Subject<void>();
 
@@ -188,8 +194,12 @@ export class CdkMenuItem implements FocusableOption, FocusableElement, Toggler,
       event.preventDefault();
       event.stopPropagation();
     } else {
-      this.trigger();
+      // Clicks dispatched by the browser for a keydown have a `detail` of 0.
+      const keepOpen = this._keepOpenOnKeyboardClick && event.detail === 0;
+      this.trigger({keepOpen});
     }
+
+    this._keepOpenOnKeyboardClick = false;
   }
 
   /**
@@ -202,8 +212,16 @@ export class CdkMenuItem implements FocusableOption, FocusableElement, Toggler,
     switch (event.keyCode) {
       case SPACE:
       case ENTER:
-        // Skip events that will trigger clicks so the handler doesn't get triggered twice.
-        if (!hasModifierKey(event) && !eventDispatchesNativeClick(this._elementRef, event)) {
+        if (!hasModifierKey(event)) {
+          const keepOpen = event.keyCode === SPACE && !this.closeOnSpacebarTrigger;
+
+          // Skip events that will trigger clicks so the handler doesn't get triggered twice.
+          // The click handler needs to know whether to keep the menu open though.
+          if (eventDispatchesNativeClick(this._elementRef, event)) {
+            this._keepOpenOnKeyboardClick = keepOpen;
+            break;
+          }
+
           const nodeName = this._elementRef.nativeElement.nodeName;
 
           // Avoid repeat events on non-native elements (see #30250). Note that we don't do this
@@ -212,7 +230,7 @@ export class CdkMenuItem implements FocusableOption, FocusableElement, Toggler,
             event.preventDefault();
           }
 
-          this.trigger({keepOpen: event.keyCode === SPACE && !this.closeOnSpacebarTrigger});
+          this.trigger({keepOpen});
         }
         break;