Trouble sending ebooks to Kindle

[Lisa1]

Hello!

I'm new to this forum. I've been using Calibre to send ebooks to my Kindle PaperWhite for quite some time (I love Calibre). However, this service doesn't seem to work anymore. I keep getting error messages like the following one. Does anyone have a solution to offer?


Starting job: Email "Don't You Know Who I Am?" to author_123@free.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 "Don't You Know Who I Am?" to author_123@free.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\\User\\AppData\\Local\\Temp\\calibre_h 5oesqab\\j7yo434jcaltmpfmt.mobi', '"Don\'t You Know Who I Am?" - Ramani Durvasula.mobi', 'author_123@free.kindle.com', 'E-book: "Don\'t You Know Who I Am?"', 'Attached, you will find the e-book\n\n"Don\'t You Know Who I Am?"\n\tby Ramani Durvasula\n\nin the MOBI format.') {'notifications': <queue.Queue object at 0x000002C70005E5E0>, 'abort': <threading.Event object at 0x000002C70005E820>, 'log': <calibre.utils.logging.GUILog object at 0x000002C70005E970>}

[DNSB]

What email provider are you sending the email through?

[kovidgoyal]

You need to setup an email relay as described in the FAQ https://manual.calibre-ebook.com/faq...-using-calibre