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Old 01-30-2022, 08:10 AM   #1
slasor
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emailing books suddenly stopped working- timing out
the email books to my kindle have suddenly stopped working.
I've checked the details (username/password) and it all seems fine.

it's using the Hotmail option to send emails.

below is the error message that comes when it can't send an email

Traceback (most recent call last):
File "calibre\gui2\wizard\send_email.py", line 208, in test_email_settings
File "calibre\utils\smtp.py", line 171, in sendmail
File "polyglot\smtplib.py", line 36, in __init__
File "smtplib.py", line 253, in __init__
File "smtplib.py", line 339, in connect
File "smtplib.py", line 308, in _get_socket
File "socket.py", line 808, in create_connection
File "socket.py", line 796, in create_connection
TimeoutError: [WinError 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


Log:
connect: ('smtp.live.com', 587)
connect: to ('smtp.live.com', 587) None
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Old 01-30-2022, 08:31 AM   #2
kovidgoyal
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your antivirus/firewall/router is blocking calibre.
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Old 01-30-2022, 07:33 PM   #3
davidfor
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I think this might be a change elsewhere. Just testing, I cannot telnet to smtp.live.com using port 587. I tested from a Windows and Linux box that do not go through the same network path.

I think this has changed to use "smtp-mail.outlook.com" instead. I have a vague memory of seeing something about this happening a while ago. They have probably just turned it off in the last couple of days.
Last edited by davidfor; 01-30-2022 at 07:36 PM.
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Old 01-30-2022, 09:21 PM   #4
kovidgoyal
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Oh fun. In that case change the server in Preferences->sharing by email from smtp.live.com to smtp-mail.outlook.com and you should be fine.
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Old 02-01-2022, 11:37 AM   #5
Myzifer
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Same issue and suggested fix worked for me.
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Old 02-05-2022, 05:38 AM   #6
slasor
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thank you that seemed to have worked.
somehow in my messing about, I've activated some form of app password.
entered this and was able to send a test email.
thank you
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