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Hello @Neluser , can you describe the steps on the Synology ? I'm blocked by the fact that it requires a private key on Cloudron side... Thanks

Hello,
I can send email from Cloudron admin menu (Email / Domains: Action send test email) with succes.
But I can't send email from Calibre. Once in the queue, it fails...
On the logs, there is the folowing traces:

DEBUG {cps.tasks.mail:194} Start sending e-mail
DEBUG {cps.tasks.mail:62} send: ehlo [172.18.19.85]
DEBUG {cps.tasks.mail:60} send: AUTH PLAIN
DEBUG {cps.tasks.mail:60} send: AUTH LOGIN
DEBUG {cps.tasks.mail:62} send: **********
ERROR {cps.tasks.mail:199} (535, b'5.7.8 Authentication failed')

(Not sure if line 62 is sensitive data, so I've replace it with stars)

The Calibre "email server settings" are the original ones:
SMTP hostname: mail
Port: 2525
Encryption: None

Thanks for your help !