First big oops of this form that I remember:
"In December 1986, the ARPANET had 7 dedicated trunk lines between NY and Boston, except that they all went through the same conduit -- which was accidentally cut by a backhoe. "
One example was a site that had fiber and coax, from different companies. They might have shared a pipe at some point along their length, hard to say. But both connections went down at the same time for digital reasons, not physical. The providers had simultaneous unrelated backend router problems and the site lost contact to both gateways.
This was with a nice SD-WAN system that routed everything dynamically across both pipes to address latency and errors, but if the packets get dropped at the first hop in both networks, there's not much you can do!
The saving grace in that case was the third redundant connection, a 4G cell modem, with a lot less bandwidth but able to keep the critical transactions going. These days I'd certainly want Starlink on the roof as well.
In any system where both sides of redundancy always carry traffic then loss of one link can cause congestion failure if any link fails. This is a very common means of failure in electrical networks that requires load shedding. Well, you can't load shed air traffic.
A more complex system that I like, but comes with it's own set of constraints and implementation issues is a system where both lines carry all the traffic at all times. This way the default state of the system is always working and your first failure isn't invisibly critical.
But this is very hard as we see in TCP when things get out of order and high latency creeps in. You have to manage a lot more state at the data level.