Cannot send mail from Apple mail client: "Impossible to send your email"

Created:

2017-01-30 18:35:08 UTC

Modified:

2017-08-16 16:10:35 UTC

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Cannot send mail from Apple mail client: "Impossible to send your email"

Applicable to:

  • Plesk for Linux
  • Plesk Onyx for Linux

Symptoms

Cannot send an email from Airmail or Apple Mail client for a domain with Let's Encrypt certificate enabled. "Impossible to send your email" error message appeared.

Cause

Apple mail clients have SSL support enabled as default. Postfix mail server on the Plesk server uses certificate assigned to server.example.com domain name. When mail client verifies the certificate, it founds a mismatch in domain name specified in mail account johndoe@example3.com and server.example.com and cannot validate it. This behavior is expected.

Resolution

1. To avoid that specify server.example.com as SMTP outgoing mail server in Apple mail client settings.

2. Use multi-domain server as the one for Postfix mail server

3. Use non-SSL connection in the mail client.

https://discussions.apple.com/thread/4164964?start=0&tstart=0 - how to turn off SSL in Mac mail client

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