If there is a good book on why software adoption/modernization fails so often I have missed it, but I have really enjoyed the work of Robert Charette on the topic. I think his first piece on it was simply titled "
Why Software Fails" and was published in IEEE Spectrum. He has written several follow ups since then. Bob is easily approachable via email and has a wealth of knowledge about these topics. By the way, he is also the author of the recent 12 part series "The EV Transition Explained," which
was also published as an ebook and demonstrates his characteristic insights into system dynamics.