Hi.
(Iterate)WebRequest uses a special CookieContainer to receive, store, and send cookies. In the case of (Iterate)WebRequest you cannot manage cookies using the Cookie header.
The CookieContainer lifecycle is tied to the runsession. The CookieContainer is created with the runsession and deleted when the runsession is completed. It can't be preserved.
That means that the whole cycle of authentication, data processing, and data sending must be executed in a single runsession.
Try to use "Reload and run" to run the entire workflow at once.