Sudden problem sending books to my phone via email

[FavSport:Reading]

I have been using Calibre for quite some time. I have always sent the books to my phone via email and saved them in an ereader app just in case I didn't have my actual ereader with me should I want to do some reading. I have never had a problem doing so. However, we just dumped our home internet service in favor of the, now retired, Verizon Prepaid Unlimited plan. Everything in the house is connected to the jetpack and working flawlessly (in fact, working better than the land line we had before....much faster). However, I cannot seem to get the Calibre emails to work. My email works without an issue for everything else. Any suggestions? I'm baffled.

[kovidgoyal]

Look at the log from the email sending jobs.

[FavSport:Reading]

I did and it says it failed to send. I have attempted it several times. In the event I can’t get it to work, could you please tell me how Calibre Companion works? I put it on my phone yesterday and know I can move the books there. My question is, are the books actually taking up space on my phone or are they in a cloud? If they are not in a cloud, is there a way to use the cloud of my choice (I use pcloud)? If I could make that work, then I wouldn’t necessarily need to bother with the email.

[Bookstooge]

There is a whole sub-forum dedicated to CC:

Calibre Companion Forum

[stumped]

with calibre companion the books have to be on your phone for you to read them. it is not a reader as such -it is a program that fetches books and associated info wirelessly from a calibre content server or a cloud library copy. then it hands the books off to be read in an app of your choice.
it works with dropbox, google drive..,. but pcloud is not yet supported

[FavSport:Reading]

Stumped, thank you for the information. What I really want to do is continue to send them via email but it simply is not working. I don't know why. I haven't done anything differently other than we switched from Consolidated Communications (formerly Fairpoint) which was a land line, to a Verizon Jetpack. The jetpack is working extremely well with everything, except for this email glitch. I just don't know what to do to fix it. Any thoughts? I was able to find the books on the computer where they were originally downloaded and share them via email, but it doesn't send the updated bookcovers, etc.

[DNSB]

Originally Posted by FavSport:Reading

Stumped, thank you for the information. What I really want to do is continue to send them via email but it simply is not working. I don't know why. I haven't done anything differently other than we switched from Consolidated Communications (formerly Fairpoint) which was a land line, to a Verizon Jetpack. The jetpack is working extremely well with everything, except for this email glitch. I just don't know what to do to fix it. Any thoughts? I was able to find the books on the computer where they were originally downloaded and share them via email, but it doesn't send the updated bookcovers, etc.

As Kovid said "look at the log from the email sending jobs".

Generally that log file has the reason for the send failure --"authentication" is one of the more common but there are all kinds of errors that can occur.

You can try posting a calibre debug log here if you are having issues seeing any useful information in the log file.

Start calibre in debug mode, try emailing your ebook and close calibre. The debug log will pop up. Copy and paste it into a message here and wrap it in spoiler tags (the eyeball with the X will wrap that tag around selected text).

It is very likely that log file has the information needed to give others the ability to diagnose your problem. As it is, you are calling your auto mechanic, saying my car is making a funny noise then expecting him to diagnose the problem with no further information.

[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.

Edited this message to delete the debugging information once Bernie solved my problem!

[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

[FavSport:Reading]

Bernie,

Thank you soooo much! You are my hero!!!!! I am now sending email from Calibre again. I can't tell you how grateful I am for your help.

[FavSport:Reading]

And a huge thank you to DNSB, as well. Without the debugging information, I would never have gotten anywhere. You folks are amazing!!!!!