The best practice for naming folders is probably to avoid using ‘special’ characters like #. Why: these could be used for special operations deep inside the Linux operating system. More details at: https://www.inmotionhosting.com/support/server/linux/best-practice-for-naming-files-in-linux/ . As you discovered, when you removed the # character, you resolved the problem.
I have tested such case on macOS and Windows – it is not a problem to use “#” character in the folder name during file upload – I have checked featured image and upload to the content.
Maybe it is an issue related to your specific linux distribution, but for sure it is not a general problem
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