diff --git a/plugins/woocommerce/changelog/update-48533-account-creation-settings b/plugins/woocommerce/changelog/update-48533-account-creation-settings
new file mode 100644
index 00000000000..63db9e1ae21
--- /dev/null
+++ b/plugins/woocommerce/changelog/update-48533-account-creation-settings
@@ -0,0 +1,4 @@
+Significance: patch
+Type: update
+
+Updated account settings descriptions for added clarity
diff --git a/plugins/woocommerce/client/legacy/css/admin.scss b/plugins/woocommerce/client/legacy/css/admin.scss
index 05e415f90c7..7b63dd7cca8 100644
--- a/plugins/woocommerce/client/legacy/css/admin.scss
+++ b/plugins/woocommerce/client/legacy/css/admin.scss
@@ -5173,6 +5173,10 @@ img.help_tip {
 			float: none;
 		}
 
+		td.disabled {
+			opacity: 0.5;
+		}
+
 		fieldset {
 			margin-top: 4px;
 
@@ -5255,6 +5259,13 @@ img.help_tip {
 		.wc_emails_wrapper {
 			padding: 0 15px 10px 0;
 		}
+
+		legend {
+			font-weight: 700;
+			line-height: 1.4;
+			padding: 5px 0 0;
+			margin: 0 0 8px !important;
+		}
 	}
 
 	.wc-shipping-zone-settings {
diff --git a/plugins/woocommerce/includes/admin/class-wc-admin-settings.php b/plugins/woocommerce/includes/admin/class-wc-admin-settings.php
index e635fce0824..a5f0de69566 100644
--- a/plugins/woocommerce/includes/admin/class-wc-admin-settings.php
+++ b/plugins/woocommerce/includes/admin/class-wc-admin-settings.php
@@ -47,7 +47,7 @@ if ( ! class_exists( 'WC_Admin_Settings', false ) ) :
 			if ( empty( self::$settings ) ) {
 				$settings = array();
 
-				include_once dirname( __FILE__ ) . '/settings/class-wc-settings-page.php';
+				include_once __DIR__ . '/settings/class-wc-settings-page.php';
 
 				$settings[] = include __DIR__ . '/settings/class-wc-settings-general.php';
 				$settings[] = include __DIR__ . '/settings/class-wc-settings-products.php';
@@ -153,7 +153,7 @@ if ( ! class_exists( 'WC_Admin_Settings', false ) ) :
 			// Get tabs for the settings page.
 			$tabs = apply_filters( 'woocommerce_settings_tabs_array', array() );
 
-			include dirname( __FILE__ ) . '/views/html-admin-settings.php';
+			include __DIR__ . '/views/html-admin-settings.php';
 		}
 
 		/**
@@ -514,11 +514,19 @@ if ( ! class_exists( 'WC_Admin_Settings', false ) ) :
 							$visibility_class[] = $value['row_class'];
 						}
 
+						$must_disable = $value['disabled'] ?? false;
+
+						if ( $must_disable ) {
+							$visibility_class[] = 'disabled';
+						}
+
 						$container_class = implode( ' ', $visibility_class );
-						$must_disable    = $value['disabled'] ?? false;
+						$has_title       = isset( $value['title'] ) && '' !== $value['title'];
+						$has_legend      = isset( $value['legend'] ) && '' !== $value['legend'];
 
 						if ( ! isset( $value['checkboxgroup'] ) || 'start' === $value['checkboxgroup'] ) {
-							$has_tooltip             = isset( $value['tooltip'] ) && '' !== $value['tooltip'];
+							$has_tooltip = isset( $value['tooltip'] ) && '' !== $value['tooltip'];
+
 							$tooltip_container_class = $has_tooltip ? 'with-tooltip' : '';
 							?>
 								<tr class="<?php echo esc_attr( $container_class ); ?>">
@@ -535,9 +543,9 @@ if ( ! class_exists( 'WC_Admin_Settings', false ) ) :
 							<?php
 						}
 
-						if ( ! empty( $value['title'] ) ) {
+						if ( $has_title || $has_legend ) {
 							?>
-								<legend class="screen-reader-text"><span><?php echo esc_html( $value['title'] ); ?></span></legend>
+								<legend class="<?php echo $has_legend ? '' : 'screen-reader-text'; ?>"><span><?php echo esc_html( $has_legend ? $value['legend'] : $value['title'] ); ?></span></legend>
 							<?php
 						}
 
@@ -550,7 +558,6 @@ if ( ! class_exists( 'WC_Admin_Settings', false ) ) :
 									type="checkbox"
 									class="<?php echo esc_attr( isset( $value['class'] ) ? $value['class'] : '' ); ?>"
 									value="1"
-									<?php disabled( $value['disabled'] ?? false ); ?>
 									<?php checked( $option_value, 'yes' ); ?>
 									<?php echo implode( ' ', $custom_attributes ); // WPCS: XSS ok. ?>
 								/> <?php echo $description; // WPCS: XSS ok. ?>
diff --git a/plugins/woocommerce/includes/admin/settings/class-wc-settings-accounts.php b/plugins/woocommerce/includes/admin/settings/class-wc-settings-accounts.php
index be1c1dd71f7..b8c18059943 100644
--- a/plugins/woocommerce/includes/admin/settings/class-wc-settings-accounts.php
+++ b/plugins/woocommerce/includes/admin/settings/class-wc-settings-accounts.php
@@ -50,8 +50,9 @@ class WC_Settings_Accounts extends WC_Settings_Page {
 				'id'    => 'account_registration_options',
 			),
 			array(
-				'title'         => __( 'Guest checkout', 'woocommerce' ),
-				'desc'          => __( 'Allow customers to place orders without an account', 'woocommerce' ),
+				'title'         => __( 'Checkout', 'woocommerce' ),
+				'desc'          => __( 'Enable guest checkout (recommended)', 'woocommerce' ),
+				'desc_tip'      => __( 'Allows customers to checkout without an account.', 'woocommerce' ),
 				'id'            => 'woocommerce_enable_guest_checkout',
 				'default'       => 'yes',
 				'type'          => 'checkbox',
@@ -60,7 +61,7 @@ class WC_Settings_Accounts extends WC_Settings_Page {
 			),
 			array(
 				'title'         => __( 'Login', 'woocommerce' ),
-				'desc'          => __( 'Allow customers to log into an existing account during checkout', 'woocommerce' ),
+				'desc'          => __( 'Enable log-in during checkout', 'woocommerce' ),
 				'id'            => 'woocommerce_enable_checkout_login_reminder',
 				'default'       => 'no',
 				'type'          => 'checkbox',
@@ -69,31 +70,38 @@ class WC_Settings_Accounts extends WC_Settings_Page {
 			),
 			array(
 				'title'         => __( 'Account creation', 'woocommerce' ),
-				'desc'          => __( 'Allow customers to create an account during checkout', 'woocommerce' ),
+				'desc'          => __( 'During checkout', 'woocommerce' ),
+				'desc_tip'      => __( 'Customers can create an account before placing their order.', 'woocommerce' ),
 				'id'            => 'woocommerce_enable_signup_and_login_from_checkout',
 				'default'       => 'no',
 				'type'          => 'checkbox',
 				'checkboxgroup' => 'start',
+				'legend'        => __( 'Allow customers to create an account:', 'woocommerce' ),
+				'autoload'      => false,
+			),
+			array(
+				'title'         => __( 'Account creation', 'woocommerce' ),
+				'desc'          => __( 'On "My account" page', 'woocommerce' ),
+				'id'            => 'woocommerce_enable_myaccount_registration',
+				'default'       => 'no',
+				'type'          => 'checkbox',
+				'checkboxgroup' => 'end',
+				'autoload'      => false,
+			),
+			array(
+				'title'         => __( 'Account creation options', 'woocommerce' ),
+				'desc'          => __( 'Use email address as account login (recommended)', 'woocommerce' ),
+				'desc_tip'      => __( 'If unchecked, customers will need to set a username during account creation.', 'woocommerce' ),
+				'id'            => 'woocommerce_registration_generate_username',
+				'default'       => 'yes',
+				'type'          => 'checkbox',
+				'checkboxgroup' => 'start',
 				'autoload'      => false,
 			),
 			array(
-				'desc'          => __( 'Allow customers to create an account on the "My account" page', 'woocommerce' ),
-				'id'            => 'woocommerce_enable_myaccount_registration',
-				'default'       => 'no',
-				'type'          => 'checkbox',
-				'checkboxgroup' => '',
-				'autoload'      => false,
-			),
-			array(
-				'desc'          => __( 'When creating an account, automatically generate an account username for the customer based on their name, surname or email', 'woocommerce' ),
-				'id'            => 'woocommerce_registration_generate_username',
-				'default'       => 'yes',
-				'type'          => 'checkbox',
-				'checkboxgroup' => '',
-				'autoload'      => false,
-			),
-			array(
-				'desc'          => __( 'When creating an account, send the new user a link to set their password', 'woocommerce' ),
+				'title'         => __( 'Account creation options', 'woocommerce' ),
+				'desc'          => __( 'Send password setup link (recommended)', 'woocommerce' ),
+				'desc_tip'      => __( 'New customers receive an email to set up their password.', 'woocommerce' ),
 				'id'            => 'woocommerce_registration_generate_password',
 				'default'       => 'yes',
 				'type'          => 'checkbox',
@@ -118,7 +126,7 @@ class WC_Settings_Accounts extends WC_Settings_Page {
 				'id'            => 'woocommerce_erasure_request_removes_download_data',
 				'type'          => 'checkbox',
 				'default'       => 'no',
-				'checkboxgroup' => 'end',
+				'checkboxgroup' => '',
 				'autoload'      => false,
 			),
 			array(
@@ -127,7 +135,7 @@ class WC_Settings_Accounts extends WC_Settings_Page {
 				'desc_tip'      => __( 'Adds an option to the orders screen for removing personal data in bulk. Note that removing personal data cannot be undone.', 'woocommerce' ),
 				'id'            => 'woocommerce_allow_bulk_remove_personal_data',
 				'type'          => 'checkbox',
-				'checkboxgroup' => 'start',
+				'checkboxgroup' => 'end',
 				'default'       => 'no',
 				'autoload'      => false,
 			),
@@ -229,10 +237,49 @@ class WC_Settings_Accounts extends WC_Settings_Page {
 			),
 		);
 
-		return apply_filters(
-			'woocommerce_' . $this->id . '_settings',
-			$account_settings
-		);
+		/**
+		 * Filter account settings.
+		 *
+		 * @hook woocommerce_account_settings
+		 * @since 3.5.0
+		 * @param array $account_settings Account settings.
+		 */
+		return apply_filters( 'woocommerce_' . $this->id . '_settings', $account_settings );
+	}
+
+	/**
+	 * Output the HTML for the settings.
+	 */
+	public function output() {
+		parent::output();
+
+		// The following code toggles disabled state on the account options based on other values.
+		?>
+		<script type="text/javascript">
+			document.addEventListener('DOMContentLoaded', function() {
+				const checkboxes = [
+					document.getElementById("woocommerce_enable_signup_and_login_from_checkout"),
+					document.getElementById("woocommerce_enable_myaccount_registration"),
+					document.getElementById("woocommerce_enable_signup_from_checkout_for_subscriptions")
+				];
+				const inputs = [
+					document.getElementById("woocommerce_registration_generate_username"),
+					document.getElementById("woocommerce_registration_generate_password")
+				];
+
+				function updateInputs() {
+					const isChecked = checkboxes.some(cb => cb && cb.checked);
+					inputs.forEach(input => {
+						input.disabled = !isChecked;
+						input.closest('td').classList.toggle("disabled", !isChecked);
+					});
+				}
+
+				checkboxes.forEach(cb => cb.addEventListener('change', updateInputs));
+				updateInputs(); // Initial state
+			});
+		</script>
+		<?php
 	}
 }
 
diff --git a/plugins/woocommerce/tests/api-core-tests/tests/settings/settings-crud.test.js b/plugins/woocommerce/tests/api-core-tests/tests/settings/settings-crud.test.js
index b8de91dcc90..e22be453720 100644
--- a/plugins/woocommerce/tests/api-core-tests/tests/settings/settings-crud.test.js
+++ b/plugins/woocommerce/tests/api-core-tests/tests/settings/settings-crud.test.js
@@ -1334,9 +1334,8 @@ test.describe.serial( 'Settings API tests: CRUD', () => {
 				expect.arrayContaining( [
 					expect.objectContaining( {
 						id: 'woocommerce_enable_guest_checkout',
-						label: 'Guest checkout',
-						description:
-							'Allow customers to place orders without an account',
+						label: 'Checkout',
+						description: 'Enable guest checkout (recommended)',
 						type: 'checkbox',
 						default: 'yes',
 						value: 'yes',
@@ -1348,8 +1347,7 @@ test.describe.serial( 'Settings API tests: CRUD', () => {
 					expect.objectContaining( {
 						id: 'woocommerce_enable_checkout_login_reminder',
 						label: 'Login',
-						description:
-							'Allow customers to log into an existing account during checkout',
+						description: 'Enable log-in during checkout',
 						type: 'checkbox',
 						default: 'no',
 						value: 'no',
@@ -1361,8 +1359,7 @@ test.describe.serial( 'Settings API tests: CRUD', () => {
 					expect.objectContaining( {
 						id: 'woocommerce_enable_signup_and_login_from_checkout',
 						label: 'Account creation',
-						description:
-							'Allow customers to create an account during checkout',
+						description: 'During checkout',
 						type: 'checkbox',
 						default: 'no',
 						value: 'no',
@@ -1373,9 +1370,8 @@ test.describe.serial( 'Settings API tests: CRUD', () => {
 				expect.arrayContaining( [
 					expect.objectContaining( {
 						id: 'woocommerce_enable_myaccount_registration',
-						label: '',
-						description:
-							'Allow customers to create an account on the "My account" page',
+						label: 'Account creation',
+						description: 'On "My account" page',
 						type: 'checkbox',
 						default: 'no',
 						value: 'no',
@@ -1386,9 +1382,9 @@ test.describe.serial( 'Settings API tests: CRUD', () => {
 				expect.arrayContaining( [
 					expect.objectContaining( {
 						id: 'woocommerce_registration_generate_username',
-						label: '',
+						label: 'Account creation options',
 						description:
-							'When creating an account, automatically generate an account username for the customer based on their name, surname or email',
+							'Use email address as account login (recommended)',
 						type: 'checkbox',
 						default: 'yes',
 						value: 'yes',
@@ -1399,9 +1395,8 @@ test.describe.serial( 'Settings API tests: CRUD', () => {
 				expect.arrayContaining( [
 					expect.objectContaining( {
 						id: 'woocommerce_registration_generate_password',
-						label: '',
-						description:
-							'When creating an account, send the new user a link to set their password',
+						label: 'Account creation options',
+						description: 'Send password setup link (recommended)',
 						type: 'checkbox',
 						default: 'yes',
 						value: 'yes',