diff --git a/bin/commander.js b/bin/commander.js
index 6aee722ae206c..0d6ef931f4767 100755
--- a/bin/commander.js
+++ b/bin/commander.js
@@ -9,6 +9,8 @@ const inquirer = require( 'inquirer' );
 const semver = require( 'semver' );
 const chalk = require( 'chalk' );
 const fs = require( 'fs' );
+const glob = require( 'fast-glob' );
+const readline = require( 'readline' );
 const rimraf = require( 'rimraf' );
 const SimpleGit = require( 'simple-git/promise' );
 const childProcess = require( 'child_process' );
@@ -427,7 +429,7 @@ async function runBumpPluginVersionAndCommitStep( version, changelog, abortMessa
 		] );
 		const commitData = await simpleGit.commit( 'Bump plugin version to ' + version );
 		commitHash = commitData.commit;
-		console.log( '>> The plugin version bump has been commited successfully.' );
+		console.log( '>> The plugin version bump has been committed successfully.' );
 	} );
 
 	return commitHash;
@@ -729,12 +731,114 @@ async function runWordPressReleaseBranchSyncStep( abortMessage ) {
 	};
 }
 
+/**
+ * Update CHANGELOG files with the new version number for those packages that
+ * contain new entries.
+ *
+ * @param {string} minimumVersionBump Minimum version bump for the packages.
+ * @param {string} abortMessage       Abort Message.
+ */
+async function updatePackageChangelogs( minimumVersionBump, abortMessage ) {
+	const changelogFiles = await glob( path.resolve( gitWorkingDirectoryPath, 'packages/*/CHANGELOG.md' ) );
+	const processedPackages = await Promise.all( changelogFiles.map( async ( changelogFile ) => {
+		const fileStream = fs.createReadStream( changelogFile );
+
+		const lines = readline.createInterface( {
+			input: fileStream,
+		} );
+
+		let changesDetected = false;
+		let versionBump = null;
+		for await ( const line of lines ) {
+			// Detect unpublished changes first.
+			if ( line.startsWith( '## Master' ) ) {
+				changesDetected = true;
+				continue;
+			}
+
+			// Skip all lines until unpublished changes found.
+			if ( ! changesDetected ) {
+				continue;
+			}
+
+			// A previous published version detected. Stop processing.
+			if ( line.startsWith( '## ' ) ) {
+				break;
+			}
+
+			// A major version bump required. Stop processing.
+			if ( line.startsWith( '### Breaking Change' ) ) {
+				versionBump = 'major';
+				break;
+			}
+
+			// A minor version bump required. Proceed to the next line.
+			if ( line.startsWith( '### New Feature' ) || line.startsWith( '### Deprecation' ) ) {
+				versionBump = 'minor';
+				continue;
+			}
+
+			// A version bump required. Found new changelog section.
+			if ( versionBump !== 'minor' && line.startsWith( '### ' ) ) {
+				versionBump = minimumVersionBump;
+			}
+		}
+		const packageName = `@wordpress/${ changelogFile.split( '/' ).reverse()[ 1 ] }`;
+		const { version } = readJSONFile( changelogFile.replace( 'CHANGELOG.md', 'package.json' ) );
+		const nextVersion = ( versionBump !== null ) ?
+			semver.inc( version, versionBump ) :
+			null;
+
+		return {
+			changelogFile,
+			packageName,
+			version,
+			nextVersion,
+		};
+	} ) );
+
+	const changelogsToUpdate = processedPackages.
+		filter( ( { nextVersion } ) => nextVersion );
+
+	if ( changelogsToUpdate.length === 0 ) {
+		console.log( '>> No changes in CHANGELOG files detected.' );
+		return;
+	}
+
+	console.log( '>> Recommended version bumps based on the changes detected in CHANGELOG files:' );
+
+	const publishDate = new Date().toISOString().split( 'T' )[ 0 ];
+	await Promise.all(
+		changelogsToUpdate
+			.map( async ( { changelogFile, packageName, nextVersion, version } ) => {
+				const content = await fs.promises.readFile( changelogFile, 'utf8' );
+				await fs.promises.writeFile( changelogFile, content.replace(
+					'## Master',
+					`## Master\n\n## ${ nextVersion } (${ publishDate })`
+				) );
+				console.log( `   - ${ packageName }: ${ version } -> ${ nextVersion }` );
+			} )
+	);
+
+	await askForConfirmationToContinue(
+		`All corresponding files were updated. Commit the changes?`,
+		true,
+		abortMessage
+	);
+	const simpleGit = SimpleGit( gitWorkingDirectoryPath );
+	await simpleGit.add( './*' );
+	await simpleGit.commit( 'Update changelog files' );
+	console.log( '>> Changelog files changes have been committed successfully.' );
+}
+
 /**
  * Prepublish to npm steps for WordPress packages.
  *
+ * @param {string} minimumVersionBump Minimum version bump for the packages.
+ *
  * @return {Object} Github release object.
  */
-async function prepublishPackages() {
+async function prepublishPackages( minimumVersionBump ) {
 	// This is a variable that contains the abort message shown when the script is aborted.
 	let abortMessage = 'Aborting!';
 	await askForConfirmationToContinue( 'Ready to go? ' );
@@ -745,6 +849,8 @@ async function prepublishPackages() {
 	// Checking out the WordPress release branch and doing sync with the last plugin release.
 	const { releaseBranch } = await runWordPressReleaseBranchSyncStep( abortMessage );
 
+	await updatePackageChangelogs( minimumVersionBump, abortMessage );
+
 	// Push the local changes
 	abortMessage = `Aborting! Make sure to push changes applied to WordPress release branch "${ releaseBranch }" manually.`;
 	await runPushGitChangesStep( releaseBranch, abortMessage );
@@ -756,15 +862,15 @@ async function prepublishPackages() {
 program
 	.command( 'prepublish-packages-stable' )
 	.alias( 'npm-stable' )
-	.description( 'Prepublish to npm steps for a stable version of WordPress packages' )
+	.description( 'Prepublish to npm steps for the next stable version of WordPress packages' )
 	.action( async () => {
 		console.log(
 			chalk.bold( '💃 Time to publish WordPress packages to npm 🕺\n\n' ),
-			'Welcome! This tool is going to help you with prepublish to npm steps for a new stable version of WordPress packages.\n',
+			'Welcome! This tool is going to help you with prepublish to npm steps for the next stable version of WordPress packages.\n',
 			'To perform a release you\'ll have to be a member of the WordPress Team on npm.\n'
 		);
 
-		await prepublishPackages();
+		await prepublishPackages( 'minor' );
 
 		console.log(
 			'\n>> 🎉 WordPress packages are ready to publish.\n',
diff --git a/docs/contributors/release.md b/docs/contributors/release.md
index 09c812df8f3ec..4b91573ee602e 100644
--- a/docs/contributors/release.md
+++ b/docs/contributors/release.md
@@ -209,7 +209,7 @@ The Gutenberg repository mirrors the [WordPress SVN repository](https://make.wor
 
 ### Synchronizing WordPress Trunk
 
-For each Gutenberg plugin release, WordPress trunk should be synchronized with this release. This involves the following steps:
+For each Gutenberg plugin release, WordPress trunk should be synchronized with this release. This involves the following steps that are automated with `./bin/commander npm-stable` command:
 
 **Note:** The WordPress `trunk` branch can be closed or in "feature-freeze" mode. Usually, this happens between the first `beta` and the first `RC` of the WordPress release cycle. During this period, the Gutenberg plugin releases should not be synchronized with WordPress Core.
 
@@ -219,12 +219,13 @@ For each Gutenberg plugin release, WordPress trunk should be synchronized with t
 3. Remove all files from the current branch: `git rm -r .`.
 4. Check out all the files from the release branch: `git checkout release/x.x -- .`.
 5. Commit all changes to the `wp/trunk` branch with `git commit -m "Merge changes published in the Gutenberg plugin vX.X release"` and push to the repository.
+6. Update the `CHANGELOG.md` files of the packages with the new publish version calculated and commit to the `wp/trunk` branch.
+Aassuming the package versions are written using this format `major.minor.patch`, make sure to bump at least the `minor` version number. For example, if the CHANGELOG of the package to be released indicates that the next unreleased version is `5.6.1`, choose `5.7.0` as a version in case of `minor` version.
 
 Now, the branch is ready to be used to publish the npm packages.
 
-1. Run the [package release process] but when asked for the version numbers to choose for each package, (assuming the package versions are written using this format `major.minor.patch`) make sure to bump at least the `minor` version number. For example, if the CHANGELOG of the package to be released indicates that the next unreleased version is `5.6.1`, choose `5.7.0` as a version.
-2. Update the `CHANGELOG.md` files of the published packages with the new released versions and commit to the `wp/trunk` branch.
-3. Cherry-pick the "Publish" (created by Lerna) and the CHANGELOG update commits into the `master` branch of Gutenberg.
+1. Run the [package release process] but when asked for the version numbers to choose for each package pick values based on the updated CHANGELOG files.
+2. Cherry-pick the "Publish" (created by Lerna) and the CHANGELOG update commits into the `master` branch of Gutenberg.
 
 Now, the npm packages should be ready and a patch can be created and committed into WordPress `trunk`.
 
@@ -254,7 +255,7 @@ Now, the branch is ready to be used to publish the npm packages.
 Now, the npm packages should be ready and a patch can be created and committed into the corresponding WordPress SVN branch.
 
 
-### Standalone Package Releases 
+### Standalone Package Releases
 
 The following workflow is needed when packages require bug fixes or security releases to be published to _npm_ outside of a WordPress release cycle.
 
@@ -276,7 +277,7 @@ Before porting commits check that the `wp/trunk` branch does not have any outsta
 
 Now _cherry-pick_ the commits from `master` to `wp/trunk`, use `-m 1 commithash` if the commit was a pull request merge commit:
 1. `git cherry-pick -m 1 cb150a2`
-2. `git push` 
+2. `git push`
 
 Whilst waiting for the Travis CI build for  `wp/trunk` [branch to pass](https://travis-ci.com/WordPress/gutenberg/branches) identify and begin updating the `CHANGELOG.md` files:
 1. `git checkout wp/trunk`
@@ -317,23 +318,23 @@ Now that the changes have been committed to the `wp/trunk` branch and the Travis
 > @wordpress/scripts
 > lerna success found 3 packages ready to publish
 > ```
-2. Run the [package release process](https://github.com/WordPress/gutenberg/blob/master/packages/README.md#releasing-packages) but when asked for the version numbers to choose for each package use the versions you made note of above when updating each packages `CHANGELOG.md` file.
+2. Run the [package release process] but when asked for the version numbers to choose for each package use the versions you made note of above when updating each packages `CHANGELOG.md` file.
 > Truncated example of publishing process output
 > ```
 > npm run publish:prod
-> 
+>
 > Build Progress: [==============================] 100%
 > lerna notice cli v3.18.2
 > lerna info versioning independent
 > ? Select a new version for @wordpress/e2e-tests (currently 1.9.0) Patch (1.9.1)
 > ? Select a new version for @wordpress/jest-preset-default (currently 5.3.0) Patch (5.3.1)
 > ? Select a new version for @wordpress/scripts (currently 6.1.0) Patch (6.1.1)
-> 
+>
 > Changes:
 >  - @wordpress/e2e-tests: 1.9.0 => 1.9.1
 >  - @wordpress/jest-preset-default: 5.3.0 => 5.3.1
 >  - @wordpress/scripts: 6.1.0 => 6.1.1
-> 
+>
 > ? Are you sure you want to publish these packages? Yes
 > lerna info execute Skipping releases
 > lerna info git Pushing tags...
@@ -359,21 +360,21 @@ Now that the packages have been published the _"chore(release): publish"_ and _"
 5. Get the commit hash from the the lerna publish commit either from the terminal or [wp/trunk commits](https://github.com/WordPress/gutenberg/commits/wp/trunk)
 6. Cherry-pick the `fe6ae0d` "chore(release): publish"_ commit made to `wp/trunk`
 7. `git cherry-pick fe6ae0d`
-8. `git push` 
+8. `git push`
 
 Confirm the packages dependancies do not contain `file://` links in the `dependencies` or `devdependencies` section of the packages released, e.g:
 > https://unpkg.com/browse/@wordpress/jest-preset-default@5.3.1/package.json
 > https://unpkg.com/browse/@wordpress/scripts@6.1.1/package.json
 > https://unpkg.com/browse/@wordpress/jest-preset-default@5.3.1/package.json
 
-Time to announce the published changes in the #core-js and #core-editor Slack channels 
+Time to announce the published changes in the #core-js and #core-editor Slack channels
 > ```
 > 📣 Successfully published:
 > • @wordpress/e2e-tests@1.9.1
 > • @wordpress/jest-preset-default@5.3.1
 > • @wordpress/scripts@6.1.1
 > Lerna success published 3 packages
-```
+> ```
 
 ---------