HI Kevin-7004,
1.Could you please enter winver in command prompt on problematial session host server and look the os version and os version number ?[for example windows 10 enterprise 1809 (os build 17763.316)]
2.What's RDS deployment on AWS? Are profile server and RDsession host server in the same network segment?
3."Why is it failing the first time"
We can try to capture the first logon fslogix log and the second logon fslogix logs,then compare which differece between them.
On the problematical rdsh, download the support tool from
https://aka.ms/fslogix_support_tool
1).Run the FSLogix Support Tool.
2).Fill in the company name (we use this to separate the information from others).
3).click "enable logging" and Select "Gather Rule files", and "Gather Dump Files".
4).Click "Gather FSLogix Content" (* Please note: this will take several minutes*)
5).Once complete, please locate the resulting zip file from C:\ProgramData\FSLogix\Support and attach it to your support ticket.
============================================
If the Answer is helpful, please click "Accept Answer" and upvote it.
Note: Please follow the steps in our documentation to enable e-mail notifications if you want to receive the related email notification for this thread.