The New New Thing by Michael Lewis

Ostensibly, this book covers Jim Clark's entreneurial works: Silicon Graphics, Netscape, Healtheon, and myCFO. Having started three companies that each at one time or another had a market capitalization greater than $1e9, you would think that might warrant some interest. But they don't. On the other hand, computers and ships do.

Jim made a bunch of money off of Silicon Graphics and wanted to build a completely monitorable, remote-controllable ship, i.e. graft SCADA from a power plant onto a sailboat. He also wanted it big, like 60 meter mast big. That level of ridiculous expense apparently forced him to push Netscape to IPO before it had made any money, so that he could take that money and sink it into his new boat. Naturally, computerizing a sailboat has its own issues.

... Lance pointed to the message on his computer screen and said, "The computer has no sense of proportion. It doesn't know whether what happened is serious or trivial. You get used to ignoring these alarm messages."
"Hey! Hey! Hey! Hey! Hey! Hey! Hey!"
This time the alarm came from a human being. Screams. They came from the galley.
"Hey! Hey! Hey! Hey! Hey!..." It was a high-pitched protest. And it was followed immediately by the sound of dishes crashing onto the floor.
... The computer programmers swiveled in their chairs. Before them unfolded a puzzling scene. A thick slice out of the middle of the table that separated the galley from the lower salon rose up into the air, as if by magic...; like everything else on the boat, it was automated.
... Steve ... punched a few more keys. The he shouted, almost triumphantly, "Lance that was you who caused that problem!"
... On Steve's sea blue computer screen a single line of code flashed. It would have been perfectly meaningless to everyone else on the boat, but to these three young men it was an important message. It said,
HYP 24 Request PLC Write P24-Control S430303-10 1:(0): null
... Whatever Lance had been doing to the movie system appeared to be the culprit. While obviously not critical in itself -- the boat could sail without movies -- the message suggested a deeper and more troubling problem: Why had Lance's computer issued this command?
... [ they make sure no human entered that command ] ...
And for some inexplicable reason everyone else decided the problem was more or less solved, which it wasn't. Tina [ the cook ] glared at the programmers and said, "If I am at the mercy of this computer, I'll be a paranoid cook." She returned to the galley.
... [ could it be a wiring problem? ] ...
"Nah," said Steve, "Hyperion 24 received an instruction. It's just unclear where that instruction came from."
More silence.
... The three young men breathed easier. The bug that sent Tina's table into the ceiling underwent a subtle change in status. No longer was it a problem bug. A critical bug. A meaningful bug. It was a bug that could be ignored. It could be hunted down tomrrow, or the next day, or even the next. Or maybe never.
-- pages 138-150

While one could argue that the bug (a table automatically folding away for storage) really had little consequence, That anecdote provides a good case study in people giving up when they don't have adequate tools. You probably can think of at least one thing that could help debug future issues. We just have to do it.

Now compare that to the following:

The sound, whatever it was, was not something the computers picked up on; there was no obvious sign of anything wrong. But the mast did make a faint clicking sound that Jaime had never heard it make, and he made a point of knowing all the sounds on the boat. This one, so faint that it barely registered, was entirely new. Click ... Click ... Click. It bothered Jaime enough that he decided to climb the mast to see what might be causing it.
This in itself seemed an act of madness. It crossed my mind that the computers had taken over so much of the business on the boat that the human beings strained their imaginations to remain relevant.
... The seas were rougher than they had been in days. The boat pitched and rolled with sufficient violence that you had to concentrate to remain upright on deck. The top of the mast was two hundred feet off the ocean, or about seventeen stories. The slightest sway on the deck was experienced at the top of the mast as a violent rock.
... Now, on our seventh evening at sea, he'd heard a sound that no one else had heard. In response to that sound he donned a thin harness shaped like a jockstrap and asked Celcelia, who was making her first long sailboat trip, to belay him up in it.
... At first Jaime had thought the sound in the mast might be the satellite dish. But he rose past the satellite dish on the second spreader, and the noise only grew louder. It grew louder, in fact, all the way to the top. Only when he arrived at the top of the mast did Jaime find its origin. The rope that had been strung up in place of the main halyard -- that is, the rope that held up the massive sail [ the main halyard had previously snapped ] -- had ripped the sail. A fresh tear nearly a yard long ran down from the top. ... The entire sail was like a giant stocking on the verge of a run, he said. A strong gust of wind would rip it in two. One half would probably blow clear off the side; the other would flap crazily from its moorings at the base of the mast. The force of this event, on a sail of this size, might easily cause the mast to snap.
-- pages 234-236

Funny to think of a sailboat as open-source, but in this case, it works just the same: any engineer could inspect the sail, they just need the impetus and the tools. Unfortunately, the boat's SCADA system didn't have the same level of tool availability....