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I'm sure it's doable, and they may end up doing it as a courtesy, but I don't think they're under any ethical obligation to do so. They announced the lifespan of the product when they sold it, everyone was clear there would be no promise of updates after that. It's not like they broke the certificate, the expiration was set long ago.
Apple could push a security patch that caused some undocumented functionality used by Office 2019 to crash. Apple says the code used by Office 2019 was insecure and they won't be modifying their security update to accommodate it. Is Microsoft still under any obligation to push out a patch to make sure it continues to function, in your view?
I totally get customer frustration with bitrot and the (seemingly unnecessarily) short lifecycle of software. One of Microsoft's great strengths for a long time was that they put a lot of effort into making sure your old unsupported software would run on new and improved Windows platforms. But this also became a major liability to them, and I also understand the need to draw a line at spending precious engineering effort fighting bitrot for products that have been superseded several times over. I would guess they will not legally pursue someone who makes, e.g., an unofficial certificate patch.
They promised the software would “continue to function”, yet they’re the ones who set the certificate to expire and now refuse to update it.
It’s not their responsibility to update the software further, including not their responsibility to fix if Apple breaks the software via OS update (although they should let someone else fix it).
It’s selling someone a product with a built-in unadvertised kill switch (planned obsolescence without plausible deniability). The seller isn’t responsible for reasonable defects outside the warranty, nor if the buyer breaks the product. But if they put in an unreasonable kill switch (from malice or incompetence) they’re responsible, even outside the warranty. DRM that expires and bricks the software (which no other DRM I’m aware of does) is an unreasonable kill switch.
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