The Preserve timestamp checkbox is disabled on your second screenshot.
That can happen in two situations:

• Synchronization (as per the note you have quoted yourself).
  
• Uploads with protocols/servers that do not support setting timestamps of uploaded files (some FTP servers, S3 protocol)
  

For details, see:
https://winscp.net/eng/docs/ui_transfer_custom#common

I assume the second point applies to you, as you are "uploading". Then you do not need to disable the option, as the timestamps are not (cannot be) preserved anyway.

Hello,
I have looked at this article and have followed the directions but no matter what I do "preserver time stamp" stays enabled (see screenshot)The only thing I couldn't find that the article mentions is the note that says "you cannot disable preserving timestamp for synchronization, unless you turn off Modification timestamp comparison criteria." For the life of me I cannot find how to turn off the "Modification timestamp criteria" I am doing this all through the GUI. Can anyone suggest a solution? https://winscp.net/eng/docs/message_preserve_time_perm