problems emailing books to kindle paperwhite

[Ginnia]

I'm having trouble sending books from calibre to my kindle via my gmail.com account. Sure could use some help...

Attached is the error message I get:



calibre, version 5.9.0 (win32, embedded-python: True)
Failed to email book: Failed: Email The Hellfire Club to ginnybo@kindle.com

Starting job: Email The Hellfire Club to ginnybo@kindle.com

Sending failed...

Traceback (most recent call last):
File "calibre\gui2\email.py", line 45, in run
File "calibre\gui2\email.py", line 129, in sendmail
File "calibre\utils\smtp.py", line 168, in sendmail
File "calibre\utils\smtp.py", line 149, in sendmail_direct
OSError: Failed to send mail: TimeoutError(10060, 'A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond', None, 10060, None)


Retrying in 1 seconds...

Waiting 1 seconds before sending, to avoid being marked as spam.
You can control this delay via Preferences->Tweaks

Sending failed...

Traceback (most recent call last):
File "calibre\gui2\email.py", line 45, in run
File "calibre\gui2\email.py", line 129, in sendmail
File "calibre\utils\smtp.py", line 168, in sendmail
File "calibre\utils\smtp.py", line 149, in sendmail_direct
OSError: Failed to send mail: TimeoutError(10060, 'A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond', None, 10060, None)

Job: "Email The Hellfire Club to ginnybo@kindle.com" failed with error:
Traceback (most recent call last):
File "calibre\gui2\threaded_jobs.py", line 83, in start_work
File "calibre\gui2\email.py", line 102, in __call__
File "calibre\gui2\email.py", line 45, in run
File "calibre\gui2\email.py", line 129, in sendmail
File "calibre\utils\smtp.py", line 168, in sendmail
File "calibre\utils\smtp.py", line 149, in sendmail_direct
OSError: Failed to send mail: TimeoutError(10060, 'A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond', None, 10060, None)

Called with args: ('C:\\Users\\Ginny\\AppData\\Local\\Temp\\calibre_ nxkkf7pc\\fxlxz0r2caltmpfmt.mobi', 'The Hellfire Club - Jake Tapper.mobi', 'ginnybo@kindle.com', 'E-book: The Hellfire Club', 'Attached, you will find the e-book\n\nThe Hellfire Club\n\tby Jake Tapper\n\nin the MOBI format.') {'notifications': <queue.Queue object at 0x00000244DD4F5910>, 'abort': <threading.Event object at 0x00000244DD4F5CD0>, 'log': <calibre.utils.logging.GUILog object at 0x00000244DD4F5DC0>}

[Ginnia]

Also attaching the resulting info fromrunning an email test from "Sharing books by email" from Preferences.

[dunhill]

They are gmail security measures, check unwanted messages or spam.

[CathyA]

Configure Calibre to use Gmail's servers to send the email to Amazon.

In your Gmail account, turn on 2-Step Verification and then generate an App Password for use with Calibre. Here's Google's Help on how to do that: https://support.google.com/accounts/answer/185833

In the Calibre email setup screen, the "Send email from" should be the Gmail username that's whitelisted in your Amazon account, Hostname is smtp.gmail.com, Port is 587, username is the Gmail username again, Password is the app password you generated specifically for Calibre, and TLS is selected.

If you use "ginnybo" for both your Gmail username and your Kindle address, then Amazon will send you a verification email for each book before it will deliver it to your Kindle. If you want to avoid that, change the Kindle address to some more random string of letters and numbers.

[PeterT]

Maybe try entering the server info for Gmail and ensure that you've enabled access to the Gmail server on your Google settings.

In my case
Hostname smtp.gmail.com Port 587
Username <my Gmail address>
Password <app specific password>
Encryption TLS

You'll have to look through your Google account settings to find out how to create an app specific password

Sent from my Pixel 4a using Tapatalk

[Ginnia]

I don't understand what you are telling me... I looked in spam folder, but did not, nor did I expect to find anything relating.

[Deskisamess]

Did you add the "sending" email to the list of approved senders in Manage Your Content and Devices in your Amazon account?

[Ginnia]

Thank you CathyA and PeterT -- I would have NEVER figured this out by myself. I can now email books to my Kindle...