Thanks for your suggestion.
Will see if more people ask for this.

(According to our stats, currently only 0.1% of users use the autoselection rules).

Is there any way to set file permission based on file type for uploading?
So if I select a tons of file on my local computer and upload it to the remote server, I want to mark *.sh and *.bin files execautable, transfer *.sh files in text mode, and *.bin in binary mode, and don't mark the rest of files as executable, e.g. *.png and *.txt, but I want these files to upload also in the same breath.

As I understand, with winscp 5.2.4 I can only define the correct Transfer Settings, and upload the *.sh first (with "other file mask"), *.bin file second and the rest of the files last. Allowing file mask in "local directory mask" at the Autoselection rule field would be great.