Having a boss who is as at least as tech competent as yourself AND is interested enough to be up to date as well is rubbish.
In the past I would have been able to ask for an SSD with some spurious reason and it wold have been signed off, now I ask, and he not only asks why, but when I mumble in agreement with him about lack of disk space, took my laptop off me and checked!
He's probably still the best person I've worked for in a very long time, just don't tell him that I said so.