diff --git a/plugins/woocommerce/changelog/51014-e2e-external-sites-update-merchant-tests-pt1 b/plugins/woocommerce/changelog/51014-e2e-external-sites-update-merchant-tests-pt1
new file mode 100644
index 00000000000..180673a625b
--- /dev/null
+++ b/plugins/woocommerce/changelog/51014-e2e-external-sites-update-merchant-tests-pt1
@@ -0,0 +1,4 @@
+Significance: patch
+Type: update
+
+Update /merchant tests (first five files), so they are passing against Pressable env.
\ No newline at end of file
diff --git a/plugins/woocommerce/tests/e2e-pw/envs/default-pressable/playwright.config.js b/plugins/woocommerce/tests/e2e-pw/envs/default-pressable/playwright.config.js
index 988e4d3bbea..b0747f37c30 100644
--- a/plugins/woocommerce/tests/e2e-pw/envs/default-pressable/playwright.config.js
+++ b/plugins/woocommerce/tests/e2e-pw/envs/default-pressable/playwright.config.js
@@ -16,6 +16,11 @@ config = {
 				'**/admin-marketing/**/*.spec.js',
 				'**/admin-tasks/**/*.spec.js',
 				'**/customize-store/**/*.spec.js',
+				'**/merchant/command-palette.spec.js',
+				'**/merchant/create-cart-block.spec.js',
+				'**/merchant/create-checkout-block.spec.js',
+				'**/merchant/create-coupon.spec.js',
+				'**/merchant/create-order.spec.js',
 			],
 			grepInvert: /@skip-on-default-pressable/,
 		},
diff --git a/plugins/woocommerce/tests/e2e-pw/tests/merchant/create-cart-block.spec.js b/plugins/woocommerce/tests/e2e-pw/tests/merchant/create-cart-block.spec.js
index b262e740846..1f612946ce5 100644
--- a/plugins/woocommerce/tests/e2e-pw/tests/merchant/create-cart-block.spec.js
+++ b/plugins/woocommerce/tests/e2e-pw/tests/merchant/create-cart-block.spec.js
@@ -5,6 +5,7 @@ const {
 	insertBlock,
 	transformIntoBlocks,
 	publishPage,
+	closeChoosePatternModal,
 } = require( '../../utils/editor' );
 const { getInstalledWordPressVersion } = require( '../../utils/wordpress' );
 
@@ -23,6 +24,8 @@ test.describe(
 		} ) => {
 			await goToPageEditor( { page } );
 
+			await closeChoosePatternModal( { page } );
+
 			await fillPageTitle( page, testPage.title );
 			const wordPressVersion = await getInstalledWordPressVersion();
 			await insertBlock( page, 'Classic Cart', wordPressVersion );
diff --git a/plugins/woocommerce/tests/e2e-pw/tests/merchant/create-checkout-block.spec.js b/plugins/woocommerce/tests/e2e-pw/tests/merchant/create-checkout-block.spec.js
index 23317b1a834..53479325a1b 100644
--- a/plugins/woocommerce/tests/e2e-pw/tests/merchant/create-checkout-block.spec.js
+++ b/plugins/woocommerce/tests/e2e-pw/tests/merchant/create-checkout-block.spec.js
@@ -7,6 +7,7 @@ const {
 	transformIntoBlocks,
 	publishPage,
 	openEditorSettings,
+	closeChoosePatternModal,
 } = require( '../../utils/editor' );
 const { getInstalledWordPressVersion } = require( '../../utils/wordpress' );
 
@@ -74,6 +75,8 @@ test.describe(
 		} ) => {
 			await goToPageEditor( { page } );
 
+			await closeChoosePatternModal( { page } );
+
 			await fillPageTitle( page, testPage.title );
 			const wordPressVersion = await getInstalledWordPressVersion();
 			await insertBlock( page, 'Classic Checkout', wordPressVersion );
diff --git a/plugins/woocommerce/tests/e2e-pw/tests/merchant/create-coupon.spec.js b/plugins/woocommerce/tests/e2e-pw/tests/merchant/create-coupon.spec.js
index 2630674a42b..785f5c0d6b3 100644
--- a/plugins/woocommerce/tests/e2e-pw/tests/merchant/create-coupon.spec.js
+++ b/plugins/woocommerce/tests/e2e-pw/tests/merchant/create-coupon.spec.js
@@ -35,7 +35,15 @@ const test = baseTest.extend( {
 	coupon: async ( { api }, use ) => {
 		const coupon = {};
 		await use( coupon );
-		await api.delete( `coupons/${ coupon.id }`, { force: true } );
+		await api
+			.delete( `coupons/${ coupon.id }`, { force: true } )
+			.then( ( response ) => {
+				console.log( 'Delete successful:', response.data );
+			} )
+			.catch( ( error ) => {
+				console.log( 'Error response data:', error.response.data );
+				throw new Error( error.response.data );
+			} );
 	},
 } );
 
diff --git a/plugins/woocommerce/tests/e2e-pw/tests/merchant/create-order.spec.js b/plugins/woocommerce/tests/e2e-pw/tests/merchant/create-order.spec.js
index aa33c49f167..087e95556b7 100644
--- a/plugins/woocommerce/tests/e2e-pw/tests/merchant/create-order.spec.js
+++ b/plugins/woocommerce/tests/e2e-pw/tests/merchant/create-order.spec.js
@@ -299,10 +299,17 @@ test.describe(
 			await page
 				.getByRole( 'textbox', { name: 'Postcode' } )
 				.fill( '12345' );
-			await page
-				.getByRole( 'textbox', { name: 'Select an option…' } )
-				.click();
-			await page.getByRole( 'option', { name: 'Florida' } ).click();
+			// eslint-disable-next-line playwright/no-conditional-in-test
+			if (
+				await page
+					.getByRole( 'textbox', { name: 'Select an option…' } )
+					.isVisible()
+			) {
+				await page
+					.getByRole( 'textbox', { name: 'Select an option…' } )
+					.click();
+				await page.getByRole( 'option', { name: 'Florida' } ).click();
+			}
 			await page
 				.getByRole( 'textbox', { name: 'Email address' } )
 				.fill( 'elbarto@example.com' );