Looking at the WinSCP options, it looks like automatic retry should be supported even with a passphrase protected key. I have the following options set:
- Transfer on background by default
No confirmations for background transfers
Automatically pop up prompts of background transfers when idle
Remember password of main session for background transfers
- Automatically reconnect session, if it breaks during transfer
Reconnect after 300 seconds
Since I have asked it to remember the password, and to automatically reconnect, I don't know why it always displays a dialog box when there is a connection error, and why it asks me for my password again. I would like you to remember my password, and automatically reconnect. Basically, I leave file transfers running for several days sometimes, and I want to be sure that they are not going to fail while I am away.