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I know it isn't a part of this PR, but maybe you remember how does context.WithTimeout has anything to do with ssh being used? The PR that introduced this doesn't mention any details here.
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Just curious - so if you remember then just some quick tldr will be enough 😄
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I'm not sure how much time I spent at the time digging into the exact cause; the timeout was helping with an issue (see #2424), and I'm not sure I was able to consistently reproduce the ssh problem locally (or only in CI?). Ultimately decided that the SSH connections were less common, so to keep diving into the issue for later (there's some other issues remaining with the ssh connection helper as well).
In case useful;
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It may be just missing functionality in the ssh connecting helper (it not handling context cancelation), but yeah, never found the time really to get myself familiar with that code or to dig into the issue.
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Thanks!