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I have the following situation:
Domain registered with ionos.
Email boxes per address to facilitate sending mail from the domain address.
Email to the domain address is forwarded by ionos to a gmail address.
Gmail is then email "client" giving all he benefits of a gmail account for email.
Gmail configured to send using the ionos mailbox credentials to send mail.
This works near perfectly, except for one sender (any user from the sender's domain).
In this failure case the email is rejected by gmail so bounces back, with the message "550-5.7.26 This message does not have authentication information or fails to 550-5.7.26 pass authentication checks".
If the same sender sends directly to the gmail address then it is not rejected.
The email headers just have the extra "Received:" headers as it's forward, it doesn't appear to have any other changes.
Sounds like an issue with the email forwarding, right? Must be doing something that's tripping gmail up.
TIA.
Do you know that it actually gets forwarded to gmail rather than rejected by ionos for lacking SPF/DKIM/whatever?
Yep, looks like it, definitely google rejecting it.
Also, slightly weird as that rejection gets send to the domain address (and then correctly forwarded to the gmail address!). I think because ionos received the rejection and sending it to the domain address rather than back to the original sender?
"
SMTP error from remote server for TEXT command, host: gmail-smtp-in.l.google.com (108.177.15.27) reason: 550-5.7.26 This message does not have authentication information or fails
to
550-5.7.26 pass authentication checks. To best protect our users from spam
, the
550-5.7.26 message has been blocked. Please visit
550-5.7.26 https://support.google.com/mail/answer/81126#authentication fo
r more
550 5.7.26 information.
"
I don't think Gmail likes mail forwarded to it. Particularly if your mate is sending email from example.com which has an SPF record saying they will always send with mailserver.example.com and Gmails seeing mail arriving from your Ionos server. Possibly also they discourage it to encourage you to use paid for Google email.
Does your Ionos setup have the option for Sender Rewriting Scheme (Or similar), so that Gmail sees the email as being From Ionos, but with a reply-to (or similar) header so when you hit reply it goes to the right place?
That does make some sense.
I guess I could either move the domain to google or change the gmail config to use pop3 to check for email on the domain accounts instead of the domain forwarding the mail. This might mean that emails are slower to arrive in gmail, but should be more reliable.