See the bit at the end
Quote:
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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]')
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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
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