Against my better judgement I did a reverse image search and found the post that you found that screenshot from [1]. The post is full of people having exactly t

Against my better judgement I did a reverse image search and found the post that you found that screenshot from [1]. The post is full of people having exactly the sort of problems you would expect from an automatic software updater, along with instructions from Jeff on how to manually update using SSH and git. These things happen. The world is messy, and whether due to technical inadequacy or run-of-the-mill software updater bugs, web backends will not always be updated. As you've noted, this could eventually lead to security problems, and I agree -- but that doesn't justify intentionally breaking their code. To say that their breakage is justifiable because they'll be 0wned at some point anyway is an absurdly darwinian argument. To address your last question, the way you update a system like the web is exactly the way we always have -- accretion. With very few exceptions, websites from the early 90s still work today. We didn't remove the `table` tag when we introduced flex boxes. We add new APIs while preserving existing functionality. If you want to see a fantastic talk on this exact subject, watch "Stewardship: The Sobering Parts" by Brian Goetz [2]. It is well worth your time. [1] https://meta.discourse.org/t/how-do-you-update-discourse/10962/2 https://meta.discourse.org/t/how-do-you-update-discourse/109... [2] https://www.youtube.com/watch?v=2y5Pv4yN0b0 https://www.youtube.com/watch?v=2y5Pv4yN0b0