Forwarding to Gmail - messages going missing?

akorvemaker · 19 Sep 2017, 01:28 AM

Background:
My wife and I have a domain for personal used. For years (10?) I've been hosting the DNS at FM, and it's worked well. The A records point to the website, and the MX records point to FM. A few domain aliases are set up. They forward my messages to my FM account, and her messages to her Gmail account.

Issue:
Recently she's found out that some messages are not getting to her. She sees online that a (small) newsletter was sent out, but it never arrived. Replies from one person she's been corresponding with never reach her (individually addressed messages, not bulk mail). Things like that. They're not in her spam folder. She just never gets them.

Question:
Do I have everything set up properly in our DNS records? Any other ideas?

Here's what I have in the FM Domains screen:
FM default settings that are active:

Quote:

MX [domain.tld] 10 in1-smtp.messagingengine.com 1 hour
MX [domain.tld] 20 in2-smtp.messagingengine.com

MX *.[domain.tld] 10 in1-smtp.messagingengine.com 1 hour
MX *.[domain.tld] 20 in2-smtp.messagingengine.com

A mail.[domain.tld] 66.111.4.147 1 hour
A mail.[domain.tld] 66.111.4.148

CNAME mesmtp._domainkey.[domain.tld] mesmtp.[domain.tld].dkim.fmhosted.com 1 hour
CNAME fm1._domainkey.[domain.tld] fm1.[domain.tld].dkim.fmhosted.com
CNAME fm2._domainkey.[domain.tld] fm2.[domain.tld].dkim.fmhosted.com
CNAME fm3._domainkey.[domain.tld] fm3.[domain.tld].dkim.fmhosted.com

The rest of the standard FM entries are disabled (A records, MX for mail.[domain.tld], TXT for SPF record, 3 SRV records).

Custom DNS settings I have entered are:

Quote:

SPF [domain.tld] v=spf1 include:aspmx.googlemail.com include:spf.messagingengine.com ~all
SPF *.[domain.tld] v=spf1 include:aspmx.googlemail.com include:spf.messagingengine.com ~all
(and a couple A records pointing to our website)

Anything look wrong? Any ideas? It has (as far as we can tell) worked flawlessly for years, and now suddenly she's having issues.

Andy

akorvemaker · 19 Sep 2017, 02:02 AM

Extra info. Under Domains, I also have the settings:

Quote:

Mail
Subdomain: Accept mail to ]anything@user.[domain.tld] and deliver it to user+anything@[domain.tld]
Routing: Route mail internally

Messages I send to wife@domain.tld and something@wife.domain.tld both get through (sending from both FM and another gmail account).

BritTim · 19 Sep 2017, 04:58 AM

I do not claim to be an expert in this area, and someone may turn up to correct my explanation, but I think this is roughly what is happening.

The first thing to understand is that there are two flavors of forwarding

A regular forward that create a new message sent from the account that originally received the message.
A redirect, where the message is sent from (in this case) FastMail's servers, but with the original headers indicating that the sender is (usually) not FastMail.

The regular forward should never be a problem. The redirect can be troublesome. In your case, Google sees a message coming from <some domain> using a server (FastMail) that is unexpected (depending on SPF, DKIM and DMARC settings for the sending domain). In most cases, since you have no control over the security settings for the sending domain, messages are subject to being discarded by Google. For any specific sending email addresses, you may be able to circumvent the issue by using a Gmail filter that instructs Google never to discard messages from that address. As a general matter, it is a known gotcha with using redirects.

TenFour · 21 Sep 2017, 08:22 AM

In Gmail make sure you have the account set up to "send as" whatever the email address is for your wife, and go through the setup process even if you never intend to "send as" from the Gmail account. That usually cures the problem, if I understand it correctly.

For example, I set up Gmail to "send as" YYYY@domain.com. As part of the setup process Gmail will send a message to that address and you have to answer to show that you really are at the address. After that, Gmail will usually successfully accept email forwarded from YYYY@domain.com. https://support.google.com/mail/answer/22370?hl=en

akorvemaker · 22 Sep 2017, 12:42 AM

Thanks for the thoughts, BritTim & TenFour. Much appreciated.

I know we have her main address (wife@domain.tld) set up as a "send as" address in gmail, but we might need to do that for various other something@wife.domain.tld addresses too. I'll look into that.

(It would be so nice if simple forwarding just worked. Too bad spammers messed that up for everyone...)

Andy

19 Sep 2017, 04:58 AM	#3
BritTim The "e" in e-mail Join Date: May 2003 Location: mostly in Thailand Posts: 3,090	I do not claim to be an expert in this area, and someone may turn up to correct my explanation, but I think this is roughly what is happening. The first thing to understand is that there are two flavors of forwarding A regular forward that create a new message sent from the account that originally received the message. A redirect, where the message is sent from (in this case) FastMail's servers, but with the original headers indicating that the sender is (usually) *not* FastMail. The regular forward should never be a problem. The redirect can be troublesome. In your case, Google sees a message coming from <some domain> using a server (FastMail) that is unexpected (depending on SPF, DKIM and DMARC settings for the sending domain). In most cases, since you have no control over the security settings for the sending domain, messages are subject to being discarded by Google. For any specific sending email addresses, you may be able to circumvent the issue by using a Gmail filter that instructs Google never to discard messages from that address. As a general matter, it is a known gotcha with using redirects.

21 Sep 2017, 08:22 AM	#4
TenFour Master of the @ Join Date: Feb 2017 Location: USA Posts: 1,721	In Gmail make sure you have the account set up to "send as" whatever the email address is for your wife, and go through the setup process even if you never intend to "send as" from the Gmail account. That usually cures the problem, if I understand it correctly. For example, I set up Gmail to "send as" YYYY@domain.com. As part of the setup process Gmail will send a message to that address and you have to answer to show that you really are at the address. After that, Gmail will usually successfully accept email forwarded from YYYY@domain.com. https://support.google.com/mail/answer/22370?hl=en

22 Sep 2017, 12:42 AM	#5
akorvemaker Master of the @ Join Date: Nov 2002 Location: Canada Posts: 1,015	Thanks for the thoughts, BritTim & TenFour. Much appreciated. I know we have her main address (wife@domain.tld) set up as a "send as" address in gmail, but we might need to do that for various other something@wife.domain.tld addresses too. I'll look into that. (It would be so nice if simple forwarding just worked. Too bad spammers messed that up for everyone...) Andy