So you have a stored session with an encrypted password which you are using regularly. And without you changing that stored session and without changing the master password, the session password suddenly cannot be decrypted. Is that what you experience? How difficult is to reproduce the problem? How often does it happen?

Thanks for the response, and sorry for my late reply. I've since had this problem a few different times, so I'm finding the master password option to be unworkable. If this is just a 'me' thing then I don't imagine there will be much traction for changing anything, but I wanted to offer the feedback.

Ultimately it would be nice if stored passwords could be viewed, much like you can in a browser password manager (I use BitWarden but I know LastPass has this functionality as well). Right now the only way to see what the stored password is involves logging passwords to disk.

Sorry, I do not remember such problem recently. So I cannot suggest, what to do to prevent the problem. An unexpected program termination should not cause it, unless it happens in a middle of changing of the master password or saving a session.

I use WinSCP with a master password. I open a connection to a local VM and after entering my master password I get the "The password cannot be decrypted" message. If I try to edit the credentials the message pops up every time I click in the password field, so I guess I'll need to delete and recreate it(?). This does not apply to all stored passwords. A WinSCP window was left open connected to SSH running from my phone (this stored password still works), and a Windows update caused my PC to reboot last night. So the unexpected program termination might have caused this.

I found a forum post about this message back in 2013, noting that it was fixed in version 5.2.3. I was not using that old of a version but I did update to the latest 5.21 on the website. It didn't change anything.

How would I go about preventing this from happening in the future? I've had it happen before, and I can access the VM via its console and reset the password on both ends. If I'm storing passwords I typically don't also have them written down on any post-its, so external passwords would be more work to recover, (a solid reason for me to quit using a master password if encrypted passwords can just get broken sometimes).