fix: (cy.prompt) add more context to the error message shown when cy.prompt() fails to download

Author: ryanthemanuel

cli/CHANGELOG.md

@@ -10,6 +10,7 @@ _Released 10/20/2025 (PENDING)_
 **Bugfixes:**
 
 - Fixes 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).
+- Added more context to the error message shown when `cy.prompt()` fails to download. Addressed in [#](https://github.com/cypress-io/cypress/pull/).
 
 **Misc:**
 

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,
@@ -99,15 +101,15 @@ export class CyPromptLifecycleManager {
         additionalHeaders: cloudHeaders,
         cyPromptHash: this.cyPromptHash,
         projectSlug: (await ctx.project.getConfig()).projectId || undefined,
-        error,
+        error: lastError,
         cyPromptMethod: 'initializeCyPromptManager',
         cyPromptMethodArgs: [],
       })
 
       // Clean up any registered listeners
       this.listeners = []
 
-      return { error }
+      return { error: lastError }
     })
 
     this.cyPromptManagerPromise = cyPromptManagerPromise

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', () => {