diff --git a/packages/block-library/src/editor.scss b/packages/block-library/src/editor.scss
index 784850095f97d2..e1f7040e88fb49 100644
--- a/packages/block-library/src/editor.scss
+++ b/packages/block-library/src/editor.scss
@@ -31,6 +31,7 @@
 @import "./spacer/editor.scss";
 @import "./subhead/editor.scss";
 @import "./table/editor.scss";
+@import "./table-of-contents/editor.scss";
 @import "./tag-cloud/editor.scss";
 @import "./text-columns/editor.scss";
 @import "./verse/editor.scss";
diff --git a/packages/block-library/src/index.js b/packages/block-library/src/index.js
index a9a9b78f34ca92..1d95150a6f808b 100644
--- a/packages/block-library/src/index.js
+++ b/packages/block-library/src/index.js
@@ -54,6 +54,7 @@ import * as shortcode from './shortcode';
 import * as spacer from './spacer';
 import * as subhead from './subhead';
 import * as table from './table';
+import * as tableOfContents from './table-of-contents';
 import * as template from './template';
 import * as textColumns from './text-columns';
 import * as verse from './verse';
@@ -119,6 +120,7 @@ export const registerCoreBlocks = () => {
 		spacer,
 		subhead,
 		table,
+		tableOfContents,
 		tagCloud,
 		template,
 		textColumns,
diff --git a/packages/block-library/src/table-of-contents/ListLevel.js b/packages/block-library/src/table-of-contents/ListLevel.js
new file mode 100644
index 00000000000000..cdbc56d871e5fe
--- /dev/null
+++ b/packages/block-library/src/table-of-contents/ListLevel.js
@@ -0,0 +1,69 @@
+/**
+ * WordPress dependencies
+ */
+import { RichText } from '@wordpress/editor';
+
+export default function ListLevel( props ) {
+	const { edit, attributes, setAttributes } = props;
+	let childnodes = null;
+
+	if ( props.children ) {
+		childnodes = props.children.map( function( childnode ) {
+			const link = getLinkElement( childnode, props );
+
+			return (
+				<li key={ childnode.block.anchor }>
+					{ link }
+					{ childnode.children ? <ListLevel
+						edit={ edit }
+						attributes={ attributes }
+						setAttributes={ setAttributes }
+					>
+						{ childnode.children }
+					</ListLevel> : null }
+				</li>
+			);
+		} );
+
+		return (
+			<ul>
+				{ childnodes }
+			</ul>
+		);
+	}
+}
+
+function getLinkElement( childnode, props ) {
+	const { edit, attributes, setAttributes } = props;
+	const { headings, autosync } = attributes;
+
+	const updateHeading = ( content ) => {
+		headings[ childnode.index ].content = content;
+		setAttributes( { headings } );
+	};
+
+	if ( autosync ) {
+		return <a href={ childnode.block.anchor } data-level={ childnode.block.level }>{ childnode.block.content }</a>;
+	}
+
+	if ( edit ) {
+		return (
+			<RichText
+				tagName="a"
+				href={ childnode.block.anchor }
+				data-level={ childnode.block.level }
+				onChange={ ( content ) => updateHeading( content ) }
+				value={ childnode.block.content }
+			/>
+		);
+	}
+
+	return (
+		<RichText.Content
+			tagName="a"
+			href={ childnode.block.anchor }
+			data-level={ childnode.block.level }
+			value={ childnode.block.content }
+		/>
+	);
+}
diff --git a/packages/block-library/src/table-of-contents/block.json b/packages/block-library/src/table-of-contents/block.json
new file mode 100644
index 00000000000000..947c5aa078ba42
--- /dev/null
+++ b/packages/block-library/src/table-of-contents/block.json
@@ -0,0 +1,4 @@
+{
+	"name": "core/table-of-contents",
+	"category": "common"
+}
\ No newline at end of file
diff --git a/packages/block-library/src/table-of-contents/edit.js b/packages/block-library/src/table-of-contents/edit.js
new file mode 100644
index 00000000000000..3dbe16ac380f0b
--- /dev/null
+++ b/packages/block-library/src/table-of-contents/edit.js
@@ -0,0 +1,128 @@
+/**
+ * Internal dependencies
+ */
+import * as Utils from './utils';
+import ListLevel from './ListLevel';
+
+/**
+ * WordPress dependencies
+ */
+import { Component } from '@wordpress/element';
+import { subscribe } from '@wordpress/data';
+import { __ } from '@wordpress/i18n';
+import {
+	IconButton,
+	Toolbar,
+	PanelBody,
+	ToggleControl,
+} from '@wordpress/components';
+import {
+	BlockControls,
+	InspectorControls,
+} from '@wordpress/editor';
+
+class TOCEdit extends Component {
+	constructor() {
+		super( ...arguments );
+
+		this.state = {
+			wpDataUnsubscribe: null,
+		};
+
+		this.toggleAttribute = this.toggleAttribute.bind( this );
+		this.refresh = this.refresh.bind( this );
+	}
+
+	toggleAttribute( propName ) {
+		const value = this.props.attributes[ propName ];
+		const { setAttributes } = this.props;
+
+		setAttributes( { [ propName ]: ! value } );
+	}
+
+	refresh() {
+		const { setAttributes } = this.props;
+		const headings = Utils.getPageHeadings();
+		setAttributes( { headings } );
+	}
+
+	componentDidMount() {
+		const { attributes, setAttributes } = this.props;
+		const headings = attributes.headings || [];
+		const wpDataUnsubscribe = subscribe( () => {
+			const pageHeadings = Utils.getPageHeadings();
+			this.setState( { pageHeadings } );
+		} );
+
+		setAttributes( { headings } );
+		this.setState( { wpDataUnsubscribe } );
+	}
+
+	componentWillUnmount() {
+		this.state.wpDataUnsubscribe();
+	}
+
+	componentDidUpdate( prevProps, prevState ) {
+		const { attributes, setAttributes } = this.props;
+		const pageHeadings = Utils.getPageHeadings();
+		if ( JSON.stringify( pageHeadings ) !== JSON.stringify( prevState.pageHeadings ) ) {
+			this.setState( { pageHeadings } );
+			if ( attributes.autosync ) {
+				setAttributes( { headings: pageHeadings } ); // this is displayed on the page
+			}
+		}
+	}
+
+	render() {
+		const { attributes, setAttributes } = this.props;
+		const { autosync } = attributes;
+		const headings = attributes.headings || [];
+		if ( headings.length === 0 ) {
+			return ( <p>{ __( 'Start adding headings to generate Table of Contents' ) }</p> );
+		}
+
+		Utils.updateHeadingBlockAnchors();
+
+		return (
+			<div className={ this.props.className }>
+				{ ! autosync &&
+					<BlockControls>
+						<Toolbar>
+							<IconButton
+								label={ __( 'Update' ) }
+								aria-pressed={ this.state.isEditing }
+								onClick={ this.refresh }
+								icon="update"
+							/>
+						</Toolbar>
+					</BlockControls>
+				}
+				{
+					<InspectorControls>
+						<PanelBody title={ __( 'Table of Contents Settings' ) }>
+							<ToggleControl
+								label={ __( 'Auto Sync' ) }
+								checked={ autosync }
+								onChange={ () => {
+									if ( ! autosync ) {
+										this.refresh();
+									}
+									this.toggleAttribute( 'autosync' );
+								} }
+							/>
+						</PanelBody>
+					</InspectorControls>
+				}
+				<ListLevel
+					edit={ true }
+					attributes={ attributes }
+					setAttributes={ setAttributes }
+				>
+					{ Utils.linearToNestedList( headings ) }
+				</ListLevel>
+			</div>
+		);
+	}
+}
+
+export default TOCEdit;
diff --git a/packages/block-library/src/table-of-contents/editor.scss b/packages/block-library/src/table-of-contents/editor.scss
new file mode 100644
index 00000000000000..5ecf514b4c9c53
--- /dev/null
+++ b/packages/block-library/src/table-of-contents/editor.scss
@@ -0,0 +1,21 @@
+.wp-block-table-of-contents {
+	.editor-block-list__block & ul {
+		padding-left: 1.3em;
+
+		a {
+			display: block;
+
+			&:focus {
+				box-shadow: none;
+			}
+		}
+
+		ul {
+			margin-bottom: 0;
+		}
+	}
+
+	p {
+		opacity: 0.5;
+	}
+}
diff --git a/packages/block-library/src/table-of-contents/index.js b/packages/block-library/src/table-of-contents/index.js
new file mode 100644
index 00000000000000..2a4e169af43ca6
--- /dev/null
+++ b/packages/block-library/src/table-of-contents/index.js
@@ -0,0 +1,39 @@
+/**
+ * WordPress dependencies
+ */
+import { __ } from '@wordpress/i18n';
+
+/**
+ * Internal dependencies
+ */
+import edit from './edit';
+import metadata from './block.json';
+import save from './save';
+
+const { name } = metadata;
+
+export { metadata, name };
+
+export const settings = {
+	title: __( 'Table of Contents' ),
+	description: __( 'Add a list of internal links allowing your readers to quickly navigate around.' ),
+	icon: 'list-view',
+	category: 'layout',
+	attributes: {
+		headings: {
+			source: 'query',
+			selector: 'a',
+			query: {
+				content: { source: 'text' },
+				anchor: { source: 'attribute', attribute: 'href' },
+				level: { source: 'attribute', attribute: 'data-level' },
+			},
+		},
+		autosync: {
+			type: 'boolean',
+			default: true,
+		},
+	},
+	edit,
+	save,
+};
diff --git a/packages/block-library/src/table-of-contents/save.js b/packages/block-library/src/table-of-contents/save.js
new file mode 100644
index 00000000000000..60c17b1ab4560d
--- /dev/null
+++ b/packages/block-library/src/table-of-contents/save.js
@@ -0,0 +1,27 @@
+/**
+ * Internal dependencies
+ */
+import * as Utils from './utils';
+import ListLevel from './ListLevel';
+
+export default function save( props ) {
+	const { attributes, setAttributes } = props;
+	const headings = attributes.headings;
+
+	if ( headings.length === 0 ) {
+		return null;
+	}
+
+	Utils.updateHeadingBlockAnchors();
+	return (
+		<nav className={ props.className }>
+			<ListLevel
+				edit={ false }
+				attributes={ attributes }
+				setAttributes={ setAttributes }
+			>
+				{ Utils.linearToNestedList( headings ) }
+			</ListLevel>
+		</nav>
+	);
+}
diff --git a/packages/block-library/src/table-of-contents/utils.js b/packages/block-library/src/table-of-contents/utils.js
new file mode 100644
index 00000000000000..9aff56cd8bac82
--- /dev/null
+++ b/packages/block-library/src/table-of-contents/utils.js
@@ -0,0 +1,118 @@
+/**
+ * WordPress dependencies
+ */
+import { select } from '@wordpress/data';
+import { cleanForSlug } from '@wordpress/editor';
+
+export function linearToNestedList( array, index = 0 ) {
+	const returnValue = [];
+
+	array.forEach( function( heading, key ) {
+		if ( typeof heading.content === 'undefined' ) {
+			return;
+		}
+
+		// Make sure we are only working with the same level as the first iteration in our set.
+		if ( heading.level === array[ 0 ].level ) {
+			// Check that the next iteration will return a value.
+			// If it does and the next level is greater than the current level,
+			// the next iteration becomes a child of the current interation.
+			if (
+				( typeof array[ key + 1 ] !== 'undefined' ) &&
+				( array[ key + 1 ].level > heading.level )
+			) {
+				// We need to calculate the last index before the next iteration that has the same level (siblings).
+				// We then use this last index to slice the array for use in recursion.
+				// This prevents duplicate nodes.
+				let endOfSlice = array.length;
+				for ( let i = ( key + 1 ); i < array.length; i++ ) {
+					if ( array[ i ].level === heading.level ) {
+						endOfSlice = i;
+						break;
+					}
+				}
+
+				// We found a child node: Push a new node onto the return array with children.
+				returnValue.push( {
+					block: heading,
+					index: index + key,
+					children: linearToNestedList( array.slice( key + 1, endOfSlice ), index + key + 1 ),
+				} );
+			} else {
+				// No child node: Push a new node onto the return array.
+				returnValue.push( {
+					block: heading,
+					index: index + key,
+					children: null,
+				} );
+			}
+		}
+	} );
+
+	return returnValue;
+}
+
+export function getPageHeadings() {
+	return convertHeadingBlocksToAttributes( getHeadingBlocks() );
+}
+
+export function getHeadingBlocks() {
+	const editor = select( 'core/block-editor' );
+	return editor.getBlocks().filter( ( block ) => block.name === 'core/heading' );
+}
+
+export function convertHeadingBlocksToAttributes( headingBlocks ) {
+	return headingBlocks.map( function( heading ) {
+		const level = heading.attributes.level.toString();
+
+		const headingContent = heading.attributes.content || '';
+		const anchorContent = heading.attributes.anchor || '';
+
+		// strip html from heading and attribute content
+		const contentDiv = document.createElement( 'div' );
+
+		contentDiv.innerHTML = headingContent;
+		const content = contentDiv.textContent || contentDiv.innerText || '';
+
+		contentDiv.innerHTML = anchorContent;
+		let anchor = contentDiv.textContent || contentDiv.innerText || '';
+
+		if ( anchor !== '' && anchor.indexOf( '#' ) === -1 ) {
+			anchor = '#' + cleanForSlug( anchor );
+		}
+
+		return { content, anchor, level };
+	} );
+}
+
+export function updateHeadingBlockAnchors() {
+	// Add anchors to any headings that don't have one.
+	getHeadingBlocks().forEach( function( heading, key ) {
+		const headingAnchorEmpty = ( typeof heading.attributes.anchor === 'undefined' || heading.attributes.anchor === '' );
+		const headingContentEmpty = ( typeof heading.attributes.content === 'undefined' || heading.attributes.content === '' );
+		const headingDefaultAnchor = ( ! headingAnchorEmpty && heading.attributes.anchor.indexOf( key + '-' ) === 0 );
+
+		if ( ! headingContentEmpty && ( headingAnchorEmpty || headingDefaultAnchor ) ) {
+			heading.attributes.anchor = key + '-' + cleanForSlug( heading.attributes.content.toString() );
+		}
+	} );
+}
+
+export function haveHeadingsChanged( oldHeadings, newHeadings ) {
+	if ( oldHeadings.length !== newHeadings.length ) {
+		return true;
+	}
+
+	const changedHeadings = oldHeadings.filter( ( heading, index ) => {
+		const newHeading = newHeadings[ index ];
+
+		return (
+			heading.content !== newHeading.content ||
+			heading.anchor !== newHeading.anchor ||
+			heading.level !== newHeading.level
+		);
+	} );
+
+	// Return boolean value from length.
+	return ! ! +changedHeadings.length;
+}
diff --git a/packages/e2e-tests/fixtures/block-transforms.js b/packages/e2e-tests/fixtures/block-transforms.js
index 7391c1bc7adb90..3e75b883210449 100644
--- a/packages/e2e-tests/fixtures/block-transforms.js
+++ b/packages/e2e-tests/fixtures/block-transforms.js
@@ -416,6 +416,12 @@ export const EXPECTED_TRANSFORMS = {
 			'Group',
 		],
 	},
+	'core__table-of-contents': {
+		originalBlock: 'Table of Contents',
+		availableTransforms: [
+			'Group',
+		],
+	},
 	'core__tag-cloud': {
 		originalBlock: 'Tag Cloud',
 		availableTransforms: [
diff --git a/packages/e2e-tests/fixtures/blocks/core__table-of-contents.html b/packages/e2e-tests/fixtures/blocks/core__table-of-contents.html
new file mode 100644
index 00000000000000..d16d4106710de1
--- /dev/null
+++ b/packages/e2e-tests/fixtures/blocks/core__table-of-contents.html
@@ -0,0 +1,3 @@
+<!-- wp:core/table-of-contents -->
+<nav class="wp-block-table-of-contents"><ul><li><a href="#0-First-Heading" data-level="2">First Heading</a><ul><li><a href="#1-Sub-Heading" data-level="3">Sub Heading</a></li><li><a href="#2-Another-Sub-Heading" data-level="3">Another Sub Heading</a></li></ul></li></ul></nav>
+<!-- /wp:core/table-of-contents -->
\ No newline at end of file
diff --git a/packages/e2e-tests/fixtures/blocks/core__table-of-contents.json b/packages/e2e-tests/fixtures/blocks/core__table-of-contents.json
new file mode 100644
index 00000000000000..861783a7f749dd
--- /dev/null
+++ b/packages/e2e-tests/fixtures/blocks/core__table-of-contents.json
@@ -0,0 +1,29 @@
+[
+    {
+        "clientId": "_clientId_0",
+        "name": "core/table-of-contents",
+        "isValid": true,
+        "attributes": {
+            "headings": [
+                {
+                    "content": "First Heading",
+                    "anchor": "#0-First-Heading",
+                    "level": "2"
+                },
+                {
+                    "content": "Sub Heading",
+                    "anchor": "#1-Sub-Heading",
+                    "level": "3"
+                },
+                {
+                    "content": "Another Sub Heading",
+                    "anchor": "#2-Another-Sub-Heading",
+                    "level": "3"
+                }
+            ],
+            "autosync": true
+        },
+        "innerBlocks": [],
+        "originalContent": "<nav class=\"wp-block-table-of-contents\"><ul><li><a href=\"#0-First-Heading\" data-level=\"2\">First Heading</a><ul><li><a href=\"#1-Sub-Heading\" data-level=\"3\">Sub Heading</a></li><li><a href=\"#2-Another-Sub-Heading\" data-level=\"3\">Another Sub Heading</a></li></ul></li></ul></nav>"
+    }
+]
diff --git a/packages/e2e-tests/fixtures/blocks/core__table-of-contents.parsed.json b/packages/e2e-tests/fixtures/blocks/core__table-of-contents.parsed.json
new file mode 100644
index 00000000000000..589603df59a0ff
--- /dev/null
+++ b/packages/e2e-tests/fixtures/blocks/core__table-of-contents.parsed.json
@@ -0,0 +1,11 @@
+[
+    {
+        "blockName": "core/table-of-contents",
+        "attrs": {},
+        "innerBlocks": [],
+        "innerHTML": "\n<nav class=\"wp-block-table-of-contents\"><ul><li><a href=\"#0-First-Heading\" data-level=\"2\">First Heading</a><ul><li><a href=\"#1-Sub-Heading\" data-level=\"3\">Sub Heading</a></li><li><a href=\"#2-Another-Sub-Heading\" data-level=\"3\">Another Sub Heading</a></li></ul></li></ul></nav>\n",
+        "innerContent": [
+            "\n<nav class=\"wp-block-table-of-contents\"><ul><li><a href=\"#0-First-Heading\" data-level=\"2\">First Heading</a><ul><li><a href=\"#1-Sub-Heading\" data-level=\"3\">Sub Heading</a></li><li><a href=\"#2-Another-Sub-Heading\" data-level=\"3\">Another Sub Heading</a></li></ul></li></ul></nav>\n"
+        ]
+    }
+]
diff --git a/packages/e2e-tests/fixtures/blocks/core__table-of-contents.serialized.html b/packages/e2e-tests/fixtures/blocks/core__table-of-contents.serialized.html
new file mode 100644
index 00000000000000..06fbdee15a85ee
--- /dev/null
+++ b/packages/e2e-tests/fixtures/blocks/core__table-of-contents.serialized.html
@@ -0,0 +1,3 @@
+<!-- wp:table-of-contents -->
+<nav class="wp-block-table-of-contents"><ul><li><a href="#0-First-Heading" data-level="2">First Heading</a><ul><li><a href="#1-Sub-Heading" data-level="3">Sub Heading</a></li><li><a href="#2-Another-Sub-Heading" data-level="3">Another Sub Heading</a></li></ul></li></ul></nav>
+<!-- /wp:table-of-contents -->