E-mail to device fails

[mazinho]

I have Calibre 6.29.0 (recommended version for my legacy Macbook OS) set up to send epub files by e-mail to my Kindle. This has worked for a long time and now fails. Error log in spoiler.

I have checked credentials for outgoing and incoming e-mail and the seem to be correct. What can be the issue?

Spoiler:

@kindle.com address masked

Starting job: Email De Camino to ****@kindle.com
connect: to ('smtp.office365.com', 587) None
reply: b'220 AS4P191CA0028.outlook.office365.com Microsoft ESMTP MAIL Service ready at Mon, 27 Jan 2025 21:23:38 +0000 [08DD3E2D12C16060]\r\n'
reply: retcode (220); Msg: b'AS4P191CA0028.outlook.office365.com Microsoft ESMTP MAIL Service ready at Mon, 27 Jan 2025 21:23:38 +0000 [08DD3E2D12C16060]'
connect: b'AS4P191CA0028.outlook.office365.com Microsoft ESMTP MAIL Service ready at Mon, 27 Jan 2025 21:23:38 +0000 [08DD3E2D12C16060]'
send: 'ehlo localhost.localdomain\r\n'
reply: b'250-AS4P191CA0028.outlook.office365.com Hello [31.21.218.121]\r\n'
reply: b'250-SIZE 157286400\r\n'
reply: b'250-PIPELINING\r\n'
reply: b'250-DSN\r\n'
reply: b'250-ENHANCEDSTATUSCODES\r\n'
reply: b'250-STARTTLS\r\n'
reply: b'250-8BITMIME\r\n'
reply: b'250-BINARYMIME\r\n'
reply: b'250-CHUNKING\r\n'
reply: b'250 SMTPUTF8\r\n'
reply: retcode (250); Msg: b'AS4P191CA0028.outlook.office365.com Hello [31.21.218.121]\nSIZE 157286400\nPIPELINING\nDSN\nENHANCEDSTATUSCODES\nS TARTTLS\n8BITMIME\nBINARYMIME\nCHUNKING\nSMTPUTF8'
send: 'STARTTLS\r\n'
reply: b'220 2.0.0 SMTP server ready\r\n'
reply: retcode (220); Msg: b'2.0.0 SMTP server ready'
send: 'ehlo localhost.localdomain\r\n'
reply: b'250-AS4P191CA0028.outlook.office365.com Hello [31.21.218.121]\r\n'
reply: b'250-SIZE 157286400\r\n'
reply: b'250-PIPELINING\r\n'
reply: b'250-DSN\r\n'
reply: b'250-ENHANCEDSTATUSCODES\r\n'
reply: b'250-AUTH LOGIN XOAUTH2\r\n'
reply: b'250-8BITMIME\r\n'
reply: b'250-BINARYMIME\r\n'
reply: b'250-CHUNKING\r\n'
reply: b'250 SMTPUTF8\r\n'
reply: retcode (250); Msg: b'AS4P191CA0028.outlook.office365.com Hello [31.21.218.121]\nSIZE 157286400\nPIPELINING\nDSN\nENHANCEDSTATUSCODES\nA UTH LOGIN XOAUTH2\n8BITMIME\nBINARYMIME\nCHUNKING\nSMTPUTF8'
send: AUTH <censored>
reply: b'334 UGFzc3dvcmQ6\r\n'
reply: retcode (334); Msg: b'UGFzc3dvcmQ6'
send: 'IWlEOTYwNDc5Kw==\r\n'
reply: b'535 5.7.139 Authentication unsuccessful, basic authentication is disabled. [AS4P191CA0028.EURP191.PROD.OUTLOOK.COM 2025-01-27T21:23:44.411Z 08DD3E2D12C16060]\r\n'
reply: retcode (535); Msg: b'5.7.139 Authentication unsuccessful, basic authentication is disabled. [AS4P191CA0028.EURP191.PROD.OUTLOOK.COM 2025-01-27T21:23:44.411Z 08DD3E2D12C16060]'

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 181, in sendmail
File "smtplib.py", line 750, in login
File "smtplib.py", line 739, in login
File "smtplib.py", line 662, in auth
smtplib.SMTPAuthenticationError: (535, b'5.7.139 Authentication unsuccessful, basic authentication is disabled. [AS4P191CA0028.EURP191.PROD.OUTLOOK.COM 2025-01-27T21:23:44.411Z 08DD3E2D12C16060]')

[PeterT]

See the bit at the end

smtplib.SMTPAuthenticationError: (535, b'5.7.139 Authentication unsuccessful, basic authentication is disabled. [AS4P191CA0028.EURP191.PROD.OUTLOOK.COM 2025-01-27T21:23:44.411Z 08DD3E2D12C16060]')

Some of the cloud based email providers including Google and Microsoft are disabling the use of passwords to access their mail services. You will need to get a different provider for calibre to use. Some use GMX for this purpose. Whatever you do use be sure to go through ALL their web settings and ensure that POP3 / SMTP access is enabled

Sent from my Pixel 7a using Tapatalk

[mazinho]

Thanks. I have changed to GMX-mail and fixed the issue. Thread can be closed.