[SOLVED] Redirect to gmail account failing

Discussions on webmail and the Professional version.
Post Reply
R4LRetro
Posts: 36
Joined: Wed Mar 25, 2020 1:32 pm

[SOLVED] Redirect to gmail account failing

Post by R4LRetro »

I'm having trouble figuring out an issue we've been having. To start, I configured MailEnable to redirect all mail to our Spam appliance so it could handle inbound and outbound. I have a couple of users who redirect mail to a Gmail account. Some emails won't actually deliver and I receive a MDF instead. Here's an example:

Code: Select all

Recipient: [SMTP:user1@gmail.com]
Reason: 550-5.7.1 [Our Public IP 12] Our system has detected that this message is likely unsolicited mail. To reduce the amount of spam sent to Gmail, this message has been blocked. Please visit https://support.google.com/mail/?p=UnsolicitedMessageError for more information. u19-20020a056e02111300b002d0f9f4e4bcsi1522857ilk.150 - gsmtp
I assume that with multiple users doing this is why Gmail suspects it as bulk. I disabled the smart host, yet the same issue persists. I've tried following their bulk email guidelines and now I'm also receiving a hard SPF fail check sometimes and an unsolicited email message:

Code: Select all

Recipient: [SMTP:user1@gmail.com] This message fails to pass SPF checks for an SPF record with a hard fail policy (-all). To best protect our users from spam and phishing, the message has been blocked. Please visit https://support.google.com/mail/answer/81126#authentication for more information. v3-20020a05620a0f0300b006a64dbdb75asi1022063qkl.308 - gsmtp
I've checked our SPF records with a number of tools online and they pass with our domain and IP using ~all. However, this seems to contradict what the above SMTP error message says. I'm not exactly sure what I should do here?

R4LRetro
Posts: 36
Joined: Wed Mar 25, 2020 1:32 pm

Re: Redirect to gmail account failing

Post by R4LRetro »

Actually I think I get what's happening. Redirected emails just sends the original email, so if my domain marks it as a soft/hard fail, that info passes onto Google. Am I right to assume that is what is happening? If I send an email from my domain to my gmail account, it passes with flying colors.

MailEnable-Ian
Site Admin
Posts: 9738
Joined: Mon Mar 22, 2004 4:44 am
Location: Melbourne, Victoria, Australia

Re: Redirect to gmail account failing

Post by MailEnable-Ian »

Hi,

You need to change the redirection handling to "Remail from mailbox address" within the postoffice connector properties. Please see:

https://www.mailenable.com/documentation/10.0/Professional/Post_office_connector_General.html
Regards,

Ian Margarone
MailEnable Support

R4LRetro
Posts: 36
Joined: Wed Mar 25, 2020 1:32 pm

Re: Redirect to gmail account failing

Post by R4LRetro »

Hi Ian,

I didn't even know that option existed. Thank you for pointing that out. I will switch it over and monitor it today, but I'm pretty sure you are right. 8)

Thanks!

EDIT: I just did a quick test and yeah, that seems to have solved the issue. Thanks again!

R4LRetro
Posts: 36
Joined: Wed Mar 25, 2020 1:32 pm

Re: [SOLVED] Redirect to gmail account failing

Post by R4LRetro »

I saw this morning I had some MDFs still, even after making the postoffice change for redirects. However, I figured out why. The mail in particular failed DKIM so our spam appliance tagged it. This then got remailed to a Gmail account, which obviously fails. As much as DKIM, SPF and DMARC are helpful they are also a PITA and pretty much require someone to monitor mail all day. I think I may have to look into an archiver or running a secondary MailEnable server for archival purposes.

Post Reply