Tried again: with Debugview, started Kobo Desktop, connected KT and click button (at about 32s time and debug answer at about 50s).
00000001 0.00000000 [4340] BTMMHOOK 21.09.2011 17:17:28 Thread<114C> Hook DLL loaded
00000002 2.87083459 [1600] Executed EEPROM Tool...47
00000003 2.87089133 [1600]
00000004 4.25265598 [236] ApplicationBase::switchTranslator::loading locale: ":/translations/trans_it_IT"
00000005 4.67367315 [236] setProxyEnabled true
00000006 4.67500353 [236] ------- [SyncClient] ------ SyncClient::start (Thread: 0x1104 )
00000007 7.77817583 [236] Object::connect: No such slot DeviceManager::startUsbUpgradeWizard()
00000008 8.12454700 [236] QCoreApplication:
ostEvent: Unexpected null receiver
00000009 8.16102982 [236] MainWindowController::checkUserDeviceID
00000010 8.16460896 [236] UserIDFilter<class Volume>::UserIDFilter Woah.. you probably don't want to filter on empty string
00000011 8.16538525 [236] UserIDFilter<class Volume>::UserIDFilter Woah.. you probably don't want to filter on empty string
00000012 8.24179459 [236] AbstractLibraryController<class Volume>::layout source has no rows
00000013 8.28110981 [236] BTMMHOOK 21.09.2011 17:17:37 Thread<1104> Hook DLL loaded
00000014 24.40891647 libusb0-sys:info [DriverEntry] loading driver
00000015 24.40987015 libusb0-sys:info [add_device] device #1 created
00000016 24.40999603 libusb0-sys:info [add_device] running in filter mode
00000017 24.40999985 libusb0-sys:info [add_device] complete status=00000000
00000018 24.41060257 libusb0-sys:info [dispatch_pnp] IRP_MN_START_DEVICE
00000019 24.72852898 libusb0-sys:info [dispatch_pnp] IRP_MN_QUERY_CAPABILITIES
00000020 26.49523735 libusb0-sys:info [get_descriptor] buffer size: 18 type: 0001 recipient: 0000 index: 0000 language id: 0000 timeout: 5000
00000021 26.49648666 libusb0-sys:info [release_all_interfaces] releasing all interfaces bound to file object 0xfe185f90
00000022 26.49724960 libusb0-sys:info [get_descriptor] buffer size: 8 type: 0002 recipient: 0000 index: 0000 language id: 0000 timeout: 1000
00000023 26.49860764 libusb0-sys:info [get_descriptor] buffer size: 32 type: 0002 recipient: 0000 index: 0000 language id: 0000 timeout: 1000
00000024 26.50422478 libusb0-sys:info [release_all_interfaces] releasing all interfaces bound to file object 0xfe185f90
00000025 26.50425529 libusb0-sys:info [get_configuration] timeout: 5000
00000026 26.50534439 libusb0-sys:info [get_configuration] current configuration is: 1
00000027 26.50535965 libusb0-sys:info [get_descriptor] buffer size: 255 type: 0003 recipient: 0000 index: 0000 language id: 0000 timeout: 1000
00000028 26.50774956 libusb0-sys:info [get_descriptor] buffer size: 255 type: 0003 recipient: 0000 index: 0003 language id: 1033 timeout: 1000
00000029 26.50867844 libusb0-sys:info [release_all_interfaces] releasing all interfaces bound to file object 0xfe185f90
00000030 26.69951439 [236] Opened the device's database. Ref count = 1
00000031 26.70840836 [236] Removed the device's database
00000032 26.72211075 [236] Opened the device's database. Ref count = 1
00000033 26.72414589 [236] Removed the device's database
00000034 26.73223495 [236] Opened the device's database. Ref count = 1
00000035 26.73448753 [236] Removed the device's database
00000036 31.94103432 [1600] Executed EEPROM Tool...48
00000037 31.94105530 [1600]
00000038 50.64150620 [236] NetworkReplyObserver:
nError 99
00000039 50.64161682 [236] WebResponseInflater::webRequestFinished FAILED 99 "Connection timed out"
00000040 50.64181519 [236] ------- [SyncClient] ------ SyncClient::~SyncClient (Thread: 0x1104 )
00000041 56.96340561 [236] Removed the DESKTOP's database
00000042 56.96343231 [236] ------- [SyncClient] ------ SyncClient::~SyncClient (Thread: 0x1104 )
00000043 56.96384048 [236] BTMMHOOK 21.09.2011 17:18:25 Thread<1104> Hook DLL unloaded
00000044 56.96445465 [236] [ESENT 0ec.1104 20110921171825] ESENT version 5.01.2600.5512 (RETAIL RTM MBCS) loaded.
00000045 56.96445465 [236] [ESENT 0ec.1104 20110921171825] Image: "C:\WINNT\system32\ESENT.dll"
00000046 56.96445465 [236] [ESENT 0ec.1104 20110921171825] Process: "C:\Program Files\Kobo\Kobo.exe"
00000047 56.96445465 [236] [ESENT 0ec.1104 20110921171825] Trace File: "C:\WINNT\Debug\ESE.TXT"
00000048 56.96445465 [236] [ESENT 0ec.1104 20110921171825] Trace Level: Full
00000049 56.96457672 [236] [ESENT 0ec.1104 20110921171825] ESENT version 5.01.2600.5512 (RETAIL RTM MBCS) unloaded.
00000050 57.61185455 [1600] Executed EEPROM Tool...49
00000051 57.61187744 [1600]