Some of the middle era SV history books are quite good, although they cover the combination of hardware, software, and startup stuff.

Fire in the Valley, Dealers of Lightning, Where the Wizards Stay up Late by Katie Hafner, Soul of a new Machine by Tracey Kidder, The Dream Machine.

There are histories of Apple, Microsoft, and many smaller (and now gone) companies and/or projects.

Showstopper (Windows NT), Insanely Great (Macintosh), Defying Gravity (Apple Newton), In the Plex (Google), Hackers (by Steven Levy), Ghost in the Wires.

More philosophical type stuff In the beginning was the command line Dreaming Code, Coders at Work

There's many worthwhile books about the history and culture of programming and hacking not listed, but this might be a useful starting point.

I'm old, but I think any list like this can't miss the Jargon File. http://www.catb.org/jargon/html/

Especially the lore section: http://www.catb.org/jargon/html/appendixa.html

There is also a jargon file from inside IBM around 1990[1], a very different culture. Many of the entries deal with company traditions and office politics instead of technical matters.

1. http://www.comlay.net/ibmjarg.pdf

Unix haters handbook. Thankfully its freely available now - http://web.mit.edu/~simsong/www/ugh.pdf .

Psycology of Computer Programming by Gerald Weinberg, from the early 1970s, lots of anecdotes.

Hackers, Heroes of the Computer Revolution by Steven Levy, long opening setion on MIT in the 1950s - 1980s, another section on the beginning of the computer games industry mostly in California in the 1970s, other sections too.

The Soul of A New Machine by Tracy Kidder

https://www.barnesandnoble.com/w/soul-of-a-new-machine-tracy...

It's mostly about the development of the Data General Nova computer. It's mostly about (80s) hardware engineering, but there's some software stuff too, IIRC.