diff --git a/packages/theme/src/cli/utilities/theme-environment/storefront-session.test.ts b/packages/theme/src/cli/utilities/theme-environment/storefront-session.test.ts
index 45bb5add6a..5d00ac6a27 100644
--- a/packages/theme/src/cli/utilities/theme-environment/storefront-session.test.ts
+++ b/packages/theme/src/cli/utilities/theme-environment/storefront-session.test.ts
@@ -80,12 +80,14 @@ describe('Storefront API', () => {
           response({
             status: 200,
             headers: {'set-cookie': ''},
+            text: () => Promise.resolve(''),
           }),
         )
         .mockResolvedValueOnce(
           response({
             status: 200,
             headers: {'set-cookie': 'storefront_digest=digest-value; path=/; HttpOnly'},
+            text: () => Promise.resolve(''),
           }),
         )
 
@@ -105,9 +107,15 @@ describe('Storefront API', () => {
           response({
             status: 200,
             headers: {'set-cookie': '_shopify_essential=:AABBCCDDEEFFGGHH==123:; path=/; HttpOnly'},
+            text: () => Promise.resolve(''),
+          }),
+        )
+        .mockResolvedValueOnce(
+          response({
+            status: 401,
+            text: () => Promise.resolve(''),
           }),
         )
-        .mockResolvedValueOnce(response({status: 401}))
 
       // When
       const cookies = getStorefrontSessionCookies('https://example-store.myshopify.com', '123456', 'wrongpassword')
@@ -121,7 +129,7 @@ describe('Storefront API', () => {
 
   // Tests rely on this function because the 'packages/theme' package cannot
   // directly access node-fetch and they use: new Response('OK', {status: 200})
-  function response(mock: {status: number; headers?: {[key: string]: string}}) {
+  function response(mock: {status: number; headers?: {[key: string]: string}; text?: () => Promise<string>}) {
     const setCookieHeader = (mock.headers ?? {})['set-cookie'] ?? ''
     const setCookieArray = [setCookieHeader]
 
diff --git a/packages/theme/src/cli/utilities/theme-environment/storefront-session.ts b/packages/theme/src/cli/utilities/theme-environment/storefront-session.ts
index 1ec68e338d..40748a12a3 100644
--- a/packages/theme/src/cli/utilities/theme-environment/storefront-session.ts
+++ b/packages/theme/src/cli/utilities/theme-environment/storefront-session.ts
@@ -2,6 +2,7 @@ import {parseCookies, serializeCookies} from './cookies.js'
 import {defaultHeaders} from './storefront-utils.js'
 import {fetch} from '@shopify/cli-kit/node/http'
 import {AbortError} from '@shopify/cli-kit/node/error'
+import {outputDebug} from '@shopify/cli-kit/node/output'
 
 export async function isStorefrontPasswordProtected(storeURL: string): Promise<boolean> {
   const response = await fetch(prependHttps(storeURL), {
@@ -104,6 +105,14 @@ async function sessionEssentialCookie(storeUrl: string, themeId: string, headers
   const setCookies = response.headers.raw()['set-cookie'] ?? []
   const shopifyEssential = getCookie(setCookies, '_shopify_essential')
 
+  if (!shopifyEssential) {
+    outputDebug(
+      `Failed to obtain _shopify_essential cookie.\n
+       -Request ID: ${response.headers.get('x-request-id') ?? 'unknown'}\n
+       -Body: ${await response.text()}`,
+    )
+  }
+
   return shopifyEssential
 }
 
@@ -129,6 +138,14 @@ async function enrichSessionWithStorefrontPassword(
   const setCookies = response.headers.raw()['set-cookie'] ?? []
   const storefrontDigest = getCookie(setCookies, 'storefront_digest')
 
+  if (!storefrontDigest) {
+    outputDebug(
+      `Failed to obtain storefront_digest cookie.\n
+       -Request ID: ${response.headers.get('x-request-id') ?? 'unknown'}\n
+       -Body: ${await response.text()}`,
+    )
+  }
+
   return storefrontDigest
 }