We just ran into this problem with another self-hosted forem community trying to move from local to cloudinary setup.
Adding the imagga crop and scale plugin (not the imagga auto tagging) to cloudinary fixed it immediately.
This shouldn't be strictly required (DEV.to uses it, but it doesn't mean it should be needed to use cloudinary), and we'll be discussing making that plugin optional.
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We just ran into this problem with another self-hosted forem community trying to move from local to cloudinary setup.
Adding the imagga crop and scale plugin (not the imagga auto tagging) to cloudinary fixed it immediately.
This shouldn't be strictly required (DEV.to uses it, but it doesn't mean it should be needed to use cloudinary), and we'll be discussing making that plugin optional.