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Old 12-14-2022, 10:49 AM   #1
tpetrich
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Error communicating with device Errno 22

When attempting to send files to my new Kindle Paper White Signature Edition 11th Generation, I receive the following error:

calibre, version 6.9.0
ERROR: Error: Error communicating with device

[Errno 22] Invalid argument: '/Volumes/Kindle/documents'

Traceback (most recent call last):
File "calibre/gui2/device.py", line 88, in run
File "calibre/gui2/device.py", line 620, in _upload_books
File "calibre/devices/usbms/driver.py", line 331, in upload_books
File "calibre/devices/usbms/device.py", line 901, in create_upload_path
File "os.py", line 215, in makedirs
File "os.py", line 225, in makedirs
OSError: [Errno 22] Invalid argument: '/Volumes/Kindle/documents'
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Old 12-14-2022, 10:53 AM   #2
kovidgoyal
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That indicates the macOS kernel is refusing to let calibre create folders on the Kindle. Apple keeps playing games in the name of security, so make sure you have enabled disk access for calibre. And check that /Volumes/Kindle is accessible and working in Finder.
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Old 12-14-2022, 12:30 PM   #3
tpetrich
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I'd done that already before joining the forum and asking for help. Calibre has full disk access and it is mounted in the finder, visible on the desktop. However when I click on it and open it, it just shows as a blank/empty folder.

Any further help would be greatly appreciated.
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Old 12-14-2022, 09:11 PM   #4
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Well the mkdir() system call is failing with an invalid argument error which indicates something is wrong at the kernel/filesystem level. Apple keeps mokeying with these system calls, so hard for anyone else to know what they broke. In general, check that you can create files and directories inside the /Volumes/Kindle/documents folder. Try resetting the Kindle. Try a different USB cable/port.
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Old 12-15-2022, 12:27 PM   #5
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Thank you for your suggestions. Not getting anywhere on my Mac mini M1, I decided to download and install the same edition of calibre 6.9.0 on older Mac my wife has. It is running Catalina, not Ventura as is the mini. When I opened the Kindle drive it showed its folders, rather than the totally empty view on my M1. All the books I'd sent to the Kindle were there, but at the root level. I simply dragged them into the documents folder and everything is now good. So, eventually it has something to do with the Mac mini M1 and its Apple Chip. Hopefully there will be a work around, as many people won't have a second older machine to use with calibre.
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Old 12-15-2022, 09:03 PM   #6
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calibre works fine with M1 and Ventura, this is something specific to your machine.
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