Continuing the discussion from 2.9.0.beta9: Security fix, bug fixes and more:
Why is this disallowed? In earlier versions it seemed to work fine with secure media.
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Secure Uploads in Chat aren’t supported at the minute, so it made that setting a little misleading. There’s more detailed info in the commit itself, as well as a workaround if you have server access: 
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Thanks @JammyDodger . Just noting as well that I am queued up on making secure media work with more areas, including chat, later in the year.
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Just a kind reminder that secure media is important and useful for some Discourse users 
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This is definitely not forgotten, I am the one that will be working on this compatibility, I just have many other things on my plate. Will post updates here when they are ready
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Sorry for being annoying about this, perhaps once every 6 month I can send a request to bump this into priority 
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