diff --git a/src/js/_enqueues/wp/updates.js b/src/js/_enqueues/wp/updates.js
index ef4b47e66093e..ea0039fd4512f 100644
--- a/src/js/_enqueues/wp/updates.js
+++ b/src/js/_enqueues/wp/updates.js
@@ -2515,6 +2515,10 @@
 			} else if ( 'themes' === pagenow || 'themes-network' === pagenow ) {
 				if ( 'update-theme' === job.action ) {
 					$message = $( '[data-slug="' + job.data.slug + '"]' ).find( '.update-message' );
+
+					if ( 'themes' === pagenow ) {
+						$message = $message.add( $( '#update-theme' ).closest( '.notice' ) );
+					}
 				} else if ( 'delete-theme' === job.action && 'themes-network' === pagenow ) {
 					$message = $( '[data-slug="' + job.data.slug + '"]' ).find( '.row-actions a.delete' );
 				} else if ( 'delete-theme' === job.action && 'themes' === pagenow ) {
diff --git a/tests/qunit/wp-admin/js/updates.js b/tests/qunit/wp-admin/js/updates.js
index 9d3948811abfd..6c10a8fea868f 100644
--- a/tests/qunit/wp-admin/js/updates.js
+++ b/tests/qunit/wp-admin/js/updates.js
@@ -158,6 +158,46 @@ jQuery( function( $ ) {
 		assert.equal( jQuery.ajax.getCall( 0 ).args[0].data.slug, 'twentyeleven' );
 	} );
 
+	QUnit.test( 'Canceling the credentials modal restores the theme details notice', function( assert ) {
+		var overlayNotice = $(
+				'<div class="notice notice-warning notice-alt notice-large" data-slug="twentyeleven">' +
+					'<h3 class="notice-title">Update Available</h3>' +
+					'<p><strong>There is a new version of Twenty Eleven available. <a id="update-theme" data-slug="twentyeleven" href="#">update now</a>.</strong></p>' +
+				'</div>'
+			).appendTo( '#qunit-fixture' ),
+			eventTarget = overlayNotice.find( '#update-theme' ),
+			rowNotice = $(
+				'<div class="theme" data-slug="twentyeleven">' +
+					'<div class="update-message notice inline notice-warning notice-alt">' +
+						'<p><strong>There is a new version of Twenty Eleven available. <a href="#">update now</a>.</strong></p>' +
+					'</div>' +
+				'</div>'
+			).appendTo( '#qunit-fixture' );
+
+		$( '<div id="request-filesystem-credentials-dialog"><form id="request-filesystem-credentials-form"></form></div>' )
+			.appendTo( '#qunit-fixture' );
+
+		wp.updates.shouldRequestFilesystemCredentials = true;
+		wp.updates.filesystemCredentials.available = false;
+
+		wp.updates.maybeRequestFilesystemCredentials( $.Event( 'click', {
+			target: eventTarget[0]
+		} ) );
+
+		wp.updates.updateTheme( { slug: 'twentyeleven' } );
+
+		assert.strictEqual( wp.updates.queue.length, 1, 'Theme update waits for credentials.' );
+		assert.true( overlayNotice.hasClass( 'updating-message' ), 'Overlay notice is marked as updating.' );
+		assert.true( rowNotice.find( '.update-message' ).hasClass( 'updating-message' ), 'Theme row notice is marked as updating.' );
+
+		wp.updates.requestForCredentialsModalCancel();
+
+		assert.false( overlayNotice.hasClass( 'updating-message' ), 'Overlay notice resets after cancel.' );
+		assert.false( rowNotice.find( '.update-message' ).hasClass( 'updating-message' ), 'Theme row notice resets after cancel.' );
+		assert.notStrictEqual( overlayNotice.text().indexOf( 'Updating...' ), 0, 'Overlay notice no longer shows the updating text.' );
+		assert.notStrictEqual( rowNotice.text().indexOf( 'Updating...' ), 0, 'Theme row notice no longer shows the updating text.' );
+	} );
+
 	QUnit.test( 'Installing a theme should call the API', function( assert ) {
 		wp.updates.installTheme( { slug: 'twentyeleven' } );
 		assert.ok( jQuery.ajax.calledOnce );
diff --git a/tools/gutenberg/download.js b/tools/gutenberg/download.js
index fd76c6c7a7836..687552c66ccb5 100644
--- a/tools/gutenberg/download.js
+++ b/tools/gutenberg/download.js
@@ -27,6 +27,7 @@ const zlib = require( 'zlib' );
 const {
 	gutenbergDir,
 	readGutenbergConfig,
+	fetchWithRetry,
 	fetchGhcrToken,
 	fetchManifest,
 } = require( './utils' );
@@ -151,11 +152,15 @@ async function main() {
 	 */
 	console.log( `\n📥 Downloading and extracting artifact...` );
 	try {
-		const response = await fetch( `https://ghcr.io/v2/${ config.ghcrRepo }/blobs/${ digest }`, {
-			headers: {
-				Authorization: `Bearer ${ token }`,
+		const response = await fetchWithRetry(
+			`https://ghcr.io/v2/${ config.ghcrRepo }/blobs/${ digest }`,
+			{
+				headers: {
+					Authorization: `Bearer ${ token }`,
+				},
 			},
-		} );
+			`blob ${ digest }`
+		);
 		if ( ! response.ok ) {
 			throw new Error( `Failed to download blob: ${ response.status } ${ response.statusText }` );
 		}
diff --git a/tools/gutenberg/utils.js b/tools/gutenberg/utils.js
index 43047b5ee5dd7..763ed800ef53f 100644
--- a/tools/gutenberg/utils.js
+++ b/tools/gutenberg/utils.js
@@ -25,6 +25,82 @@ const hashFilePath = path.join( gutenbergDir, '.gutenberg-hash' );
 const SHA_PATTERN = /^[a-f0-9]{40}$/i;
 
 const MANIFEST_ACCEPT = 'application/vnd.oci.image.manifest.v1+json';
+const RETRYABLE_HTTP_STATUSES = new Set( [ 429, 500, 502, 503, 504 ] );
+const MAX_FETCH_RETRIES = 3;
+const RETRY_DELAY_MS = 1000;
+
+/**
+ * Pause execution for a short duration between transient fetch retries.
+ *
+ * @param {number} delayMs Delay in milliseconds.
+ * @return {Promise<void>}
+ */
+function sleep( delayMs ) {
+	return new Promise( ( resolve ) => {
+		setTimeout( resolve, delayMs );
+	} );
+}
+
+/**
+ * Determine whether a fetch failure should be retried.
+ *
+ * @param {Response | undefined} response Fetch response when available.
+ * @param {unknown} error Fetch error when the request failed before a response.
+ * @return {boolean} Whether the failure appears transient.
+ */
+function shouldRetryFetch( response, error ) {
+	if ( response ) {
+		return RETRYABLE_HTTP_STATUSES.has( response.status );
+	}
+
+	return error instanceof TypeError;
+}
+
+/**
+ * Fetch a URL with retries for transient GHCR and network failures.
+ *
+ * @param {string} url Request URL.
+ * @param {RequestInit} options Fetch options.
+ * @param {string} resourceLabel Human-readable resource name for logs.
+ * @return {Promise<Response>} The successful or final response.
+ */
+async function fetchWithRetry( url, options, resourceLabel ) {
+	let lastError;
+
+	for ( let attempt = 1; attempt <= MAX_FETCH_RETRIES; attempt++ ) {
+		let response;
+
+		try {
+			response = await fetch( url, options );
+		} catch ( error ) {
+			lastError = error;
+
+			if ( attempt === MAX_FETCH_RETRIES || ! shouldRetryFetch( undefined, error ) ) {
+				throw error;
+			}
+
+			console.warn(
+				`Retrying ${ resourceLabel } after network failure (${ attempt }/${ MAX_FETCH_RETRIES })...`
+			);
+			await sleep( RETRY_DELAY_MS * attempt );
+			continue;
+		}
+
+		if ( response.ok || ! shouldRetryFetch( response, undefined ) || attempt === MAX_FETCH_RETRIES ) {
+			return response;
+		}
+
+		lastError = new Error(
+			`Failed to fetch ${ resourceLabel }: ${ response.status } ${ response.statusText }`
+		);
+		console.warn(
+			`Retrying ${ resourceLabel } after ${ response.status } ${ response.statusText } (${ attempt }/${ MAX_FETCH_RETRIES })...`
+		);
+		await sleep( RETRY_DELAY_MS * attempt );
+	}
+
+	throw lastError;
+}
 
 /**
  * Read Gutenberg configuration from package.json.
@@ -64,8 +140,10 @@ function readGutenbergConfig() {
  * @return {Promise<string>} The bearer token.
  */
 async function fetchGhcrToken( ghcrRepo ) {
-	const response = await fetch(
-		`https://ghcr.io/token?scope=repository:${ ghcrRepo }:pull&service=ghcr.io`
+	const response = await fetchWithRetry(
+		`https://ghcr.io/token?scope=repository:${ ghcrRepo }:pull&service=ghcr.io`,
+		{},
+		'GHCR token'
 	);
 	if ( ! response.ok ) {
 		throw new Error(
@@ -88,14 +166,15 @@ async function fetchGhcrToken( ghcrRepo ) {
  * @return {Promise<Record<string, any>>} Parsed manifest JSON.
  */
 async function fetchManifest( ref, ghcrRepo, token ) {
-	const response = await fetch(
+	const response = await fetchWithRetry(
 		`https://ghcr.io/v2/${ ghcrRepo }/manifests/${ ref }`,
 		{
 			headers: {
 				Authorization: `Bearer ${ token }`,
 				Accept: MANIFEST_ACCEPT,
 			},
-		}
+		},
+		`manifest for "${ ref }"`
 	);
 	if ( ! response.ok ) {
 		const error = /** @type {Error & { status?: number }} */ (
@@ -241,6 +320,7 @@ module.exports = {
 	gutenbergDir,
 	readGutenbergConfig,
 	verifyGutenbergVersion,
+	fetchWithRetry,
 	fetchGhcrToken,
 	fetchManifest,
 	resolveExpectedSha,
diff --git a/tools/local-env/scripts/install.js b/tools/local-env/scripts/install.js
index 038ecc3a67d5e..cba7f1169e3ad 100644
--- a/tools/local-env/scripts/install.js
+++ b/tools/local-env/scripts/install.js
@@ -9,8 +9,8 @@ const local_env_utils = require( './utils' );
 
 dotenvExpand.expand( dotenv.config() );
 
-// Create wp-config.php.
-wp_cli( `config create --dbname=wordpress_develop --dbuser=root --dbpass=password --dbhost=mysql --force --config-file="wp-config.php"` );
+// Create wp-config.php without waiting on the database to accept connections.
+wp_cli( `config create --dbname=wordpress_develop --dbuser=root --dbpass=password --dbhost=mysql --skip-check --force --config-file="wp-config.php"` );
 
 // Add the debug settings to wp-config.php.
 // Windows requires this to be done as an additional step, rather than using the --extra-php option in the previous step.
diff --git a/tools/local-env/scripts/start.js b/tools/local-env/scripts/start.js
index 66559d4c10b85..caef49de2bf14 100644
--- a/tools/local-env/scripts/start.js
+++ b/tools/local-env/scripts/start.js
@@ -5,6 +5,12 @@ const dotenvExpand = require( 'dotenv-expand' );
 const { execSync, spawnSync } = require( 'child_process' );
 const local_env_utils = require( './utils' );
 const { constants, copyFile } = require( 'node:fs' );
+const RETRYABLE_DOCKER_PULL_ERRORS = [
+	'context deadline exceeded',
+	'Client.Timeout exceeded while awaiting headers',
+	'request canceled while waiting for connection',
+];
+const MAX_DOCKER_START_ATTEMPTS = 3;
 
 // Copy the default .env file when one is not present.
 copyFile( '.env.example', '.env', constants.COPYFILE_EXCL, () => {
@@ -32,18 +38,46 @@ if ( process.env.LOCAL_PHP_MEMCACHED === 'true' ) {
 	containers.push( 'memcached' );
 }
 
-spawnSync(
-	'docker',
-	[
-		'compose',
-		...composeFiles.map( ( composeFile ) => [ '-f', composeFile ] ).flat(),
-		'up',
-		'--quiet-pull',
-		'-d',
-		...containers,
-	],
-	{ stdio: 'inherit' }
-);
+let dockerUpResult;
+for ( let attempt = 1; attempt <= MAX_DOCKER_START_ATTEMPTS; attempt++ ) {
+	dockerUpResult = spawnSync(
+		'docker',
+		[
+			'compose',
+			...composeFiles.map( ( composeFile ) => [ '-f', composeFile ] ).flat(),
+			'up',
+			'--quiet-pull',
+			'-d',
+			...containers,
+		],
+		{ encoding: 'utf8' }
+	);
+
+	if ( dockerUpResult.stdout ) {
+		process.stdout.write( dockerUpResult.stdout );
+	}
+
+	if ( dockerUpResult.stderr ) {
+		process.stderr.write( dockerUpResult.stderr );
+	}
+
+	if ( dockerUpResult.status === 0 ) {
+		break;
+	}
+
+	const output = `${ dockerUpResult.stdout || '' }\n${ dockerUpResult.stderr || '' }`;
+	const isRetryable = RETRYABLE_DOCKER_PULL_ERRORS.some( ( errorText ) =>
+		output.includes( errorText )
+	);
+
+	if ( ! isRetryable || attempt === MAX_DOCKER_START_ATTEMPTS ) {
+		process.exit( dockerUpResult.status || 1 );
+	}
+
+	console.warn(
+		`Retrying Docker environment startup after transient registry failure (${ attempt }/${ MAX_DOCKER_START_ATTEMPTS })...`
+	);
+}
 
 // If Docker Toolbox is being used, we need to manually forward LOCAL_PORT to the Docker VM.
 if ( process.env.DOCKER_TOOLBOX_INSTALL_PATH ) {