This is something I strive quite hard to ensure, using tools like html-proofer and comparing against old sitemaps when I change things considerably with my site. It's also something that is quite infuriating when following links to a site that has now rewritten their URLs, so I've learned from that too!
Recommended read: Don't ever break a URL if you can help it https://www.hanselman.com/blog/dont-ever-break-a-url-if-you-can-help-it
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