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: 
https://github.com/discourse/discourse-chat/commit/93ab81c725faeca23fbe0bb597a5038382a711e3
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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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6 months have passed and It’s me again 
Please allow uploads to chat when secure_uploads is enabled
See you in 6 months 
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In a recent Discourse update, thumbnail preview of images uploaded in chat is broken when secure-uploads is enabled.
I know “This condition can be overridden with DISCOURSE_ALLOW_UNSECURE_CHAT_UPLOADS at operator risk”, but I wonder if there’s any temporary solution for it? @martin
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