Troubleshooting 10060 error "emailing to kindle"

[HowardH]

Hello,
When I right click on a file and select "email to [kindle address]",
it fails with the error below.
I can drag and drop the same file into the Kindle desktop app, "send to Kindle" or email the file with my Outlook program as an attachment. Both of them work fine.

What am I missing?
Thanks, Howard



calibre, version 6.1.0 (win32, embedded-python: True)
Failed to email book: Failed: Email Mother Jones to
[kindle address]@kindle.com

Starting job: Email Mother Jones to
[kindle address]@kindle.com

Sending failed...

Traceback (most recent call last):
File "calibre\gui2\email.py", line 48, in run
File "calibre\gui2\email.py", line 137, in sendmail
File "calibre\utils\smtp.py", line 162, in sendmail
File "calibre\utils\smtp.py", line 142, 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 48, in run
File "calibre\gui2\email.py", line 137, in sendmail
File "calibre\utils\smtp.py", line 162, in sendmail
File "calibre\utils\smtp.py", line 142, 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 Mother Jones to [kindle address]@kindle.com" failed with error:
Traceback (most recent call last):
File "calibre\gui2\threaded_jobs.py", line 82, in start_work
File "calibre\gui2\email.py", line 105, in __call__
File "calibre\gui2\email.py", line 48, in run
File "calibre\gui2\email.py", line 137, in sendmail
File "calibre\utils\smtp.py", line 162, in sendmail
File "calibre\utils\smtp.py", line 142, 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\\halve\\AppData\\Local\\Temp\\calibre_ ghz_rh55\\odfvn1ykcaltmpfmt.mobi', 'Mother Jones - calibre.mobi', '[kindle address]@kindle.com', 'E-book: Mother Jones', 'Attached, you will find the e-book\n\nMother Jones\n\tby calibre\n\nin the MOBI format.') {'notifications': <queue.Queue object at 0x0000018C1FB79B70>, 'abort': <threading.Event object at 0x0000018C1FB783A0>, 'log': <calibre.utils.logging.GUILog object at 0x0000018C1FB78970>}

[DNSB]

The 'None' in your error message suggests that no SMTP server has been configured in calibre.

What SMTP server do you have configured in calibre? What port? Check in Preferences => Sharing books by email. Is the Hostname a valid SMTP server? Is the Port a valid port for that SMTP server? Does using the Test email button report a successful connection?

[HowardH]

Thank you, David.

I was attacked by a bad case of brainfartism.

I'm new to calibre, and, as cool as calibre is, it does not have the ability to magically set up an SMTP server.

My brain was maxed out on a complex process to get a large quantity of PDF files OCR'd and converted to flowable and searchable ebooks that have to be down converted to azw (not azw3) for an old Kindle DX. Mobi files are searchable (and also quotable) but wreck the formatting in the DX. The azw file are close to perfect. Now I can actually read the files on a big screen (I hate my paperwhite's baby screen), and search and pull notes from the files. (the DX is a portable, searchable, readable, research library)

And thanks to your tip, I now have a GMX account with aliases for my book publishing project and can keep all that stuff separate from my main email.

Thanks again.

Regards, Howard