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PuTTY's saved sessions list box is fine for people with only a few saved sessions, but some people (such as sysadmins) might plausibly have a much larger number of them and might find the list box unwieldy.
One solution to this is to invent a means of categorising saved sessions, perhaps by introducing a hierarchical directory structure within the saved-sessions list. (Some list entries would be directories, which you could click on to go down a level; in any non-root directory there would be a `back up a level' item you could click on to go back up.)
A smaller and simpler alternative would be simply to allow the PuTTY config box to be resized - and grow the saved sessions list box as the window grows. We've been deliberately keeping the config box small for the benefit of people with 640x480 screens, but if a particular user were to want to expand their own config box there'd be no reason to prevent them. For this to be really useful I suppose PuTTY would have to remember the size of its config box...
Another possibility would be to sort the sessions based on most recent access time. I'm not sure how users would cope with their sessions' being shuffled all the time, though.
It's not impossible that we might want to do all of these things, or something else entirely. Some design is required.
There are various third-party forks and tools which try to address this problem on our Links page.
Audit trail for this wish.