I've purchased cheap retail/OEM (not volume) Windows 10 and 11 keys through multiple vendors, including Kinguin and BitsDuJour (one of many StackCommerce storefronts that sell them). They activated just fine as retail keys, and my desktop Windows 11 Pro is still working 2 years later. I used the other keys for VMs that also still work. As I mentioned before, I had to get one key replaced when it looked like it had been used already, and that was pretty painless. Just sent them a screenshot of the activation failure and they sent another key that worked. These dealers have been in business for years and are well established, they're not some fly-by-night operation.
I've also recently bought two Adobe Acrobat Pro 2023 keys (one for Windows, one for Mac) from SoftwareShore, who also sells Windows licenses which I've not tried. I'm not as familiar with Adobe's license key schemes, but these looked like they might have been volume licenses. In fact I think Adobe only offers perpetual licenses to Acrobat 2023 through volume licenses now, regular retail customers must subscribe to get anything newer than the 2020 version. So who knows for long they'll work, but for now they do. AFAICT from their domain registration, SoftwareShore has been around for about a year now, and they even accept Klarna as a payment option which would seem to grant them some degree of legitimacy. While they're almost certainly some unauthorized grey market software dealer, if they were outright ripping people off I doubt they'd still be in business under the same DBA. Most of those sites tend to advertise heavily, make a lot of sales, and disappear before popping up under a new DBA. But YMMV -- I'm not trying to vouch for them other than to say I took a chance and it went fine (so far).
At the prices we're talking about, the risk is pretty low, but always take precautions. When I'm dealing with an unknown vendor where I don't have trusted references to vouch for them, I'll use a one-time CC number for the purchase. Either through Privacy.com or one of my CC providers that offer virtual numbers. I set the virtual limit to just over the purchase amount, and then to be doubly sure I close the virtual card immediately after the purchase. That way I don't have to worry about any fraudulent additional charges later.