Major issue with Calibre email functionality

[muellerbenjamin]

Hi all,

I've spent a couple of hours trying to set up Calibre to send books to my Kindle via Gmail. No success, unfortunately.

In essence, I always get the same error message when sendning a test e-mail:

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 113, in sendmail
File "site-packages/calibre/utils/smtplib.py", line 617, in login
SMTPAuthenticationError: (535, '5.7.8 Username and Password not accepted. Learn more at\n5.7.8 http://support.google.com/mail/bin/answer.py?answer=14257 mb7sm3889396wic.10 - gsmtp')

Username and password are correct. I have tried the following:
1. Create & use application-specific password
2. Create new dedicated Gmail account for Calibre and use with & without application-specific password
3. Changing SMTP Port from 587 to 465 and encryption from TLS to SSL

None of these worked. With method 3, interestingly, Calibre regularly froze and had to be force-closed.

So I've run out of ideas regarding how to fix this.

Does anyone have any suggestions?

[theducks]

Did you follow these tips from the FAQ
http://manual.calibre-ebook.com/faq.html#id32

[muellerbenjamin]

Originally Posted by theducks

Did you follow these tips from the FAQ
http://manual.calibre-ebook.com/faq.html#id32

Yes I have. My AV program's Mail shield shows no activity so that shouldn't be the reason.

As the error description indicates, the issue is related to Google rejecting the username/password as well as application-specific passwords. Is there a workaround?

[kovidgoyal]

This is most likely caused by something incorrect in your gmail config. What that might be, I haven't the foggiest idea, though the link to the gmail help docs in that error message provides several clues.

I will note that I personally use gmail with calibre's email sending functionality every day.

[muellerbenjamin]

Originally Posted by kovidgoyal

This is most likely caused by something incorrect in your gmail config. What that might be, I haven't the foggiest idea, though the link to the gmail help docs in that error message provides several clues.

I will note that I personally use gmail with calibre's email sending functionality every day.

Well there is hardly something 'incorrect' in my Gmail config, since my Gmail works just fine. I use Gmail for a whole host of external applications ('connected applications'): ITunes Google Sync; ipad mail; iphone chrome; Mac calendar; Mac mail; Mac notes; dropbox, camscanner etc. etc.

What all of the above have in common is that their Google logon node is built into the Gmail API.

I think a more sober assessment would be: there is some unknown compatiblity/configuration issue that Calibre has regarding email sending functionality in Gmail.

My hunch is it is an issue with 2-step verification accounts. I think Calibre's 'ad hoc'/independent/unverified login node is likely to be treated with suspicion by Google's servers.

You should explore the possibility with Google of making Calibre's Gmail functionality official.

[GoSharks]

Originally Posted by muellerbenjamin

You should ......

I always love when someone is asking for help and begins their last sentence with this phrase.

[theducks]

If Calibre was a Google product:

You would have to register to use most functionality
Be connected so Google could harvest all your book search results.
Watch 32 Ads before being allowed to Click OK
Receive endless updates to get around various blocking tools you now employ.

[DoctorOhh]

Originally Posted by muellerbenjamin

My hunch is it is an issue with 2-step verification accounts.

Since sending books from calibre using gmail works fine for me you may be correct in pointing out that 2-step verification may be the hitch preventing your account from functioning. If this proves to be the case then the simple work around (until calibre works with 2-step verification) would be to create an account for simply sending books and leave the account setup with standard authentication.

[PeterT]

I thought two step security also allowed the creation of application specific passwords, is back to the classic single password.

[DoctorOhh]

Originally Posted by PeterT

I thought two step security also allowed the creation of application specific passwords, is back to the classic single password.

I don't know how it works, but a quick look shows the OP can exempt that computer after logging in one time.

During sign-in, you can tell us not to ask for a code again on that particular computer. From then on, that computer will only ask for your password when you sign in.

[PeterT]

Also see Sign in using application-specific passwords

[DoctorOhh]

Originally Posted by PeterT

Also see Sign in using application-specific passwords

So it looks like there may be something 'incorrect' in the OP's Gmail config, since Gmail makes available the necessary tools to allow gmail to work just fine with calibre.

[PeterT]

Exactly! My calibre / gmail setup has been using an application specific password for a very long time now.

[kovidgoyal]

calibre's email sending functionality uses the bog standard SMTP protocol as implemented in the python standard library. I really dont see any scope for bugs in it, but, anything is possible As I said, I haven't a clue as to what the bug could be, but, patches are always welcome.

[muellerbenjamin]

Originally Posted by GoSharks

I always love when someone is asking for help and begins their last sentence with this phrase.

I have a problem with Calibre. I tried to fix it by running through all conceivable scenarios (see my OP), and run against some invisible obstacle. Instead of just complaining, I offer a suggestion as to what that invisible obstacle *may* be. So I don't see your logic at all. You're the one who is moaning for moaning's sake instead of being constructive. Thanks for a completely unnecessary and ignorant post.

Originally Posted by theducks

If Calibre was a Google product...

Patently untrue. Look at how Dropbox has integrated Gmail, or CamScanner, or most applications with some kind of email functionality. I'm not saying sell Calibre to Google, I'm suggesting that Calibre integrates Gmail's API for its email capability, which should make it more stable. The current situation where some users are simply unable to use Gmail in Calibre - the forums are full of users reporting this issue! - is unsatisfactory, and is probably due to the ad-hoc integration of Gmail.

Originally Posted by DoctorOhh

create an account for simply sending books and leave the account setup with standard authentication.

Thank you for the constructive suggestion. As per my OP (see point 2.) I have tried this approach, unsuccessfully, unfortunately.

Originally Posted by PeterT

I thought two step security also allowed the creation of application specific passwords, is back to the classic single password.

Thank you for the helpful tip. I tried this approach (see OP), it didn't work unfortunately.

Originally Posted by DoctorOhh

So it looks like there may be something 'incorrect' in the OP's Gmail config

I won't discount that possibility. However, I haven't a clue as to what I should configure differently. Any ideas?

It is interesting how some users react to my problem in a defensive/sarcastic manner. I harbour no ill intentions, I simply have an issue with Calibre that I wanted to seek some advice for, and suggest potential solutions. As it stands, I still cannot send emails through Calibre. I am also willing to set up a new account with a different email provider, and use their SMTP server, but I don't know of any alternatives.