Thanks, prikryl!

The option can be enabled permanently here:
https://winscp.net/eng/docs/ui_pref_security

It will be on be default in the next release:
https://winscp.net/tracker/1409

Thanks for the great software. Here's one way to improve it for a daily workflow:

Every time I connect with WinSCP and type my password, I need to manually check "[ ] Remember password for this session". If I don't, I have to re-type the password up to dozens of times during one session.

The option of not remembering a password for the session seems completely unnecessary, but in any case its default is the wrong way around. At least 99% of the time I'd like the password to be remembered. Having to check "[ ] Remember" manually every time is a nuisance.

Solution

Remove the option. When the user wants a typed password to be forgotten, they disconnect. This is the industry standard.

Or, if this checkbox is really needed

1. Either default it to the value used the last time, or
2. offer a setting to choose the default, or
3. default it to checked (same as now but reverse).