Here's the log from Windows version:
Spoiler:
calibre Debug log
calibre 2.7 [64bit] isfrozen: True is64bit: True
Windows-7-6.1.7601-SP1 Windows ('64bit', 'WindowsPE')
('Windows', '7', '6.1.7601')
Python 2.7.8
Windows: ('7', '6.1.7601', 'SP1', 'Multiprocessor Free')
Successfully initialized third party plugins: Kindle and Mobipocket DeDRM && Inept Epub DeDRM && Quality Check && Kindle 2, 3, 4, Touch, PaperWhite Device Interface Paperwhite thumbnail FIX MOD
Starting up...
Started up in 6.29 seconds with 333 books
Job: 1 Get device information started
DeviceJob: 1 Get device information done, calling callback
DeviceJob: 1 Get device information callback returned
Job: 2 Set library information started
DeviceJob: 2 Set library information done, calling callback
DeviceJob: 2 Set library information callback returned
Job: 3 Get list of books on device started
DEBUG: 0.0 USBMS: Fetching list of books from device. Device= KINDLE2 oncard= None
DEBUG: 0.0 USBMS: dirs are: E:\ documents
DEBUG: 0.1 USBMS: scan from root False E:\documents
Job: 2 Set library information finished
No details available.
Job: 1 Get device information finished
No details available.
DEBUG: 0.3 USBMS: count found in cache: 15, count of files in metadata: 15, need_sync: False
DEBUG: 0.3 USBMS: Finished fetching list of books from device. oncard= None
DEBUG: 0.3 USBMS: Fetching list of books from device. Device= KINDLE2 oncard= carda
DEBUG: 0.3 USBMS: Fetching list of books from device. Device= KINDLE2 oncard= cardb
DeviceJob: 3 Get list of books on device done, calling callback
DeviceJob: metadata_downloaded: Starting set_books_in_library
DeviceJob: set_books_in_library: books to process= 15
DeviceJob: set_books_in_library finished: time= 0.00399994850159
DeviceJob: metadata_downloaded: updating views
DeviceJob: metadata_downloaded: syncing
DeviceJob: metadata_downloaded: refreshing ondevice
DeviceJob: metadata_downloaded: sending metadata_available signal
DeviceJob: 3 Get list of books on device callback returned
Job: 3 Get list of books on device finished
No details available.
Job: 4 Upload 1 books to device:The Long Walk started
Device using plugboard azw3 KINDLE2 None
Setting metadata in: The Long Walk at: C:\Users\Cath\AppData\Local\Temp\calibre_pvo2m6\k3 42dncaltmpfmt.azw3
DEBUG: 8.5 USBMS: uploading 1 books
APNX META: guid: fd6e063b
APNX META: ASIN: 8c3e5bac-2e79-442b-ba3f-cac012e3ad36
APNX META: CDE: EBOK
APNX META: format: MOBI_8
APNX META: Name: The_Long_Walk
APNX Content Header: {"contentGuid":"fd6e063b","asin":"8c3e5bac-2e79-442b-ba3f-cac012e3ad36","cdeType":"EBOK","format":"MOBI_8"," fileRevisionId":"1","acr":"The_Long_Walk"}
DEBUG: 9.3 USBMS: finished uploading 1 books
DeviceJob: 4 Upload 1 books to device:The Long Walk done, calling callback
DEBUG: 9.3 USBMS: adding metadata for 1 books
DEBUG: 9.3 USBMS: finished adding metadata
DeviceJob: set_books_in_library: books to process= 16
DeviceJob: set_books_in_library finished: time= 0.00100016593933
DeviceJob: 4 Upload 1 books to device:The Long Walk callback returned
Job: 5 Send metadata to device started
DEBUG: 9.4 USBMS: starting sync_booklists
DEBUG: 9.6 USBMS: finished sync_booklists
DeviceJob: 5 Send metadata to device done, calling callback
DeviceJob: 5 Send metadata to device callback returned
Job: 4 Upload 1 books to device:The Long Walk finished
No details available.
Job: 5 Send metadata to device finished
No details available.
Job: 6 Delete books from device started
DEBUG: 41.9 USBMS: deleting 1 books
DEBUG: 42.0 USBMS: finished deleting 1 books
DeviceJob: 6 Delete books from device done, calling callback
DEBUG: 42.0 USBMS: removing metadata for 1 books
DEBUG: 42.0 USBMS: finished removing metadata for 1 books
DeviceJob: set_books_in_library: books to process= 15
DeviceJob: set_books_in_library finished: time= 0.00399994850159
DeviceJob: 6 Delete books from device callback returned
Job: 7 Send metadata to device started
DEBUG: 42.1 USBMS: starting sync_booklists
DEBUG: 42.3 USBMS: finished sync_booklists
DeviceJob: 7 Send metadata to device done, calling callback
DeviceJob: 7 Send metadata to device callback returned
Job: 7 Send metadata to device finished
And here's the log from the portable version:
Spoiler:
calibre Debug log
calibre 2.7 Portable isfrozen: True is64bit: False
Windows-7-6.1.7601-SP1 Windows ('32bit', 'WindowsPE')
32bit process running on 64bit windows
('Windows', '7', '6.1.7601')
Python 2.7.8
Windows: ('7', '6.1.7601', 'SP1', 'Multiprocessor Free')
Starting up...
Started up in 3.63 seconds with 0 books
Job: 1 Get device information started
DeviceJob: 1 Get device information done, calling callback
DeviceJob: 1 Get device information callback returned
Job: 2 Set library information started
DeviceJob: 2 Set library information done, calling callback
DeviceJob: 2 Set library information callback returned
Job: 3 Get list of books on device started
DEBUG: 0.0 USBMS: Fetching list of books from device. Device= KINDLE2 oncard= None
DEBUG: 0.0 USBMS: dirs are: E:\ documents
DEBUG: 0.1 USBMS: scan from root False E:\documents
Job: 1 Get device information finished
No details available.
Job: 2 Set library information finished
No details available.
DEBUG: 0.3 USBMS: count found in cache: 18, count of files in metadata: 18, need_sync: False
DEBUG: 0.3 USBMS: Finished fetching list of books from device. oncard= None
DEBUG: 0.3 USBMS: Fetching list of books from device. Device= KINDLE2 oncard= carda
DEBUG: 0.3 USBMS: Fetching list of books from device. Device= KINDLE2 oncard= cardb
DeviceJob: 3 Get list of books on device done, calling callback
DeviceJob: metadata_downloaded: Starting set_books_in_library
DeviceJob: set_books_in_library: books to process= 18
DeviceJob: set_books_in_library finished: time= 0.0159997940063
DeviceJob: metadata_downloaded: updating views
DeviceJob: metadata_downloaded: syncing
DeviceJob: metadata_downloaded: refreshing ondevice
DeviceJob: metadata_downloaded: sending metadata_available signal
DeviceJob: 3 Get list of books on device callback returned
Job: 3 Get list of books on device finished
No details available.
DeviceJob: set_books_in_library: books to process= 18
DeviceJob: set_books_in_library finished: time= 0.374000072479
Job: 4 Set library information started
DeviceJob: 4 Set library information done, calling callback
DeviceJob: 4 Set library information callback returned
Job: 4 Set library information finished
No details available.
Job: 5 Upload 1 books to device:Neverwhere started
Device using plugboard azw3 KINDLE2 None
Setting metadata in: Neverwhere at: C:\Users\Cath\AppData\Local\Temp\calibre_mzcl88\qw 9ht7caltmpfmt.azw3
DEBUG: 38.9 USBMS: uploading 1 books
APNX META: guid: 4f2cb88f
APNX META: ASIN: 6c29e792-40fc-4ce2-a248-f0d0d0dd61db
APNX META: CDE: EBOK
APNX META: format: MOBI_8
APNX META: Name: Neverwhere
APNX Content Header: {"contentGuid":"4f2cb88f","asin":"6c29e792-40fc-4ce2-a248-f0d0d0dd61db","cdeType":"EBOK","format":"MOBI_8"," fileRevisionId":"1","acr":"Neverwhere"}
DEBUG: 40.0 USBMS: finished uploading 1 books
DeviceJob: 5 Upload 1 books to device:Neverwhere done, calling callback
DEBUG: 40.0 USBMS: adding metadata for 1 books
DEBUG: 40.0 USBMS: finished adding metadata
DeviceJob: set_books_in_library: books to process= 19
DeviceJob: set_books_in_library finished: time= 0.0
DeviceJob: 5 Upload 1 books to device:Neverwhere callback returned
Job: 6 Send metadata to device started
DEBUG: 40.2 USBMS: starting sync_booklists
DEBUG: 40.4 USBMS: finished sync_booklists
DeviceJob: 6 Send metadata to device done, calling callback
DeviceJob: 6 Send metadata to device callback returned
Job: 5 Upload 1 books to device:Neverwhere finished
No details available.
Job: 6 Send metadata to device finished
No details available.
Kovid quoted some of the code that sends the book. It looks like it checks to see what kindle it is and sends the larger thumbnail if it's a Voyage. Is there any way to see what kind of kindle Calibre thinks is attached? There is a reference to "KINDLE2" in both of the above logs.