Cool, thanks. How could I overlook this setting? Anyway, I switched from an installed WinSCP to WinSCP portable on my machines, maybe I had this setting enabled in the installed version before or it was enabled by default in the past.

Greets,
spackmat

You need to enable preference option Remember password for duration of the session:
https://winscp.net/eng/docs/ui_pref_security

This hasn't changed recently.

Were not for below bug you'd also have an option to remember the password per session:
https://winscp.net/tracker/1159

Hi,

I don't exacly remember when it started, but since an update of WinSCP a few months ago, I have to reenter the passphrase for my private key on the first upload of an edited file. After login (entering the passphrase the first time), I can upload and download as many files I want. But when I edit the first file and save it, WinSCP asks for the passphrase again. Seems as if editing opens a second connection or something.

Any suggestions, how I get WinSCP to only ask me once for a private key's passphrase?

My passphrase is complicated and I have to get it from my passwort manager every time. I often have to do just small updates of config files on several servers over the day and getting the passphrase twice every time ist quite annoying. Pageant would be an extra step and is no solution for my situation.

Greets,
spackmat