[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.