The authentication you’re talking about is called STIR/SHAKEN and it’s an ongoing retrofit. I will describe the status quo based on my brief time in a business VoIP form.
The concept of a “phone line” with a fixed number belongs to residential service. Pretty much any business premise has a PBX on it, and that PBX is connected to the PSTN by a bundle of circuits including some voice channels and some signaling channels. Some number of inbound numbers may be routed there. Or not! But that has nothing to do with the signaling on outbound calls.
Now for a small business it would probably be sensible to limit outgoing caller IDs to the inbound numbers routed there. In a larger business, PBXes at different sites are connected to each other by an enterprise network, and to the PSTN through different telecoms in different regions. You may have branch offices that only receive calls via the enterprise network, but make outbound calls on local transit. You may route a call from elsewhere on the enterprise network to exit to the PSTN via that branch office, for cost or redundancy reasons. That’s how Twilio itself works. Lots of IT departments have internal Twilios, in that sense.
The upshot is that you need a fairly sophisticated cross-telecom standard for establishing authorization to present a number on caller ID, and no one got around to building or driving adoption of that until pretty recently.