You can make a batch file (.bat) that first runs WinSCP script and then OpenSSL.
For scripting part, see https://winscp.net/eng/docs/guide_automation

Hi All, I am new to WinSCP, and am looking at it to automate the download and decryption of encrypted files from an SFTP server.

The download of the files using the WinSCP command line has been straight forward and that is working well. Only three (Excel) .CSV files are downloaded daily.

As the files I am downloading are encrypted, once downloaded, I run a Windows batch file that I have created using OpenSSL.exe to decrypt the files.

If possible, I would like to use WinSCP to combine the two tasks, by downloading the files and parsing the filenames to the OpenSSL batch file to decrypt them in one process.

Thanks in advance, cheers Brad.