Using Pageant for Authentication - WinSCP
https://winscp.net/eng/docs/ui_pageant06.12.2021 · Pageant can automatically load one or more private keys when it starts up, if you provide them on the Pageant command line. Your command line might then look like: "C:\Program Files\WinSCP\PuTTY\pageant.exe" d:\main.ppk d:\secondary.ppk. If the keys are stored encrypted, Pageant will request the passphrases on startup.