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It could be Amazon.
Linux users running wine USED to be able to run the Windows App. Then they couldn't, with exact same sympton.
Recent version now doesn't install on Wine. Gets to 97% install and fails. The Play On Linux version is older and won't log in, just like you describe.
Without a log in, the DRM isn't activated and bought Amazon titles with DRM won't work.
So I use my actual Kindle DXG as selected device, and download for transfer via PC to use the files with Calibre. I convert to ePub for Kobo and have my Kindle serial number in a Calibre Plug-in.
Not illegal in Ireland.
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