That will not be difficult to implement, except maybe the migration point when WinSCP is updated, in which case I guess it makes sense for every existing session to simply inherit the common history, which will provide the usual behavior, for a while, and then every session will start developing its own history, gradually replacing the common inherited part.
By inheriting the common history I mean make a copy of it to every session's registry branch, or - as in that case the total registry data size might turn out to be too big - the data can be moved to a dedicated file as well. Even if the file is lost, it's not critical, just a history of commands.
In the case when WinSCP stores its settings in a file already, the solution is analogous.
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