Honeypots are good fun. This book introduced me to them many years ago at university.
- Silicon Cowboys - https://www.imdb.com/title/tt4938484/
It covers the creation of Compaq
- American Experience: Silicon Velley - http://www.pbs.org/wgbh/americanexperience/films/silicon/
About how Silicon Valley came to be.
- Naughty Dog 30th Anniversary - https://m.youtube.com/watch?v=cdr7THH0zo8
Kind of a PR video, but interesting and free. Covers the history of Naughty Dog games.
- Cukoo’s Egg - https://www.amazon.com/Cuckoos-Egg-Tracking-Computer-Espiona...
Has some interesting technical detail, and gives perspective on a very different time on the internet.
- Revolution in the Valley - https://www.amazon.com/Revolution-Valley-Insanely-Great-Stor...
You can read these stories on folklore.org, but I enjoyed the collected book. Covers the creation of the Macintosh.
For a gripping tale of technology and hacking, The Cuckoo's Egg never fails: https://www.amazon.com/Cuckoos-Egg-Tracking-Computer-Espiona...
And, as someone reminded me in the thread about Xerox and Fujifilm, Dealers of Lightning tells the story of Xerox PARC, the Alto, Steve Jobs' visit, etc: https://www.amazon.com/Dealers-Lightning-Xerox-PARC-Computer...
So I called a friend, who is now a physics professor at MIT, and said “Our machines are infected, could you please break in, go root, clean the infection, and send an email to our sysadmin explaining to him you did this at my request?” All he said was “Ok, get some sleep” and yes even though we’d just spent almost 24 hours locking down every possible attack vector into our machines and network we woke up to clean machines with a polite email in the sysadmin’s inbox. I never have figured out whether that was more a measure of the state of network security in the late 1980’s or of the kind of mad skills it takes to become tenure track at a place like MIT.
There is a good telling of the worm story in the final chapters of Cliff Stoll’s amazing book on discovering a case of internet-hacking meets East-German-spies meets 2400-baud-modems and three-letter-agencies back in the mid 1980’s (which spent 42 weeks on the NYTimes bestseller list and is a ton of fun to read)
Others have listed some great, entertaining reads already:
Soul Of A New Machine (which won a Pulitzer),
Cringley's PBS series Triumph Of The Nerds (available on YouTube),
Where Wizards Stay Up Late
Some not mentioned so far (as I write):
The ancient, online Jargon File is a large glossary that captures a lot of early computer subculture through its lexicon. Eric S. Raymond maintains it today, but it originated way back in the 1970s: http://www.catb.org/jargon/html/
"American Experience," on PBS, did a stellar documentary on the origins of Silicon Valley and the pervasive startup mentality there. It's all about the rise of the semiconductor industry, starting with transistors. Watch online: http://www.pbs.org/wgbh/americanexperience/films/silicon/
Dropping LSD was, it turns out, crucial to the origins of personal computing! This I learned from Jaron Lanier and Kevin Kelly, who recommended John Markoff's What The Dormouse Said: http://www.amazon.com/What-Dormouse-Said-Personal-Computer-e...
The Difference Engine: Charles Babbage and the Quest to Build the First Computer is a short book but also a fun read. Doron Swade, technology historian and assistant director of London's Science Museum, races to build a copy of Charles Babbage's "difference engine" before the anniversary of said machine; he tells his travails in building it while giving Charles Babbage's story at the same time: http://www.amazon.com/Difference-Engine-Charles-Babbage-Comp...
No one has mentioned books covering the dark side of hacking. There are some great reads out there, and infosec is a crucial part of computer history.
CYBERPUNK: Outlaws and Hackers on the Computer Frontier covers Kevin Mitnick, the Chaos Computer Club, and Robert Tappin Morris (who, somewhat inadvertently, wrote the first Internet worm). Mitnick disputes his section of the book, but it's fascinating nonetheless. Worth it for the Morris part alone: http://www.amazon.com/CYBERPUNK-Outlaws-Hackers-Computer-Fro...
The Cuckoo's Egg: Tracking a Spy Through the Maze of Computer Espionage by Clifford Stoll is a fun read. Stoll is an astronomer by trade, and his analytical thinking can be an inspiration: http://www.amazon.com/The-Cuckoos-Egg-Tracking-Espionage/dp/...
The Watchman is a true crime thriller you won't be able to put down. The author set out to write a book on Mitnick but wound up detouring to do a story on Kevin Poulsen, who is now an excellent infosec writer at Wired. You will not believe what Poulsen does in this book. http://www.amazon.com/Watchman-Twisted-Crimes-Serial-Poulsen...
The Hacker Crackdown by acclaimed sci fi author Bruce Sterling is a great work on an infamous cross-country bust of many hackers. You'll get a look into the BBS subculture, Phrack Magazine, and the phreaker scene. http://www.amazon.com/Hacker-Crackdown-Disorder-Electronic-F...?
And let's not forget gaming:
Masters of Doom: How Two Guys Created an Empire and Transformed Pop Culture gives a great history of ID Software and the origins of the FPS: http://www.amazon.com/Masters-Doom-Created-Transformed-Cultu...
My recommendations would add:
http://www.amazon.com/The-Codebreakers-Comprehensive-Communi... by David Kahn. Many stories of the whole history of secret communications, with lessons in op-sec, not changing the codes frequently enough, they can't possibly break this.
The John LaCarre http://en.wikipedia.org/wiki/John_le_Carr%C3%A9 books. Do you remember the point where someone says to Smiley "There is no reason to think that they tapped the phone" to which Smiley replies "There is Every reason".
A must read, I tell my students in my Security Awareness training classes is The Cuckoo's Egg http://www.amazon.com/The-Cuckoos-Egg-Tracking-Espionage/dp/.... Examples like default service accounts on Dec Vax with username Field and password Service. Note when this is written and are our habits really any better with junk hung on the internet? Concepts pioneered in his book, as effective as they are, are not practiced. Note the alarms going off, ignored, at a large retailer last thanksgiving. Or another retailer recently, "Wait, what, we are being attacked? I didn't feel anything".
Most vulnerable is the thinking "Well, they can't get our X because <thing we did>". I have a matrix of attacker motives and what they are after. There motives and targetsyou haven't thought of.
Another couple of possibilities might be:
The Soul of a New Machine - Tracy Kidder
The Cuckoo's Egg: Tracking a Spy Through the Maze of Computer Espionage - Clifford Stoll
Hackers & Painters - Paul Graham (yes, that Paul Graham)
By the way, there's a bonus at the end of the book: he mentions Paul Graham (in the context of Robert Morris' worm). Was a pleasant surprise when I read the book.
Amazon link: http://www.amazon.com/Cuckoos-Egg-Tracking-Computer-Espionag...
Wiki about the book: http://en.wikipedia.org/wiki/The_Cuckoo%27s_Egg_%28book%29
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