If you are having trouble uploading files using the web service this offers an easy alternative

• Use the following URL to upload files: https://www.trainingpeaks.com/TPWebServices/EasyFileUpload.ashx?username=yourusername&password=******
• Make sure you encode the username and password as they may have special characters that aren't friendly to querystring. 
• If you are using Xcode, use setHTTPBody to set the body to the bytes, and use the url above with a post and it should work,
  (no need to encode) and it should be processed by the server and return "OK" on the response.
• PWX File Format: http://www.peaksware.com/PWX/1/0/pwx.xsd 
• Sample PWX Files (.zip file containing several examples)