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Post links of the form http://{site}/q/{PostId}/ and http://{site}/a/{PostId}/ do not onebox in chat. I think they should. (Origin of such links: I'm in the habit of deleting UserId from short links, which leaves them ending with a slash as above.)
The slash-less counterparts do create a onebox: http://{site}/q/{PostId} and http://{site}/a/{PostId} both work.
And when "q" is expanded to "questions", the trailing slash is no longer an issue: http://{site}/questions/{PostId}/ oneboxes.
Ultimately, that isn't an actual official link - and is not one that the site ever produces; we produce it with the user-id if logged in, and without either the user-id or the trailing slash if anonymous, like this (taken in incognito mode):
So I don't think it is automatic that it would be assumed to work, but: it also isn't much work to allow it to work; this should now be available.
