Apologies, don't see an Edit button on the previous post, but wanted to add the initial output of debug device detection:
Spoiler:
calibre 6.26 embedded-python: True
macOS-13.5.1-arm64-arm-64bit Darwin ('64bit', '')
('Darwin', '22.6.0', 'Darwin Kernel Version 22.6.0: Wed Jul 5 22:17:35 PDT 2023; root:xnu-8796.141.3~6/RELEASE_ARM64_T8112')
Python 3.10.1
OSX: ('13.5.1', ('', '', ''), 'arm64')
Interface language: None
Successfully initialized third party plugins: Set KFX metadata (from KFX Output) (2, 3, 0) && KFX Output (2, 3, 0) && KePub Metadata Reader (3, 4, 3) && KePub Metadata Writer (3, 4, 3) && KePub Output (3, 6, 5) && Kobo Utilities (2, 16, 10) && KoboTouchExtended (3, 6, 5) && Obok DeDRM (10, 0, 3)
USB devices on system:
[['0x1058',
'0x25a3',
'0x1031',
'Western Digital',
'Elements 25A3',
'3546473534555754'],
['0x1949', '0x9981', '0x223', 'Amazon', 'Kindle Scribe', 'G0923L07245500T5'],
['0x5ac',
'0x1460',
'0x235',
'Apple Inc.',
'USB-C Digital AV Multiport Adapter',
'DLC7156047SG2KQA0\x00']]
Disabled plugins: KOBOTOUCH
Looking for devices of type: MTP_DEVICE
No MTP devices connected to system
Looking for devices of type: SMART_DEVICE_APP
All IP addresses {'lo0': [{'addr': '127.0.0.1', 'netmask': '255.0.0.0', 'peer': '127.0.0.1'}], 'en0': [{'addr': '192.168.1.4', 'netmask': '255.255.255.0', 'broadcast': '192.168.1.255'}]}
No device is connected
Looking for devices...
Devices possibly connected: None