Just a bystander opinion, I have no official stake or say on the matter:
There are a few problems with this proposal:
- Not actionable: The visitor to a website with outdated software can do nothing about the warning and does not even know what the risks a particular "outdated software" presents.
- Warning shown to the wrong person: It's the website owner that can do something about outdated software, not the visitor.
- Technically difficult: There are many HTTP servers out there, collecting a list of all of them and determining which versions are outdated, then keeping this list up-to-date, would be very time-consuming. And the major serving HTTP stacks are not necessarily open/versionable.
- Warning fatigue: My understanding is that Chrome tries to minimize the number of warnings shown to users to avoid training users to skip/ignore warnings.
In short, it would be a lot of technical work for dubious benefit (no guarantee that owners of websites running on outdated software would update just to avoid a skippable warning).
Eran