Gmail password working, then failing

[jmw082]

I set up an application specific password for Gmail (required because I have two-step verification enabled for my Gmail account), and the password works for Calibre, but the next day, it fails and I have to revoke my password and create a new one. I can tell from the error message that the password is the issue.

Traceback (most recent call last):
File "site-packages\calibre\gui2\email.py", line 43, in run
File "site-packages\calibre\gui2\email.py", line 130, in sendmail
File "site-packages\calibre\utils\smtp.py", line 135, 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 https://support.google.com/mail/answer/14257 t133sm4817360ywe.54 - gsmtp')


So again, I do a new password, and it works for a day, then fails. My computer remains on with Calibre open (as I have it as a server).

[PeterT]

When I read https://support.google.com/accounts/answer/185833?hl=en I see

Every App password is only used once. But don't worry, you can always generate a new App password whenever you need one, even for a device or application you've authorized before

I take that to mean it's a one use password.

[jmw082]

"Most of the time, you’ll only have to enter an App password once per app or device, so don’t worry about memorizing it."

For example, I have Thunderbird email application on my PC. I do not have to create a new password to access my gmail through Thunderbird each time I use Thunderbird. This issue only has come up for Calibre.

[PeterT]

I think you will find that apps like Thunderbird contain support for the security being used by Gmail (I sense that during the initial authentication a token is applied by Gmail to the application and look subsequent authentications the token is exchanged) and calibre does not contain special support.

[kovidgoyal]

Gmail is an email monopoly play disguised as a free service. Just use GMX or Hotmail or pretty much any other free email service that properly supports the SMTP standard.