[gbm]

Originally Posted by FavSport:Reading

This is the debug log you asked for. This was done after the latest Calibre update. Still can't send email. Always could. Never had a problem until recently. Hope this can help. It means absolutely nothing to me.

Spoiler:

[calibre Debug log
calibre 3.44 [64bit] embedded-python: True is64bit: True
Windows-10-10.0.17134-SP0 Windows ('64bit', 'WindowsPE')
('Windows', '10', '10.0.17134')
Python 2.7.15+
Windows: ('10', '10.0.17134', 'SP0', u'Multiprocessor Free')
Interface language: None
Successfully initialized third party plugins: Gather KFX-ZIP (from KFX Input) (1, 17, 1) && DeDRM (6, 6, 3) && Package KFX (from KFX Input) (1, 17, 1) && Barnes & Noble (1, 2, 15) && Resize Cover (1, 0, 2) && Obok DeDRM (6, 5, 4) && Prettify Cover 0.9.12 && KFX metadata reader (from KFX Input) (1, 17, 1) && KFX Input (1, 17, 1) && Modify ePub (1, 3, 13) && Kobo Books (1, 6, 0) && Set KFX metadata (from KFX Output) (1, 30, 0) && KFX Output (1, 30, 0) && Kobo Utilities (2, 8, 0)
calibre 3.44 [64bit] embedded-python: True is64bit: True
Windows-10-10.0.17134-SP0 Windows ('64bit', 'WindowsPE')
('Windows', '10', '10.0.17134')
Python 2.7.15+
Windows: ('10', '10.0.17134', 'SP0', u'Multiprocessor Free')
Interface language: None
Successfully initialized third party plugins: Gather KFX-ZIP (from KFX Input) (1, 17, 1) && DeDRM (6, 6, 3) && Package KFX (from KFX Input) (1, 17, 1) && Barnes & Noble (1, 2, 15) && Resize Cover (1, 0, 2) && Obok DeDRM (6, 5, 4) && Prettify Cover 0.9.12 && KFX metadata reader (from KFX Input) (1, 17, 1) && KFX Input (1, 17, 1) && Modify ePub (1, 3, 13) && Kobo Books (1, 6, 0) && Set KFX metadata (from KFX Output) (1, 30, 0) && KFX Output (1, 30, 0) && Kobo Utilities (2, 8, 0)
Turning on automatic hidpi scaling
devicePixelRatio: 1.0
logicalDpi: 96.0 x 96.0
physicalDpi: 100.569275362 x 100.55257732
Using calibre Qt style: True
[0.00] Starting up...
[0.00] Showing splash screen...
[0.14] splash screen shown
[0.14] Initializing db...
[0.20] db initialized
[0.20] Constructing main UI...
DEBUG: 0.0 obok::utilities.py - loading translations
DEBUG: 0.0 obok::dialogs.py - loading translations
DEBUG: 0.0 obok::config.py - loading translations
DEBUG: 0.0 obok::action_err.py - loading translations
DEBUG: 0.0 KoboUtilites::action.py - loading translations
DEBUG: 0.0 KoboUtilites::dialogs.py - loading translations
DEBUG: 0.0 KoboUtilites::action.py - loading translations
DEBUG: 1.8 No Kobo Touch, Glo or Mini appears to be connected
DEBUG: 1.8 rebuild_menus - self.supports_ratings=None, self.supports_tiles=None
DEBUG: 1.8 KoboUtilities:set_toolbar_button_tooltip - start: text='None'
DEBUG: 1.8 device_driver_name - could not load extended driver. Exception= No module named kobotouch_extended.device.driver
DEBUG: 1.8 KoboUtilities:set_toolbar_button_tooltip - setting to text='Utilities to use with Kobo ereaders

Driver: KoboTouch'
DEBUG: 1.8 device_driver_name - could not load extended driver. Exception= No module named kobotouch_extended.device.driver
[2.42] main UI initialized...
[2.42] Hiding splash screen
SMART_DEV ( 0.00: 0.004) _attach_to_port try ip address "" on port 9090
SMART_DEV ( 1.02: 0.835) _startup_on_demand listening on port 9090
SMART_DEV ( 1.10: 0.001) _attach_to_port try ip address "" on port 54982
SMART_DEV ( 1.17: 0.000) _startup_on_demand broadcast socket listening on port 54982
SMART_DEV ( 2.27: 1.033) run All IP addresses {'{49A92197-0147-42BD-B4B1-0EAC436ACDD5}': [{'addr': u'192.168.1.5', 'broadcast': u'192.168.1.5', 'netmask': u'255.255.255.255'}], '{0EF41E05-07D9-11E8-8F6E-806E6F6E6963}': [{'addr': u'127.0.0.1', 'broadcast': u'127.0.0.1', 'netmask': u'255.255.255.255'}]}
[35.17] splash screen hidden
[35.17] Started up in 35.17 seconds with 579 books
Device using plugboard epub email None
Job: 0 Email Show Me Good Land to Pondview02@icloud.com finished
Starting job: Email Show Me Good Land to Pondview02@icloud.com
connect: (u'smtp.gmail.com', 25)
connect: (u'smtp.gmail.com', 25)
reply: '220 smtp.gmail.com ESMTP t8sm4094336qtc.80 - gsmtp\r\n'
reply: retcode (220); Msg: smtp.gmail.com ESMTP t8sm4094336qtc.80 - gsmtp
connect: smtp.gmail.com ESMTP t8sm4094336qtc.80 - gsmtp
send: u'ehlo [192.168.1.5]\r\n'
reply: '250-smtp.gmail.com at your service, [2600:1000:b05a:25fc:3404:b40:b3ad:a35f]\r\n'
reply: '250-SIZE 35882577\r\n'
reply: '250-8BITMIME\r\n'
reply: '250-STARTTLS\r\n'
reply: '250-ENHANCEDSTATUSCODES\r\n'
reply: '250-PIPELINING\r\n'
reply: '250-CHUNKING\r\n'
reply: '250 SMTPUTF8\r\n'
reply: retcode (250); Msg: smtp.gmail.com at your service, [2600:1000:b05a:25fc:3404:b40:b3ad:a35f]
SIZE 35882577
8BITMIME
STARTTLS
ENHANCEDSTATUSCODES
PIPELINING
CHUNKING
SMTPUTF8
send: 'STARTTLS\r\n'
reply: '220 2.0.0 Ready to start TLS\r\n'
reply: retcode (220); Msg: 2.0.0 Ready to start TLS
send: u'ehlo [192.168.1.5]\r\n'
reply: '250-smtp.gmail.com at your service, [2600:1000:b05a:25fc:3404:b40:b3ad:a35f]\r\n'
reply: '250-SIZE 35882577\r\n'
reply: '250-8BITMIME\r\n'
reply: '250-AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH\r\n'
reply: '250-ENHANCEDSTATUSCODES\r\n'
reply: '250-PIPELINING\r\n'
reply: '250-CHUNKING\r\n'
reply: '250 SMTPUTF8\r\n'
reply: retcode (250); Msg: smtp.gmail.com at your service, [2600:1000:b05a:25fc:3404:b40:b3ad:a35f]
SIZE 35882577
8BITMIME
AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH
ENHANCEDSTATUSCODES
PIPELINING
CHUNKING
SMTPUTF8
send: u'mail FROM:<wmshomestead@gmail.com> size=1106801\r\n'
reply: '530-5.5.1 Authentication Required. Learn more at\r\n'
reply: '530 5.5.1 https://support.google.com/mail/?p=WantAuthError t8sm4094336qtc.80 - gsmtp\r\n'
reply: retcode (530); Msg: 5.5.1 Authentication Required. Learn more at
5.5.1 https://support.google.com/mail/?p=WantAuthError t8sm4094336qtc.80 - gsmtp
send: 'rset\r\n'
reply: '250 2.1.5 Flushed t8sm4094336qtc.80 - gsmtp\r\n'
reply: retcode (250); Msg: 2.1.5 Flushed t8sm4094336qtc.80 - gsmtp
send: 'quit\r\n'
reply: '221 2.0.0 closing connection t8sm4094336qtc.80 - gsmtp\r\n'
reply: retcode (221); Msg: 2.0.0 closing connection t8sm4094336qtc.80 - gsmtp

Sending failed...

Traceback (most recent call last):
File "site-packages\calibre\gui2\email.py", line 45, in run
File "site-packages\calibre\gui2\email.py", line 135, in sendmail
File "site-packages\calibre\utils\smtp.py", line 163, in sendmail
File "site-packages\calibre\utils\smtplib.py", line 762, in sendmail
SMTPSenderRefused: (530, '5.5.1 Authentication Required. Learn more at\n5.5.1 https://support.google.com/mail/?p=WantAuthError t8sm4094336qtc.80 - gsmtp', u'wmshomestead@gmail.com')


Retrying in 301 seconds...

Waiting 301 seconds before sending, to avoid being marked as spam.
You can control this delay via Preferences->Tweaks
Aborted job: Email Show Me Good Land to Pondview02@icloud.com

reply: '530-5.5.1 Authentication Required. Learn more at\r\n'
reply: '530 5.5.1 https://support.google.com/mail/?p=WantAuthError t8sm4094336qtc.80 - gsmtp\r\n'
reply: retcode (530); Msg: 5.5.1 Authentication Required. Learn more at
5.5.1 https://support.google.com/mail/?p=WantAuthError t8sm4094336qtc.80 - gsmtp

go to this link the steps you want are:

• Use an App Password: If you use 2-Step Verification, try signing in with an App Password.
• Allow less secure apps: If you don't use 2-Step Verification, you might need to allow less secure apps to access your account.

bernie