About 10 years ago, my then-employer had an Oracle audit and they were found to owe over $500,000 in licensing fees (the initial cost was much higher but they negotiated it down). They were blatantly violating their agreement by owning a single socket license and using Oracle on a half dozen large production servers and a bunch of dev servers. The DBA that ran the licensing script said "You know we're not in compliance right?" and the company execs said "No worries, we'll negotiate a good deal".
When I started, I asked about licensing while setting up a new production server and the CTO admitted they were under licensed and were planning to true up licenses next quarter, but over a year went by and they never did. I suggested that they work on porting to Postgres or MySQL/MariaDB and get off Oracle (or at least consolidate into fewer servers to reduce the socket count), but they never had the time to do that.
The company went out of business shortly after the bill from Oracle came due (not sure if Oracle ever got any money). I'd already left by then since I saw the writing on the wall -- as soon as they stopped providing snacks in the break room and the coffee switched from Peets to Folgers, I knew they were running out of money.