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There is a very similar question (Different SSL states as seen by Safari, Chrome and Firefox) but with a different failure reason so I am posting this one as I think it is slightly different debug.

enter image description here

I have been trying to clear various browser states. Is there somewhere else (DNS?) that I should be clearing that could be causing this?

The other interesting information is one time when I tried to check ssl.com on ssllabs.com tool, it took a very long time to succeed. Not all checks took a while.

I have also tried to clear various DNS (and socket) state in chrome via chrome://net-internals/#events but I suspect something might be to do with the network or even old libraries on old macs.

I am noticing this problem is occurring more on two older macs in particular.

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    You show only a single case, not different ones for different browsers. And you show only an image but fail to describe an actual problem. And is not clear what "two older macs" specifically means - Macs which don't receive any more software updates? Also it is pretty normal that SSLLabs takes a long time since they check far more than just the certificates.
    – Steffen Ullrich
    Jan 5 at 22:08
  • @SteffenUllrich Thanks but I figured it out. Will post solution below as it might help others.
    – mathtick
    Jan 5 at 22:24

1 Answer 1

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The problem was caused by expired root certificates on very old macs. The clue is that apparently Mozilla runs its own root cert store somehow.

The fix was to find a new mac, export the root certs and copy and add them as per here:

https://apple.stackexchange.com/questions/422332/how-do-i-update-my-root-certificates-on-an-older-version-of-mac-os-e-g-el-capi

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  • "The clue is that apparently Mozilla runs its own root cert store somehow." - yes, Firefox comes with its own certificate store. Chrome uses the system store on Mac and Windows but its own on Linux too. Various tools (Python, Java, ...) come with their own certificate stores too.
    – Steffen Ullrich
    Jan 5 at 22:33
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