Windows path length limitations will come into play when the fully qualified file name exceeds 260 characters, or the directory name is greater than 248 characters.
The error will look like this in the AdminWebservice Log
TaskService - UploadFile(): Exception while uploading file System.Web.Services.Protocols.SoapException: Unable to create target folder on server! PathTooLongException ---> System.IO.PathTooLongException: The specified path, file name, or both are too long. The fully qualified file name must be less than 260 characters, and the directory name must be less than 248 characters.
There is a configuration change that can be made on the task servers (versions 22.1.11