From 3eed65b68eba1c52c3211fbf2e38fb6af33ff8e5 Mon Sep 17 00:00:00 2001
From: Dave Smith <getdavemail@gmail.com>
Date: Tue, 6 Jul 2021 13:29:57 +0100
Subject: [PATCH 01/14] Initial pass at grouping by feature

---
 bin/plugin/commands/changelog.js      | 57 +++++++++++++++++++++++++++
 bin/plugin/commands/test/changelog.js | 41 +++++++++++++++++++
 2 files changed, 98 insertions(+)

diff --git a/bin/plugin/commands/changelog.js b/bin/plugin/commands/changelog.js
index 9384bc6540f43..418adf6a22c72 100644
--- a/bin/plugin/commands/changelog.js
+++ b/bin/plugin/commands/changelog.js
@@ -92,6 +92,21 @@ const LABEL_TYPE_MAPPING = {
 	'[Type] Security': 'Security',
 };
 
+const LABEL_FEATURE_MAPPING = {
+	'[Package] Block editor': 'Block Editor',
+	'[Package] Editor': 'Editor',
+	'[Package] Edit Widgets': 'Widgets',
+	'[Package] Widgets Customizer': 'Widgets',
+	'[Feature] Widgets Screen': 'Widgets',
+	'[Block] Legacy Widget': 'Widgets',
+	'[Package] Components': 'Components',
+	'[Feature] UI Components': 'Components',
+	'[Feature] Component System': 'Components',
+	'[Package] Block Library': 'Block Library',
+	'[Feature] Blocks': 'Block Library',
+	'New Block': 'Block Library',
+};
+
 /**
  * Order in which to print group titles. A value of `undefined` is used as slot
  * in which unrecognized headings are to be inserted.
@@ -152,6 +167,24 @@ function getTypesByLabels( labels ) {
 	);
 }
 
+function getIssuesByFeature( labels ) {
+	return uniq(
+		labels
+			.filter( ( label ) =>
+				Object.keys( LABEL_FEATURE_MAPPING ).includes( label )
+			)
+			.map( ( label ) => LABEL_FEATURE_MAPPING[ label ] )
+	);
+}
+
+function getBlockSpecificIssues( labels ) {
+	return uniq(
+		labels
+			.filter( ( label ) => label.startsWith( '[Block] ' ) )
+			.map( () => 'Block Library' )
+	);
+}
+
 /**
  * Returns type candidates based on given issue title.
  *
@@ -180,6 +213,7 @@ function getTypesByTitle( title ) {
  */
 function getIssueType( issue ) {
 	const labels = issue.labels.map( ( { name } ) => name );
+
 	const candidates = [
 		...getTypesByLabels( labels ),
 		...getTypesByTitle( issue.title ),
@@ -188,6 +222,17 @@ function getIssueType( issue ) {
 	return candidates.length ? candidates.sort( sortType )[ 0 ] : 'Various';
 }
 
+function getIssueFeature( issue ) {
+	const labels = issue.labels.map( ( { name } ) => name );
+
+	const candidates = [
+		...getIssuesByFeature( labels ),
+		...getBlockSpecificIssues( labels ),
+	];
+
+	return candidates.length ? candidates.sort( sortType )[ 0 ] : 'Unknown';
+}
+
 /**
  * Sort comparator, comparing two label candidates.
  *
@@ -485,6 +530,7 @@ async function getChangelog( settings ) {
 	let changelog = '';
 
 	const groupedPullRequests = groupBy( pullRequests, getIssueType );
+
 	const sortedGroups = Object.keys( groupedPullRequests ).sort( sortGroup );
 	for ( const group of sortedGroups ) {
 		const groupPullRequests = groupedPullRequests[ group ];
@@ -495,6 +541,16 @@ async function getChangelog( settings ) {
 		if ( ! groupEntries.length ) {
 			continue;
 		}
+		// console.log( groupPullRequests );
+		console.log(
+			groupBy(
+				groupPullRequests.map( ( item ) => ( {
+					title: item.title,
+					labels: item.labels,
+				} ) ),
+				getIssueFeature
+			)
+		);
 
 		changelog += '### ' + group + '\n\n';
 		groupEntries.forEach( ( entry ) => ( changelog += entry + '\n' ) );
@@ -562,6 +618,7 @@ async function getReleaseChangelog( options ) {
 	getNormalizedTitle,
 	getReleaseChangelog,
 	getIssueType,
+	getIssueFeature,
 	sortGroup,
 	getTypesByLabels,
 	getTypesByTitle,
diff --git a/bin/plugin/commands/test/changelog.js b/bin/plugin/commands/test/changelog.js
index bdde2e92926c9..1e0aceaaae1dc 100644
--- a/bin/plugin/commands/test/changelog.js
+++ b/bin/plugin/commands/test/changelog.js
@@ -12,6 +12,7 @@ import {
 	sortGroup,
 	getTypesByLabels,
 	getTypesByTitle,
+	getIssueFeature,
 } from '../changelog';
 
 describe( 'getNormalizedTitle', () => {
@@ -172,6 +173,46 @@ describe( 'getIssueType', () => {
 	} );
 } );
 
+describe( 'getIssueFeature', () => {
+	it( 'returns "Unknown" if unable to find appropriate feature by label', () => {
+		const result = getIssueFeature( { labels: [] } );
+
+		expect( result ).toBe( 'Unknown' );
+	} );
+
+	it( 'returns "Block Library" for all PRs that have a block specific label', () => {
+		const result = getIssueFeature( {
+			labels: [
+				{
+					name: '[Block] Some Block',
+				},
+			],
+		} );
+
+		expect( result ).toEqual( 'Block Library' );
+	} );
+
+	it.each( [
+		{
+			labels: [
+				{
+					name: '[Package] Edit Widgets',
+				},
+			],
+			feature: 'Widgets',
+		},
+	] )(
+		'returns appropriate feature for all PRs that have a specific label',
+		( testData ) => {
+			const result = getIssueFeature( {
+				labels: testData.labels,
+			} );
+
+			expect( result ).toEqual( testData.feature );
+		}
+	);
+} );
+
 describe( 'sortGroup', () => {
 	it( 'returns groups in order', () => {
 		const result = [

From 75539a9627361a86ed65ea72ce864f212464e3ce Mon Sep 17 00:00:00 2001
From: Dave Smith <getdavemail@gmail.com>
Date: Tue, 6 Jul 2021 16:59:02 +0100
Subject: [PATCH 02/14] Basic sort by feature implementation

---
 bin/plugin/commands/changelog.js      | 70 +++++++++++++++++----------
 bin/plugin/commands/test/changelog.js | 63 ++++++++++++++++--------
 2 files changed, 87 insertions(+), 46 deletions(-)

diff --git a/bin/plugin/commands/changelog.js b/bin/plugin/commands/changelog.js
index 418adf6a22c72..d713a0d555e29 100644
--- a/bin/plugin/commands/changelog.js
+++ b/bin/plugin/commands/changelog.js
@@ -1,7 +1,7 @@
 /**
  * External dependencies
  */
-const { groupBy, escapeRegExp, uniq } = require( 'lodash' );
+const { countBy, groupBy, escapeRegExp, uniq } = require( 'lodash' );
 const Octokit = require( '@octokit/rest' );
 const { sprintf } = require( 'sprintf-js' );
 const semver = require( 'semver' );
@@ -93,7 +93,7 @@ const LABEL_TYPE_MAPPING = {
 };
 
 const LABEL_FEATURE_MAPPING = {
-	'[Package] Block editor': 'Block Editor',
+	'[Package] Block Editor': 'Block Editor',
 	'[Package] Editor': 'Editor',
 	'[Package] Edit Widgets': 'Widgets',
 	'[Package] Widgets Customizer': 'Widgets',
@@ -167,17 +167,15 @@ function getTypesByLabels( labels ) {
 	);
 }
 
-function getIssuesByFeature( labels ) {
-	return uniq(
-		labels
-			.filter( ( label ) =>
-				Object.keys( LABEL_FEATURE_MAPPING ).includes( label )
-			)
-			.map( ( label ) => LABEL_FEATURE_MAPPING[ label ] )
-	);
+function getIssueFeatures( labels ) {
+	return labels
+		.filter( ( label ) =>
+			Object.keys( LABEL_FEATURE_MAPPING ).includes( label )
+		)
+		.map( ( label ) => LABEL_FEATURE_MAPPING[ label ] );
 }
 
-function getBlockSpecificIssues( labels ) {
+function getIsBlockSpecificIssue( labels ) {
 	return uniq(
 		labels
 			.filter( ( label ) => label.startsWith( '[Block] ' ) )
@@ -225,12 +223,31 @@ function getIssueType( issue ) {
 function getIssueFeature( issue ) {
 	const labels = issue.labels.map( ( { name } ) => name );
 
+	const blockSpecificLabels = getIsBlockSpecificIssue( labels );
+
+	if ( blockSpecificLabels.length ) {
+		return blockSpecificLabels[ 0 ];
+	}
+
 	const candidates = [
-		...getIssuesByFeature( labels ),
-		...getBlockSpecificIssues( labels ),
+		...blockSpecificLabels,
+		...getIssueFeatures( labels ),
 	];
 
-	return candidates.length ? candidates.sort( sortType )[ 0 ] : 'Unknown';
+	if ( ! candidates.length ) {
+		return 'Unknown';
+	}
+
+	// Get occurances of the feature labels.
+	const featureCounts = countBy( candidates );
+
+	// Check which matching label occurs most often.
+	const rankedFeatures = Object.keys( featureCounts ).sort(
+		( a, b ) => featureCounts[ b ] - featureCounts[ a ]
+	);
+
+	// Return the one that appeared most often.
+	return rankedFeatures[ 0 ];
 }
 
 /**
@@ -541,19 +558,22 @@ async function getChangelog( settings ) {
 		if ( ! groupEntries.length ) {
 			continue;
 		}
-		// console.log( groupPullRequests );
-		console.log(
-			groupBy(
-				groupPullRequests.map( ( item ) => ( {
-					title: item.title,
-					labels: item.labels,
-				} ) ),
-				getIssueFeature
-			)
-		);
+
+		const featureGroups = groupBy( groupPullRequests, getIssueFeature );
 
 		changelog += '### ' + group + '\n\n';
-		groupEntries.forEach( ( entry ) => ( changelog += entry + '\n' ) );
+
+		Object.keys( featureGroups ).forEach( ( feature ) => {
+			const featureGroup = featureGroups[ feature ];
+			changelog += '- ' + feature + '\n';
+			const featureGroupEntries = featureGroup
+				.map( getEntry )
+				.filter( Boolean );
+			featureGroupEntries.forEach(
+				( entry ) => ( changelog += `  ${ entry }\n` )
+			);
+			changelog += '\n';
+		} );
 		changelog += '\n';
 	}
 
diff --git a/bin/plugin/commands/test/changelog.js b/bin/plugin/commands/test/changelog.js
index 1e0aceaaae1dc..b2f145c492b53 100644
--- a/bin/plugin/commands/test/changelog.js
+++ b/bin/plugin/commands/test/changelog.js
@@ -174,43 +174,64 @@ describe( 'getIssueType', () => {
 } );
 
 describe( 'getIssueFeature', () => {
-	it( 'returns "Unknown" if unable to find appropriate feature by label', () => {
+	it( 'returns "Unknown" as feature if unable to find appropriate feature by label', () => {
 		const result = getIssueFeature( { labels: [] } );
 
 		expect( result ).toBe( 'Unknown' );
 	} );
 
-	it( 'returns "Block Library" for all PRs that have a block specific label', () => {
+	it( 'returns "Block Library" as feature for all PRs that have a block specific label', () => {
+		const widgetFavouringLabels = [
+			{
+				name: '[Block] Some Block',
+			},
+			{
+				name: '[Package] Edit Widgets',
+			},
+			{
+				name: '[Feature] Widgets Screen',
+			},
+			{
+				name: '[Package] Widgets Customizer',
+			},
+		];
+
 		const result = getIssueFeature( {
-			labels: [
-				{
-					name: '[Block] Some Block',
-				},
-			],
+			labels: widgetFavouringLabels,
 		} );
 
 		expect( result ).toEqual( 'Block Library' );
 	} );
 
-	it.each( [
-		{
+	it( 'returns a single best match feature for a given issue', () => {
+		const result = getIssueFeature( {
 			labels: [
+				{
+					name: '[Package] Components',
+				},
 				{
 					name: '[Package] Edit Widgets',
 				},
+				{
+					name: '[Package] Block Editor',
+				},
+				{
+					name: '[Package] Editor',
+				},
+				{
+					name: '[Feature] UI Components',
+				},
+				{
+					name: '[Feature] Component System',
+				},
+				{
+					name: '[Package] Block Library', // 2. mapped to "Block Library"
+				},
 			],
-			feature: 'Widgets',
-		},
-	] )(
-		'returns appropriate feature for all PRs that have a specific label',
-		( testData ) => {
-			const result = getIssueFeature( {
-				labels: testData.labels,
-			} );
-
-			expect( result ).toEqual( testData.feature );
-		}
-	);
+		} );
+
+		expect( result ).toEqual( 'Components' );
+	} );
 } );
 
 describe( 'sortGroup', () => {

From 4ae6a6edb566f9b10310bd8e6b2985b336e23421 Mon Sep 17 00:00:00 2001
From: Dave Smith <getdavemail@gmail.com>
Date: Tue, 6 Jul 2021 17:15:35 +0100
Subject: [PATCH 03/14] Prefer Group by feature label if present

---
 bin/plugin/commands/changelog.js      | 10 ++++++++++
 bin/plugin/commands/test/changelog.js | 21 +++++++++++++++++++++
 2 files changed, 31 insertions(+)

diff --git a/bin/plugin/commands/changelog.js b/bin/plugin/commands/changelog.js
index d713a0d555e29..c612158f34587 100644
--- a/bin/plugin/commands/changelog.js
+++ b/bin/plugin/commands/changelog.js
@@ -183,6 +183,10 @@ function getIsBlockSpecificIssue( labels ) {
 	);
 }
 
+function getFeatureSpecificLabel( labels ) {
+	return labels.find( ( label ) => label.startsWith( '[Feature] ' ) );
+}
+
 /**
  * Returns type candidates based on given issue title.
  *
@@ -223,6 +227,12 @@ function getIssueType( issue ) {
 function getIssueFeature( issue ) {
 	const labels = issue.labels.map( ( { name } ) => name );
 
+	const featureSpecificLabel = getFeatureSpecificLabel( labels );
+
+	if ( featureSpecificLabel ) {
+		return featureSpecificLabel.replace( '[Feature] ', '' );
+	}
+
 	const blockSpecificLabels = getIsBlockSpecificIssue( labels );
 
 	if ( blockSpecificLabels.length ) {
diff --git a/bin/plugin/commands/test/changelog.js b/bin/plugin/commands/test/changelog.js
index b2f145c492b53..41c52ab7fe68b 100644
--- a/bin/plugin/commands/test/changelog.js
+++ b/bin/plugin/commands/test/changelog.js
@@ -180,6 +180,27 @@ describe( 'getIssueFeature', () => {
 		expect( result ).toBe( 'Unknown' );
 	} );
 
+	it( 'returns the feature label for any PRs marked with a specific feature label', () => {
+		const result = getIssueFeature( {
+			labels: [
+				{
+					name: '[Block] Some Block',
+				},
+				{
+					name: '[Package] Edit Widgets',
+				},
+				{
+					name: '[Feature] Widgets Screen',
+				},
+				{
+					name: '[Package] Widgets Customizer',
+				},
+			],
+		} );
+
+		expect( result ).toEqual( 'Widgets Screen' );
+	} );
+
 	it( 'returns "Block Library" as feature for all PRs that have a block specific label', () => {
 		const widgetFavouringLabels = [
 			{

From b3addc0042e60633b84f5fda21e5c298bb5aa87e Mon Sep 17 00:00:00 2001
From: Dave Smith <getdavemail@gmail.com>
Date: Tue, 6 Jul 2021 17:27:39 +0100
Subject: [PATCH 04/14] Sort Unknown to be the last feature group

---
 bin/plugin/commands/changelog.js | 37 +++++++++++++++++++++-----------
 1 file changed, 25 insertions(+), 12 deletions(-)

diff --git a/bin/plugin/commands/changelog.js b/bin/plugin/commands/changelog.js
index c612158f34587..68a9eb991e5bf 100644
--- a/bin/plugin/commands/changelog.js
+++ b/bin/plugin/commands/changelog.js
@@ -19,6 +19,8 @@ const config = require( '../config' );
 // @ts-ignore
 const manifest = require( '../../../package.json' );
 
+const UNKNOWN = 'Unknown';
+
 /** @typedef {import('@octokit/rest')} GitHub */
 /** @typedef {import('@octokit/rest').IssuesListForRepoResponseItem} IssuesListForRepoResponseItem */
 /** @typedef {import('@octokit/rest').IssuesListMilestonesForRepoResponseItem} OktokitIssuesListMilestonesForRepoResponseItem */
@@ -245,7 +247,7 @@ function getIssueFeature( issue ) {
 	];
 
 	if ( ! candidates.length ) {
-		return 'Unknown';
+		return UNKNOWN;
 	}
 
 	// Get occurances of the feature labels.
@@ -573,17 +575,28 @@ async function getChangelog( settings ) {
 
 		changelog += '### ' + group + '\n\n';
 
-		Object.keys( featureGroups ).forEach( ( feature ) => {
-			const featureGroup = featureGroups[ feature ];
-			changelog += '- ' + feature + '\n';
-			const featureGroupEntries = featureGroup
-				.map( getEntry )
-				.filter( Boolean );
-			featureGroupEntries.forEach(
-				( entry ) => ( changelog += `  ${ entry }\n` )
-			);
-			changelog += '\n';
-		} );
+		Object.keys( featureGroups )
+			.sort() // natural sort first
+			.sort( ( a, b ) => {
+				// sort "Unknown" to always be at the end
+				if ( a === 'Unknown' ) {
+					return 1;
+				} else if ( b === 'Unknown' ) {
+					return -1;
+				}
+				return 0;
+			} )
+			.forEach( ( feature ) => {
+				const featureGroup = featureGroups[ feature ];
+				changelog += '- ' + feature + '\n';
+				const featureGroupEntries = featureGroup
+					.map( getEntry )
+					.filter( Boolean );
+				featureGroupEntries.forEach(
+					( entry ) => ( changelog += `  ${ entry }\n` )
+				);
+				changelog += '\n';
+			} );
 		changelog += '\n';
 	}
 

From 902a1302a906aea5f6583c6a0b614dd9e1df15b3 Mon Sep 17 00:00:00 2001
From: Dave Smith <getdavemail@gmail.com>
Date: Tue, 6 Jul 2021 17:31:47 +0100
Subject: [PATCH 05/14] Strip feature name from entry

---
 bin/plugin/commands/changelog.js | 12 +++++++++---
 1 file changed, 9 insertions(+), 3 deletions(-)

diff --git a/bin/plugin/commands/changelog.js b/bin/plugin/commands/changelog.js
index 68a9eb991e5bf..bcd785c86e70f 100644
--- a/bin/plugin/commands/changelog.js
+++ b/bin/plugin/commands/changelog.js
@@ -588,13 +588,19 @@ async function getChangelog( settings ) {
 			} )
 			.forEach( ( feature ) => {
 				const featureGroup = featureGroups[ feature ];
+				// Start new markdown list
 				changelog += '- ' + feature + '\n';
 				const featureGroupEntries = featureGroup
 					.map( getEntry )
 					.filter( Boolean );
-				featureGroupEntries.forEach(
-					( entry ) => ( changelog += `  ${ entry }\n` )
-				);
+				featureGroupEntries.forEach( ( entry ) => {
+					// Strip feature name from entry if present.
+					entry = entry && entry.replace( `[${ feature } - `, '[' );
+
+					// Add a new bullet point to the list.
+					changelog += `  ${ entry }\n`;
+				} );
+				// End the markdown list.
 				changelog += '\n';
 			} );
 		changelog += '\n';

From 1cbf284352a5c1bfc07d47d0b05ba0f87c519cc7 Mon Sep 17 00:00:00 2001
From: Dave Smith <getdavemail@gmail.com>
Date: Mon, 19 Jul 2021 16:03:45 +0100
Subject: [PATCH 06/14] Improve function naming and simplify

---
 bin/plugin/commands/changelog.js | 71 ++++++++++++++++++++++++--------
 1 file changed, 54 insertions(+), 17 deletions(-)

diff --git a/bin/plugin/commands/changelog.js b/bin/plugin/commands/changelog.js
index bcd785c86e70f..44f001c52f276 100644
--- a/bin/plugin/commands/changelog.js
+++ b/bin/plugin/commands/changelog.js
@@ -169,7 +169,15 @@ function getTypesByLabels( labels ) {
 	);
 }
 
-function getIssueFeatures( labels ) {
+/**
+ * Returns candidates by retrieving the appropriate mapping
+ * from the label -> feature lookup.
+ *
+ * @param {string[]} labels Label names.
+ *
+ * @return {string[]} Feature candidates.
+ */
+function mapLabelsToFeatures( labels ) {
 	return labels
 		.filter( ( label ) =>
 			Object.keys( LABEL_FEATURE_MAPPING ).includes( label )
@@ -177,15 +185,26 @@ function getIssueFeatures( labels ) {
 		.map( ( label ) => LABEL_FEATURE_MAPPING[ label ] );
 }
 
+/**
+ * Returns whether not the given labels contain the block specific
+ * label "block library".
+ *
+ * @param {string[]} labels Label names.
+ *
+ * @return {boolean} whether or not the issue's is labbeled as block specific
+ */
 function getIsBlockSpecificIssue( labels ) {
-	return uniq(
-		labels
-			.filter( ( label ) => label.startsWith( '[Block] ' ) )
-			.map( () => 'Block Library' )
-	);
+	return !! labels.find( ( label ) => label.startsWith( '[Block] ' ) );
 }
 
-function getFeatureSpecificLabel( labels ) {
+/**
+ * Returns the first feature specific label from the given labels.
+ *
+ * @param {string[]} labels Label names.
+ *
+ * @return {string|undefined} the feature specific label.
+ */
+function getFeatureSpecificLabels( labels ) {
 	return labels.find( ( label ) => label.startsWith( '[Feature] ' ) );
 }
 
@@ -226,32 +245,50 @@ function getIssueType( issue ) {
 	return candidates.length ? candidates.sort( sortType )[ 0 ] : 'Various';
 }
 
+/**
+ * Removes any `[Feature]` prefix from a given label.
+ *
+ * @param {string} label The label potentially containing a prefix.
+ *
+ * @return {string} the label without the prefix.
+ */
+function stripFeaturePrefix( label ) {
+	return label.replace( '[Feature] ', '' );
+}
+
+/**
+ * Returns the most appropriate feature category for the given issue based
+ * on a basic heuristic.
+ *
+ * @param {IssuesListForRepoResponseItem} issue Issue object.
+ *
+ * @return {string} the feature name.
+ */
 function getIssueFeature( issue ) {
 	const labels = issue.labels.map( ( { name } ) => name );
 
-	const featureSpecificLabel = getFeatureSpecificLabel( labels );
+	const featureSpecificLabel = getFeatureSpecificLabels( labels );
 
+	// If it's marked as as `[Feature]` label then use that feature name.
 	if ( featureSpecificLabel ) {
-		return featureSpecificLabel.replace( '[Feature] ', '' );
+		return stripFeaturePrefix( featureSpecificLabel );
 	}
 
 	const blockSpecificLabels = getIsBlockSpecificIssue( labels );
 
-	if ( blockSpecificLabels.length ) {
-		return blockSpecificLabels[ 0 ];
+	// If it's block specific issue then use the block specific label.
+	if ( blockSpecificLabels ) {
+		return 'Block Library';
 	}
 
-	const candidates = [
-		...blockSpecificLabels,
-		...getIssueFeatures( labels ),
-	];
+	const featureCandidates = mapLabelsToFeatures( labels );
 
-	if ( ! candidates.length ) {
+	if ( ! featureCandidates.length ) {
 		return UNKNOWN;
 	}
 
 	// Get occurances of the feature labels.
-	const featureCounts = countBy( candidates );
+	const featureCounts = countBy( featureCandidates );
 
 	// Check which matching label occurs most often.
 	const rankedFeatures = Object.keys( featureCounts ).sort(

From f5e8939355d3b792d3e91126f4ef32ebc7799258 Mon Sep 17 00:00:00 2001
From: =?UTF-8?q?H=C3=A9ctor?= <27339341+priethor@users.noreply.github.com>
Date: Thu, 8 Jul 2021 17:59:53 +0200
Subject: [PATCH 07/14] Update "Widgets" changelog mapping name to "Widgets
 Editor"

Co-authored-by: Dave Smith <getdavemail@gmail.com>
---
 bin/plugin/commands/changelog.js | 8 ++++----
 1 file changed, 4 insertions(+), 4 deletions(-)

diff --git a/bin/plugin/commands/changelog.js b/bin/plugin/commands/changelog.js
index 44f001c52f276..ff407fcdcfc52 100644
--- a/bin/plugin/commands/changelog.js
+++ b/bin/plugin/commands/changelog.js
@@ -97,10 +97,10 @@ const LABEL_TYPE_MAPPING = {
 const LABEL_FEATURE_MAPPING = {
 	'[Package] Block Editor': 'Block Editor',
 	'[Package] Editor': 'Editor',
-	'[Package] Edit Widgets': 'Widgets',
-	'[Package] Widgets Customizer': 'Widgets',
-	'[Feature] Widgets Screen': 'Widgets',
-	'[Block] Legacy Widget': 'Widgets',
+	'[Package] Edit Widgets': 'Widgets Editor',
+	'[Package] Widgets Customizer': 'Widgets Editor',
+	'[Feature] Widgets Screen': 'Widgets Editor',
+	'[Block] Legacy Widget': 'Widgets Editor',
 	'[Package] Components': 'Components',
 	'[Feature] UI Components': 'Components',
 	'[Feature] Component System': 'Components',

From 2929c67eca993c92714e9f6e1e7f77e0b892a86a Mon Sep 17 00:00:00 2001
From: Dave Smith <getdavemail@gmail.com>
Date: Mon, 19 Jul 2021 16:18:54 +0100
Subject: [PATCH 08/14] Add feature mapping as provided by Hector

See https://github.com/WordPress/gutenberg/pull/33229#pullrequestreview-701879448
---
 bin/plugin/commands/changelog.js | 29 ++++++++++++++++++++++++-----
 1 file changed, 24 insertions(+), 5 deletions(-)

diff --git a/bin/plugin/commands/changelog.js b/bin/plugin/commands/changelog.js
index ff407fcdcfc52..27147b9661e1b 100644
--- a/bin/plugin/commands/changelog.js
+++ b/bin/plugin/commands/changelog.js
@@ -94,18 +94,37 @@ const LABEL_TYPE_MAPPING = {
 	'[Type] Security': 'Security',
 };
 
+/**
+ * Mapping of label names to arbitary features in the release notes.
+ *
+ * Mapping a given label to a feature will guarantee it will be categorised
+ * under that feature name in the changelog within each section.
+ *
+ * @type {Record<string,string>}
+ */
 const LABEL_FEATURE_MAPPING = {
+	'[Feature] Widgets Screen': 'Widgets Editor',
+	'[Feature] Design Tools': 'Design Tools',
+	'[Feature] UI Components': 'Components',
+	'[Feature] Component System': 'Components',
+	'[Feature] Template Editing Mode': 'Template Editor',
+	'[Feature] Blocks': 'Block Library',
+	'[Feature] Inserter': 'Block Editor',
+	'[Feature] Drag and Drop': 'Block Editor',
+	'[Feature] Block Multi Selection': 'Block Editor',
+	'[Feature] Link Editing': 'Block Editor',
+	'[Package] Edit Post': 'Post Editor',
+	'[Package] Icons': 'Icons',
 	'[Package] Block Editor': 'Block Editor',
 	'[Package] Editor': 'Editor',
 	'[Package] Edit Widgets': 'Widgets Editor',
 	'[Package] Widgets Customizer': 'Widgets Editor',
-	'[Feature] Widgets Screen': 'Widgets Editor',
-	'[Block] Legacy Widget': 'Widgets Editor',
 	'[Package] Components': 'Components',
-	'[Feature] UI Components': 'Components',
-	'[Feature] Component System': 'Components',
 	'[Package] Block Library': 'Block Library',
-	'[Feature] Blocks': 'Block Library',
+	'[Package] Rich text': 'Block Editor',
+	'[Package] Data': 'Data Layer',
+	'[Block] Legacy Widget': 'Widgets Editor',
+	'REST API Interaction': 'REST API',
 	'New Block': 'Block Library',
 };
 

From 0f27dc39c57b5469a4f19cf591c430c52eb45e80 Mon Sep 17 00:00:00 2001
From: Dave Smith <getdavemail@gmail.com>
Date: Mon, 19 Jul 2021 16:56:23 +0100
Subject: [PATCH 09/14] Give priority to explicit label to feature mapping and
 update tests

---
 bin/plugin/commands/changelog.js      | 38 ++++++-------
 bin/plugin/commands/test/changelog.js | 78 ++++++++++++++-------------
 2 files changed, 62 insertions(+), 54 deletions(-)

diff --git a/bin/plugin/commands/changelog.js b/bin/plugin/commands/changelog.js
index 27147b9661e1b..355cc62345b92 100644
--- a/bin/plugin/commands/changelog.js
+++ b/bin/plugin/commands/changelog.js
@@ -286,36 +286,38 @@ function stripFeaturePrefix( label ) {
 function getIssueFeature( issue ) {
 	const labels = issue.labels.map( ( { name } ) => name );
 
+	const featureCandidates = mapLabelsToFeatures( labels );
+
+	// 1. Prefer explicit mapping of label to feature.
+	if ( featureCandidates.length ) {
+		// Get occurances of the feature labels.
+		const featureCounts = countBy( featureCandidates );
+
+		// Check which matching label occurs most often.
+		const rankedFeatures = Object.keys( featureCounts ).sort(
+			( a, b ) => featureCounts[ b ] - featureCounts[ a ]
+		);
+
+		// Return the one that appeared most often.
+		return rankedFeatures[ 0 ];
+	}
+
+	// 2. `[Feature]` labels
 	const featureSpecificLabel = getFeatureSpecificLabels( labels );
 
-	// If it's marked as as `[Feature]` label then use that feature name.
 	if ( featureSpecificLabel ) {
 		return stripFeaturePrefix( featureSpecificLabel );
 	}
 
+	// 3. Block specific labels.
 	const blockSpecificLabels = getIsBlockSpecificIssue( labels );
 
-	// If it's block specific issue then use the block specific label.
 	if ( blockSpecificLabels ) {
 		return 'Block Library';
 	}
 
-	const featureCandidates = mapLabelsToFeatures( labels );
-
-	if ( ! featureCandidates.length ) {
-		return UNKNOWN;
-	}
-
-	// Get occurances of the feature labels.
-	const featureCounts = countBy( featureCandidates );
-
-	// Check which matching label occurs most often.
-	const rankedFeatures = Object.keys( featureCounts ).sort(
-		( a, b ) => featureCounts[ b ] - featureCounts[ a ]
-	);
-
-	// Return the one that appeared most often.
-	return rankedFeatures[ 0 ];
+	// Fallback - if we couldn't find a good match.
+	return UNKNOWN;
 }
 
 /**
diff --git a/bin/plugin/commands/test/changelog.js b/bin/plugin/commands/test/changelog.js
index 41c52ab7fe68b..d348d90436985 100644
--- a/bin/plugin/commands/test/changelog.js
+++ b/bin/plugin/commands/test/changelog.js
@@ -174,84 +174,90 @@ describe( 'getIssueType', () => {
 } );
 
 describe( 'getIssueFeature', () => {
-	it( 'returns "Unknown" as feature if unable to find appropriate feature by label', () => {
+	it( 'returns "Unknown" as feature if there are no labels', () => {
 		const result = getIssueFeature( { labels: [] } );
 
 		expect( result ).toBe( 'Unknown' );
 	} );
 
-	it( 'returns the feature label for any PRs marked with a specific feature label', () => {
+	it( 'falls by to "Unknown" as the feature if unable to classify by other means', () => {
 		const result = getIssueFeature( {
 			labels: [
 				{
-					name: '[Block] Some Block',
-				},
-				{
-					name: '[Package] Edit Widgets',
+					name: 'Some Label',
 				},
 				{
-					name: '[Feature] Widgets Screen',
+					name: '[Package] Example Package', // 1. has explicit mapping
 				},
 				{
-					name: '[Package] Widgets Customizer',
+					name: '[Package] Another One',
 				},
 			],
 		} );
 
-		expect( result ).toEqual( 'Widgets Screen' );
+		expect( result ).toEqual( 'Unknown' );
 	} );
 
-	it( 'returns "Block Library" as feature for all PRs that have a block specific label', () => {
-		const widgetFavouringLabels = [
-			{
-				name: '[Block] Some Block',
-			},
-			{
-				name: '[Package] Edit Widgets',
-			},
-			{
-				name: '[Feature] Widgets Screen',
-			},
-			{
-				name: '[Package] Widgets Customizer',
-			},
-		];
-
+	it( 'gives precedence to manual feature mapping', () => {
 		const result = getIssueFeature( {
-			labels: widgetFavouringLabels,
+			labels: [
+				{
+					name: '[Block] Some Block', // 3. Block-specific label
+				},
+				{
+					name: '[Package] Edit Widgets', // 1. has explicit mapping
+				},
+				{
+					name: '[Feature] Some Feature', // 2. Feature label.
+				},
+				{
+					name: '[Package] Another One',
+				},
+			],
 		} );
 
-		expect( result ).toEqual( 'Block Library' );
+		const mappingForPackageEditWidgets = 'Widgets Editor';
+
+		expect( result ).toEqual( mappingForPackageEditWidgets );
 	} );
 
-	it( 'returns a single best match feature for a given issue', () => {
+	it( 'gives secondary priority to feature labels when manually mapped label is not present', () => {
 		const result = getIssueFeature( {
 			labels: [
 				{
-					name: '[Package] Components',
+					name: '[Block] Some Block', // block specific label
 				},
 				{
-					name: '[Package] Edit Widgets',
+					name: '[Package] This package',
 				},
 				{
-					name: '[Package] Block Editor',
+					name: '[Feature] Cool Feature', // should have priority despite prescence of block specific label
 				},
 				{
-					name: '[Package] Editor',
+					name: '[Package] Another One',
 				},
+			],
+		} );
+
+		expect( result ).toEqual( 'Cool Feature' );
+	} );
+
+	it( 'gives tertiary priority to "Block Library" as feature for all PRs that have a block specific label (and where manually mapped or feature label not present)', () => {
+		const result = getIssueFeature( {
+			labels: [
 				{
-					name: '[Feature] UI Components',
+					name: '[Block] Some Block',
 				},
 				{
-					name: '[Feature] Component System',
+					name: '[Package] This package',
 				},
 				{
-					name: '[Package] Block Library', // 2. mapped to "Block Library"
+					name: '[Package] Another One',
 				},
 			],
 		} );
 
-		expect( result ).toEqual( 'Components' );
+		expect( result ).toEqual( 'Block Library' );
 	} );
 } );
 

From c39c778d01d495ec28c36833276bfab9dc9e255f Mon Sep 17 00:00:00 2001
From: Dave Smith <getdavemail@gmail.com>
Date: Mon, 19 Jul 2021 17:05:36 +0100
Subject: [PATCH 10/14] Sort features within section by total number of PR
 entries

---
 bin/plugin/commands/changelog.js | 5 +++--
 1 file changed, 3 insertions(+), 2 deletions(-)

diff --git a/bin/plugin/commands/changelog.js b/bin/plugin/commands/changelog.js
index 355cc62345b92..2732602533ae4 100644
--- a/bin/plugin/commands/changelog.js
+++ b/bin/plugin/commands/changelog.js
@@ -630,11 +630,12 @@ async function getChangelog( settings ) {
 		}
 
 		const featureGroups = groupBy( groupPullRequests, getIssueFeature );
-
 		changelog += '### ' + group + '\n\n';
 
 		Object.keys( featureGroups )
-			.sort() // natural sort first
+			.sort( ( a, b ) => {
+				return featureGroups[ b ].length - featureGroups[ a ].length;
+			} )
 			.sort( ( a, b ) => {
 				// sort "Unknown" to always be at the end
 				if ( a === 'Unknown' ) {

From 9e19907d6db5427e83dfbe98e1451f2c0ad7b234 Mon Sep 17 00:00:00 2001
From: Dave Smith <getdavemail@gmail.com>
Date: Mon, 19 Jul 2021 17:14:24 +0100
Subject: [PATCH 11/14] Simplify and unify sorting mechanic

---
 bin/plugin/commands/changelog.js | 6 ++----
 1 file changed, 2 insertions(+), 4 deletions(-)

diff --git a/bin/plugin/commands/changelog.js b/bin/plugin/commands/changelog.js
index 2732602533ae4..1691a4d4bc7b0 100644
--- a/bin/plugin/commands/changelog.js
+++ b/bin/plugin/commands/changelog.js
@@ -108,6 +108,7 @@ const LABEL_FEATURE_MAPPING = {
 	'[Feature] UI Components': 'Components',
 	'[Feature] Component System': 'Components',
 	'[Feature] Template Editing Mode': 'Template Editor',
+	'[Feature] Writing Flow': 'Block Editor',
 	'[Feature] Blocks': 'Block Library',
 	'[Feature] Inserter': 'Block Editor',
 	'[Feature] Drag and Drop': 'Block Editor',
@@ -633,9 +634,6 @@ async function getChangelog( settings ) {
 		changelog += '### ' + group + '\n\n';
 
 		Object.keys( featureGroups )
-			.sort( ( a, b ) => {
-				return featureGroups[ b ].length - featureGroups[ a ].length;
-			} )
 			.sort( ( a, b ) => {
 				// sort "Unknown" to always be at the end
 				if ( a === 'Unknown' ) {
@@ -643,7 +641,7 @@ async function getChangelog( settings ) {
 				} else if ( b === 'Unknown' ) {
 					return -1;
 				}
-				return 0;
+				return featureGroups[ b ].length - featureGroups[ a ].length;
 			} )
 			.forEach( ( feature ) => {
 				const featureGroup = featureGroups[ feature ];

From b5cda0c638885040f80771cc41801f722c3b4aad Mon Sep 17 00:00:00 2001
From: Dave Smith <getdavemail@gmail.com>
Date: Tue, 20 Jul 2021 10:03:49 +0100
Subject: [PATCH 12/14] Improve code formatting and update UNKNOWN type

---
 bin/plugin/commands/changelog.js      | 92 ++++++++++++++++++---------
 bin/plugin/commands/test/changelog.js |  4 +-
 2 files changed, 65 insertions(+), 31 deletions(-)

diff --git a/bin/plugin/commands/changelog.js b/bin/plugin/commands/changelog.js
index 1691a4d4bc7b0..5d4752364a251 100644
--- a/bin/plugin/commands/changelog.js
+++ b/bin/plugin/commands/changelog.js
@@ -19,7 +19,7 @@ const config = require( '../config' );
 // @ts-ignore
 const manifest = require( '../../../package.json' );
 
-const UNKNOWN = 'Unknown';
+const UNKNOWN_FEATURE_FALLBACK_NAME = 'Uncategorized';
 
 /** @typedef {import('@octokit/rest')} GitHub */
 /** @typedef {import('@octokit/rest').IssuesListForRepoResponseItem} IssuesListForRepoResponseItem */
@@ -318,7 +318,7 @@ function getIssueFeature( issue ) {
 	}
 
 	// Fallback - if we couldn't find a good match.
-	return UNKNOWN;
+	return UNKNOWN_FEATURE_FALLBACK_NAME;
 }
 
 /**
@@ -620,6 +620,7 @@ async function getChangelog( settings ) {
 	const groupedPullRequests = groupBy( pullRequests, getIssueType );
 
 	const sortedGroups = Object.keys( groupedPullRequests ).sort( sortGroup );
+
 	for ( const group of sortedGroups ) {
 		const groupPullRequests = groupedPullRequests[ group ];
 		const groupEntries = groupPullRequests
@@ -630,42 +631,75 @@ async function getChangelog( settings ) {
 			continue;
 		}
 
-		const featureGroups = groupBy( groupPullRequests, getIssueFeature );
+		// Start a new section within the changelog.
 		changelog += '### ' + group + '\n\n';
 
-		Object.keys( featureGroups )
-			.sort( ( a, b ) => {
-				// sort "Unknown" to always be at the end
-				if ( a === 'Unknown' ) {
-					return 1;
-				} else if ( b === 'Unknown' ) {
-					return -1;
-				}
-				return featureGroups[ b ].length - featureGroups[ a ].length;
-			} )
-			.forEach( ( feature ) => {
-				const featureGroup = featureGroups[ feature ];
-				// Start new markdown list
-				changelog += '- ' + feature + '\n';
-				const featureGroupEntries = featureGroup
-					.map( getEntry )
-					.filter( Boolean );
-				featureGroupEntries.forEach( ( entry ) => {
-					// Strip feature name from entry if present.
-					entry = entry && entry.replace( `[${ feature } - `, '[' );
-
-					// Add a new bullet point to the list.
-					changelog += `  ${ entry }\n`;
-				} );
-				// End the markdown list.
-				changelog += '\n';
+		// Group PRs within this section into "Features".
+		const featureGroups = groupBy( groupPullRequests, getIssueFeature );
+
+		const featuredGroupNames = sortFeatureGroups( featureGroups );
+
+		// Start output of Features within the section.
+		featuredGroupNames.forEach( ( featureName ) => {
+			const featureGroupPRs = featureGroups[ featureName ];
+
+			const featureGroupEntries = featureGroupPRs
+				.map( getEntry )
+				.filter( Boolean );
+
+			// Don't create feature sections when there are no PRs.
+			if ( ! featureGroupEntries.length ) {
+				return;
+			}
+
+			// Start new <ul> for the Feature group.
+			changelog += '- ' + featureName + '\n';
+
+			// Add a <li> for each PR in the Feature.
+			featureGroupEntries.forEach( ( entry ) => {
+				// Strip feature name from entry if present.
+				entry = entry && entry.replace( `[${ featureName } - `, '[' );
+
+				// Add a new bullet point to the list.
+				changelog += `  ${ entry }\n`;
 			} );
+
+			// Close the <ul> for the Feature group.
+			changelog += '\n';
+		} );
+
 		changelog += '\n';
 	}
 
 	return changelog;
 }
 
+/**
+ * Sorts the feature groups by the feature which contains the greatest number of PRs
+ * ready for output into the changelog.
+ *
+ * @param {Object[]} featureGroups feature specific PRs keyed by feature name.
+ * @return {string[]} sorted list of feature names.
+ */
+function sortFeatureGroups( featureGroups ) {
+	return Object.keys( featureGroups ).sort(
+		( featureAName, featureBName ) => {
+			// Sort "Unknown" to always be at the end
+			if ( featureAName === UNKNOWN_FEATURE_FALLBACK_NAME ) {
+				return 1;
+			} else if ( featureBName === UNKNOWN_FEATURE_FALLBACK_NAME ) {
+				return -1;
+			}
+
+			// Sort by greatest number of PRs in the group first.
+			return (
+				featureGroups[ featureBName ].length -
+				featureGroups[ featureAName ].length
+			);
+		}
+	);
+}
+
 /**
  * Generates and logs changelog for a milestone.
  *
diff --git a/bin/plugin/commands/test/changelog.js b/bin/plugin/commands/test/changelog.js
index d348d90436985..773609949873b 100644
--- a/bin/plugin/commands/test/changelog.js
+++ b/bin/plugin/commands/test/changelog.js
@@ -177,7 +177,7 @@ describe( 'getIssueFeature', () => {
 	it( 'returns "Unknown" as feature if there are no labels', () => {
 		const result = getIssueFeature( { labels: [] } );
 
-		expect( result ).toBe( 'Unknown' );
+		expect( result ).toBe( 'Uncategorized' );
 	} );
 
 	it( 'falls by to "Unknown" as the feature if unable to classify by other means', () => {
@@ -195,7 +195,7 @@ describe( 'getIssueFeature', () => {
 			],
 		} );
 
-		expect( result ).toEqual( 'Unknown' );
+		expect( result ).toEqual( 'Uncategorized' );
 	} );
 
 	it( 'gives precedence to manual feature mapping', () => {

From 68abcf31d55894941c37f5ee56bbb1cf3a84d1bc Mon Sep 17 00:00:00 2001
From: Dave Smith <getdavemail@gmail.com>
Date: Tue, 20 Jul 2021 10:08:27 +0100
Subject: [PATCH 13/14] Normalize function name

---
 bin/plugin/commands/changelog.js | 24 ++++++++++++------------
 1 file changed, 12 insertions(+), 12 deletions(-)

diff --git a/bin/plugin/commands/changelog.js b/bin/plugin/commands/changelog.js
index 5d4752364a251..39021ce9ba83d 100644
--- a/bin/plugin/commands/changelog.js
+++ b/bin/plugin/commands/changelog.js
@@ -265,17 +265,6 @@ function getIssueType( issue ) {
 	return candidates.length ? candidates.sort( sortType )[ 0 ] : 'Various';
 }
 
-/**
- * Removes any `[Feature]` prefix from a given label.
- *
- * @param {string} label The label potentially containing a prefix.
- *
- * @return {string} the label without the prefix.
- */
-function stripFeaturePrefix( label ) {
-	return label.replace( '[Feature] ', '' );
-}
-
 /**
  * Returns the most appropriate feature category for the given issue based
  * on a basic heuristic.
@@ -307,7 +296,7 @@ function getIssueFeature( issue ) {
 	const featureSpecificLabel = getFeatureSpecificLabels( labels );
 
 	if ( featureSpecificLabel ) {
-		return stripFeaturePrefix( featureSpecificLabel );
+		return removeFeaturePrefix( featureSpecificLabel );
 	}
 
 	// 3. Block specific labels.
@@ -458,6 +447,17 @@ function removeRedundantTypePrefix( title, issue ) {
 	);
 }
 
+/**
+ * Removes any `[Feature] ` prefix from a given string.
+ *
+ * @param {string} text The string of text potentially containing a prefix.
+ *
+ * @return {string} the text without the prefix.
+ */
+function removeFeaturePrefix( text ) {
+	return text.replace( '[Feature] ', '' );
+}
+
 /**
  * Array of normalizations applying to title, each returning a new string, or
  * undefined to indicate an entry which should be omitted.

From 08ace56fa354577c1828d75b4825738c042f3822 Mon Sep 17 00:00:00 2001
From: Dave Smith <getdavemail@gmail.com>
Date: Tue, 20 Jul 2021 10:16:47 +0100
Subject: [PATCH 14/14] Fix typings

---
 bin/plugin/commands/changelog.js | 2 +-
 1 file changed, 1 insertion(+), 1 deletion(-)

diff --git a/bin/plugin/commands/changelog.js b/bin/plugin/commands/changelog.js
index 39021ce9ba83d..0e769daab44f1 100644
--- a/bin/plugin/commands/changelog.js
+++ b/bin/plugin/commands/changelog.js
@@ -678,7 +678,7 @@ async function getChangelog( settings ) {
  * Sorts the feature groups by the feature which contains the greatest number of PRs
  * ready for output into the changelog.
  *
- * @param {Object[]} featureGroups feature specific PRs keyed by feature name.
+ * @param {Object.<string, IssuesListForRepoResponseItem[]>} featureGroups feature specific PRs keyed by feature name.
  * @return {string[]} sorted list of feature names.
  */
 function sortFeatureGroups( featureGroups ) {