Command Line "Start" of the \KeepUptoDate switch

I currently am using the command line to auto start the WinSCP at boot up.
But it opens the "Keep Up to Date" dialog box and I am forced to manually click "START".
I need it to automatically click "START" for me. How can I accomplish this using the Command line?

Use the /defaults switch:
https://winscp.net/eng/docs/commandline#defaults

Or consider using scripting, with its keepuptodate command:
https://winscp.net/eng/docs/scriptcommand_keepuptodate

I was using the command winscp.exe Axium /keepuptodate /defualts, and it was starting my Axium named Site and opening up the Keep Remote Directory up to date dialog box and it clicked the "Start" button (all was well). Then all of a sudden the /defaults switch quit clicking the "Start" button automatically. Any thoughts as what to try? I did not change anything. I also reinstalled WinSCP just to be sure that was not the issue.

Please double check your command. It's /defaults, not /defualts.
If it does not help, please post session log file.