Gmail thinks messagingengine.com is spam

[trikotret]

Originally Posted by silverwolff

I'm using the DNS from my website host, but I have the MX records, CNAME records, and TXT record all set up correctly there, and the Domains area in Fastmail set up correctly. When I look at Domains > mydomain.com, I see:

• The MX servers for your domain are set correctly: your email is hosted at Fastmail.
• DKIM is correctly configured.
• SPF is correctly configured.

Also, I have asked FM Support for help by opening a ticket, but that was Thursday and they still haven't fixed it. So I'm looking for more things that I can do, with your help perhaps, to solve!

I have emails from a few different domains set up at Fastmail, set up a few different ways, and they've all worked fine for years. It suddenly changed this past Thursday, and all of them are now being marked a spam by Gmail.

Are you sure you dont have your DNS records setup somewhere else also? I used to get this error when I had my DNS records setup at simplelogin and domain host. I deleted the simplelogin dns records and it started working fine.

[jarland]

If you can send any email from Fastmail and land in Gmail's inbox, you can be sure their support will only be able to make a confused gesture. At best you'll get sympathy but no solution. I know a lot of people like to think there's these hidden channels where companies can resolve these issues in private but they really don't exist. There are only a handful of people at Google who will talk about filters and they won't make any changes on request by anyone, they're not allowed to. The ones who are allowed aren't speaking to anyone outside of the company about the topic.

This to say, don't wait on Fastmail support for this. Go for the gold:

https://support.google.com/mail/answ...926052666&rd=1

https://support.google.com/mail/answ..._topic=7279058

And don't forget to mark the emails as not spam in Gmail. If you score a 10/10 on mail-tester or even close to it, you're working against a machine learning algorithm that has targeted you. While it's possible that the algorithm in question considers Fastmail + you to be the full trigger (where Fastmail minus you does not), it can only be changed by training their filters regardless, and that is something which users are largely involved in.

It is absolutely possible to wreck a domain reputation without intending to. Poorly configured cron job notifications blasting to Gmail, forwarding an excess of spam using SRS (and you want to be using SRS if forwarding), or even and especially legitimately upsetting recipients who report you as spam. The latter is what Postmaster Tools are best for giving insight on.

And finally, drop your email signature and check the result. The use of images and shortlinks in email signatures is rampant and very often responsible for spam filtering. Trust me, this one I've seen too many times.

[silverwolff]

Ultimately, I solved the problem by setting up my domains within Fastmail and changing my MX records etc. It took a few hours to settle and once it did my emails stopped being marked as Spam. I still think this is a FM/Gmail problem, and I shouldn't have to move my domains to FM to solve it.

Fastmail also never got back to my ticket.

[JeremyNicoll]

Originally Posted by silverwolff

Fastmail also never got back to my ticket.

Do you mean you haven't yet even had their first-level response, or that - if it was passed onto someone else, that they haven't replied?

Have you read this thread: http://www.emaildiscussions.com/showthread.php?t=78940

[BritTim]

Originally Posted by silverwolff

Ultimately, I solved the problem by setting up my domains within Fastmail and changing my MX records etc. It took a few hours to settle and once it did my emails stopped being marked as Spam. I still think this is a FM/Gmail problem, and I shouldn't have to move my domains to FM to solve it.

Fastmail also never got back to my ticket.

Bear in mind that the cessation of the problem may have nothing to do with any changes you made. Personally, I think it most likely that there was a temporary glitch in Gmail's very complex filtering system which has now been found and fixed.

[silverwolff]

Originally Posted by JeremyNicoll

Do you mean you haven't yet even had their first-level response, or that - if it was passed onto someone else, that they haven't replied

I initially reported the problem on March 18 in the late afternoon, including full email headers and a screenshot.

I got a response 6 hours later saying "I’ve escalated your ticket to our developers, as they are best suited to assist with this issue."

I sent updates on the 19th and 20th. I still haven't gotten a second or a useful response (it's been 5 days).

[silverwolff]

Originally Posted by BritTim

Bear in mind that the cessation of the problem may have nothing to do with any changes you made. Personally, I think it most likely that there was a temporary glitch in Gmail's very complex filtering system which has now been found and fixed.

The problem has been fixed for the 3 domains that I have now pointing at Fastmail (emails from those domains to gmail are not marked as spam).

The problem remains for the 2 domains that I haven't changed (emails sent from those domains go straight to spam in gmail, even for recipients who have that email in their addressbooks and with whom I've emailed in the past).

[jarland]

Changing where inbound email goes to isn't going to impact that. I'm confused that sending an email from fastmail, from a domain, goes to spam and then sending an email from fastmail, from a domain, after changing it's MX records, doesn't go to spam. It sounds like there's a missing detail. Like maybe you're correctly setting the SPF record at the same time that you're changing MX? And why are you sending email from fastmail, from a domain, if you don't have that domain on fastmail to begin with?

[placebo]

Originally Posted by jarland

Changing where inbound email goes to isn't going to impact that. I'm confused that sending an email from fastmail, from a domain, goes to spam and then sending an email from fastmail, from a domain, after changing it's MX records, doesn't go to spam. It sounds like there's a missing detail. Like maybe you're correctly setting the SPF record at the same time that you're changing MX? And why are you sending email from fastmail, from a domain, if you don't have that domain on fastmail to begin with?

I took "setting up my domains within Fastmail" to mean silverwolff is now using Fastmail's DNS servers for those domains. One advantage of doing that is that things like SPF and DKIM will be set up automatically and correctly, which reduces the likelihood of outgoing email being marked as spam.

Before, silverwolff was using the webhost DNS servers, which suggests to me that there was something wrong with the setup which Google may have overlooked before but is now enforcing.

It might be helpful to see the full headers of one of the messages that ended up in the spam folder on Gmail to see how it was processed by Google's spam filters.

[silverwolff]

Originally Posted by placebo

Before, silverwolff was using the webhost DNS servers, which suggests to me that there was something wrong with the setup which Google may have overlooked before but is now enforcing.

Hmm, that does make some sense. I would sure like to know what's wrong with my setup so that I can fix it for my remaining two domains, which I can't move into Fastmail.

Originally Posted by placebo

It might be helpful to see the full headers of one of the messages that ended up in the spam folder on Gmail to see how it was processed by Google's spam filters.

The grey message from Google, which I see when viewing the message in my test gmail account's Spam folder, says "Why is this message in spam? Lots of messages from messagingengine.com were identified as spam in the past."

Below is a full header from a "marked as spam" email I sent just now. DKIM and SPF are both listed as "pass."

Delivered-To: xxxxxxxxx@gmail.com
Received: by 2002:a05:6840:b502:b0:bb2:9f64:6159 with SMTP id k2csp2270954nli;
        Wed, 23 Mar 2022 13:59:50 -0700 (PDT)
X-Google-Smtp-Source: ABdhPJzTGs9HTNXCYp7UO6IuzAmqeraJ6bNtjIgUS6Tgflr7lZU+SmIqMItw9Z1Ca9/TWS/wEKxt
X-Received: by 2002:a81:8106:0:b0:2dc:1f07:920b with SMTP id r6-20020a818106000000b002dc1f07920bmr2031765ywf.330.1648069190443;
        Wed, 23 Mar 2022 13:59:50 -0700 (PDT)
ARC-Seal: i=1; a=rsa-sha256; t=1648069190; cv=none;
        d=google.com; s=arc-20160816;
        b=s1Sjd1uxw9Mh0ry1tU73MXwtNqpaf8WVMkkwb3k8f0WtLBdr51BucfBnq9voUNtRgO
         ms0FmsGh08FnkVO//QnnelKqs2vbhhu41oMzTOyQkpVaBWw/F9mpUNyQO9/Dq1z8/g8g
         ELhYv53J/EnT+yD5rAiuwQedDqMlsuyqm4cfjR/PgCVx026/7JKlLWZcD5JcIPAhd2O6
         tLHsA+0YdHIhLS/Xf5cTLq0cX5X+Y/d9TiCD1Exu/4tb/dA7dFP7qhha4naPBz7rtuNa
         2zTJeOREePtNbLyPpArQbnXo70gWa96xh3bPKDa9RORj8b7bLw1VUOKsQKlOj+JMSB2w
         VdAQ==
ARC-Message-Signature: i=1; a=rsa-sha256; c=relaxed/relaxed; d=google.com; s=arc-20160816;
        h=subject:to:from:date:message-id:mime-version:user-agent
         :dkim-signature;
        bh=iYHlRXgEsv+ikSIVeBDEHmbdSzOKDQhpwZCoym2J26I=;
        b=EQwFfeKoOrAUVYo+7UU/D4EqgdaTlQq7VWJyk2D4MCxo8qVAo3T91nrGnBTGojvAJA
         K405Z11vwW+5H2INqYlHawa89Yp3LlXIY/uVZSxBm9djHwY7g6vejAonMnm6SwnGodGy
         Z3KkxYxG3jEJNAvu0y5ZvuTsP6hLx9RUvCHHXegHJSxYWVB9YnAFOtkB3Ub+wBvdcbxB
         6XfT4dYQLwJ4Xct3AnfShntpVM49Wzs2XZMlIEJhCOoTr2dJJ+K44DxlqasSh1y5I24q
         Q222sSI4Oaz6FfCjh0YEwCWAgfh0FBkY8bbgzs0zY/ko79da+J9vb33VKsIU0qH0J/MC
         xCzg==
ARC-Authentication-Results: i=1; mx.google.com;
       dkim=pass header.i=@messagingengine.com header.s=fm3 header.b=VJ8+Y5lF;
       spf=pass (google.com: domain of xxx@xxxxxx.info designates 66.111.4.26 as permitted sender) smtp.mailfrom=xxx@xxxxxx.info
Return-Path: <xxx@xxxxxx.info>
Received: from out2-smtp.messagingengine.com (out2-smtp.messagingengine.com. [66.111.4.26])
        by mx.google.com with ESMTPS id l7-20020a25bf87000000b0063399404621si17017099ybk.651.2022.03.23.13.59.50
        for <xxxxxxxxx@gmail.com>
        (version=TLS1_3 cipher=TLS_AES_256_GCM_SHA384 bits=256/256);
        Wed, 23 Mar 2022 13:59:50 -0700 (PDT)
Received-SPF: pass (google.com: domain of xxx@xxxxxx.info designates 66.111.4.26 as permitted sender) client-ip=66.111.4.26;
Authentication-Results: mx.google.com;
       dkim=pass header.i=@messagingengine.com header.s=fm3 header.b=VJ8+Y5lF;
       spf=pass (google.com: domain of xxx@xxxxxx.info designates 66.111.4.26 as permitted sender) smtp.mailfrom=xxx@xxxxxx.info
Received: from compute3.internal (compute3.nyi.internal [10.202.2.43]) by mailout.nyi.internal (Postfix) with ESMTP id EB1A05C01D6 for <xxxxxxxxx@gmail.com>; Wed, 23 Mar 2022 16:59:49 -0400 (EDT)
Received: from imap41 ([10.202.2.91])
  by compute3.internal (MEProxy); Wed, 23 Mar 2022 16:59:49 -0400
DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed; d= messagingengine.com; h=cc:content-type:date:date:from:from :in-reply-to:message-id:mime-version:reply-to:sender:subject :subject:to:to:x-me-proxy:x-me-proxy:x-me-sender:x-me-sender :x-sasl-enc; s=fm3; bh=iYHlRXgEsv+ikSIVeBDEHmbdSzOKDQhpwZCoym2J2 6I=; b=VJ8+Y5lFDqhExWWjEk0OB7RH7xUx/Ih4DQQLKGYMkNnmllouXgXCn+THV ARtjqqSxzKA8e78fLyXNljRz0R/PunCoJrhVQmfJr5Pw/X3+aINqAW0/gvYfF2uD M4JKqYebxqfA4VaEm0p3ku1y1COoAY1twdIoPmu64iiyLYyYv+ZYaIkSij41sIVQ +p7yloxTIK0ivvmeJd1om5z439vaTlNiuCw+diqv4nMKw6cEcExC6E0GU01HcYzd 01/eG4wIORriUioaNNVKliLi2x8Uy/N+b381zmCs4NapFRhKW71X6cu8nULLbzdL a8Kxeqd4/sfNmFItNqEQ6DyGJlsuQ==
X-ME-Sender: <xms:RYo7YlGzxUfLe6NAhw98VXQLE8WKPtpMJhi1HNKDvaGy42JR7b7mWA>
    <xme:RYo7YqU76gIQ2vB6NWVOVtZdXhv7wM5wwwBL1mxAmf5cKYrsXBg2mEYGtppomzzRs
    pKKqC2DuTu9ag>
X-ME-Proxy-Cause: gggruggvucftvghtrhhoucdtuddrgedvvddrudegjedgudeggecutefuodetggdotefrod
    ftvfcurfhrohhfihhlvgemucfhrghsthforghilhdpqfgfvfdpuffrtefokffrpgfnqfgh
    necuuegrihhlohhuthemuceftddtnecunecujfgurhepofgfggfkfffhvffutgesrgdtre
    erreertdenucfhrhhomhepfdetrghrohhnucfjohgughgvucfuihhlvhgvrhdfuceorggr
    rhhonhesthgvrghmshhilhhvvghrrdhinhhfoheqnecuggftrfgrthhtvghrnhephfeuue
    egkefgjeduveffleeiueelveevjeegtdetueeiffekfeetkeevveeggfelnecuvehluhhs
    thgvrhfuihiivgeptdenucfrrghrrghmpehmrghilhhfrhhomheprggrrhhonhesthgvrg
    hmshhilhhvvghrrdhinhhfoh
X-ME-Proxy: <xmx:RYo7YnL7zbgllGKBGCgraB-hPhuvv-1Qcq9rv3o4e6J8kW58Eo_2pw>
    <xmx:RYo7YrHnl62z99fKjNci-4Lvam6GoNBuOmS2uzVVr54IyaqByIK2GQ>
    <xmx:RYo7YrVwRrXFMsnNMJXqG1Y55zzxJzT93bhNHqbSPUG_Oyfp7LDI2A>
    <xmx:RYo7YmQGyPmGFthLQDg1T2F8FKya1Gh8igpP_K8dBToDoGdDVTMsJQ>
Received: by mailuser.nyi.internal (Postfix, from userid 501) id 5AAAC3C00CF; Wed, 23 Mar 2022 16:59:49 -0400 (EDT)
X-Mailer: MessagingEngine.com Webmail Interface
User-Agent: Cyrus-JMAP/3.5.0-alpha0-4911-g925b585eab-fm-20220323.003-g925b585e
Mime-Version: 1.0
Message-Id: <19180822-5421-4d0c-855e-3413f953b28d@www.fastmail.com>
Date: Wed, 23 Mar 2022 15:59:28 -0500
From: XXX XXXXX <xxx@xxxxxx.info>
To: XXX XXXXX <xxxxxxxxx@gmail.com>
Subject: another test
Content-Type: multipart/alternative; boundary=613463dd7b3b4da7be2df7289585acaa

--613463dd7b3b4da7be2df7289585acaa
Content-Type: text/plain

This is another test.
--613463dd7b3b4da7be2df7289585acaa
Content-Type: text/html

<!DOCTYPE html><html><head><title></title><style type="text/css">p.MsoNormal,p.MsoNoSpacing{margin:0}</style></head><body><div>This is another test.<br></div><div><br></div></body></html>
--613463dd7b3b4da7be2df7289585acaa--

[FredOnline]

Helen Horstmann-Allen (COO @Fastmail) on Twitter:

If you’re sending mail from your own domain, go check the domain settings page to make sure DKIM is set up. Google got more aggressive about it recently!

https://twitter.com/pazpena/status/1510358585783595012

[placebo]

Originally Posted by silverwolff

Below is a full header from a "marked as spam" email I sent just now. DKIM and SPF are both listed as "pass."

I just sent a message from my Fastmail-hosted domain to compare. The headers on my message also had DKIM lines my domain in addition to mail.messagingengine.com. In other words, there were two DKIM signatures and two DKIM passes.

[silverwolff]

Fastmail support finally got back to me. The problem is that I had added those email addresses a long time ago, before Fastmail required external SMTP information to be added for external addresses.

I deleted the identities and added them anew, this time entering external SMTP credentials. The problem is now solved and I can send from those identities.

A pretty simple solution. Just wish FM Support had gotten back to me sooner!

[trikotret]

Originally Posted by silverwolff

Fastmail support finally got back to me. The problem is that I had added those email addresses a long time ago, before Fastmail required external SMTP information to be added for external addresses.

I deleted the identities and added them anew, this time entering external SMTP credentials. The problem is now solved and I can send from those identities.

A pretty simple solution. Just wish FM Support had gotten back to me sooner!

So it took them 10 days to respond?

[aoeuaoeu]

Originally Posted by silverwolff

Fastmail support finally got back to me. The problem is that I had added those email addresses a long time ago, before Fastmail required external SMTP information to be added for external addresses.

I deleted the identities and added them anew, this time entering external SMTP credentials. The problem is now solved and I can send from those identities.

A pretty simple solution. Just wish FM Support had gotten back to me sooner!

Is it really necessary to delete the identity and then create it again? Or can one just add, to the existing configuration, the external server?

I appreciate this info from silverwolff and from the very many other kind readers. Bummed about this change though!