Function uploadFile

src/services/api/filesApi.ts:378–552

(
  filePath: string,
  relativePath: string,
  config: FilesApiConfig,
  opts?: { signal?: AbortSignal },
)

 * @returns Upload result with success/failure status
 */
export async function uploadFile(
  filePath: string,
  relativePath: string,
  config: FilesApiConfig,
  opts?: { signal?: AbortSignal },
): Promise<UploadResult> {
  const baseUrl = config.baseUrl || getDefaultApiBaseUrl()
  const url = `${baseUrl}/v1/files`

  const headers = {
    Authorization: `Bearer ${config.oauthToken}`,
    'anthropic-version': ANTHROPIC_VERSION,
    'anthropic-beta': FILES_API_BETA_HEADER,
  }

  logDebug(`Uploading file ${filePath} as ${relativePath}`)

  // Read file content first (outside retry loop since it's not a network operation)
  let content: Buffer
  try {
    content = await fs.readFile(filePath)
  } catch (error) {
    logEvent('tengu_file_upload_failed', {
      error_type:
        'file_read' as AnalyticsMetadata_I_VERIFIED_THIS_IS_NOT_CODE_OR_FILEPATHS,
    })
    return {
      path: relativePath,
      error: errorMessage(error),
      success: false,
    }
  }

  const fileSize = content.length

  if (fileSize > MAX_FILE_SIZE_BYTES) {
    logEvent('tengu_file_upload_failed', {
      error_type:
        'file_too_large' as AnalyticsMetadata_I_VERIFIED_THIS_IS_NOT_CODE_OR_FILEPATHS,
    })
    return {
      path: relativePath,
      error: `File exceeds maximum size of ${MAX_FILE_SIZE_BYTES} bytes (actual: ${fileSize})`,
      success: false,
    }
  }

  // Use crypto.randomUUID for boundary to avoid collisions when uploads start same millisecond
  const boundary = `----FormBoundary${randomUUID()}`
  const filename = path.basename(relativePath)

  // Build the multipart body
  const bodyParts: Buffer[] = []

  // File part
  bodyParts.push(
    Buffer.from(
      `--${boundary}\r\n` +