Thanks for your suggestion. This request has been added to the tracker:
https://winscp.net/tracker/779

Also note that, while it probably does not help in your complex scenario, you can search for session alreadty by typing beginning of its name.

short version:
- search function
- expand/collapse all session folder
- taging

long version:
a search, where i can quickly lookup sessions, would be really great.
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just enter a hostname or a session description or maybe also lookup usernames (make a ini settiong, so the user can decide what should be searchable for him) to quickly lookup session entries which are burried deep inside many folders.

little extra would be to add expand/collapse all feature

a big feature would be to make a session taggable and the tags searchable, so big environments are easily manageable with winscp.



you can see the search function in action in keepass:
https://keepass.info/
its also opensource, maybe you can reuse some code