envkey-app

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it would be great to be able to reorder the sidebar and maybe even create a divider so I can group systems (legacy etc)

I "solved" this just by adding - to the ones we care about so they reorder first

Would an option to order by last updated help?

no that would make the experience worse. you don't need to have a drag-n-drop experience. simple arrows will work or even having it hidden away in org settings work too