From e3d1d5b646eaf3c07fb8d253865c48af857683df Mon Sep 17 00:00:00 2001
From: Ryan Manuel <ryanm@cypress.io>
Date: Sat, 25 Oct 2025 07:19:20 -0500
Subject: [PATCH] fix: (cy.prompt) add more context to the error message shown
 when cy.prompt() fails to download (#32822)

---
 cli/CHANGELOG.md                              |  1 +
 .../cy-prompt/CyPromptLifecycleManager.ts     |  6 +-
 .../CyPromptLifecycleManager_spec.ts          | 79 +++++++++++++++++++
 3 files changed, 84 insertions(+), 2 deletions(-)

diff --git a/cli/CHANGELOG.md b/cli/CHANGELOG.md
index 4af8d8bd1c..734f96fa73 100644
--- a/cli/CHANGELOG.md
+++ b/cli/CHANGELOG.md
@@ -12,6 +12,7 @@ _Released 10/20/2025 (PENDING)_
 - Fixed an issue where grouped command text jumps up and down when expanding and collapsing in the command log. Addressed in [#32757](https://github.com/cypress-io/cypress/pull/32757).
 - Fixed an issue where command snapshots were not correctly displayed in Studio. Addressed in [#32808](https://github.com/cypress-io/cypress/pull/32808).
 - Fixed an issue with grouped console prop items having a hard to read blue color in the console log and duplicate `:` characters being displayed. Addressed in [#32776](https://github.com/cypress-io/cypress/pull/32776).
+- Added more context to the error message shown when `cy.prompt()` fails to download. Addressed in [#32822](https://github.com/cypress-io/cypress/pull/32822).
 
 **Misc:**
 
diff --git a/packages/server/lib/cloud/cy-prompt/CyPromptLifecycleManager.ts b/packages/server/lib/cloud/cy-prompt/CyPromptLifecycleManager.ts
index efb2a7cbd0..2fd5f212f8 100644
--- a/packages/server/lib/cloud/cy-prompt/CyPromptLifecycleManager.ts
+++ b/packages/server/lib/cloud/cy-prompt/CyPromptLifecycleManager.ts
@@ -88,6 +88,8 @@ export class CyPromptLifecycleManager {
       const cloudUrl = ctx.cloud.getCloudUrl(cloudEnv)
       const cloudHeaders = await ctx.cloud.additionalHeaders()
 
+      const lastError = error instanceof AggregateError ? error.errors[error.errors.length - 1] : error
+
       reportCyPromptError({
         cloudApi: {
           cloudUrl,
@@ -99,7 +101,7 @@ export class CyPromptLifecycleManager {
         additionalHeaders: cloudHeaders,
         cyPromptHash: this.cyPromptHash,
         projectSlug: (await ctx.project.getConfig()).projectId || undefined,
-        error,
+        error: lastError,
         cyPromptMethod: 'initializeCyPromptManager',
         cyPromptMethodArgs: [],
       })
@@ -107,7 +109,7 @@ export class CyPromptLifecycleManager {
       // Clean up any registered listeners
       this.listeners = []
 
-      return { error }
+      return { error: lastError }
     })
 
     this.cyPromptManagerPromise = cyPromptManagerPromise
diff --git a/packages/server/test/unit/cloud/cy-prompt/CyPromptLifecycleManager_spec.ts b/packages/server/test/unit/cloud/cy-prompt/CyPromptLifecycleManager_spec.ts
index 762981dda3..7ceae9b79c 100644
--- a/packages/server/test/unit/cloud/cy-prompt/CyPromptLifecycleManager_spec.ts
+++ b/packages/server/test/unit/cloud/cy-prompt/CyPromptLifecycleManager_spec.ts
@@ -566,6 +566,85 @@ describe('CyPromptLifecycleManager', () => {
         },
       })
     })
+
+    it('handles errors from ensureCyPromptBundle', async () => {
+      const actualError = new Error('Test error')
+
+      ensureCyPromptBundleStub.rejects(actualError)
+      cyPromptLifecycleManager.initializeCyPromptManager({
+        cloudDataSource: mockCloudDataSource,
+        ctx: mockCtx,
+        record: false,
+        key: '123e4567-e89b-12d3-a456-426614174000',
+      })
+
+      // @ts-expect-error - accessing private property
+      const cyPromptPromise = cyPromptLifecycleManager.cyPromptManagerPromise
+
+      expect(cyPromptPromise).to.not.be.null
+
+      const { error } = (await cyPromptPromise) as { error: Error }
+
+      expect(error.message).to.equal('Test error')
+
+      expect(reportCyPromptErrorStub).to.be.calledWith({
+        cloudApi: {
+          cloudUrl: 'https://cloud.cypress.io',
+          CloudRequest,
+          createCloudRequest,
+          isRetryableError,
+          asyncRetry,
+        },
+        cyPromptHash: 'abc',
+        projectSlug: 'test-project-id',
+        error: actualError,
+        cyPromptMethod: 'initializeCyPromptManager',
+        cyPromptMethodArgs: [],
+        additionalHeaders: {
+          'Authorization': 'Bearer test-token',
+        },
+      })
+    })
+
+    it('handles AggregateErrors from ensureCyPromptBundle', async () => {
+      const aggregateError = new AggregateError([new Error('Test error'), new Error('Second error')], 'Multiple errors')
+
+      ensureCyPromptBundleStub.rejects(aggregateError)
+
+      cyPromptLifecycleManager.initializeCyPromptManager({
+        cloudDataSource: mockCloudDataSource,
+        ctx: mockCtx,
+        record: false,
+        key: '123e4567-e89b-12d3-a456-426614174000',
+      })
+
+      // @ts-expect-error - accessing private property
+      const cyPromptPromise = cyPromptLifecycleManager.cyPromptManagerPromise
+
+      expect(cyPromptPromise).to.not.be.null
+
+      const { error } = (await cyPromptPromise) as { error: Error }
+
+      expect(error.message).to.equal('Second error')
+
+      expect(reportCyPromptErrorStub).to.be.calledWith({
+        cloudApi: {
+          cloudUrl: 'https://cloud.cypress.io',
+          CloudRequest,
+          createCloudRequest,
+          isRetryableError,
+          asyncRetry,
+        },
+        cyPromptHash: 'abc',
+        projectSlug: 'test-project-id',
+        error: aggregateError.errors[aggregateError.errors.length - 1],
+        cyPromptMethod: 'initializeCyPromptManager',
+        cyPromptMethodArgs: [],
+        additionalHeaders: {
+          'Authorization': 'Bearer test-token',
+        },
+      })
+    })
   })
 
   describe('getCyPrompt', () => {