diff --git a/edit-post/components/header/fixed-toolbar-toggle/index.js b/edit-post/components/header/fixed-toolbar-toggle/index.js
index eb7080d2c653f1..c80452c12a7f32 100644
--- a/edit-post/components/header/fixed-toolbar-toggle/index.js
+++ b/edit-post/components/header/fixed-toolbar-toggle/index.js
@@ -17,6 +17,7 @@ function FixedToolbarToggle( { onToggle, isActive } ) {
 			icon={ isActive && 'yes' }
 			isSelected={ isActive }
 			onClick={ onToggle }
+			role="menuitemcheckbox"
 		>
 			{ __( 'Fix Toolbar to Top' ) }
 		</MenuItem>
diff --git a/edit-post/components/header/index.js b/edit-post/components/header/index.js
index 41e9afe41e63e9..35549ef7818118 100644
--- a/edit-post/components/header/index.js
+++ b/edit-post/components/header/index.js
@@ -19,6 +19,7 @@ import './style.scss';
 import MoreMenu from './more-menu';
 import HeaderToolbar from './header-toolbar';
 import PinnedPlugins from './pinned-plugins';
+import shortcuts from '../../keyboard-shortcuts';
 
 function Header( {
 	isEditorSidebarOpened,
@@ -59,6 +60,7 @@ function Header( {
 						onClick={ toggleGeneralSidebar }
 						isToggled={ isEditorSidebarOpened }
 						aria-expanded={ isEditorSidebarOpened }
+						shortcut={ shortcuts.toggleSidebar.display }
 					>
 						<DotTip id="core/editor.settings">
 							{ __( 'You’ll find more settings for your page and blocks in the sidebar. Click ‘Settings’ to open it.' ) }
diff --git a/edit-post/components/header/mode-switcher/index.js b/edit-post/components/header/mode-switcher/index.js
index 527e77f1011172..9b1e9198821f64 100644
--- a/edit-post/components/header/mode-switcher/index.js
+++ b/edit-post/components/header/mode-switcher/index.js
@@ -29,7 +29,7 @@ const MODES = [
 function ModeSwitcher( { onSwitch, mode } ) {
 	const choices = MODES.map( ( choice ) => {
 		if ( choice.value !== mode ) {
-			return { ...choice, shortcut: shortcuts.toggleEditorMode.label };
+			return { ...choice, shortcut: shortcuts.toggleEditorMode.display };
 		}
 		return choice;
 	} );
diff --git a/edit-post/components/header/plugin-sidebar-more-menu-item/index.js b/edit-post/components/header/plugin-sidebar-more-menu-item/index.js
index fa36e95c38b412..403e8aeb1c3e7e 100644
--- a/edit-post/components/header/plugin-sidebar-more-menu-item/index.js
+++ b/edit-post/components/header/plugin-sidebar-more-menu-item/index.js
@@ -17,6 +17,7 @@ const PluginSidebarMoreMenuItem = ( { children, icon, isSelected, onClick } ) =>
 			<MenuItem
 				icon={ isSelected ? 'yes' : icon }
 				isSelected={ isSelected }
+				role="menuitemcheckbox"
 				onClick={ compose( onClick, fillProps.onClose ) }
 			>
 				{ children }
diff --git a/edit-post/components/header/tips-toggle/index.js b/edit-post/components/header/tips-toggle/index.js
index 807fd3eb652edb..3ad90c80daf995 100644
--- a/edit-post/components/header/tips-toggle/index.js
+++ b/edit-post/components/header/tips-toggle/index.js
@@ -15,6 +15,7 @@ function TipsToggle( { onToggle, isActive } ) {
 		<MenuItem
 			icon={ isActive && 'yes' }
 			isSelected={ isActive }
+			role="menuitemcheckbox"
 			onClick={ onToggle }
 		>
 			{ __( 'Show Tips' ) }
diff --git a/edit-post/components/keyboard-shortcuts/index.js b/edit-post/components/keyboard-shortcuts/index.js
index 91667b2b54fda4..625f29e99bccd2 100644
--- a/edit-post/components/keyboard-shortcuts/index.js
+++ b/edit-post/components/keyboard-shortcuts/index.js
@@ -16,6 +16,7 @@ class EditorModeKeyboardShortcuts extends Component {
 		super( ...arguments );
 
 		this.toggleMode = this.toggleMode.bind( this );
+		this.toggleSidebar = this.toggleSidebar.bind( this );
 	}
 
 	toggleMode() {
@@ -23,12 +24,26 @@ class EditorModeKeyboardShortcuts extends Component {
 		switchMode( mode === 'visual' ? 'text' : 'visual' );
 	}
 
+	toggleSidebar( event ) {
+		// This shortcut has no known clashes, but use preventDefault to prevent any
+		// obscure shortcuts from triggering.
+		event.preventDefault();
+		const { isEditorSidebarOpen, closeSidebar, openSidebar } = this.props;
+
+		if ( isEditorSidebarOpen ) {
+			closeSidebar();
+		} else {
+			openSidebar();
+		}
+	}
+
 	render() {
 		return (
 			<KeyboardShortcuts
 				bindGlobal
 				shortcuts={ {
-					[ shortcuts.toggleEditorMode.value ]: this.toggleMode,
+					[ shortcuts.toggleEditorMode.raw ]: this.toggleMode,
+					[ shortcuts.toggleSidebar.raw ]: this.toggleSidebar,
 				} }
 			/>
 		);
@@ -36,16 +51,19 @@ class EditorModeKeyboardShortcuts extends Component {
 }
 
 export default compose( [
-	withSelect( ( select ) => {
-		return {
-			mode: select( 'core/edit-post' ).getEditorMode(),
-		};
-	} ),
-	withDispatch( ( dispatch ) => {
-		return {
-			switchMode: ( mode ) => {
-				dispatch( 'core/edit-post' ).switchEditorMode( mode );
-			},
-		};
-	} ),
+	withSelect( ( select ) => ( {
+		mode: select( 'core/edit-post' ).getEditorMode(),
+		isEditorSidebarOpen: select( 'core/edit-post' ).isEditorSidebarOpened(),
+		hasBlockSelection: !! select( 'core/editor' ).getBlockSelectionStart(),
+	} ) ),
+	withDispatch( ( dispatch, { hasBlockSelection } ) => ( {
+		switchMode( mode ) {
+			dispatch( 'core/edit-post' ).switchEditorMode( mode );
+		},
+		openSidebar() {
+			const sidebarToOpen = hasBlockSelection ? 'edit-post/block' : 'edit-post/document';
+			dispatch( 'core/edit-post' ).openGeneralSidebar( sidebarToOpen );
+		},
+		closeSidebar: dispatch( 'core/edit-post' ).closeGeneralSidebar,
+	} ) ),
 ] )( EditorModeKeyboardShortcuts );
diff --git a/edit-post/components/sidebar/sidebar-header/index.js b/edit-post/components/sidebar/sidebar-header/index.js
index b548b4e28c4de2..19b58e26ab5c0b 100644
--- a/edit-post/components/sidebar/sidebar-header/index.js
+++ b/edit-post/components/sidebar/sidebar-header/index.js
@@ -16,6 +16,7 @@ import { withDispatch, withSelect } from '@wordpress/data';
  * Internal dependencies
  */
 import './style.scss';
+import shortcuts from '../../../keyboard-shortcuts';
 
 const SidebarHeader = ( { children, className, closeLabel, closeSidebar, title } ) => {
 	return (
@@ -36,6 +37,7 @@ const SidebarHeader = ( { children, className, closeLabel, closeSidebar, title }
 					onClick={ closeSidebar }
 					icon="no-alt"
 					label={ closeLabel }
+					shortcut={ shortcuts.toggleSidebar.display }
 				/>
 			</div>
 		</Fragment>
diff --git a/edit-post/components/visual-editor/block-inspector-button.js b/edit-post/components/visual-editor/block-inspector-button.js
index e6014d55e025b9..f29f081f8a2c8d 100644
--- a/edit-post/components/visual-editor/block-inspector-button.js
+++ b/edit-post/components/visual-editor/block-inspector-button.js
@@ -7,10 +7,15 @@ import { flow, noop } from 'lodash';
  * WordPress dependencies
  */
 import { __ } from '@wordpress/i18n';
-import { IconButton, withSpokenMessages } from '@wordpress/components';
+import { MenuItem, withSpokenMessages } from '@wordpress/components';
 import { withSelect, withDispatch } from '@wordpress/data';
 import { compose } from '@wordpress/compose';
 
+/**
+ * Internal dependencies
+ */
+import shortcuts from '../../keyboard-shortcuts';
+
 export function BlockInspectorButton( {
 	areAdvancedSettingsOpened,
 	closeSidebar,
@@ -18,7 +23,6 @@ export function BlockInspectorButton( {
 	onClick = noop,
 	small = false,
 	speak,
-	role,
 } ) {
 	const speakMessage = () => {
 		if ( areAdvancedSettingsOpened ) {
@@ -31,15 +35,15 @@ export function BlockInspectorButton( {
 	const label = areAdvancedSettingsOpened ? __( 'Hide Block Settings' ) : __( 'Show Block Settings' );
 
 	return (
-		<IconButton
+		<MenuItem
 			className="editor-block-settings-menu__control"
 			onClick={ flow( areAdvancedSettingsOpened ? closeSidebar : openEditorSidebar, speakMessage, onClick ) }
 			icon="admin-generic"
 			label={ small ? label : undefined }
-			role={ role }
+			shortcut={ shortcuts.toggleSidebar.display }
 		>
 			{ ! small && label }
-		</IconButton>
+		</MenuItem>
 	);
 }
 
diff --git a/edit-post/components/visual-editor/index.js b/edit-post/components/visual-editor/index.js
index df1852492117e3..eb4cc9523e531b 100644
--- a/edit-post/components/visual-editor/index.js
+++ b/edit-post/components/visual-editor/index.js
@@ -34,7 +34,7 @@ function VisualEditor() {
 				</ObserveTyping>
 			</WritingFlow>
 			<_BlockSettingsMenuFirstItem>
-				{ ( { onClose } ) => <BlockInspectorButton onClick={ onClose } role="menuitem" /> }
+				{ ( { onClose } ) => <BlockInspectorButton onClick={ onClose } /> }
 			</_BlockSettingsMenuFirstItem>
 			<_BlockSettingsMenuPluginsExtension>
 				{ ( { clientIds, onClose } ) => <PluginBlockSettingsMenuGroup.Slot fillProps={ { clientIds, onClose } } /> }
diff --git a/edit-post/keyboard-shortcuts.js b/edit-post/keyboard-shortcuts.js
index 100ad546c063e3..be46a74a601864 100644
--- a/edit-post/keyboard-shortcuts.js
+++ b/edit-post/keyboard-shortcuts.js
@@ -5,7 +5,11 @@ import { rawShortcut, displayShortcut } from '@wordpress/keycodes';
 
 export default {
 	toggleEditorMode: {
-		value: rawShortcut.secondary( 'm' ),
-		label: displayShortcut.secondary( 'm' ),
+		raw: rawShortcut.secondary( 'm' ),
+		display: displayShortcut.secondary( 'm' ),
+	},
+	toggleSidebar: {
+		raw: rawShortcut.primaryShift( ',' ),
+		display: displayShortcut.primaryShift( ',' ),
 	},
 };
diff --git a/packages/components/src/menu-item/index.js b/packages/components/src/menu-item/index.js
index 8bbdf95c03e00b..27460ce0e0f1ec 100644
--- a/packages/components/src/menu-item/index.js
+++ b/packages/components/src/menu-item/index.js
@@ -21,7 +21,7 @@ import IconButton from '../icon-button';
  *
  * @return {WPElement} More menu item.
  */
-function MenuItem( { children, className, icon, onClick, shortcut, isSelected = false } ) {
+function MenuItem( { children, className, icon, onClick, shortcut, isSelected, role = 'menuitem', ...props } ) {
 	className = classnames( 'components-menu-item__button', className, {
 		'has-icon': icon,
 	} );
@@ -40,7 +40,9 @@ function MenuItem( { children, className, icon, onClick, shortcut, isSelected =
 				className={ className }
 				icon={ icon }
 				onClick={ onClick }
-				aria-pressed={ isSelected }
+				aria-checked={ isSelected }
+				role={ role }
+				{ ...props }
 			>
 				{ children }
 				<Shortcut shortcut={ shortcut } />
@@ -52,7 +54,9 @@ function MenuItem( { children, className, icon, onClick, shortcut, isSelected =
 		<Button
 			className={ className }
 			onClick={ onClick }
-			aria-pressed={ isSelected }
+			aria-checked={ isSelected }
+			role={ role }
+			{ ...props }
 		>
 			{ children }
 			<Shortcut shortcut={ shortcut } />
diff --git a/packages/components/src/menu-item/style.scss b/packages/components/src/menu-item/style.scss
index 23d446bc145c7b..fc2b1db41ef2bf 100644
--- a/packages/components/src/menu-item/style.scss
+++ b/packages/components/src/menu-item/style.scss
@@ -3,7 +3,7 @@
 	width: 100%;
 	padding: 8px;
 	text-align: left;
-	padding-left: 25px;
+	padding-left: 2rem;
 	color: $dark-gray-500;
 
 	// Target plugin icons that can have arbitrary classes by using an aggressive selector.
@@ -19,7 +19,7 @@
 	}
 
 	&.has-icon {
-		padding-left: 0;
+		padding-left: 0.5rem;
 	}
 
 	&:hover:not(:disabled):not([aria-disabled="true"]) {
@@ -33,13 +33,12 @@
 	// Colorize plugin icons to ensure contrast and cohesion, but allow plugin developers to override.
 	svg,
 	svg * {
-		stroke: $dark-gray-500;
 		fill: $dark-gray-500;
 	}
 
 	&:hover svg,
 	&:hover svg * {
-		stroke: $dark-gray-900 !important;
+		// !important allows icons from plugins to be overriden and given a dark-gray fill
 		fill: $dark-gray-900 !important;
 	}
 }
diff --git a/packages/components/src/menu-item/test/__snapshots__/index.js.snap b/packages/components/src/menu-item/test/__snapshots__/index.js.snap
index 214cc157d630ac..be23d018ed82ca 100644
--- a/packages/components/src/menu-item/test/__snapshots__/index.js.snap
+++ b/packages/components/src/menu-item/test/__snapshots__/index.js.snap
@@ -2,10 +2,25 @@
 
 exports[`MenuItem should match snapshot when all props provided 1`] = `
 <IconButton
-  aria-pressed={true}
+  aria-checked={true}
   className="components-menu-item__button my-class has-icon"
   icon="wordpress"
   onClick={[Function]}
+  role="menuitemcheckbox"
+>
+  My item
+  <MenuItemsShortcut
+    shortcut="mod+shift+alt+w"
+  />
+</IconButton>
+`;
+
+exports[`MenuItem should match snapshot when isSelected and role are optionally provided 1`] = `
+<IconButton
+  className="components-menu-item__button my-class has-icon"
+  icon="wordpress"
+  onClick={[Function]}
+  role="menuitem"
 >
   My item
   <MenuItemsShortcut
@@ -16,8 +31,8 @@ exports[`MenuItem should match snapshot when all props provided 1`] = `
 
 exports[`MenuItem should match snapshot when only label provided 1`] = `
 <Button
-  aria-pressed={false}
   className="components-menu-item__button"
+  role="menuitem"
 >
   My item
   <MenuItemsShortcut />
diff --git a/packages/components/src/menu-item/test/index.js b/packages/components/src/menu-item/test/index.js
index 5706b7804bb19c..1e3f89fbc05c79 100644
--- a/packages/components/src/menu-item/test/index.js
+++ b/packages/components/src/menu-item/test/index.js
@@ -2,6 +2,7 @@
  * External dependencies
  */
 import { shallow } from 'enzyme';
+import { noop } from 'lodash';
 
 /**
  * Internal dependencies
@@ -27,7 +28,23 @@ describe( 'MenuItem', () => {
 				className="my-class"
 				icon="wordpress"
 				isSelected={ true }
-				onClick={ () => {} }
+				role="menuitemcheckbox"
+				onClick={ noop }
+				shortcut="mod+shift+alt+w"
+			>
+				My item
+			</MenuItem>
+		);
+
+		expect( wrapper ).toMatchSnapshot();
+	} );
+
+	test( 'should match snapshot when isSelected and role are optionally provided', () => {
+		const wrapper = shallow(
+			<MenuItem
+				className="my-class"
+				icon="wordpress"
+				onClick={ noop }
 				shortcut="mod+shift+alt+w"
 			>
 				My item
diff --git a/packages/components/src/menu-items-choice/index.js b/packages/components/src/menu-items-choice/index.js
index 50edc61df89505..2311fd3a0435dd 100644
--- a/packages/components/src/menu-items-choice/index.js
+++ b/packages/components/src/menu-items-choice/index.js
@@ -13,6 +13,7 @@ export default function MenuItemsChoice( {
 		return (
 			<MenuItem
 				key={ item.value }
+				role="menuitemradio"
 				icon={ isSelected && 'yes' }
 				isSelected={ isSelected }
 				shortcut={ item.shortcut }
diff --git a/packages/editor/src/components/block-list/block.js b/packages/editor/src/components/block-list/block.js
index efb8a0f33d2c39..9c38b2be13eca2 100644
--- a/packages/editor/src/components/block-list/block.js
+++ b/packages/editor/src/components/block-list/block.js
@@ -393,7 +393,7 @@ export class BlockListBlock extends Component {
 		const shouldAppearSelectedParent = ! showSideInserter && hasSelectedInnerBlock && ! isTypingWithinBlock;
 		// We render block movers and block settings to keep them tabbale even if hidden
 		const shouldRenderMovers = ( isSelected || hoverArea === 'left' ) && ! showEmptyBlockSideInserter && ! isMultiSelecting && ! isPartOfMultiSelection && ! isTypingWithinBlock;
-		const shouldRenderBlockSettings = ( isSelected || hoverArea === 'right' ) && ! isMultiSelecting && ! isPartOfMultiSelection && ! isTypingWithinBlock;
+		const shouldRenderBlockSettings = ( isSelected || hoverArea === 'right' ) && ! isMultiSelecting && ! isPartOfMultiSelection;
 		const shouldShowBreadcrumb = isHovered && ! isEmptyDefaultBlock;
 		const shouldShowContextualToolbar = ! showSideInserter && ( ( isSelected && ! isTypingWithinBlock && isValid ) || isFirstMultiSelected ) && ( ! hasFixedToolbar || ! isLargeViewport );
 		const shouldShowMobileToolbar = shouldAppearSelected;
@@ -499,7 +499,7 @@ export class BlockListBlock extends Component {
 					<BlockSettingsMenu
 						clientIds={ clientId }
 						rootClientId={ rootClientId }
-						isHidden={ ! ( isHovered || isSelected ) || hoverArea !== 'right' }
+						isHidden={ ! ( isHovered || isSelected ) || hoverArea !== 'right' || isTypingWithinBlock }
 					/>
 				) }
 				{ shouldShowBreadcrumb && (
diff --git a/packages/editor/src/components/block-settings-menu/block-convert-button.js b/packages/editor/src/components/block-settings-menu/block-convert-button.js
index c5446dc5cd5810..992292e04a5f52 100644
--- a/packages/editor/src/components/block-settings-menu/block-convert-button.js
+++ b/packages/editor/src/components/block-settings-menu/block-convert-button.js
@@ -2,23 +2,22 @@
  * WordPress dependencies
  */
 import { __ } from '@wordpress/i18n';
-import { IconButton } from '@wordpress/components';
+import { MenuItem } from '@wordpress/components';
 
-export default function BlockConverter( { shouldRender, onClick, small, role } ) {
+export default function BlockConvertButton( { shouldRender, onClick, small } ) {
 	if ( ! shouldRender ) {
 		return null;
 	}
 
 	const label = __( 'Convert to Blocks' );
 	return (
-		<IconButton
+		<MenuItem
 			className="editor-block-settings-menu__control"
 			onClick={ onClick }
 			icon="screenoptions"
 			label={ small ? label : undefined }
-			role={ role }
 		>
 			{ ! small && label }
-		</IconButton>
+		</MenuItem>
 	);
 }
diff --git a/packages/editor/src/components/block-settings-menu/block-duplicate-button.js b/packages/editor/src/components/block-settings-menu/block-duplicate-button.js
deleted file mode 100644
index 72c7e4be27c185..00000000000000
--- a/packages/editor/src/components/block-settings-menu/block-duplicate-button.js
+++ /dev/null
@@ -1,68 +0,0 @@
-/**
- * External dependencies
- */
-import { flow, noop, last, every, first, castArray } from 'lodash';
-
-/**
- * WordPress dependencies
- */
-import { __ } from '@wordpress/i18n';
-import { IconButton } from '@wordpress/components';
-import { compose } from '@wordpress/compose';
-import { withSelect, withDispatch } from '@wordpress/data';
-import { cloneBlock, hasBlockSupport } from '@wordpress/blocks';
-
-export function BlockDuplicateButton( { blocks, onDuplicate, onClick = noop, isLocked, small = false, role } ) {
-	const canDuplicate = every( blocks, ( block ) => {
-		return hasBlockSupport( block.name, 'multiple', true );
-	} );
-	if ( isLocked || ! canDuplicate ) {
-		return null;
-	}
-
-	const label = __( 'Duplicate' );
-
-	return (
-		<IconButton
-			className="editor-block-settings-menu__control"
-			onClick={ flow( onDuplicate, onClick ) }
-			icon="admin-page"
-			label={ small ? label : undefined }
-			role={ role }
-		>
-			{ ! small && label }
-		</IconButton>
-	);
-}
-
-export default compose(
-	withSelect( ( select, { clientIds, rootClientId } ) => {
-		const {
-			getBlocksByClientId,
-			getBlockIndex,
-			getTemplateLock,
-		} = select( 'core/editor' );
-
-		return {
-			blocks: getBlocksByClientId( clientIds ),
-			index: getBlockIndex( last( castArray( clientIds ) ), rootClientId ),
-			isLocked: !! getTemplateLock( rootClientId ),
-		};
-	} ),
-	withDispatch( ( dispatch, { blocks, index, rootClientId } ) => ( {
-		onDuplicate() {
-			const clonedBlocks = blocks.map( ( block ) => cloneBlock( block ) );
-			dispatch( 'core/editor' ).insertBlocks(
-				clonedBlocks,
-				index + 1,
-				rootClientId
-			);
-			if ( clonedBlocks.length > 1 ) {
-				dispatch( 'core/editor' ).multiSelect(
-					first( clonedBlocks ).clientId,
-					last( clonedBlocks ).clientId
-				);
-			}
-		},
-	} ) ),
-)( BlockDuplicateButton );
diff --git a/packages/editor/src/components/block-settings-menu/block-mode-toggle.js b/packages/editor/src/components/block-settings-menu/block-mode-toggle.js
index bb5899bb1a6088..a8702f58f25748 100644
--- a/packages/editor/src/components/block-settings-menu/block-mode-toggle.js
+++ b/packages/editor/src/components/block-settings-menu/block-mode-toggle.js
@@ -7,12 +7,12 @@ import { noop } from 'lodash';
  * WordPress dependencies
  */
 import { __ } from '@wordpress/i18n';
-import { IconButton } from '@wordpress/components';
+import { MenuItem } from '@wordpress/components';
 import { getBlockType, hasBlockSupport } from '@wordpress/blocks';
 import { withSelect, withDispatch } from '@wordpress/data';
 import { compose } from '@wordpress/compose';
 
-export function BlockModeToggle( { blockType, mode, onToggleMode, small = false, role } ) {
+export function BlockModeToggle( { blockType, mode, onToggleMode, small = false } ) {
 	if ( ! hasBlockSupport( blockType, 'html', true ) ) {
 		return null;
 	}
@@ -22,15 +22,14 @@ export function BlockModeToggle( { blockType, mode, onToggleMode, small = false,
 		__( 'Edit visually' );
 
 	return (
-		<IconButton
+		<MenuItem
 			className="editor-block-settings-menu__control"
 			onClick={ onToggleMode }
 			icon="html"
 			label={ small ? label : undefined }
-			role={ role }
 		>
 			{ ! small && label }
-		</IconButton>
+		</MenuItem>
 	);
 }
 
diff --git a/packages/editor/src/components/block-settings-menu/block-remove-button.js b/packages/editor/src/components/block-settings-menu/block-remove-button.js
deleted file mode 100644
index 7b4b5ac849f4c7..00000000000000
--- a/packages/editor/src/components/block-settings-menu/block-remove-button.js
+++ /dev/null
@@ -1,55 +0,0 @@
-/**
- * External dependencies
- */
-import { castArray, flow, noop, some, omit } from 'lodash';
-
-/**
- * WordPress dependencies
- */
-import { __ } from '@wordpress/i18n';
-import { IconButton } from '@wordpress/components';
-import { compose } from '@wordpress/compose';
-import { withDispatch, withSelect } from '@wordpress/data';
-
-export function BlockRemoveButton( { onRemove, onClick = noop, isLocked, role, ...props } ) {
-	if ( isLocked ) {
-		return null;
-	}
-
-	const label = __( 'Remove Block' );
-
-	return (
-		<IconButton
-			className="editor-block-settings-menu__control"
-			onClick={ flow( onRemove, onClick ) }
-			icon="trash"
-			label={ label }
-			role={ role }
-			{ ...omit( props, 'clientIds' ) }
-		>
-			{ label }
-		</IconButton>
-	);
-}
-
-export default compose(
-	withDispatch( ( dispatch, { clientIds } ) => ( {
-		onRemove() {
-			dispatch( 'core/editor' ).removeBlocks( clientIds );
-		},
-	} ) ),
-	withSelect( ( select, { clientIds } ) => {
-		const {
-			getBlockRootClientId,
-			getTemplateLock,
-		} = select( 'core/editor' );
-
-		return {
-			isLocked: some( castArray( clientIds ), ( clientId ) => {
-				const rootClientId = getBlockRootClientId( clientId );
-				const templateLock = getTemplateLock( rootClientId );
-				return templateLock === 'all';
-			} ),
-		};
-	} ),
-)( BlockRemoveButton );
diff --git a/packages/editor/src/components/block-settings-menu/index.js b/packages/editor/src/components/block-settings-menu/index.js
index bf7372600b7167..9b6aa24e4441fc 100644
--- a/packages/editor/src/components/block-settings-menu/index.js
+++ b/packages/editor/src/components/block-settings-menu/index.js
@@ -2,22 +2,23 @@
  * External dependencies
  */
 import classnames from 'classnames';
-import { castArray } from 'lodash';
+import { castArray, first, last, every, flow } from 'lodash';
 
 /**
  * WordPress dependencies
  */
 import { __ } from '@wordpress/i18n';
 import { Component } from '@wordpress/element';
-import { IconButton, Dropdown, NavigableMenu } from '@wordpress/components';
-import { withDispatch } from '@wordpress/data';
+import { IconButton, Dropdown, NavigableMenu, MenuItem, KeyboardShortcuts } from '@wordpress/components';
+import { withSelect, withDispatch } from '@wordpress/data';
+import { compose } from '@wordpress/compose';
+import { cloneBlock, hasBlockSupport } from '@wordpress/blocks';
+import { rawShortcut, displayShortcut } from '@wordpress/keycodes';
 
 /**
  * Internal dependencies
  */
 import BlockModeToggle from './block-mode-toggle';
-import BlockDuplicateButton from './block-duplicate-button';
-import BlockRemoveButton from './block-remove-button';
 import ReusableBlockConvertButton from './reusable-block-convert-button';
 import ReusableBlockDeleteButton from './reusable-block-delete-button';
 import BlockHTMLConvertButton from './block-html-convert-button';
@@ -25,6 +26,18 @@ import BlockUnknownConvertButton from './block-unknown-convert-button';
 import _BlockSettingsMenuFirstItem from './block-settings-menu-first-item';
 import _BlockSettingsMenuPluginsExtension from './block-settings-menu-plugins-extension';
 
+const preventDefault = ( event ) => {
+	event.preventDefault();
+	return event;
+};
+
+const shortcuts = {
+	duplicate: {
+		raw: rawShortcut.primaryShift( 'd' ),
+		display: displayShortcut.primaryShift( 'd' ),
+	},
+};
+
 export class BlockSettingsMenu extends Component {
 	constructor() {
 		super( ...arguments );
@@ -52,8 +65,11 @@ export class BlockSettingsMenu extends Component {
 			clientIds,
 			onSelect,
 			focus,
-			rootClientId,
 			isHidden,
+			onDuplicate,
+			onRemove,
+			canDuplicate,
+			isLocked,
 		} = this.props;
 		const { isFocused } = this.state;
 		const blockClientIds = castArray( clientIds );
@@ -62,6 +78,14 @@ export class BlockSettingsMenu extends Component {
 
 		return (
 			<div className="editor-block-settings-menu">
+				<KeyboardShortcuts
+					bindGlobal
+					shortcuts={ {
+						// Prevents bookmark all Tabs shortcut in Chrome when devtools are closed.
+						// Prevents reposition Chrome devtools pane shortcut when devtools are open.
+						[ shortcuts.duplicate.raw ]: flow( preventDefault, onDuplicate ),
+					} }
+				/>
 				<Dropdown
 					contentClassName="editor-block-settings-menu__popover"
 					position="bottom left"
@@ -98,31 +122,32 @@ export class BlockSettingsMenu extends Component {
 								<BlockModeToggle
 									clientId={ firstBlockClientId }
 									onToggle={ onClose }
-									role="menuitem"
 								/>
 							) }
 							{ count === 1 && (
 								<BlockUnknownConvertButton
 									clientId={ firstBlockClientId }
-									role="menuitem"
 								/>
 							) }
 							{ count === 1 && (
 								<BlockHTMLConvertButton
 									clientId={ firstBlockClientId }
-									role="menuitem"
 								/>
 							) }
-							<BlockDuplicateButton
-								clientIds={ clientIds }
-								rootClientId={ rootClientId }
-								role="menuitem"
-							/>
+							{ ! isLocked && canDuplicate && (
+								<MenuItem
+									className="editor-block-settings-menu__control"
+									onClick={ onDuplicate }
+									icon="admin-page"
+									shortcut={ shortcuts.duplicate.display }
+								>
+									{ __( 'Duplicate' ) }
+								</MenuItem>
+							) }
 							{ count === 1 && (
 								<ReusableBlockConvertButton
 									clientId={ firstBlockClientId }
 									onToggle={ onClose }
-									itemsRole="menuitem"
 								/>
 							) }
 							<_BlockSettingsMenuPluginsExtension.Slot fillProps={ { clientIds, onClose } } />
@@ -131,13 +156,17 @@ export class BlockSettingsMenu extends Component {
 								<ReusableBlockDeleteButton
 									clientId={ firstBlockClientId }
 									onToggle={ onClose }
-									itemsRole="menuitem"
 								/>
 							) }
-							<BlockRemoveButton
-								clientIds={ clientIds }
-								role="menuitem"
-							/>
+							{ ! isLocked && (
+								<MenuItem
+									className="editor-block-settings-menu__control"
+									onClick={ onRemove }
+									icon="trash"
+								>
+									{ __( 'Remove Block' ) }
+								</MenuItem>
+							) }
 						</NavigableMenu>
 					) }
 				/>
@@ -146,8 +175,56 @@ export class BlockSettingsMenu extends Component {
 	}
 }
 
-export default withDispatch( ( dispatch ) => ( {
-	onSelect( clientId ) {
-		dispatch( 'core/editor' ).selectBlock( clientId );
-	},
-} ) )( BlockSettingsMenu );
+export default compose( [
+	withSelect( ( select, { clientIds, rootClientId } ) => {
+		const {
+			getBlocksByClientId,
+			getBlockIndex,
+			getTemplateLock,
+		} = select( 'core/editor' );
+
+		const blocks = getBlocksByClientId( clientIds );
+
+		const canDuplicate = every( blocks, ( block ) => {
+			return !! block && hasBlockSupport( block.name, 'multiple', true );
+		} );
+
+		return {
+			index: getBlockIndex( last( castArray( clientIds ) ), rootClientId ),
+			isLocked: !! getTemplateLock( rootClientId ),
+			blocks,
+			canDuplicate,
+			shortcuts,
+		};
+	} ),
+	withDispatch( ( dispatch, { clientIds, rootClientId, blocks, index, isLocked, canDuplicate } ) => {
+		const { insertBlocks, multiSelect, removeBlocks, selectBlock } = dispatch( 'core/editor' );
+
+		return {
+			onDuplicate() {
+				if ( isLocked || ! canDuplicate ) {
+					return;
+				}
+
+				const clonedBlocks = blocks.map( ( block ) => cloneBlock( block ) );
+				insertBlocks(
+					clonedBlocks,
+					index + 1,
+					rootClientId
+				);
+				if ( clonedBlocks.length > 1 ) {
+					multiSelect(
+						first( clonedBlocks ).clientId,
+						last( clonedBlocks ).clientId
+					);
+				}
+			},
+			onRemove() {
+				removeBlocks( clientIds );
+			},
+			onSelect( clientId ) {
+				selectBlock( clientId );
+			},
+		};
+	} ),
+] )( BlockSettingsMenu );
diff --git a/packages/editor/src/components/block-settings-menu/reusable-block-convert-button.js b/packages/editor/src/components/block-settings-menu/reusable-block-convert-button.js
index 7683569d45b9a8..8178ef66162fbc 100644
--- a/packages/editor/src/components/block-settings-menu/reusable-block-convert-button.js
+++ b/packages/editor/src/components/block-settings-menu/reusable-block-convert-button.js
@@ -7,7 +7,7 @@ import { noop } from 'lodash';
  * WordPress dependencies
  */
 import { Fragment } from '@wordpress/element';
-import { IconButton } from '@wordpress/components';
+import { MenuItem } from '@wordpress/components';
 import { __ } from '@wordpress/i18n';
 import { isReusableBlock } from '@wordpress/blocks';
 import { withSelect, withDispatch } from '@wordpress/data';
@@ -18,7 +18,6 @@ export function ReusableBlockConvertButton( {
 	isStaticBlock,
 	onConvertToStatic,
 	onConvertToReusable,
-	itemsRole,
 } ) {
 	if ( ! isVisible ) {
 		return null;
@@ -27,24 +26,22 @@ export function ReusableBlockConvertButton( {
 	return (
 		<Fragment>
 			{ isStaticBlock && (
-				<IconButton
+				<MenuItem
 					className="editor-block-settings-menu__control"
 					icon="controls-repeat"
 					onClick={ onConvertToReusable }
-					role={ itemsRole }
 				>
 					{ __( 'Add to Reusable Blocks' ) }
-				</IconButton>
+				</MenuItem>
 			) }
 			{ ! isStaticBlock && (
-				<IconButton
+				<MenuItem
 					className="editor-block-settings-menu__control"
 					icon="controls-repeat"
 					onClick={ onConvertToStatic }
-					role={ itemsRole }
 				>
 					{ __( 'Convert to Regular Block' ) }
-				</IconButton>
+				</MenuItem>
 			) }
 		</Fragment>
 	);
diff --git a/packages/editor/src/components/block-settings-menu/reusable-block-delete-button.js b/packages/editor/src/components/block-settings-menu/reusable-block-delete-button.js
index a01dab2a790b95..537af329a9d3aa 100644
--- a/packages/editor/src/components/block-settings-menu/reusable-block-delete-button.js
+++ b/packages/editor/src/components/block-settings-menu/reusable-block-delete-button.js
@@ -7,26 +7,25 @@ import { noop } from 'lodash';
  * WordPress dependencies
  */
 import { compose } from '@wordpress/compose';
-import { IconButton } from '@wordpress/components';
+import { MenuItem } from '@wordpress/components';
 import { __ } from '@wordpress/i18n';
 import { isReusableBlock } from '@wordpress/blocks';
 import { withSelect, withDispatch } from '@wordpress/data';
 
-export function ReusableBlockDeleteButton( { reusableBlock, onDelete, itemsRole } ) {
+export function ReusableBlockDeleteButton( { reusableBlock, onDelete } ) {
 	if ( ! reusableBlock ) {
 		return null;
 	}
 
 	return (
-		<IconButton
+		<MenuItem
 			className="editor-block-settings-menu__control"
 			icon="no"
 			disabled={ reusableBlock.isTemporary }
 			onClick={ () => onDelete( reusableBlock.id ) }
-			role={ itemsRole }
 		>
 			{ __( 'Remove from Reusable Blocks' ) }
-		</IconButton>
+		</MenuItem>
 	);
 }
 
diff --git a/packages/editor/src/components/block-settings-menu/test/__snapshots__/block-remove-button.js.snap b/packages/editor/src/components/block-settings-menu/test/__snapshots__/block-remove-button.js.snap
deleted file mode 100644
index a3083cb02e3029..00000000000000
--- a/packages/editor/src/components/block-settings-menu/test/__snapshots__/block-remove-button.js.snap
+++ /dev/null
@@ -1,13 +0,0 @@
-// Jest Snapshot v1, https://goo.gl/fbAQLP
-
-exports[`BlockRemoveButton matches the snapshot 1`] = `
-<IconButton
-  className="editor-block-settings-menu__control"
-  icon="trash"
-  label="Remove Block"
-  onClick={[Function]}
-  role="menuitem"
->
-  Remove Block
-</IconButton>
-`;
diff --git a/packages/editor/src/components/block-settings-menu/test/__snapshots__/reusable-block-delete-button.js.snap b/packages/editor/src/components/block-settings-menu/test/__snapshots__/reusable-block-delete-button.js.snap
index 95614e673c4584..fe0ee5827c4998 100644
--- a/packages/editor/src/components/block-settings-menu/test/__snapshots__/reusable-block-delete-button.js.snap
+++ b/packages/editor/src/components/block-settings-menu/test/__snapshots__/reusable-block-delete-button.js.snap
@@ -1,11 +1,11 @@
 // Jest Snapshot v1, https://goo.gl/fbAQLP
 
 exports[`ReusableBlockDeleteButton matches the snapshot 1`] = `
-<IconButton
+<MenuItem
   className="editor-block-settings-menu__control"
   icon="no"
   onClick={[Function]}
 >
   Remove from Reusable Blocks
-</IconButton>
+</MenuItem>
 `;
diff --git a/packages/editor/src/components/block-settings-menu/test/block-mode-toggle.js b/packages/editor/src/components/block-settings-menu/test/block-mode-toggle.js
index 026f03c528dd92..61f819da34dbad 100644
--- a/packages/editor/src/components/block-settings-menu/test/block-mode-toggle.js
+++ b/packages/editor/src/components/block-settings-menu/test/block-mode-toggle.js
@@ -24,7 +24,7 @@ describe( 'BlockModeToggle', () => {
 				mode="visual"
 			/>
 		);
-		const text = wrapper.find( 'IconButton' ).first().prop( 'children' );
+		const text = wrapper.find( 'MenuItem' ).first().prop( 'children' );
 
 		expect( text ).toEqual( 'Edit as HTML' );
 	} );
@@ -36,7 +36,7 @@ describe( 'BlockModeToggle', () => {
 				mode="html"
 			/>
 		);
-		const text = wrapper.find( 'IconButton' ).first().prop( 'children' );
+		const text = wrapper.find( 'MenuItem' ).first().prop( 'children' );
 
 		expect( text ).toEqual( 'Edit visually' );
 	} );
diff --git a/packages/editor/src/components/block-settings-menu/test/block-remove-button.js b/packages/editor/src/components/block-settings-menu/test/block-remove-button.js
deleted file mode 100644
index 3eaf12a2280adb..00000000000000
--- a/packages/editor/src/components/block-settings-menu/test/block-remove-button.js
+++ /dev/null
@@ -1,37 +0,0 @@
-/**
- * External dependencies
- */
-import { shallow } from 'enzyme';
-import { noop } from 'lodash';
-
-/**
- * Internal dependencies
- */
-import { BlockRemoveButton } from '../block-remove-button';
-
-describe( 'BlockRemoveButton', () => {
-	it( 'matches the snapshot', () => {
-		const wrapper = shallow(
-			<BlockRemoveButton
-				role="menuitem"
-				onRemove={ noop }
-			/>
-		);
-
-		expect( wrapper ).toMatchSnapshot();
-	} );
-
-	it( 'calls the onClick function when the IconButton is clicked', () => {
-		const onClick = jest.fn();
-		const wrapper = shallow(
-			<BlockRemoveButton
-				role="menuitem"
-				onRemove={ noop }
-				onClick={ onClick }
-			/>
-		);
-		wrapper.find( 'IconButton' ).first().simulate( 'click' );
-
-		expect( onClick ).toHaveBeenCalled();
-	} );
-} );
diff --git a/packages/editor/src/components/block-settings-menu/test/reusable-block-convert-button.js b/packages/editor/src/components/block-settings-menu/test/reusable-block-convert-button.js
index 92759fb414be7e..84b8b7085f8ff2 100644
--- a/packages/editor/src/components/block-settings-menu/test/reusable-block-convert-button.js
+++ b/packages/editor/src/components/block-settings-menu/test/reusable-block-convert-button.js
@@ -25,7 +25,7 @@ describe( 'ReusableBlockConvertButton', () => {
 				onConvertToReusable={ onConvert }
 			/>
 		);
-		const button = wrapper.find( 'IconButton' ).first();
+		const button = wrapper.find( 'MenuItem' ).first();
 		expect( button.children().text() ).toBe( 'Add to Reusable Blocks' );
 		button.simulate( 'click' );
 		expect( onConvert ).toHaveBeenCalled();
@@ -40,7 +40,7 @@ describe( 'ReusableBlockConvertButton', () => {
 				onConvertToStatic={ onConvert }
 			/>
 		);
-		const button = wrapper.find( 'IconButton' ).first();
+		const button = wrapper.find( 'MenuItem' ).first();
 		expect( button.children().text() ).toBe( 'Convert to Regular Block' );
 		button.simulate( 'click' );
 		expect( onConvert ).toHaveBeenCalled();
diff --git a/packages/editor/src/components/block-settings-menu/test/reusable-block-delete-button.js b/packages/editor/src/components/block-settings-menu/test/reusable-block-delete-button.js
index 53a100add43f87..63caddb28a5911 100644
--- a/packages/editor/src/components/block-settings-menu/test/reusable-block-delete-button.js
+++ b/packages/editor/src/components/block-settings-menu/test/reusable-block-delete-button.js
@@ -31,7 +31,7 @@ describe( 'ReusableBlockDeleteButton', () => {
 			/>
 		);
 
-		wrapper.find( 'IconButton' ).simulate( 'click' );
+		wrapper.find( 'MenuItem' ).simulate( 'click' );
 		expect( onDelete ).toHaveBeenCalledWith( 123 );
 	} );
 } );
diff --git a/packages/keycodes/src/index.js b/packages/keycodes/src/index.js
index f5ab3ea87ce13b..98d29362774877 100644
--- a/packages/keycodes/src/index.js
+++ b/packages/keycodes/src/index.js
@@ -12,7 +12,7 @@
 /**
  * External dependencies
  */
-import { get, mapValues, includes } from 'lodash';
+import { get, mapValues, includes, capitalize } from 'lodash';
 
 export const BACKSPACE = 8;
 export const TAB = 9;
@@ -47,6 +47,7 @@ export function isMacOS( _window = window ) {
 const modifiers = {
 	primary: ( _isMac ) => _isMac() ? [ COMMAND ] : [ CTRL ],
 	primaryShift: ( _isMac ) => _isMac() ? [ SHIFT, COMMAND ] : [ CTRL, SHIFT ],
+	primaryAlt: ( _isMac ) => _isMac() ? [ ALT, COMMAND ] : [ CTRL, ALT ],
 	secondary: ( _isMac ) => _isMac() ? [ SHIFT, ALT, COMMAND ] : [ CTRL, SHIFT, ALT ],
 	access: ( _isMac ) => _isMac() ? [ CTRL, ALT ] : [ SHIFT, ALT ],
 };
@@ -81,13 +82,13 @@ export const displayShortcut = mapValues( modifiers, ( modifier ) => {
 		};
 		const shortcut = [
 			...modifier( _isMac ).map( ( key ) => get( replacementKeyMap, key, key ) ),
-			character.toUpperCase(),
+			capitalize( character ),
 		].join( '+' );
 
 		// Because we use just the clover symbol for MacOS's "command" key, remove
 		// the key join character ("+") between it and the final character if that
 		// final character is alphanumeric. ⌘S looks nicer than ⌘+S.
-		return shortcut.replace( /⌘\+([A-Z0-9])$/g, '⌘$1' );
+		return shortcut.replace( /⌘\+(.+)$/g, '⌘$1' );
 	};
 } );
 
diff --git a/packages/keycodes/src/test/index.js b/packages/keycodes/src/test/index.js
index e17c534ee6b941..36d8316875fd14 100644
--- a/packages/keycodes/src/test/index.js
+++ b/packages/keycodes/src/test/index.js
@@ -21,6 +21,11 @@ describe( 'displayShortcut', () => {
 			const shortcut = displayShortcut.primary( 'm', isMacOSTrue );
 			expect( shortcut ).toEqual( '⌘M' );
 		} );
+
+		it( 'outputs command Del on MacOS (works for multiple character keys)', () => {
+			const shortcut = displayShortcut.primary( 'del', isMacOSTrue );
+			expect( shortcut ).toEqual( '⌘Del' );
+		} );
 	} );
 
 	describe( 'primaryShift', () => {
@@ -33,6 +38,11 @@ describe( 'displayShortcut', () => {
 			const shortcut = displayShortcut.primaryShift( 'm', isMacOSTrue );
 			expect( shortcut ).toEqual( 'Shift+⌘M' );
 		} );
+
+		it( 'outputs shift+command Del on MacOS (works for multiple character keys)', () => {
+			const shortcut = displayShortcut.primaryShift( 'del', isMacOSTrue );
+			expect( shortcut ).toEqual( 'Shift+⌘Del' );
+		} );
 	} );
 
 	describe( 'secondary', () => {