: From your description I assume your setup is:
Environment > Window > Workspaces > Automatically save workspace on exit
Environment > Windows > Miscellaneous > Show Login dialog on startup and when the last session is closed
With that setup, WinSCP restores the previous workspace on startup automatically.
But it won't connect any session.
It would connect a session only if:
– You explicitly selected the workspace or session on an initial Login dialog (assuming your have the latter option On).
– You have started WinSCP with workspace/session name on its commandline
Afaik, nothing has changed about this behavior in any recent version of WinSCP.
If you have a different experience, we will need more detailed step-by-step instructions for reproducing the problem. Some screenshots might help too.