Hey, I was actually in this position at work a few years ago, when I set up a couple of internal (monitoring stuff) servers for my own use. I used Let's Encrypt

Hey, I was actually in this position at work a few years ago, when I set up a couple of internal (monitoring stuff) servers for my own use. I used Let's Encrypt, because I use them (for free) at home (media server), and know how it works. I wanted to throw them some (of work's) cash, and... the only two options were "Sponsor", and "Donate". Sponsorship was, uh, wrong for my use-case: it starts at some multiple-thousands of dollars. Donating would be the obviously correct choice, but putting something marked "donation" onto a corporate card would occasion a... Weird conversation, in which "you could have got this for free, but you're choosing to send them money?" would likely have been raised. I went with free, and was sad about it. Yes, corporate expectations and affordances around FOSS should change - and, I probably could have persuaded my employer that a few dollars a month for Let's Encrypt was the Right Thing To Do, so I'm a little bit of a coward - but LE would make it so much easier if there was a Send Us Money option that looks like a fee for service, rather than a donation. (Maybe being a 501c(3) precludes that? I don't know.) There's the "Corporate doesn't understand FOSS" problem, but there's also a "FOSS doesn't speak Corporatese" obstacle there, too. In the end I sent LE $20, or something, of my own money (I've had years of trouble-free use on my media server, and should have before), but they'd have had $5 / month of work's cash for years if they'd made that easier to do.