If there is a valid internet connection then the request will work. If there is no valid connection then it will fail until there is a connection. What I'm trying to say is that in most cases retrying to send the request will not help much.
I was finding when I was sending the request to the remote server (remote server not handled by me), it was returning success = False for the HTTPJob.
Error message was showing: The server cannot service the request because the media type is unsupported.
If I send the request again the second time it worked fine.
So I was adding, if it failed the first time then try and send it again, and if it fails the second time then give up and notify the user.
Strange thing is it doesn't happen all the time.