diff --git a/.gitignore b/.gitignore
index cbd461d2102..1044d8cf962 100644
--- a/.gitignore
+++ b/.gitignore
@@ -17,3 +17,6 @@ built
 /phpcs.xml
 /phpunit.xml
 /*.sql
+
+# Generated via bin/transform-readme.php
+/readme.txt
diff --git a/Gruntfile.js b/Gruntfile.js
index a5bbf0f3335..234f73c4bed 100644
--- a/Gruntfile.js
+++ b/Gruntfile.js
@@ -10,7 +10,6 @@ module.exports = function( grunt ) {
 		'assets',
 		'back-compat',
 		'includes',
-		'README.md',
 		'src',
 		'templates',
 		'vendor',
@@ -71,6 +70,9 @@ module.exports = function( grunt ) {
 				stdout: true,
 				stderr: true,
 			},
+			transform_readme: {
+				command: 'php bin/transform-readme.php',
+			},
 			verify_matching_versions: {
 				command: 'php bin/verify-version-consistency.php',
 			},
@@ -147,6 +149,9 @@ module.exports = function( grunt ) {
 				return true;
 			} );
 
+			grunt.task.run( 'shell:transform_readme' );
+			paths.push( 'readme.txt' );
+
 			paths.push( 'composer.*' ); // Copy in order to be able to do run composer_install.
 			paths.push( 'assets/js/**/*.js' );
 			paths.push( 'assets/js/**/*.asset.php' );
diff --git a/README.md b/README.md
index 7080dd0a801..4435e631072 100644
--- a/README.md
+++ b/README.md
@@ -1,18 +1,17 @@
-# AMP
+# AMP Plugin for WordPress
 
-Contributors: google, xwp, automattic, westonruter, albertomedina, schlessera, swissspidy, pierlo, johnwatkins0, joshuawold, ryankienstra  
-Tags: amp, mobile, optimization, accelerated mobile pages, framework, components, blocks, performance, ux, seo, official  
-Requires at least: 4.9  
-Tested up to: 5.6  
-Stable tag: 2.0.10  
-License: GPLv2 or later  
-License URI: http://www.gnu.org/licenses/gpl-2.0.html  
-Requires PHP: 5.6  
-
-![The Official AMP Plugin for WordPress](.wordpress-org/banner-1544x500.png)
+![Banner](.wordpress-org/banner-1544x500.png)
 
 The official AMP Plugin, supported by the AMP team. Formerly Accelerated Mobile Pages, AMP enables great experiences across both mobile and desktop.
 
+**Contributors:** [google](https://profiles.wordpress.org/google), [xwp](https://profiles.wordpress.org/xwp), [automattic](https://profiles.wordpress.org/automattic), [westonruter](https://profiles.wordpress.org/westonruter), [albertomedina](https://profiles.wordpress.org/albertomedina), [schlessera](https://profiles.wordpress.org/schlessera), [swissspidy](https://profiles.wordpress.org/swissspidy), [pierlo](https://profiles.wordpress.org/pierlo), [johnwatkins0](https://profiles.wordpress.org/johnwatkins0), [joshuawold](https://profiles.wordpress.org/joshuawold), [ryankienstra](https://profiles.wordpress.org/ryankienstra)  
+**Tags:** [amp](https://wordpress.org/plugins/tags/amp), [mobile](https://wordpress.org/plugins/tags/mobile), [optimization](https://wordpress.org/plugins/tags/optimization), [accelerated mobile pages](https://wordpress.org/plugins/tags/accelerated-mobile-pages), [framework](https://wordpress.org/plugins/tags/framework), [components](https://wordpress.org/plugins/tags/components), [blocks](https://wordpress.org/plugins/tags/blocks), [performance](https://wordpress.org/plugins/tags/performance), [ux](https://wordpress.org/plugins/tags/ux), [seo](https://wordpress.org/plugins/tags/seo), [official](https://wordpress.org/plugins/tags/official)  
+**Requires at least:** 4.9  
+**Tested up to:** 5.6  
+**Stable tag:** 2.0.10  
+**License:** [GPLv2 or later](http://www.gnu.org/licenses/gpl-2.0.html)  
+**Requires PHP:** 5.6
+
 [![Build Status](https://github.com/ampproject/amp-wp/workflows/Build,%20test%20&%20measure/badge.svg)](https://github.com/ampproject/amp-wp/actions?query=branch%3Adevelop+workflow%3A%22Build%2C+test+%26+measure%22)
 [![Coverage Status](https://img.shields.io/codecov/c/github/ampproject/amp-wp/develop.svg)](https://codecov.io/gh/ampproject/amp-wp)
 [![Built with Grunt](https://gruntjs.com/cdn/builtwith.svg)](http://gruntjs.com)
@@ -21,11 +20,11 @@ The official AMP Plugin, supported by the AMP team. Formerly Accelerated Mobile
 
 This official plugin from the AMP project enables AMP content publishing with WordPress in a way that is fully and seamlessly integrated with the standard mechanisms of the platform.
 
-https://www.youtube.com/watch?v=s52JNMT59s8&list=PLXTOW_XMsIDRGRr5QDffrvND8Qh1RndFb
+[![Play video on YouTube](https://i1.ytimg.com/vi/s52JNMT59s8/hqdefault.jpg)](https://www.youtube.com/watch?v=s52JNMT59s8&list=PLXTOW_XMsIDRGRr5QDffrvND8Qh1RndFb)
 
 For more videos like this, check out the ongoing [AMP for WordPress video series](https://www.youtube.com/playlist?list=PLXTOW_XMsIDRGRr5QDffrvND8Qh1RndFb).
 
-The key features are the following:
+The plugin's key features include:
 
 1. **Automate the process of generating AMP-valid markup as much as possible**, letting users follow the standard workflows they are used to in WordPress.
 2. **Provide effective validation tools** to help users deal with AMP incompatibilities when they happen, including mechanisms for **identifying**, **contextualizing**, and **resolving issues caused by validation errors**.
@@ -88,17 +87,29 @@ Please see the [FAQs on amp-wp.org](https://amp-wp.org/documentation/frequently-
 
 ## Screenshots
 
-1. New onboarding wizard to help you get started.<br>![New onboarding wizard to help you get started.](.wordpress-org/screenshot-1.png)
+### New onboarding wizard to help you get started.
+
+![New onboarding wizard to help you get started.](.wordpress-org/screenshot-1.png)
+
+### Built for developers and non-technical content creators alike.
+
+![Built for developers and non-technical content creators alike.](.wordpress-org/screenshot-2.png)
+
+### Theme selection to enhance the Reader mode experience.
+
+![Theme selection to enhance the Reader mode experience.](.wordpress-org/screenshot-3.png)
+
+### Preview how your site looks across desktop and mobile before finalising changes.
 
-2. Built for developers and non-technical content creators alike.<br>![Built for developers and non-technical content creators alike.](.wordpress-org/screenshot-2.png)
+![Preview how your site looks across desktop and mobile before finalising changes.](.wordpress-org/screenshot-4.png)
 
-3. Theme selection to enhance the Reader mode experience.<br>![Theme selection to enhance the Reader mode experience.](.wordpress-org/screenshot-3.png)
+### Customize the design of AMP pages in the Customizer.
 
-4. Preview how your site looks across desktop and mobile before finalising changes.<br>![Preview how your site looks across desktop and mobile before finalising changes.](.wordpress-org/screenshot-4.png)
+![Customize the design of AMP pages in the Customizer.](.wordpress-org/screenshot-5.png)
 
-5. Customize the design of AMP pages in the Customizer.<br>![Customize the design of AMP pages in the Customizer.](.wordpress-org/screenshot-5.png)
+### Reopen the onboarding wizard, change individual options, or manage advanced settings.
 
-6. Reopen the onboarding wizard, change individual options, or manage advanced settings.<br>![Reopen the onboarding wizard, change individual options, or manage advanced settings.](.wordpress-org/screenshot-6.png)
+![Reopen the onboarding wizard, change individual options, or manage advanced settings.](.wordpress-org/screenshot-6.png)
 
 ## Changelog
 
diff --git a/bin/transform-readme.php b/bin/transform-readme.php
new file mode 100755
index 00000000000..6e9350e7829
--- /dev/null
+++ b/bin/transform-readme.php
@@ -0,0 +1,178 @@
+#!/usr/bin/env php
+<?php
+/**
+ * Rewrite README.md into WordPress's readme.txt
+ *
+ * @codeCoverageIgnore
+ * @package AMP
+ */
+
+if ( 'cli' !== php_sapi_name() ) {
+	fwrite( STDERR, "Must run from CLI.\n" );
+	exit( __LINE__ );
+}
+
+$readme_md = file_get_contents( __DIR__ . '/../README.md' );
+
+$readme_txt = $readme_md;
+
+// Transform the sections above the description.
+$readme_txt = preg_replace_callback(
+	'/^.+?(?=## Description)/s',
+	static function ( $matches ) {
+		// Delete lines with images.
+		$input = trim( preg_replace( '/\[?!\[.+/', '', $matches[0] ) );
+
+		$parts = preg_split( '/\n\n+/', $input );
+
+		if ( 3 !== count( $parts ) ) {
+			fwrite( STDERR, "Too many sections in header found.\n" );
+			exit( __LINE__ );
+		}
+
+		// Replace verbose name on GitHub with short name for plugin directory.
+		$header = '# AMP';
+
+		$description = $parts[1];
+		if ( strlen( $description ) > 150 ) {
+			fwrite( STDERR, "The short description is too long: $description\n" );
+			exit( __LINE__ );
+		}
+
+		$metadata = [];
+		foreach ( explode( "\n", $parts[2] ) as $meta ) {
+			$meta = trim( $meta );
+			if ( ! preg_match( '/^\*\*(?P<key>.+?):\*\* (?P<value>.+)/', $meta, $matches ) ) {
+				fwrite( STDERR, "Parse error for meta line: $meta.\n" );
+				exit( __LINE__ );
+			}
+
+			$unlinked_value = preg_replace( '/\[(.+?)]\(.+?\)/', '$1', $matches['value'] );
+
+			$metadata[ $matches['key'] ] = $unlinked_value;
+
+			// Extract License URI from link.
+			if ( 'License' === $matches['key'] ) {
+				$license_uri = preg_replace( '/\[.+?]\((.+?)\)/', '$1', $matches['value'] );
+
+				if ( 0 !== strpos( $license_uri, 'http' ) ) {
+					fwrite( STDERR, "Unable to extract License URI from: $meta.\n" );
+					exit( __LINE__ );
+				}
+
+				$metadata['License URI'] = $license_uri;
+			}
+		}
+
+		$expected_metadata = [
+			'Contributors',
+			'Tags',
+			'Requires at least',
+			'Tested up to',
+			'Stable tag',
+			'License',
+			'License URI',
+			'Requires PHP',
+		];
+		foreach ( $expected_metadata as $key ) {
+			if ( empty( $metadata[ $key ] ) ) {
+				fwrite( STDERR, "Failed to parse metadata. Missing: $key\n" );
+				exit( __LINE__ );
+			}
+		}
+
+		$replaced = "$header\n";
+		foreach ( $metadata as $key => $value ) {
+			$replaced .= "$key: $value\n";
+		}
+		$replaced .= "\n$description\n\n";
+
+		return $replaced;
+	},
+	$readme_txt
+);
+
+// Replace image-linked YouTube videos with bare URLs.
+$readme_txt = preg_replace(
+	'#\[!\[.+?]\(.+?\)]\((https://www\.youtube\.com/.+?)\)#',
+	'$1',
+	$readme_txt
+);
+
+// Fix up the screenshots.
+$screenshots_captioned = 0;
+$readme_txt            = preg_replace_callback(
+	'/(?<=## Screenshots\n\n)(.+?)(?=## Changelog)/s',
+	static function ( $matches ) use ( &$screenshots_captioned ) {
+		if ( ! preg_match_all( '/### (.+)/', $matches[0], $screenshot_matches ) ) {
+			fwrite( STDERR, "Unable to parse screenshot headings.\n" );
+			exit( __LINE__ );
+		}
+
+		$screenshot_txt = '';
+		foreach ( $screenshot_matches[1] as $i => $screenshot_caption ) {
+			$screenshot_txt .= sprintf( "%d. %s\n", $i + 1, $screenshot_caption );
+			$screenshots_captioned++;
+		}
+		$screenshot_txt .= "\n";
+
+		return $screenshot_txt;
+	},
+	$readme_txt,
+	1,
+	$replace_count
+);
+if ( 0 === $replace_count ) {
+	fwrite( STDERR, "Unable to transform screenshots.\n" );
+	exit( __LINE__ );
+}
+
+$screenshot_files = glob( __DIR__ . '/../.wordpress-org/screenshot-*' );
+if ( count( $screenshot_files ) !== $screenshots_captioned ) {
+	fwrite( STDERR, "Number of screenshot files does not match number of screenshot captions.\n" );
+	exit( __LINE__ );
+}
+foreach ( $screenshot_files as $i => $screenshot_file ) {
+	if ( 0 !== strpos( basename( $screenshot_file ), sprintf( 'screenshot-%d.', $i + 1 ) ) ) {
+		fwrite( STDERR, "Screenshot filename is not sequential: $screenshot_file.\n" );
+		exit( __LINE__ );
+	}
+}
+
+// Convert markdown headings into WP readme headings for good measure.
+$readme_txt = preg_replace_callback(
+	'/^(#+)\s(.+)/m',
+	static function ( $matches ) {
+		$md_heading_level = strlen( $matches[1] );
+		$heading_text     = $matches[2];
+
+		// #: ===
+		// ##: ==
+		// ###: =
+		$txt_heading_level = 4 - $md_heading_level;
+		if ( $txt_heading_level <= 0 ) {
+			fwrite( STDERR, "Heading too small to transform: {$matches[0]}.\n" );
+			exit( __LINE__ );
+		}
+
+		return sprintf(
+			'%1$s %2$s %1$s',
+			str_repeat( '=', $txt_heading_level ),
+			$heading_text
+		);
+	},
+	$readme_txt,
+	-1,
+	$replace_count
+);
+if ( 0 === $replace_count ) {
+	fwrite( STDERR, "Unable to transform headings.\n" );
+	exit( __LINE__ );
+}
+
+if ( ! file_put_contents( __DIR__ . '/../readme.txt', $readme_txt ) ) {
+	fwrite( STDERR, "Failed to write readme.txt.\n" );
+	exit( __LINE__ );
+}
+
+fwrite( STDOUT, "Validated README.md and generated readme.txt\n" );
diff --git a/bin/verify-version-consistency.php b/bin/verify-version-consistency.php
index 635358ecf03..0b9a0dc0bad 100755
--- a/bin/verify-version-consistency.php
+++ b/bin/verify-version-consistency.php
@@ -15,7 +15,7 @@
 $versions = [];
 
 $readme_md = file_get_contents( dirname( __FILE__ ) . '/../README.md' );
-if ( ! preg_match( '/Stable tag:\s+(?P<version>\S+)/i', $readme_md, $matches ) ) {
+if ( ! preg_match( '/\*\*Stable tag:\*\*\s+(?P<version>\S+)/i', $readme_md, $matches ) ) {
 	echo "Could not find stable tag in readme\n";
 	exit( 1 );
 }