File Name

Whenever transferring files to my Xbox with a long filename i get the following message:

[22:01:23] Transfer failed. Use the Transfer Queue for automatic retries.

I know it has to do with long file names, because if I go into the folder i am transferring and change the long file name, it will work. Is there anyway to automate this so that i don't have to do it manually all the time?

No. But there are tools to automatically rename a batch of files.