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Both Retrocomputing and Super User deal with questions about the use and abuse of computers; Retrocomputing deals with questions involving “old” hardware or software, while Super User’s focus is on newer systems. We also have other dedicated Stack Exchanges for some particular computer topics; Stack Overflow deals with programming, Server Fault focusses on server administration, Ask Ubuntu is for questions about (duh) Ubuntu, Ask Different covers questions regarding Apple software and hardware, and Unix & Linux is for non-Ubuntu-or-macOS-specific questions about Unices and Unix-likes, just to name a few.

Problem is, computers (hardware or software - it’s true for both) don’t fall neatly into “old” and “new” categories, but exist on a continuum; thus, there has to be an arbitrary boundary drawn somewhere. Which creates difficulties when trying to ask questions that fall near, or on, the boundary:

  • For instance, Windows ME (released in late 2000) falls in Retrocomputing’s bailiwick, while XP, released the very next year, is generally a topic for Super User. But what about Windows 2000 (released a few months before ME, but remaining supported by Microsoft until 2010, while ME left extended support in 2006)? Where would a question about installing XP on a very-late-model PS/2 go? What about trying to run Windows 7 on a computer that originally shipped with Windows 98, or questions about floppy-disk support in Windows 8.1?
  • Ask Different explicitly supports, and has questions about, Macs and other Apple products stretching at least all the way back to the original 128k, and the Lisa before it; yet, we at Retrocomputing ourselves have a bunch of questions involving very early Macs, and Apple II questions generally end up here. Where’s the boundary?
  • The first Linux versions date back all the way to late 1991, and various Unices already had a long and storied history even then; do questions about these very early Unix and Unix-like OSs belong on Unix and Linux despite their antiquity, or should those early ones come here to Retrocomputing?

Not a duplicate of this question, the answers to which give some general explanations of what is on-topic here, but don't clear up the question of where, exactly, the boundary is.

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    That issue gets even more complicated with other SE sites moving questions which I'd consider generic to RC.SE just because it's not about the latest Buzzword. – Raffzahn Apr 13 at 15:11
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    Plus, there's the potential for healthy overlap in scopes, with each site bringing a different set of expertise to questions, such that a very small subset of questions could be posted on multiple sites with identical wording and receive entirely different, correct, answers. – wizzwizz4 Apr 13 at 17:00
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    We cannot clear up the question of where exactly the boundary is because there is not, and cannot be, an exact boundary. – Chenmunka Apr 13 at 17:34
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...there has to be an arbitrary boundary drawn somewhere.

No, there need not be, and there isn't one.

Certainly date alone cannot be used as a boundary because, as you have pointed out, there are obsolete systems out there that are chronologically newer than systems still considered current.

It's generally not the topic matter but the focus of the question that plays the biggest role in determining where the question belongs, especially for systems that have been used over two or more decades. A question about how to implement a particular thing in C might be best on:

  • StackOverflow if the focus is on the language itself, and the answers have some relevance to how people currently program in C.
  • Retrocomputing if the focus is on how and why that thing was historically done and why that differs (if it even does) from modern practice.
  • Ask Different if it happens to be about a Mac-specific thing that wouldn't really apply to other systems.

Another example would be a "how do I set up a network interface" question: whether it belongs in SuperUser, Retrocomputing or Ask Different depends on the details and why one is asking.

Retrocomputing may produce significantly different answers for certain types of questions, such as "go do this hack" rather than, say, "upgrade your system; you current one is unusably insecure." These sorts of expectations are built in to the community in which you ask.

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