[CRITICAL] File upload completely broken - 404 error on all file uploads (claude.com web interface, mobile, desktop)

Preflight Checklist

• [x] I have searched existing issues and this hasn't been reported yet
• [x] This is a single bug report (please file separate reports for different bugs)
• [x] I am using the latest version of Claude Code

What's Wrong?

Complete file upload failure on claude.com web interface. Cannot upload ANY files - images, documents, Skills, or any other file type.

Error in browser console:
api/organizations/{org-id}/conversations/{conv-id}/wiggle/upload-file: 404 Not Found

The /wiggle/upload-file endpoint returns 404, breaking all file upload functionality across the entire web interface.

What's affected:

• ❌ Cannot upload images to conversations
• ❌ Cannot upload documents for analysis
• ❌ Cannot upload Skills (Settings → Capabilities)
• ❌ Cannot upload any file type whatsoever

Additional context:

• Team Admin plan
• Code execution enabled
• File uploads worked on Friday (October 24-25, 2025)
• Reproduces across ALL devices (desktop + mobile)
• Reproduces across ALL browsers (Chrome, Safari, mobile browsers)
• Affects all file upload scenarios, not just Skills

This is a critical regression affecting core platform functionality.

What Should Happen?

Users should be able to upload files (images, documents, Skills, etc.) through the web interface. The /wiggle/upload-file endpoint should accept file uploads and process them correctly.

Error Messages/Logs

Browser console errors (Chrome DevTools):

  api/organizations/99ef4912-44ea-4ac5-bea8-768f2539fcc5/conversations/685edf43-5b15-4e1d-b2d7-943616775dcf/wiggle/upload-file:1
  Failed to load resource: the server responded with a status of 404 ()

  This error appears for:
  - Image uploads in chat
  - Document uploads for analysis
  - Skills uploads in Settings
  - Any file upload attempt

  Additional schema compilation error:
  Error compiling schema, function code: var refVal1 = refVal[1]; var validate = function(data, dataPath, parentData, parentDataProperty, rootData) { 'use strict'; var vErrors = null; var errors = 0; if (rootData === undefined) rootData = data; var errs_1 = errors; 
  var errs_2 = errors; if ((typeof data !== "number" || (data % 1) || data !== data)) { validate.errors = [ { keyword: 'type' , dataPath: (dataPath || '') + "" , schemaPath: '#/definitions/nonNegativeInteger/type' , params: { type: 'integer' } , message: 'should be
  integer' } ]; return false; }

Steps to Reproduce

Steps to Reproduce:

Test 1 - Upload image in conversation:

1. Go to https://claude.com and start a new conversation
2. Try to upload an image (click attachment button or drag-and-drop)
3. Open browser DevTools → Network tab
4. Observe: /wiggle/upload-file returns 404
5. Result: Upload fails

Test 2 - Upload document:

1. Try to upload any document (PDF, DOCX, etc.) to a conversation
2. Same 404 error occurs
3. File is not uploaded

Test 3 - Upload Skill:

1. Navigate to Settings → Capabilities → Skills
2. Click "Upload skill"
3. Try to select any ZIP file
4. Same 404 error occurs
5. Upload fails

Test 4 - Check endpoint directly:

1. Open DevTools → Network tab
2. Simply navigate to Settings → Capabilities
3. Observe: api/.../skills/list-skills also returns 404
4. This suggests multiple upload-related endpoints are down

All file upload functionality is broken system-wide.

Claude Model

None

Is this a regression?

Yes, this worked in a previous version

Last Working Version

_No response_

Claude Code Version

Web interface - approximately October 24-25, 2025, Mobile app the latest, Desktop the latest.

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Terminal.app (macOS)

Additional Information

CRITICAL ISSUE - Complete file upload failure

Scope:
This is NOT a Skills-specific issue. The entire file upload system on claude.com is non-functional.

Affected endpoints:

• /wiggle/upload-file - 404 (main upload endpoint)
• /skills/list-skills - 404 (Skills listing)
• Likely other file-related endpoints

Environment:

• Platform: claude.com web interface
• Account: Team Admin plan
• Browsers: Chrome, Safari, mobile browsers (all affected)
• Devices: Desktop macOS + mobile devices (all affected)

Timeline:

• Last working: Friday, October 24-25, 2025
• Broken since: October 27, 2025
• Duration: 48+ hours of downtime

Impact:

• ❌ Cannot upload any files to conversations
• ❌ Cannot analyze documents
• ❌ Cannot share images with Claude
• ❌ Cannot upload Skills
• ❌ Core platform functionality completely broken

Workaround:
None available for web interface. This is a complete service outage for file uploads.

Urgency:
HIGH - This breaks fundamental platform features that many users rely on daily.

Please escalate to web infrastructure team immediately.