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Old 08-12-2014, 05:08 PM   #1
jbuller
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Unhappy Gmail test fails except when "Access for less secure apps" enabled

Hi

I'm trying to setup Calibre for the first time.
I've entered my Gmail details and getting the error message below when I test it. I got security alert emails from Google which suggested changing a setting to allow "Access for less secure apps". When I do this and test again in Calibre I get "Mail sent"!
I was suprised not find any other metion of this else where.
Obviously I'd rather not be vunerable so any suggestions?

My settings are smtp.gmail.com 465 SSL
Port 587 and TLS doesn't work either.


Code:
Traceback (most recent call last):
File "site-packages\calibre\gui2\wizard\send_email.py", line 173, in test_email_settings
File "site-packages\calibre\utils\smtp.py", line 135, in sendmail
File "site-packages\calibre\utils\smtplib.py", line 617, in login
SMTPAuthenticationError: (534, '5.7.14 <https://accounts.google.com/ContinueSignIn?sarp=1&scc=1&plt=AKgnsbtXn\n5.7.14 PHjm6Npb0J3JeUNrvqXYCzmiMsbBdmpKiM_Y6DKeavQRZtqu8cfv_KvIHr41R_SNbGtitI\n5.7.14 sE_AKqeNltMaPBowK8438bApB7HjCW2-90TMBkiM1SzF9BOd6lXqH3jxxEIMC7vcRiLPcQ\n5.7.14 Q6LnO-228sB7f2Jh9COaIQGNQzYkmHfja8jGm6Wirg1weLD8tBsO7l1GNddNBwhFY-Lj3f\n5.7.14 UbmxMTg> Please log in via your web browser and then try again.\n5.7.14 Learn more at\n5.7.14 https://support.google.com/mail/bin/answer.py?answer=78754 r20sm60143126wik.0 - gsmtp')


Log:
connect: (u'smtp.gmail.com', 465)
connect: (u'smtp.gmail.com', 465)
reply: '220 mx.google.com ESMTP r20sm60143126wik.0 - gsmtp\r\n'
reply: retcode (220); Msg: mx.google.com ESMTP r20sm60143126wik.0 - gsmtp
connect: mx.google.com ESMTP r20sm60143126wik.0 - gsmtp
send: 'ehlo [192.168.11.2]\r\n'
reply: '250-mx.google.com at your service, [87.113.95.178]\r\n'
reply: '250-SIZE 35882577\r\n'
reply: '250-8BITMIME\r\n'
reply: '250-AUTH LOGIN PLAIN XOAUTH XOAUTH2 PLAIN-CLIENTTOKEN\r\n'
reply: '250-ENHANCEDSTATUSCODES\r\n'
reply: '250-CHUNKING\r\n'
reply: '250 SMTPUTF8\r\n'
reply: retcode (250); Msg: mx.google.com at your service, [87.113.95.178]
SIZE 35882577
8BITMIME
AUTH LOGIN PLAIN XOAUTH XOAUTH2 PLAIN-CLIENTTOKEN
ENHANCEDSTATUSCODES
CHUNKING
SMTPUTF8
send: 'AUTH PLAIN AGphbWVzLnAuYnVsbGVyQGdtYWlsLmNvbQBaSzFmd2xiMS5wYjA=\r\n'
reply: '534-5.7.14 <https://accounts.google.com/ContinueSignIn?sarp=1&scc=1&plt=AKgnsbtXn\r\n'
reply: '534-5.7.14 PHjm6Npb0J3JeUNrvqXYCzmiMsbBdmpKiM_Y6DKeavQRZtqu8cfv_KvIHr41R_SNbGtitI\r\n'
reply: '534-5.7.14 sE_AKqeNltMaPBowK8438bApB7HjCW2-90TMBkiM1SzF9BOd6lXqH3jxxEIMC7vcRiLPcQ\r\n'
reply: '534-5.7.14 Q6LnO-228sB7f2Jh9COaIQGNQzYkmHfja8jGm6Wirg1weLD8tBsO7l1GNddNBwhFY-Lj3f\r\n'
reply: '534-5.7.14 UbmxMTg> Please log in via your web browser and then try again.\r\n'
reply: '534-5.7.14 Learn more at\r\n'
reply: '534 5.7.14 https://support.google.com/mail/bin/answer.py?answer=78754 r20sm60143126wik.0 - gsmtp\r\n'
reply: retcode (534); Msg: 5.7.14 <https://accounts.google.com/ContinueSignIn?sarp=1&scc=1&plt=AKgnsbtXn
5.7.14 PHjm6Npb0J3JeUNrvqXYCzmiMsbBdmpKiM_Y6DKeavQRZtqu8cfv_KvIHr41R_SNbGtitI
5.7.14 sE_AKqeNltMaPBowK8438bApB7HjCW2-90TMBkiM1SzF9BOd6lXqH3jxxEIMC7vcRiLPcQ
5.7.14 Q6LnO-228sB7f2Jh9COaIQGNQzYkmHfja8jGm6Wirg1weLD8tBsO7l1GNddNBwhFY-Lj3f
5.7.14 UbmxMTg> Please log in via your web browser and then try again.
5.7.14 Learn more at
5.7.14 https://support.google.com/mail/bin/answer.py?answer=78754 r20sm60143126wik.0 - gsmtp
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Old 08-12-2014, 10:30 PM   #2
kovidgoyal
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There's nothing insecure about TLS. gmail just wants you to use it only from webapps with oauth. In any case if you dont want to disable oauth, then create a dummy gmail account and use it only for calibre.
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Old 08-13-2014, 05:01 AM   #3
jbuller
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Right so Gmail have change their requirements in the past month (July 2014)
http://windowsitpro.com/security/goo...synching-gmail
A more technical explanation about Google requiring Oauth 2.0 and not Basic authentication is in the 2nd post at http://forums.mozillazine.org/viewto...f=39&t=2852231

So this would appear that Calibre needs to at least provide some kind of warning about or catch this problem during set up. Else lots of other people are going to run in to this same problem an not be as able or keen as me to figure it out. Especially since the error message is not informative.

The separate Gmail account is a decent idea, with the added benefit of not cluttering my account with automated mails. A bit annoying though.
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Old 08-13-2014, 06:11 AM   #4
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I'm not particularly inclined to jump through hoops just to try to workaround one broken smtp provider. Most likely I will just remove the use gmail button from the email preferences. People can use hotmail or their ISP email providers. If google are actually requiring oauth to use smtp, by default, for all accounts, I dont see how they can claim to support smtp with a straight face.
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Old 08-13-2014, 03:40 PM   #5
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What is Google trying to do, lend weight to the arguments that they are evil and shouldn't be trusted with your data? Keep it up and I just might listen...

...

Seems I have been automatically opted in to less security? I never touched that setting, but but it is set to Enable less secure apps.
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Old 08-13-2014, 03:57 PM   #6
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Quote:
Originally Posted by eschwartz View Post
What is Google trying to do, lend weight to the arguments that they are evil and shouldn't be trusted with your data? Keep it up and I just might listen...

...

Seems I have been automatically opted in to less security? I never touched that setting, but but it is set to Enable less secure apps.
I wondered why I wasn't seeing any such options; turns out if you have two-step security enabled, then that option does not exist.
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Old 08-13-2014, 10:15 PM   #7
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As far as I can see, you now have to have either of two options to use SMTP:

1) Two pass authentication with application passwords
2) One pass authentication with "less secure" enabled
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Old 09-27-2017, 02:25 AM   #8
grovalmitch
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smtp

It is because Google blocks sign-in attempts from apps which do not use modern security standards (mentioned on their support page). You can however, turn on/off this safety feature by going to the link below:

Go to this link and select Turn On

https://www.google.com/settings/security/lesssecureapps

more on...smtp mail
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Old 09-27-2017, 03:03 AM   #9
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The "modern security standards" is bullshit. They just want to discourage use of the SMTP protocol so they can show you more ads.
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Old 09-27-2017, 05:47 AM   #10
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Quote:
Originally Posted by grovalmitch View Post
It is because Google blocks sign-in attempts from apps which do not use modern security standards (mentioned on their support page). You can however, turn on/off this safety feature by going to the link below:
Moderator Notice
Do us all a favor and do not respond to ancient threads. The original poster in this thread has not been on Mobileread in 3 years.
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