diff --git a/Gruntfile.js b/Gruntfile.js
index fba4a6153f3c0..0a9270f436847 100644
--- a/Gruntfile.js
+++ b/Gruntfile.js
@@ -12,6 +12,15 @@ module.exports = function(grunt) {
 		SOURCE_DIR = 'src/',
 		BUILD_DIR = 'build/',
 		WORKING_DIR = grunt.option( 'dev' ) ? SOURCE_DIR : BUILD_DIR,
+		/*
+		 * With --symlink, when building into /src, the wp-admin and wp-includes scripts that are copied unchanged from
+		 * /src/js/_enqueues are symlinked instead, so that edits to them take effect without a rebuild.
+		 *
+		 * This is opt-in because Docker Desktop's file sharing can keep serving the previous entry for a path whose
+		 * file is replaced, by a symlink or by a file in place of one, failing to read it until the containers are
+		 * restarted (`npm run env:restart`). For the same reason, the links in place are kept by later builds.
+		 */
+		linkScripts = WORKING_DIR === SOURCE_DIR && grunt.option( 'symlink' ) === true,
 		BANNER_TEXT = '/*! This file is auto-generated */',
 		autoprefixer = require( 'autoprefixer' ),
 		sass = require( 'sass' ),
@@ -140,8 +149,7 @@ module.exports = function(grunt) {
 			'copy',
 			'cssmin',
 			'jshint',
-			'uglify',
-			'watch'
+			'uglify'
 		],
 		'standard': [
 			'banner',
@@ -261,14 +269,28 @@ module.exports = function(grunt) {
 			css: cssFiles.map( function( file ) {
 				return setFilePath( WORKING_DIR, file );
 			} ),
-			js: jsFiles.map( function( file ) {
+			js: linkScripts ? {
+				// Clean the files in wp-admin/js one by one, so that the links in place are kept. See the link task.
+				src: jsFiles.map( function( file ) {
+					return setFilePath( WORKING_DIR, 'wp-admin/js/' === file ? 'wp-admin/js/**' : file );
+				} ),
+				filter: function( filepath ) {
+					return ! isLinkedScriptPath( filepath );
+				}
+			} : jsFiles.map( function( file ) {
 				return setFilePath( WORKING_DIR, file );
 			} ),
 
 			// Clean files built by Webpack.
-			'webpack-assets': webpackFiles.map( function( file ) {
-				return setFilePath( WORKING_DIR, file );
-			} ),
+			'webpack-assets': {
+				src: webpackFiles.map( function( file ) {
+					return setFilePath( WORKING_DIR, file );
+				} ),
+				// Keep the link to media-editor.js, which media-*.js matches. See the link task.
+				filter: function( filepath ) {
+					return ! linkScripts || ! isLinkedScriptPath( filepath );
+				}
+			},
 
 			/*
 			 * Clean files sourced from the downloaded zip file built by the Gutenberg repository.
@@ -1648,29 +1670,37 @@ module.exports = function(grunt) {
 		},
 		_watch: {
 			options: {
-				interval: 2000
+				// Directories that are never watched, so that they are not searched.
+				ignored: [
+					'**/.{svn,git}/**',
+					'**/node_modules/**',
+					'vendor/**',
+					BUILD_DIR + '**',
+					// Third-party plugins, other than those that the build copies.
+					SOURCE_DIR + 'wp-content/plugins/!(index.php|hello.php|akismet)/**',
+					// Third-party themes.
+					SOURCE_DIR + 'wp-content/themes/!(twenty*|ipsum|index.php)/**',
+					// Uploads, translations, and other content that is not part of the build.
+					SOURCE_DIR + 'wp-content/!(index.php|plugins|themes)/**'
+				]
 			},
+			/*
+			 * Copies changed files from /src to /build. Its files are those of the copy:files task, set below, so
+			 * that the same files are copied as by the build. When building into /src with --dev, there is nothing to
+			 * copy, so this target is removed.
+			 */
 			all: {
-				files: [
-					SOURCE_DIR + '**',
-					'!' + SOURCE_DIR + 'js/**/*.js',
-					// Ignore version control directories.
-					'!' + SOURCE_DIR + '**/.{svn,git}/**',
-					// Ignore third-party plugins.
-					'!' + SOURCE_DIR + 'wp-content/plugins/**'
-				],
-				tasks: ['clean:dynamic', 'copy:dynamic'],
+				files: [],
+				tasks: ['watch-dynamic:all', 'clean:dynamic', 'copy:dynamic', 'copy:dynamic-js'],
 				options: {
-					dot: true,
-					spawn: false
+					dot: true
 				}
 			},
 			'js-enqueues': {
 				files: [SOURCE_DIR + 'js/_enqueues/**/*.js'],
-				tasks: ['clean:dynamic', 'copy:dynamic-js', 'uglify:dynamic'],
+				tasks: ['watch-dynamic:js-enqueues', 'clean:dynamic', 'copy:dynamic-js', 'uglify:dynamic', 'watch-uglify'],
 				options: {
-					dot: true,
-					spawn: false
+					dot: true
 				}
 			},
 			'js-webpack': {
@@ -1679,31 +1709,33 @@ module.exports = function(grunt) {
 					'!' + SOURCE_DIR + 'js/_enqueues/**/*.js',
 					'webpack-dev.config.js'
 				],
-				tasks: ['clean:dynamic', 'webpack:dev', 'uglify:dynamic'],
+				tasks: ['watch-dynamic:js-webpack', 'clean:dynamic', 'webpack:dev'],
 				options: {
-					dot: true,
-					spawn: false
+					dot: true
 				}
 			},
 			config: {
 				files: [
 					'Gruntfile.js',
 					'webpack.config.js'
-				]
+				],
+				options: {
+					reload: true
+				}
 			},
 			colors: {
-				files: [SOURCE_DIR + 'wp-admin/css/colors/**'],
+				files: [SOURCE_DIR + 'wp-admin/css/colors/**/*.scss'],
 				tasks: ['sass:colors']
 			},
 			rtl: {
 				files: [
 					SOURCE_DIR + 'wp-admin/css/*.css',
-					SOURCE_DIR + 'wp-includes/css/*.css'
+					SOURCE_DIR + 'wp-includes/css/*.css',
+					// Built stylesheets, written next to the sources with --dev.
+					'!' + SOURCE_DIR + '{wp-admin,wp-includes}/css/*.min.css',
+					'!' + SOURCE_DIR + '{wp-admin,wp-includes}/css/*-rtl*.css'
 				],
-				tasks: ['rtlcss:dynamic'],
-				options: {
-					spawn: false
-				}
+				tasks: ['watch-dynamic:rtl', 'rtlcss:dynamic']
 			},
 			test: {
 				files: [
@@ -1722,6 +1754,35 @@ module.exports = function(grunt) {
 		grunt.config.set( 'copy.files.files', copyFilesOptions );
 	}
 
+	if ( WORKING_DIR === SOURCE_DIR ) {
+		// When building into /src, there is nothing for the `all` watch target to copy, so its files are not watched.
+		delete grunt.config.data._watch.all;
+	} else {
+		/*
+		 * Watch the files that the copy:files task copies, so that a change is copied as by the build, including
+		 * the sources it copies to other paths, such as _index.php, and wp-config-sample.php from the root.
+		 */
+		grunt.config( [ '_watch', 'all', 'files' ], grunt.config( 'copy.files.files' )[0].src.map( function( pattern ) {
+			return pattern.charAt( 0 ) === '!' ? '!' + SOURCE_DIR + pattern.slice( 1 ) : SOURCE_DIR + pattern;
+		} ).concat( Object.keys( getMappedBuildFiles() ).map( function( dest ) {
+			return getMappedBuildFiles()[ dest ];
+		} ) ) );
+	}
+
+	/*
+	 * The `phpunit` watch target, also added here rather than only by the `watch` task, so that the watch task has
+	 * it after restarting for a change to this file.
+	 */
+	if ( /^_?watch:phpunit$/.test( grunt.cli.tasks[ 0 ] ) || 'undefined' !== typeof grunt.option( 'phpunit' ) ) {
+		grunt.config( [ '_watch', 'phpunit' ], {
+			files: [
+				SOURCE_DIR + '**/*.php',
+				'tests/phpunit/**/*.php'
+			],
+			tasks: [ 'phpunit:default' ]
+		} );
+	}
+
 
 	// Register tasks.
 
@@ -1800,20 +1861,13 @@ module.exports = function(grunt) {
 		} );
 	} );
 
-	grunt.renameTask( 'watch', '_watch' );
+	grunt.registerTask( '_watch', 'Runs the tasks of the watch targets whose files change.', require( './tools/watch/task.js' )( grunt ) );
 
 	grunt.registerTask( 'watch', 'Watches files for changes and runs the related tasks. Use watch:phpunit or --phpunit to also run PHPUnit tests.', function() {
 		if ( ! this.args.length || this.args.indexOf( 'webpack' ) > -1 ) {
 			grunt.task.run( 'build' );
 		}
 
-		if ( 'watch:phpunit' === grunt.cli.tasks[ 0 ] || 'undefined' !== typeof grunt.option( 'phpunit' ) ) {
-			grunt.config.data._watch.phpunit = {
-				files: [ '**/*.php' ],
-				tasks: [ 'phpunit:default' ]
-			};
-		}
-
 		grunt.task.run( '_' + this.nameArgs );
 	} );
 
@@ -1988,10 +2042,123 @@ module.exports = function(grunt) {
 	grunt.registerTask( 'copy:js', 'Copies JavaScript files from npm packages, vendor libraries, wp-admin, and wp-includes.', [
 		'copy:npm-packages',
 		'copy:vendor-js',
-		'copy:admin-js',
-		'copy:includes-js'
+		linkScripts ? 'link:admin-js' : 'copy:admin-js',
+		linkScripts ? 'link:includes-js' : 'copy:includes-js'
 	] );
 
+	/**
+	 * Checks whether a path is a symlink, including one whose target no longer exists.
+	 *
+	 * @param {string} filepath Path to check.
+	 * @return {boolean} Whether the path is a symlink.
+	 */
+	function isSymlink( filepath ) {
+		try {
+			return fs.lstatSync( filepath ).isSymbolicLink();
+		} catch ( e ) {
+			return false;
+		}
+	}
+
+	// The scripts' symlinks in place before the build, and the directories that hold them, keyed by path.
+	var linkedScriptPaths = null;
+
+	/**
+	 * Checks whether a path is a script's symlink as created by the link task, or a directory that holds one.
+	 *
+	 * @param {string} filepath Path to check.
+	 * @return {boolean} Whether the path is or holds a script's symlink.
+	 */
+	function isLinkedScriptPath( filepath ) {
+		var files, dest;
+
+		// Collect the links and the directories that hold them once, as the clean tasks check each path.
+		if ( ! linkedScriptPaths ) {
+			linkedScriptPaths = {};
+			files = Object.assign( {},
+				grunt.config( [ 'copy', 'admin-js', 'files' ] ),
+				grunt.config( [ 'copy', 'includes-js', 'files' ] )
+			);
+			Object.keys( files ).forEach( function( linkPath ) {
+				if ( ! isSymlink( linkPath ) || fs.readlinkSync( linkPath ) !== path.relative( path.dirname( linkPath ), files[ linkPath ][ 0 ] ) ) {
+					return;
+				}
+				linkedScriptPaths[ linkPath ] = true;
+				for ( dest = path.dirname( linkPath ); dest !== '.' && ! linkedScriptPaths[ dest ]; dest = path.dirname( dest ) ) {
+					linkedScriptPaths[ dest ] = true;
+				}
+			} );
+		}
+
+		return !! linkedScriptPaths[ filepath.replace( /\/$/, '' ) ];
+	}
+
+	grunt.registerTask( 'link', 'Symlinks the files of a copy task to their sources, falling back to copying them where symlinks cannot be created.', function( target ) {
+		var files = grunt.config( [ 'copy', target, 'files' ] );
+		var linked = 0;
+		var unchanged = 0;
+		var copied = 0;
+		var canLink = true;
+
+		if ( ! files ) {
+			grunt.fail.warn( 'The copy:' + target + ' task has no files to link.' );
+			return;
+		}
+
+		Object.keys( files ).forEach( function( dest ) {
+			var src = files[ dest ][ 0 ];
+			var linkTarget = path.relative( path.dirname( dest ), src );
+
+			/*
+			 * Keep a link that is already in place. Docker Desktop's file sharing can keep serving the previous
+			 * entry for a path that is replaced, failing to read it until the containers are restarted.
+			 */
+			if ( isSymlink( dest ) && fs.readlinkSync( dest ) === linkTarget && grunt.file.exists( src ) ) {
+				unchanged++;
+				return;
+			}
+
+			// Remove the previous copy or link, so that neither is written through.
+			if ( isSymlink( dest ) || grunt.file.exists( dest ) ) {
+				fs.unlinkSync( dest );
+			}
+
+			// Like the copy task, skip a source that does not exist.
+			if ( ! grunt.file.exists( src ) ) {
+				grunt.verbose.writeln( 'Source file ' + src + ' not found.' );
+				return;
+			}
+			grunt.file.mkdir( path.dirname( dest ) );
+
+			if ( canLink ) {
+				try {
+					// A relative link also resolves inside the Docker containers, which mount the repository elsewhere.
+					fs.symlinkSync( linkTarget, dest, 'file' );
+					linked++;
+					return;
+				} catch ( e ) {
+					// Creating symlinks on Windows requires Developer Mode or administrator rights.
+					if ( [ 'EPERM', 'EACCES', 'ENOTSUP', 'ENOSYS' ].indexOf( e.code ) === -1 ) {
+						throw e;
+					}
+					canLink = false;
+					grunt.log.writeln( 'Symlinks cannot be created (' + e.code + '), so the files are copied instead.' );
+				}
+			}
+
+			grunt.file.copy( src, dest );
+			copied++;
+		} );
+
+		grunt.log.ok( 'Linked ' + linked + ' ' + grunt.util.pluralize( linked, 'file/files' ) +
+			( unchanged ? ', kept ' + unchanged + ' existing ' + grunt.util.pluralize( unchanged, 'link/links' ) : '' ) +
+			( copied ? ', copied ' + copied + ' ' + grunt.util.pluralize( copied, 'file/files' ) : '' ) + '.' );
+
+		if ( linked ) {
+			grunt.log.writeln( 'If the local environment cannot read the linked files, restart it with `npm run env:restart`.' );
+		}
+	} );
+
 	grunt.registerTask( 'uglify:all', 'Minifies all JavaScript files.', [
 		'uglify:core',
 		'uglify:emoji-loader',
@@ -2498,104 +2665,227 @@ module.exports = function(grunt) {
 	grunt.registerTask('default', 'Runs the build task.', ['build']);
 
 	/*
-	 * Automatically updates the `:dynamic` configurations
-	 * so that only the changed files are updated.
+	 * Changes seen by each watch target since its tasks last ran, keyed by file path.
+	 *
+	 * The watch task runs the tasks of a target once for all the changes made within its debounce delay, so the
+	 * changes are collected here and the `:dynamic` configurations are set from all of them when the tasks run,
+	 * by the `watch-dynamic` task, which each target runs first.
 	 */
-	grunt.event.on( 'watch', function( action, filepath, target ) {
-		var src;
+	var watchedChanges = {};
 
-		// Only configure the dynamic tasks based on known targets.
-		if ( [ 'all', 'rtl', 'webpack', 'js-enqueues', 'js-webpack' ].indexOf( target ) === -1 ) {
+	// The uglify targets to run for the changed scripts that the uglify:core task does not minify.
+	var watchedUglifyTargets = [];
+
+	grunt.event.on( 'watch', function( action, filepath, target ) {
+		if ( [ 'all', 'rtl', 'js-enqueues', 'js-webpack' ].indexOf( target ) === -1 ) {
 			return;
 		}
 
+		watchedChanges[ target ] = watchedChanges[ target ] || {};
+
 		// Normalize filepath for Windows.
-		filepath = filepath.replace( /\\/g, '/' );
-
-		// If the target is a file in the restructured js src.
-		if ( target === 'js-enqueues' ) {
-			var files = {};
-			var configs, dest;
-
-			// If it's a vendor file which are configured with glob matchers.
-			if ( filepath.indexOf( SOURCE_DIR + 'js/_enqueues/vendor/' ) === 0 ) {
-				// Grab the glob matchers from the copy task.
-				configs = grunt.config( [ 'copy', 'vendor-js', 'files' ] );
-
-				// For each glob matcher check if it matches and if so set the variables for our dynamic tasks.
-				for ( var i = 0; i < configs.length; i++ ) {
-					var config = configs[ i ];
-					var relative = path.relative( config.cwd, filepath );
-					var minimatch = require('minimatch');
-
-					if ( minimatch.match( config.src, relative, {} ) ) {
-						dest = config.dest + relative;
-						src = [ path.relative( WORKING_DIR, dest ) ];
-						files[ dest ] = [ filepath ];
-						break;
-					}
+		watchedChanges[ target ][ filepath.replace( /\\/g, '/' ) ] = action;
+	} );
+
+	/**
+	 * Gets the destination of a file in the restructured js src, relative to the working directory.
+	 *
+	 * @param {string} filepath Path of the source file.
+	 * @return {?{dest: string, src: string}} The destination and source of the copy, or null if the file is not copied.
+	 */
+	function getEnqueuedScriptCopy( filepath ) {
+		var configs, i, dest, relative;
+
+		// If it's a vendor file which are configured with glob matchers.
+		if ( filepath.indexOf( SOURCE_DIR + 'js/_enqueues/vendor/' ) === 0 ) {
+			configs = grunt.config( [ 'copy', 'vendor-js', 'files' ] );
+
+			// Find the glob matcher that copies it. The other entries map files from node_modules.
+			for ( i = 0; i < configs.length; i++ ) {
+				if ( ! configs[ i ].cwd ) {
+					continue;
 				}
-			// Or if it's another file which has a straight mapping.
-			} else {
-				configs = Object.assign( {},
-					grunt.config( [ 'copy', 'admin-js', 'files' ] ),
-					grunt.config( [ 'copy', 'includes-js', 'files' ] )
-				);
+				relative = path.relative( configs[ i ].cwd, filepath ).replace( /\\/g, '/' );
 
-				for ( dest in configs ) {
-					// If a file in the mapping matches then set the variables for our dynamic tasks.
-					if ( dest && configs.hasOwnProperty( dest ) && configs[ dest ][0] === './' + filepath ) {
-						files[ dest ] = configs[ dest ];
-						src = [ path.relative( WORKING_DIR, dest ) ];
-						break;
-					}
+				if ( relative.indexOf( '../' ) !== 0 && grunt.file.isMatch( configs[ i ].src, relative ) ) {
+					return { dest: configs[ i ].dest + relative, src: filepath };
 				}
 			}
+			return null;
+		}
+
+		// Or if it's another file which has a straight mapping.
+		configs = Object.assign( {},
+			grunt.config( [ 'copy', 'admin-js', 'files' ] ),
+			grunt.config( [ 'copy', 'includes-js', 'files' ] )
+		);
 
-			// Configure our dynamic-js copy task which uses a file mapping rather than simply copying from src to build.
-			if ( action !== 'deleted' ) {
-				grunt.config( [ 'copy', 'dynamic-js', 'files' ], files );
+		for ( dest in configs ) {
+			if ( configs.hasOwnProperty( dest ) && configs[ dest ][ 0 ] === './' + filepath ) {
+				return { dest: dest, src: configs[ dest ][ 0 ] };
 			}
-		// For the webpack builds configure the task to only check those files built by webpack.
-		} else if ( target === 'js-webpack' ) {
-			src = [
-				'wp-includes/js/media-audiovideo.js',
-				'wp-includes/js/media-grid.js',
-				'wp-includes/js/media-models.js',
-				'wp-includes/js/media-views.js'
-			];
-		// Else simply use the path relative to the source directory.
-		} else {
-			src = [ path.relative( SOURCE_DIR, filepath ) ];
 		}
+		return null;
+	}
 
-		if ( ! src ) {
-			grunt.warn( 'Failed to determine the destination file.' );
-			return;
-		}
+	/**
+	 * Gets the files that the copy:files task copies other than by its glob patterns in /src: those it copies to
+	 * another path, such as _index.php to index.php, and wp-config-sample.php from the root.
+	 *
+	 * @return {Object<string, string>} Source paths, keyed by their destinations.
+	 */
+	function getMappedBuildFiles() {
+		var mapped = {};
 
-		if ( action === 'deleted' ) {
-			// Clean up only those files that were deleted.
-			grunt.config( [ 'clean', 'dynamic', 'src' ], src );
-		} else {
-			if ( ! grunt.option( 'dev' ) ) {
-				// Otherwise copy over only the changed file.
-				grunt.config(['copy', 'dynamic', 'src'], src);
+		grunt.config( 'copy.files.files' ).forEach( function( files ) {
+			// Skip the entries of glob patterns, which have a cwd.
+			if ( files.cwd ) {
+				return;
 			}
+			// A single file copied into a directory, such as wp-config-sample.php.
+			if ( files.src ) {
+				[].concat( files.src ).forEach( function( src ) {
+					mapped[ files.dest + path.basename( src ) ] = src;
+				} );
+				return;
+			}
+			Object.keys( files ).forEach( function( dest ) {
+				if ( 0 === files[ dest ][ 0 ].indexOf( SOURCE_DIR ) ) {
+					mapped[ dest ] = files[ dest ][ 0 ];
+				}
+			} );
+		} );
 
-			// For javascript also minify and validate the changed file.
-			if ( target === 'js-enqueues' ) {
-				grunt.config( [ 'uglify', 'dynamic', 'src' ], src );
-				grunt.config( [ 'dynamic', 'files', 'src' ], src.map( function( dir ) { return  WORKING_DIR + dir; } ) );
+		return mapped;
+	}
+
+	/**
+	 * Gets the uglify target that minifies a script in the build.
+	 *
+	 * @param {string} dest Path of the script, relative to the working directory.
+	 * @return {?string} The name of the uglify target, or null if the script is not minified.
+	 */
+	function getUglifyTarget( dest ) {
+		var targets = grunt.config( 'uglify' );
+
+		return Object.keys( targets ).filter( function( name ) {
+			var target = targets[ name ];
+			var relative;
+
+			if ( 'options' === name || 'dynamic' === name ) {
+				return false;
 			}
-			// For webpack only validate the file, minification is handled by webpack itself.
-			if ( target === 'js-webpack' ) {
-				grunt.config( [ 'dynamic', 'files', 'src' ], src.map( function( dir ) { return  WORKING_DIR + dir; } ) );
+			if ( ! target.expand ) {
+				return target.src === WORKING_DIR + dest;
 			}
-			// For css run the rtl task on just the changed file.
-			if ( target === 'rtl' ) {
-				grunt.config( [ 'rtlcss', 'dynamic', 'src' ], src );
+			relative = path.relative( target.cwd, WORKING_DIR + dest ).replace( /\\/g, '/' );
+			return relative.indexOf( '../' ) !== 0 && grunt.file.isMatch( target.src, relative );
+		} )[ 0 ] || null;
+	}
+
+	/*
+	 * Updates the `:dynamic` configurations so that only the changed files are updated.
+	 *
+	 * Every configuration a target uses is set each time, so that none is left over from an earlier run.
+	 */
+	grunt.registerTask( 'watch-dynamic', 'Configures the dynamic tasks of a watch target for the files changed since they last ran.', function( target ) {
+		var changes = watchedChanges[ target ] || {};
+		var mappedBuildFiles = getMappedBuildFiles();
+		var deleted = [];
+		var copyFiles = {};
+		var minify = [];
+		var uglifyTargets = [];
+		var changed = [];
+
+		delete watchedChanges[ target ];
+
+		Object.keys( changes ).forEach( function( filepath ) {
+			var action = changes[ filepath ];
+			var copy, dest, uglifyTarget;
+
+			if ( target === 'js-enqueues' ) {
+				copy = getEnqueuedScriptCopy( filepath );
+				if ( ! copy ) {
+					grunt.log.writeln( 'Not built: ' + filepath );
+					return;
+				}
+				dest = path.relative( WORKING_DIR, copy.dest ).replace( /\\/g, '/' );
+
+				if ( action === 'deleted' ) {
+					// A symlink to the deleted file no longer exists for the clean task, so it is removed here.
+					if ( isSymlink( copy.dest ) ) {
+						fs.unlinkSync( copy.dest );
+					} else {
+						deleted.push( dest );
+					}
+					// Every uglify target writes the minified script next to the script, with a .min.js extension.
+					if ( getUglifyTarget( dest ) ) {
+						deleted.push( dest.replace( /\.js$/, '.min.js' ) );
+					}
+					return;
+				}
+
+				// A symlink already has the changes, and copying onto it would write the file onto itself.
+				if ( ! isSymlink( copy.dest ) ) {
+					copyFiles[ copy.dest ] = [ copy.src ];
+				}
+
+				// Minify the script as the build does: with uglify:core, or by running the target that minifies it.
+				uglifyTarget = getUglifyTarget( dest );
+				if ( 'core' === uglifyTarget ) {
+					minify.push( dest );
+				} else if ( uglifyTarget && uglifyTargets.indexOf( uglifyTarget ) === -1 ) {
+					uglifyTargets.push( uglifyTarget );
+				}
+			} else if ( target === 'js-webpack' ) {
+				// Check only the files built by webpack.
+				if ( action === 'deleted' ) {
+					deleted = [
+						'wp-includes/js/media-audiovideo.js',
+						'wp-includes/js/media-grid.js',
+						'wp-includes/js/media-models.js',
+						'wp-includes/js/media-views.js'
+					];
+				}
+			} else if ( target === 'all' && Object.keys( mappedBuildFiles ).some( function( mappedDest ) {
+				return mappedBuildFiles[ mappedDest ] === filepath;
+			} ) ) {
+				// Copy a file that the build copies to another path, such as _index.php to index.php, or delete the copy.
+				Object.keys( mappedBuildFiles ).forEach( function( mappedDest ) {
+					if ( mappedBuildFiles[ mappedDest ] !== filepath ) {
+						return;
+					}
+					if ( action === 'deleted' ) {
+						deleted.push( path.relative( WORKING_DIR, mappedDest ).replace( /\\/g, '/' ) );
+					} else {
+						copyFiles[ mappedDest ] = [ filepath ];
+					}
+				} );
+			} else if ( action === 'deleted' ) {
+				deleted.push( path.relative( SOURCE_DIR, filepath ) );
+			} else {
+				changed.push( path.relative( SOURCE_DIR, filepath ) );
 			}
+		} );
+
+		grunt.config( [ 'clean', 'dynamic', 'src' ], deleted );
+
+		if ( target === 'all' ) {
+			grunt.config( [ 'copy', 'dynamic', 'src' ], changed );
+			grunt.config( [ 'copy', 'dynamic-js', 'files' ], copyFiles );
+		} else if ( target === 'rtl' ) {
+			grunt.config( [ 'rtlcss', 'dynamic', 'src' ], changed );
+		} else if ( target === 'js-enqueues' ) {
+			grunt.config( [ 'copy', 'dynamic-js', 'files' ], copyFiles );
+			grunt.config( [ 'uglify', 'dynamic', 'src' ], minify );
+			watchedUglifyTargets = uglifyTargets;
 		}
-	});
+	} );
+
+	grunt.registerTask( 'watch-uglify', 'Runs the uglify targets for the changed scripts that uglify:core does not minify.', function() {
+		grunt.task.run( watchedUglifyTargets.map( function( name ) {
+			return 'uglify:' + name;
+		} ) );
+		watchedUglifyTargets = [];
+	} );
 };
diff --git a/README.md b/README.md
index 0f41da84643bd..a0fd93673885f 100644
--- a/README.md
+++ b/README.md
@@ -76,6 +76,18 @@ npm run dev
 
 To stop the watcher, press `ctrl+c`.
 
+The watcher relies on the file system events of your operating system. Where these are not delivered, such as on a network drive or for a Windows drive accessed from WSL, set the `CHOKIDAR_USEPOLLING=1` environment variable to check the files for changes periodically instead.
+
+The JavaScript files in `src/wp-admin/js` and `src/wp-includes/js` that are copied unchanged from `src/js/_enqueues` can be symlinked instead, so that changes to them take effect without the watcher:
+
+```
+npm run build:dev -- --symlink
+```
+
+The option also applies to the build that the watcher runs when it starts, as in `npm run dev -- --symlink`. Later builds with the option keep the links in place, while a build without it replaces them with copies again.
+
+If the local environment then cannot load these files, which can happen with Docker Desktop after switching between links and copies, restart it with `npm run env:restart`.
+
 #### To run a [WP-CLI](https://make.wordpress.org/cli/handbook/) command
 
 ```
diff --git a/package-lock.json b/package-lock.json
index 5b497251c419d..c327ba65167fc 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -57,6 +57,7 @@
 				"@wordpress/prettier-config": "4.51.0",
 				"@wordpress/scripts": "33.0.0",
 				"autoprefixer": "10.5.3",
+				"chokidar": "4.0.3",
 				"dotenv": "17.4.2",
 				"dotenv-expand": "13.0.0",
 				"grunt": "1.6.2",
@@ -67,7 +68,6 @@
 				"grunt-contrib-cssmin": "~5.0.0",
 				"grunt-contrib-jshint": "3.2.0",
 				"grunt-contrib-uglify": "~5.2.2",
-				"grunt-contrib-watch": "~1.1.0",
 				"grunt-file-append": "0.0.7",
 				"grunt-jsdoc": "2.4.1",
 				"grunt-legacy-util": "^2.0.2",
@@ -3013,18 +3013,6 @@
 				"url": "https://github.com/chalk/ansi-styles?sponsor=1"
 			}
 		},
-		"node_modules/@jest/core/node_modules/braces": {
-			"version": "3.0.3",
-			"resolved": "https://registry.npmjs.org/braces/-/braces-3.0.3.tgz",
-			"integrity": "sha512-yQbXgO/OSZVD2IsiLlro+7Hf6Q18EJrKSEsdoMzKePKXct3gvD8oLcOQdIzGupr5Fj+EDe8gO/lxc1BzfMpxvA==",
-			"dev": true,
-			"dependencies": {
-				"fill-range": "^7.1.1"
-			},
-			"engines": {
-				"node": ">=8"
-			}
-		},
 		"node_modules/@jest/core/node_modules/chalk": {
 			"version": "4.1.2",
 			"resolved": "https://registry.npmjs.org/chalk/-/chalk-4.1.2.tgz",
@@ -3059,18 +3047,6 @@
 			"integrity": "sha512-dOy+3AuW3a2wNbZHIuMZpTcgjGuLU/uBL/ubcZF9OXbDo8ff4O8yVp5Bf0efS8uEoYo5q4Fx7dY9OgQGXgAsQA==",
 			"dev": true
 		},
-		"node_modules/@jest/core/node_modules/fill-range": {
-			"version": "7.1.1",
-			"resolved": "https://registry.npmjs.org/fill-range/-/fill-range-7.1.1.tgz",
-			"integrity": "sha512-YsGpe3WHLK8ZYi4tWDg2Jy3ebRz2rXowDxnld4bkQB00cc/1Zw9AWnC0i9ztDJitivtQvaI9KaLyKrc+hBW0yg==",
-			"dev": true,
-			"dependencies": {
-				"to-regex-range": "^5.0.1"
-			},
-			"engines": {
-				"node": ">=8"
-			}
-		},
 		"node_modules/@jest/core/node_modules/has-flag": {
 			"version": "4.0.0",
 			"resolved": "https://registry.npmjs.org/has-flag/-/has-flag-4.0.0.tgz",
@@ -3080,15 +3056,6 @@
 				"node": ">=8"
 			}
 		},
-		"node_modules/@jest/core/node_modules/is-number": {
-			"version": "7.0.0",
-			"resolved": "https://registry.npmjs.org/is-number/-/is-number-7.0.0.tgz",
-			"integrity": "sha512-41Cifkg6e8TylSpdtTpeLVMqvSBEVzTttHvERD741+pnZ8ANv0004MRL43QKPDlK9cGvNp6NZWZUBlbGXYxxng==",
-			"dev": true,
-			"engines": {
-				"node": ">=0.12.0"
-			}
-		},
 		"node_modules/@jest/core/node_modules/micromatch": {
 			"version": "4.0.8",
 			"resolved": "https://registry.npmjs.org/micromatch/-/micromatch-4.0.8.tgz",
@@ -3127,18 +3094,6 @@
 				"node": ">=8"
 			}
 		},
-		"node_modules/@jest/core/node_modules/to-regex-range": {
-			"version": "5.0.1",
-			"resolved": "https://registry.npmjs.org/to-regex-range/-/to-regex-range-5.0.1.tgz",
-			"integrity": "sha512-65P7iz6X5yEr1cwcgvQxbbIw7Uk3gOy5dIdtZ4rDveLqhrdJP+Li/Hx6tyK0NEb+2GCyneCMJiGqrADCSNk8sQ==",
-			"dev": true,
-			"dependencies": {
-				"is-number": "^7.0.0"
-			},
-			"engines": {
-				"node": ">=8.0"
-			}
-		},
 		"node_modules/@jest/environment": {
 			"version": "29.7.0",
 			"resolved": "https://registry.npmjs.org/@jest/environment/-/environment-29.7.0.tgz",
@@ -3802,18 +3757,6 @@
 				"url": "https://github.com/chalk/ansi-styles?sponsor=1"
 			}
 		},
-		"node_modules/@jest/transform/node_modules/braces": {
-			"version": "3.0.3",
-			"resolved": "https://registry.npmjs.org/braces/-/braces-3.0.3.tgz",
-			"integrity": "sha512-yQbXgO/OSZVD2IsiLlro+7Hf6Q18EJrKSEsdoMzKePKXct3gvD8oLcOQdIzGupr5Fj+EDe8gO/lxc1BzfMpxvA==",
-			"dev": true,
-			"dependencies": {
-				"fill-range": "^7.1.1"
-			},
-			"engines": {
-				"node": ">=8"
-			}
-		},
 		"node_modules/@jest/transform/node_modules/chalk": {
 			"version": "4.1.2",
 			"resolved": "https://registry.npmjs.org/chalk/-/chalk-4.1.2.tgz",
@@ -3854,18 +3797,6 @@
 			"integrity": "sha512-Kvp459HrV2FEJ1CAsi1Ku+MY3kasH19TFykTz2xWmMeq6bk2NU3XXvfJ+Q61m0xktWwt+1HSYf3JZsTms3aRJg==",
 			"dev": true
 		},
-		"node_modules/@jest/transform/node_modules/fill-range": {
-			"version": "7.1.1",
-			"resolved": "https://registry.npmjs.org/fill-range/-/fill-range-7.1.1.tgz",
-			"integrity": "sha512-YsGpe3WHLK8ZYi4tWDg2Jy3ebRz2rXowDxnld4bkQB00cc/1Zw9AWnC0i9ztDJitivtQvaI9KaLyKrc+hBW0yg==",
-			"dev": true,
-			"dependencies": {
-				"to-regex-range": "^5.0.1"
-			},
-			"engines": {
-				"node": ">=8"
-			}
-		},
 		"node_modules/@jest/transform/node_modules/has-flag": {
 			"version": "4.0.0",
 			"resolved": "https://registry.npmjs.org/has-flag/-/has-flag-4.0.0.tgz",
@@ -3875,15 +3806,6 @@
 				"node": ">=8"
 			}
 		},
-		"node_modules/@jest/transform/node_modules/is-number": {
-			"version": "7.0.0",
-			"resolved": "https://registry.npmjs.org/is-number/-/is-number-7.0.0.tgz",
-			"integrity": "sha512-41Cifkg6e8TylSpdtTpeLVMqvSBEVzTttHvERD741+pnZ8ANv0004MRL43QKPDlK9cGvNp6NZWZUBlbGXYxxng==",
-			"dev": true,
-			"engines": {
-				"node": ">=0.12.0"
-			}
-		},
 		"node_modules/@jest/transform/node_modules/micromatch": {
 			"version": "4.0.8",
 			"resolved": "https://registry.npmjs.org/micromatch/-/micromatch-4.0.8.tgz",
@@ -3910,18 +3832,6 @@
 				"node": ">=8"
 			}
 		},
-		"node_modules/@jest/transform/node_modules/to-regex-range": {
-			"version": "5.0.1",
-			"resolved": "https://registry.npmjs.org/to-regex-range/-/to-regex-range-5.0.1.tgz",
-			"integrity": "sha512-65P7iz6X5yEr1cwcgvQxbbIw7Uk3gOy5dIdtZ4rDveLqhrdJP+Li/Hx6tyK0NEb+2GCyneCMJiGqrADCSNk8sQ==",
-			"dev": true,
-			"dependencies": {
-				"is-number": "^7.0.0"
-			},
-			"engines": {
-				"node": ">=8.0"
-			}
-		},
 		"node_modules/@jest/types": {
 			"version": "29.6.3",
 			"resolved": "https://registry.npmjs.org/@jest/types/-/types-29.6.3.tgz",
@@ -4789,45 +4699,6 @@
 				"url": "https://opencollective.com/parcel"
 			}
 		},
-		"node_modules/@parcel/watcher/node_modules/braces": {
-			"version": "3.0.3",
-			"resolved": "https://registry.npmjs.org/braces/-/braces-3.0.3.tgz",
-			"integrity": "sha512-yQbXgO/OSZVD2IsiLlro+7Hf6Q18EJrKSEsdoMzKePKXct3gvD8oLcOQdIzGupr5Fj+EDe8gO/lxc1BzfMpxvA==",
-			"dev": true,
-			"license": "MIT",
-			"optional": true,
-			"dependencies": {
-				"fill-range": "^7.1.1"
-			},
-			"engines": {
-				"node": ">=8"
-			}
-		},
-		"node_modules/@parcel/watcher/node_modules/fill-range": {
-			"version": "7.1.1",
-			"resolved": "https://registry.npmjs.org/fill-range/-/fill-range-7.1.1.tgz",
-			"integrity": "sha512-YsGpe3WHLK8ZYi4tWDg2Jy3ebRz2rXowDxnld4bkQB00cc/1Zw9AWnC0i9ztDJitivtQvaI9KaLyKrc+hBW0yg==",
-			"dev": true,
-			"license": "MIT",
-			"optional": true,
-			"dependencies": {
-				"to-regex-range": "^5.0.1"
-			},
-			"engines": {
-				"node": ">=8"
-			}
-		},
-		"node_modules/@parcel/watcher/node_modules/is-number": {
-			"version": "7.0.0",
-			"resolved": "https://registry.npmjs.org/is-number/-/is-number-7.0.0.tgz",
-			"integrity": "sha512-41Cifkg6e8TylSpdtTpeLVMqvSBEVzTttHvERD741+pnZ8ANv0004MRL43QKPDlK9cGvNp6NZWZUBlbGXYxxng==",
-			"dev": true,
-			"license": "MIT",
-			"optional": true,
-			"engines": {
-				"node": ">=0.12.0"
-			}
-		},
 		"node_modules/@parcel/watcher/node_modules/micromatch": {
 			"version": "4.0.8",
 			"resolved": "https://registry.npmjs.org/micromatch/-/micromatch-4.0.8.tgz",
@@ -4843,20 +4714,6 @@
 				"node": ">=8.6"
 			}
 		},
-		"node_modules/@parcel/watcher/node_modules/to-regex-range": {
-			"version": "5.0.1",
-			"resolved": "https://registry.npmjs.org/to-regex-range/-/to-regex-range-5.0.1.tgz",
-			"integrity": "sha512-65P7iz6X5yEr1cwcgvQxbbIw7Uk3gOy5dIdtZ4rDveLqhrdJP+Li/Hx6tyK0NEb+2GCyneCMJiGqrADCSNk8sQ==",
-			"dev": true,
-			"license": "MIT",
-			"optional": true,
-			"dependencies": {
-				"is-number": "^7.0.0"
-			},
-			"engines": {
-				"node": ">=8.0"
-			}
-		},
 		"node_modules/@paulirish/trace_engine": {
 			"version": "0.0.39",
 			"resolved": "https://registry.npmjs.org/@paulirish/trace_engine/-/trace_engine-0.0.39.tgz",
@@ -9316,15 +9173,6 @@
 				"node": ">=8"
 			}
 		},
-		"node_modules/async": {
-			"version": "2.6.4",
-			"resolved": "https://registry.npmjs.org/async/-/async-2.6.4.tgz",
-			"integrity": "sha512-mzo5dfJYwAn29PeiJ0zvwTo04zj8HDJj0Mn8TD7sno7q12prdbnasKJHhkm2c1LgrhlJ0teaea8860oxi51mGA==",
-			"dev": true,
-			"dependencies": {
-				"lodash": "^4.17.14"
-			}
-		},
 		"node_modules/async-function": {
 			"version": "1.0.0",
 			"resolved": "https://registry.npmjs.org/async-function/-/async-function-1.0.0.tgz",
@@ -9958,12 +9806,16 @@
 			}
 		},
 		"node_modules/binary-extensions": {
-			"version": "2.1.0",
-			"resolved": "https://registry.npmjs.org/binary-extensions/-/binary-extensions-2.1.0.tgz",
-			"integrity": "sha512-1Yj8h9Q+QDF5FzhMs/c9+6UntbD5MkRfRwac8DoEm9ZfUBZ7tZ55YcGVAzEe4bXsdQHEk+s9S5wsOKVdZrw0tQ==",
+			"version": "2.3.0",
+			"resolved": "https://registry.npmjs.org/binary-extensions/-/binary-extensions-2.3.0.tgz",
+			"integrity": "sha512-Ceh+7ox5qe7LJuLHoY0feh3pHuUDHAcRUeyL2VYghZwfpkNIy/+8Ocg0a3UuSoYzavmylwuLWQOf3hl0jjMMIw==",
 			"dev": true,
+			"license": "MIT",
 			"engines": {
 				"node": ">=8"
+			},
+			"funding": {
+				"url": "https://github.com/sponsors/sindresorhus"
 			}
 		},
 		"node_modules/bluebird": {
@@ -9972,18 +9824,6 @@
 			"integrity": "sha512-XpNj6GDQzdfW+r2Wnn7xiSAd7TM3jzkxGXBGTtWKuSXv1xUV+azxAm8jdWZN06QTQk+2N2XB9jRDkvbmQmcRtg==",
 			"dev": true
 		},
-		"node_modules/body": {
-			"version": "5.1.0",
-			"resolved": "https://registry.npmjs.org/body/-/body-5.1.0.tgz",
-			"integrity": "sha1-5LoM5BCkaTYyM2dgnstOZVMSUGk=",
-			"dev": true,
-			"dependencies": {
-				"continuable-cache": "^0.3.1",
-				"error": "^7.0.0",
-				"raw-body": "~1.1.0",
-				"safe-json-parse": "~1.0.1"
-			}
-		},
 		"node_modules/body-parser": {
 			"version": "1.20.6",
 			"resolved": "https://registry.npmjs.org/body-parser/-/body-parser-1.20.6.tgz",
@@ -10070,33 +9910,6 @@
 				"node": ">= 0.8"
 			}
 		},
-		"node_modules/body/node_modules/bytes": {
-			"version": "1.0.0",
-			"resolved": "https://registry.npmjs.org/bytes/-/bytes-1.0.0.tgz",
-			"integrity": "sha512-/x68VkHLeTl3/Ll8IvxdwzhrT+IyKc52e/oyHhA2RwqPqswSnjVbSddfPRwAsJtbilMAPSRWwAlpxdYsSWOTKQ==",
-			"dev": true
-		},
-		"node_modules/body/node_modules/raw-body": {
-			"version": "1.1.7",
-			"resolved": "https://registry.npmjs.org/raw-body/-/raw-body-1.1.7.tgz",
-			"integrity": "sha512-WmJJU2e9Y6M5UzTOkHaM7xJGAPQD8PNzx3bAd2+uhZAim6wDk6dAZxPVYLF67XhbR4hmKGh33Lpmh4XWrCH5Mg==",
-			"dev": true,
-			"license": "MIT",
-			"dependencies": {
-				"bytes": "1",
-				"string_decoder": "0.10"
-			},
-			"engines": {
-				"node": ">= 0.8.0"
-			}
-		},
-		"node_modules/body/node_modules/string_decoder": {
-			"version": "0.10.31",
-			"resolved": "https://registry.npmjs.org/string_decoder/-/string_decoder-0.10.31.tgz",
-			"integrity": "sha512-ev2QzSzWPYmy9GuqfIVildA4OdcGLeFZQrq5ys6RtiuF+RQQiZWr8TZNyAcuVXyQRYfEO+MsoB/1BuQVhOJuoQ==",
-			"dev": true,
-			"license": "MIT"
-		},
 		"node_modules/bonjour-service": {
 			"version": "1.2.1",
 			"resolved": "https://registry.npmjs.org/bonjour-service/-/bonjour-service-1.2.1.tgz",
@@ -10124,6 +9937,19 @@
 				"concat-map": "0.0.1"
 			}
 		},
+		"node_modules/braces": {
+			"version": "3.0.3",
+			"resolved": "https://registry.npmjs.org/braces/-/braces-3.0.3.tgz",
+			"integrity": "sha512-yQbXgO/OSZVD2IsiLlro+7Hf6Q18EJrKSEsdoMzKePKXct3gvD8oLcOQdIzGupr5Fj+EDe8gO/lxc1BzfMpxvA==",
+			"dev": true,
+			"license": "MIT",
+			"dependencies": {
+				"fill-range": "^7.1.1"
+			},
+			"engines": {
+				"node": ">=8"
+			}
+		},
 		"node_modules/browserslist": {
 			"version": "4.28.6",
 			"resolved": "https://registry.npmjs.org/browserslist/-/browserslist-4.28.6.tgz",
@@ -10521,73 +10347,19 @@
 			}
 		},
 		"node_modules/chokidar": {
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-			}
-		},
 		"node_modules/stylelint/node_modules/write-file-atomic": {
 			"version": "5.0.1",
 			"resolved": "https://registry.npmjs.org/write-file-atomic/-/write-file-atomic-5.0.1.tgz",
@@ -27089,29 +26423,6 @@
 				"globrex": "^0.1.2"
 			}
 		},
-		"node_modules/tiny-lr": {
-			"version": "1.1.1",
-			"resolved": "https://registry.npmjs.org/tiny-lr/-/tiny-lr-1.1.1.tgz",
-			"integrity": "sha512-44yhA3tsaRoMOjQQ+5v5mVdqef+kH6Qze9jTpqtVufgYjYt08zyZAwNwwVBj3i1rJMnR52IxOW0LK0vBzgAkuA==",
-			"dev": true,
-			"dependencies": {
-				"body": "^5.1.0",
-				"debug": "^3.1.0",
-				"faye-websocket": "~0.10.0",
-				"livereload-js": "^2.3.0",
-				"object-assign": "^4.1.0",
-				"qs": "^6.4.0"
-			}
-		},
-		"node_modules/tiny-lr/node_modules/debug": {
-			"version": "3.2.7",
-			"resolved": "https://registry.npmjs.org/debug/-/debug-3.2.7.tgz",
-			"integrity": "sha512-CFjzYYAi4ThfiQvizrFQevTTXHtnCqWfe7x1AhgEscTz6ZbLbfoLRLPugTQyBth6f8ZERVUSyWHFD/7Wu4t1XQ==",
-			"dev": true,
-			"dependencies": {
-				"ms": "^2.1.1"
-			}
-		},
 		"node_modules/tinyglobby": {
 			"version": "0.2.17",
 			"resolved": "https://registry.npmjs.org/tinyglobby/-/tinyglobby-0.2.17.tgz",
@@ -27189,6 +26500,19 @@
 			"integrity": "sha512-3f0uOEAQwIqGuWW2MVzYg8fV/QNnc/IpuJNG837rLuczAaLVHslWHZQj4IGiEl5Hs3kkbhwL9Ab7Hrsmuj+Smw==",
 			"dev": true
 		},
+		"node_modules/to-regex-range": {
+			"version": "5.0.1",
+			"resolved": "https://registry.npmjs.org/to-regex-range/-/to-regex-range-5.0.1.tgz",
+			"integrity": "sha512-65P7iz6X5yEr1cwcgvQxbbIw7Uk3gOy5dIdtZ4rDveLqhrdJP+Li/Hx6tyK0NEb+2GCyneCMJiGqrADCSNk8sQ==",
+			"dev": true,
+			"license": "MIT",
+			"dependencies": {
+				"is-number": "^7.0.0"
+			},
+			"engines": {
+				"node": ">=8.0"
+			}
+		},
 		"node_modules/toidentifier": {
 			"version": "1.0.1",
 			"resolved": "https://registry.npmjs.org/toidentifier/-/toidentifier-1.0.1.tgz",
@@ -28326,12 +27650,50 @@
 				"ajv": "^8.8.2"
 			}
 		},
+		"node_modules/webpack-dev-server/node_modules/chokidar": {
+			"version": "3.6.0",
+			"resolved": "https://registry.npmjs.org/chokidar/-/chokidar-3.6.0.tgz",
+			"integrity": "sha512-7VT13fmjotKpGipCW9JEQAusEPE+Ei8nl6/g4FBAmIm0GOOLMua9NDDo/DWp0ZAxCr3cPq5ZpBqmPAQgDda2Pw==",
+			"dev": true,
+			"license": "MIT",
+			"dependencies": {
+				"anymatch": "~3.1.2",
+				"braces": "~3.0.2",
+				"glob-parent": "~5.1.2",
+				"is-binary-path": "~2.1.0",
+				"is-glob": "~4.0.1",
+				"normalize-path": "~3.0.0",
+				"readdirp": "~3.6.0"
+			},
+			"engines": {
+				"node": ">= 8.10.0"
+			},
+			"funding": {
+				"url": "https://paulmillr.com/funding/"
+			},
+			"optionalDependencies": {
+				"fsevents": "~2.3.2"
+			}
+		},
 		"node_modules/webpack-dev-server/node_modules/json-schema-traverse": {
 			"version": "1.0.0",
 			"resolved": "https://registry.npmjs.org/json-schema-traverse/-/json-schema-traverse-1.0.0.tgz",
 			"integrity": "sha512-NM8/P9n3XjXhIZn1lLhkFaACTOURQXjWhV4BA/RnOv8xvgqtqpAX9IO4mRQxSx1Rlo4tqzeqb0sOlruaOy3dug==",
 			"dev": true
 		},
+		"node_modules/webpack-dev-server/node_modules/readdirp": {
+			"version": "3.6.0",
+			"resolved": "https://registry.npmjs.org/readdirp/-/readdirp-3.6.0.tgz",
+			"integrity": "sha512-hOS089on8RduqdbhvQ5Z37A0ESjsqz6qnRcffsMU3495FuTdqSm+7bhJ29JvIOsBDEEnan5DPu9t3To9VRlMzA==",
+			"dev": true,
+			"license": "MIT",
+			"dependencies": {
+				"picomatch": "^2.2.1"
+			},
+			"engines": {
+				"node": ">=8.10.0"
+			}
+		},
 		"node_modules/webpack-dev-server/node_modules/rimraf": {
 			"version": "3.0.2",
 			"resolved": "https://registry.npmjs.org/rimraf/-/rimraf-3.0.2.tgz",
diff --git a/package.json b/package.json
index 4b29c829fb5a0..6f429eb4c7504 100644
--- a/package.json
+++ b/package.json
@@ -55,6 +55,7 @@
 		"@wordpress/prettier-config": "4.51.0",
 		"@wordpress/scripts": "33.0.0",
 		"autoprefixer": "10.5.3",
+		"chokidar": "4.0.3",
 		"dotenv": "17.4.2",
 		"dotenv-expand": "13.0.0",
 		"grunt": "1.6.2",
@@ -65,7 +66,6 @@
 		"grunt-contrib-cssmin": "~5.0.0",
 		"grunt-contrib-jshint": "3.2.0",
 		"grunt-contrib-uglify": "~5.2.2",
-		"grunt-contrib-watch": "~1.1.0",
 		"grunt-file-append": "0.0.7",
 		"grunt-jsdoc": "2.4.1",
 		"grunt-legacy-util": "^2.0.2",
diff --git a/tools/watch/task.js b/tools/watch/task.js
new file mode 100644
index 0000000000000..525036b6fe164
--- /dev/null
+++ b/tools/watch/task.js
@@ -0,0 +1,430 @@
+/**
+ * Watch Task
+ *
+ * Runs the tasks of the `_watch` targets whose files change. It replaces
+ * grunt-contrib-watch, which missed changes: it polls each watched file through
+ * gaze, which finds every file in the directories that a target's patterns
+ * exclude before filtering them out; it recreates its watchers after each run,
+ * missing the changes made meanwhile; and it leaves the changes seen while
+ * another target's tasks run waiting for the next change.
+ *
+ * Files are watched with chokidar, through the native file system events of
+ * each platform. Set `CHOKIDAR_USEPOLLING=1` to poll instead, where the events
+ * are not delivered, as on network drives or for Windows drives under WSL.
+ *
+ * Each target takes `files` patterns, the `tasks` to run when one of them
+ * changes, and the options `dot`, to match files whose names begin with a dot,
+ * and `reload`, to restart the watch task, as for a change to the Gruntfile.
+ * The `ignored` option of the task lists the patterns of the directories that
+ * are never watched.
+ *
+ * The tasks run in the watch process, and a `watch` event is emitted for each
+ * change of a target before they run, so that a listener can configure them for
+ * the changed files. Changes made while tasks run are run once they finish. When
+ * a task fails, the rest of its target's tasks are skipped, and those of the
+ * other targets still run. A reload happens after the tasks of the other
+ * changes made with it, or while its tasks ran, have run. The new process is
+ * handed the changes made while it starts, which the previous one still watches.
+ *
+ * A target's tasks must not write files that match its own patterns, which
+ * would run them again without end.
+ *
+ * @package WordPress
+ */
+
+const path = require( 'path' );
+const { spawn } = require( 'child_process' );
+const chokidar = require( 'chokidar' );
+
+/**
+ * Time to wait for more changes before running the tasks, in milliseconds.
+ *
+ * An editor or a version control checkout often changes several files at once.
+ */
+const DEBOUNCE_DELAY = 250;
+
+/**
+ * Environment variable set for a watch process started by a reload, which takes over the changes that the
+ * previous process saw while it started.
+ */
+const HAND_OFF_ENV = 'WP_WATCH_HAND_OFF';
+
+/**
+ * Change actions, keyed by the chokidar event names.
+ */
+const ACTIONS = {
+	add: 'added',
+	change: 'changed',
+	unlink: 'deleted',
+};
+
+/**
+ * Gets the directory that a pattern searches, before any part with glob syntax.
+ *
+ * @param {string} pattern The pattern.
+ *
+ * @return {string} The directory, or the file when the pattern has no glob syntax.
+ */
+function getPatternBase( pattern ) {
+	const segments = [];
+
+	for ( const segment of pattern.split( '/' ) ) {
+		if ( /[*?[\]{}()!+@]/.test( segment ) ) {
+			break;
+		}
+		segments.push( segment );
+	}
+
+	return segments.join( '/' ) || '.';
+}
+
+/**
+ * Gets the paths to watch for the patterns, without those inside another one.
+ *
+ * @param {string[]} patterns The patterns.
+ *
+ * @return {string[]} The paths to watch.
+ */
+function getWatchPaths( patterns ) {
+	const bases = [ ...new Set(
+		patterns
+			.filter( ( pattern ) => ! pattern.startsWith( '!' ) )
+			.map( getPatternBase )
+	) ];
+	const isInside = ( child, parent ) => parent === '.' || child.startsWith( parent + '/' );
+
+	return bases.filter( ( base ) => ! bases.some( ( other ) => other !== base && isInside( base, other ) ) );
+}
+
+/**
+ * Builds the watch task.
+ *
+ * @param {Object} grunt The grunt instance.
+ *
+ * @return {Function} The task function.
+ */
+module.exports = ( grunt ) => {
+	let watcher = null;
+	let taskName = '_watch';
+	let targetNames = [];
+	let nameArgs = '';
+	let resume = null;
+	let timer = null;
+	let reload = false;
+	let restartPending = false;
+	let startedAt = null;
+	let currentTarget = null;
+	let failureReported = false;
+
+	// The changes seen while restarting, as chokidar event names and paths, to hand to the new process.
+	let handOffChanges = null;
+
+	// Changed files since the tasks last ran, keyed by path, and the targets to run for them.
+	const changes = new Map();
+	const queuedTargets = new Set();
+
+	// The targets whose tasks are queued in the current run, until each one's tasks finish.
+	let runningTargets = [];
+
+	grunt.registerTask( '_watch-target', 'Marks the tasks of a watch target as started or finished.', ( step, name ) => {
+		failureReported = false;
+		if ( 'start' === step ) {
+			currentTarget = name;
+		} else {
+			currentTarget = null;
+			runningTargets = runningTargets.filter( ( running ) => running !== name );
+		}
+	} );
+
+	/**
+	 * Gets the configuration of a target.
+	 *
+	 * @param {string} name The target name.
+	 *
+	 * @return {{files: string[], tasks: string[], options: Object}} The target configuration.
+	 */
+	function getTarget( name ) {
+		const target = grunt.config( [ taskName, name ] );
+
+		return {
+			files: [].concat( target.files || [] ).map( ( pattern ) => grunt.config.process( pattern ) ),
+			tasks: [].concat( target.tasks || [] ),
+			options: target.options || {},
+		};
+	}
+
+	/**
+	 * Gets the tasks to run for targets, each between the tasks that mark it as started and finished.
+	 *
+	 * @param {string[]} names The target names.
+	 *
+	 * @return {string[]} The tasks.
+	 */
+	function getTasks( names ) {
+		return names.flatMap( ( name ) => [ '_watch-target:start:' + name ].concat(
+			getTarget( name ).tasks,
+			'_watch-target:done:' + name
+		) );
+	}
+
+	/**
+	 * Records a change, for each target whose patterns match the file.
+	 *
+	 * @param {string} event    The chokidar event name.
+	 * @param {string} filepath The path of the changed file.
+	 */
+	function recordChange( event, filepath ) {
+		const action = ACTIONS[ event ];
+		let matched = false;
+
+		if ( ! action ) {
+			return;
+		}
+
+		// Once restarting, the changes are for the new process, which is handed them when it is ready.
+		if ( handOffChanges ) {
+			handOffChanges.push( [ event, filepath ] );
+			return;
+		}
+
+		filepath = path.relative( process.cwd(), filepath ).replace( /\\/g, '/' );
+
+		targetNames.forEach( ( name ) => {
+			const target = getTarget( name );
+
+			if ( ! grunt.file.isMatch( { dot: !! target.options.dot }, target.files, filepath ) ) {
+				return;
+			}
+
+			matched = true;
+			queuedTargets.add( name );
+			if ( target.options.reload ) {
+				reload = true;
+			}
+
+			grunt.event.emit( 'watch', action, filepath, name );
+		} );
+
+		if ( matched ) {
+			changes.set( filepath, action );
+			clearTimeout( timer );
+			timer = setTimeout( runQueued, DEBOUNCE_DELAY );
+		}
+	}
+
+	/**
+	 * Runs the tasks of the targets that have changes, unless tasks are running.
+	 *
+	 * The changes are then kept until the tasks finish and the watch task resumes.
+	 */
+	function runQueued() {
+		const done = resume;
+
+		timer = null;
+		if ( ! done ) {
+			return;
+		}
+
+		changes.forEach( ( action, filepath ) => {
+			grunt.log.ok( 'File "' + filepath + '" ' + action + '.' );
+		} );
+
+		// Restart once the tasks for the other changes have run, as the new process does not see those changes.
+		if ( reload ) {
+			restartPending = true;
+			reload = false;
+		}
+
+		runningTargets = targetNames.filter( ( name ) => queuedTargets.has( name ) );
+		changes.clear();
+		queuedTargets.clear();
+		resume = null;
+		startedAt = Date.now();
+
+		// Run the watch task again after the tasks, to wait for the next changes.
+		grunt.task.run( getTasks( runningTargets ).concat( nameArgs ) );
+		done();
+	}
+
+	/**
+	 * Restarts the watch task in a new process, so that it loads the changed configuration.
+	 */
+	function restart() {
+		grunt.log.writeln( 'Reloading watch config...'.cyan );
+
+		/*
+		 * Keep watching until the new process is ready, which can take several seconds for its initial scan, and
+		 * hand it the changes seen meanwhile, which it would otherwise miss.
+		 */
+		handOffChanges = [];
+
+		const child = spawn(
+			process.execPath,
+			process.execArgv.concat( process.argv[ 1 ], nameArgs, grunt.option.flags() ),
+			{
+				stdio: [ 'inherit', 'inherit', 'inherit', 'ipc' ],
+				env: { ...process.env, [ HAND_OFF_ENV ]: '1' },
+			}
+		);
+		child.on( 'message', ( message ) => {
+			if ( ! message || 'watch-ready' !== message.type ) {
+				return;
+			}
+			watcher.close();
+			child.send( { type: 'watch-changes', changes: handOffChanges }, () => child.disconnect() );
+			handOffChanges = [];
+		} );
+		child.on( 'exit', ( code ) => process.exit( code === null ? 1 : code ) );
+
+		// Stop the new process with this one, which only waits for it.
+		[ 'SIGINT', 'SIGTERM', 'SIGHUP' ].forEach( ( signal ) => {
+			process.on( signal, () => child.kill( signal ) );
+		} );
+	}
+
+	/**
+	 * Takes over the changes that the previous watch process saw while this one started, when started by a reload.
+	 *
+	 * The previous process keeps watching until this one reports that it is ready, then hands over its changes.
+	 */
+	function takeOverChanges() {
+		if ( ! process.send || ! process.env[ HAND_OFF_ENV ] ) {
+			return;
+		}
+
+		process.on( 'message', ( message ) => {
+			if ( message && 'watch-changes' === message.type ) {
+				message.changes.forEach( ( [ event, filepath ] ) => recordChange( event, filepath ) );
+			}
+		} );
+		process.send( { type: 'watch-ready' } );
+	}
+
+	/**
+	 * Keeps the watch task running when a task fails, instead of exiting.
+	 *
+	 * The failure is logged, and the watch task resumes, waiting for the next changes.
+	 */
+	function keepWatchingOnFailure() {
+		/*
+		 * Exit once the output can no longer be written, as when the terminal is closed. Otherwise, the error
+		 * of each attempt to log would be reported as another failure, without end.
+		 */
+		[ process.stdout, process.stderr ].forEach( ( stream ) => {
+			stream.on( 'error', ( error ) => {
+				if ( error.code === 'EPIPE' ) {
+					process.exit( 1 );
+				}
+			} );
+		} );
+
+		/*
+		 * Skip the rest of the failed target's tasks, but still run those of the other targets in the run.
+		 */
+		function rerun() {
+			runningTargets = runningTargets.filter( ( running ) => running !== currentTarget );
+			currentTarget = null;
+			grunt.task.clearQueue();
+			grunt.task.run( getTasks( runningTargets ).concat( nameArgs ) );
+		}
+
+		/*
+		 * Unlike grunt's own handlers, which exit, these return to the failed task, which can then fail again on
+		 * the result it did not get, as grunt-contrib-uglify does after "Uglification failed.". Only the first
+		 * failure is reported, until the next task starts.
+		 */
+		function reportFailure( prefix, error ) {
+			const message = prefix + ( typeof error === 'string' ? error : error.message );
+
+			if ( failureReported ) {
+				grunt.verbose.writeln( message );
+				return;
+			}
+			failureReported = true;
+			grunt.log.writeln( 'Fatal error: ' === prefix ? message.red : message.yellow );
+			rerun();
+		}
+
+		grunt.warn = grunt.fail.warn = ( error ) => {
+			if ( grunt.option( 'force' ) ) {
+				grunt.log.writeln( ( 'Warning: ' + ( typeof error === 'string' ? error : error.message ) ).yellow );
+				return;
+			}
+			reportFailure( 'Warning: ', error );
+		};
+		grunt.fatal = grunt.fail.fatal = ( error ) => {
+			reportFailure( 'Fatal error: ', error );
+		};
+	}
+
+	/**
+	 * Starts watching the files of the targets.
+	 *
+	 * @param {Function} onReady Called once the initial scan is complete.
+	 */
+	function startWatching( onReady ) {
+		// Compiled once, as every path found is checked against them.
+		const ignored = ( grunt.config( [ taskName, 'options', 'ignored' ] ) || [] )
+			.flatMap(
+				// Match each ignored directory itself, so that it is not searched.
+				( pattern ) => pattern.endsWith( '/**' ) ? [ pattern, pattern.slice( 0, -3 ) ] : [ pattern ]
+			)
+			// Grunt's own minimatch, which it provides for its file matching.
+			.map( ( pattern ) => new grunt.file.minimatch.Minimatch( pattern, { dot: true } ) );
+		const patterns = targetNames.flatMap( ( name ) => getTarget( name ).files );
+
+		watcher = chokidar.watch( getWatchPaths( patterns ), {
+			ignoreInitial: true,
+			ignored: ( filepath ) => {
+				const relative = path.relative( process.cwd(), filepath ).replace( /\\/g, '/' );
+				return ignored.some( ( matcher ) => matcher.match( relative ) );
+			},
+		} );
+
+		watcher.on( 'all', recordChange );
+		watcher.on( 'error', ( error ) => grunt.log.error( 'Watch error: ' + error.message ) );
+		watcher.once( 'ready', onReady );
+	}
+
+	return function( target ) {
+		const config = grunt.config( this.name ) || {};
+
+		taskName = this.name;
+		nameArgs = this.nameArgs;
+		resume = this.async();
+		failureReported = false;
+
+		if ( watcher ) {
+			if ( startedAt ) {
+				grunt.log.writeln( ( 'Completed in ' + ( ( Date.now() - startedAt ) / 1000 ).toFixed( 3 ) + 's at ' + new Date().toString() ).cyan + ' - Waiting...' );
+				startedAt = null;
+			}
+
+			// Run the changes made while the tasks ran, now or once the debounce timer fires, before any restart.
+			if ( changes.size ) {
+				if ( ! timer ) {
+					runQueued();
+				}
+				return;
+			}
+
+			if ( restartPending ) {
+				restart();
+			}
+			return;
+		}
+
+		targetNames = target ? [ target ] : Object.keys( config ).filter( ( name ) => name !== 'options' );
+		const missing = targetNames.filter( ( name ) => ! config[ name ] );
+		if ( missing.length ) {
+			grunt.fail.warn( 'No "' + this.name + '" targets found: ' + missing.join( ', ' ) );
+			return;
+		}
+
+		keepWatchingOnFailure();
+		startWatching( () => {
+			grunt.log.writeln( 'Waiting...' );
+			takeOverChanges();
+		} );
+	};
+};