Gmail thinks messagingengine.com is spam

[silverwolff]

Originally Posted by trikotret

So it took them 10 days to respond?

Yes.

March 18 - me: reported problem, with urgency.
March 19 - FM: I've escalated your ticket.
March 19 - me: hello?
March 20 - me: problem is worse; now affecting other domains!
March 28 - FM: Looks like your DKIM and SPF are correct. Are you still having the problem?
March 28 - me: Yes! Still having this problem!
March 31 - FM: provides answer about needing to use external SMTP

That's 13 days, almost 2 weeks, from me reporting the problem to a solution.

[ioneja]

Originally Posted by silverwolff

That's 13 days, almost 2 weeks, from me reporting the problem to a solution.

I mean, it could be worse. In all seriousness, they escalated it within 1 day, which was a decent start... but then... that gap between Mar 20 and Mar 28 is definitely a bummer. Disappointing TBH.

When I see reports like this I do get concerned over Fastmail. I've been with them for a long time, and they've been generally good for me. I like the people there too, so I want them to be successful (even though I might end up leaving them due to Australian government intrusion, which just keeps getting worse, like they've lost their minds -- and which is obviously not Fastmail's fault).

I also spread my email needs around a bunch of providers. But this story (and others I've read in the last few years) makes me wonder if they need to offer a premium paid support service. Something better than what they've been delivering... (Maybe they do and I just don't know about it.) It also makes me wonder if their current support system is stretched too thin... which might mean they don't have the budget to hire enough people... who knows... but it's not reassuring that if I got into a similar situation that I can count on them to resolve it quickly.

I've personally never had truly *bad* service from them (that I can recall, it's been many years), but my queries might have been easier to answer. However, I've also never had *spectacular* service from them either, and if this was a mission-critical business email situation and I had a huge time gap like that on something important, I'd probably have given up and migrated away to another service.

[Terry]

I have found with gmail an ms if I use Terry it often get flagged as spam so perhaps it has something to do with the Op's domain name.

[TenFour]

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.

Wasn't the problem that Gmail was marking emails you sent as spam? You were able to send those emails obviously, so not sure exactly what you mean by "entering external SMTP credentials."

[silverwolff]

Originally Posted by TenFour

Wasn't the problem that Gmail was marking emails you sent as spam? You were able to send those emails obviously, so not sure exactly what you mean by "entering external SMTP credentials."

I guess that previously, I was able to send those emails using FastMail's builtin SMTP information. Suddenly, Gmail must have decided that there was some kind of mismatch it didn't like. Entering the SMTP credentials for the matching server to the email address must have fixed that concern? I don't really understand it.

[placebo]

Originally Posted by silverwolff

I guess that previously, I was able to send those emails using FastMail's builtin SMTP information. Suddenly, Gmail must have decided that there was some kind of mismatch it didn't like. Entering the SMTP credentials for the matching server to the email address must have fixed that concern? I don't really understand it.

I think what's confusing some of us is that we thought you were hosting your domain's email at Fastmail. That means you'd normally be using Fastmail's SMTP server for sending email, not an external server. But now you're referring to external SMTP credentials, which suggests you're using a non-Fastmail SMTP server for some reason.

The headers you posted earlier show that in your previous setup, Fastmail's server was authorized to send email for your domain as both DKIM and SPF passed. Yet now you're suggesting you're using a different server, and that solved the problem. Does this mean you updated the DKIM and SPF records for your domain as well? If so, that might be the actual reason the problem was resolved.

[PON]

I've just had this problem for the first time ever (FM user for 20+ years): an important email I sent to a gmail user last week was not received. Just discovered it today. Ended up sending twice more before it was reported as filed in spam because it came from messagingengine.

I use my own domain, with MX records pointing to Fastmail, SPF and DKIM set up correctly.

The reports of poor response from Fastmail are worrying. I routinely recommend Fastmail as an alternative to Gmail.

I don't have time to dig into this just now, just want to add a "me too" for now. Will get back to this later.

[ioneja]

Sadly, I'll have to add a deliverability concern too, but in my case from FastMail to Microsoft 365 for Business -- I had an important email to a client get flagged as spam, and I've sent many, many emails over the years to this same client with the same kind of content. Same email server settings, everything set up properly with Fastmail on my custom domain, SPF, DKIM, etc., all good. But this one straight to her spam. She only discovered it after a phone call from me. She has since marked that email as not spam, and I think she whitelisted me, and I think it's solved for now, but this thread makes me wonder how many other emails fall through the cracks like this. I don't like having a conversation with a client asking them to check their spam box. So all in all, I'm a little frustrated right now, and if this happens again, I will be considering moving business email off of Fastmail.

[TenFour]

but in my case from FastMail to Microsoft 365 for Business -- I had an important email to a client get flagged as spam,

Microsoft for Business is notorious for this. I use it at work and have to check my Junk folder every day, and every day there are important emails there. Even some of our own internal emails sent through Microsoft 365 within the organization go into the Junk folders of users. You can whitelist, mark as Not Junk, do whatever you want, and it doesn't make one bit of difference. Microsoft 365 filters have a mind of their own.

[ioneja]

Originally Posted by TenFour

Microsoft for Business is notorious for this.

Well, I guess that's good news for me then?

Bummer to hear your experience with them, I migrated away from them for my business years ago -- can't remember the reasons why though.

In any case, your experience might explain why my client didn't mind checking her spam/junk folder. Maybe it happens to her with other people too. It was the first time that I knew of with my own email to her from Fastmail though.

[aoeuaoeu]

Originally Posted by placebo

I think what's confusing some of us is that we thought you were hosting your domain's email at Fastmail. That means you'd normally be using Fastmail's SMTP server for sending email, not an external server. But now you're referring to external SMTP credentials, which suggests you're using a non-Fastmail SMTP server for some reason.

Is it reasonable for me to expect that my using an external (non-Fastmail) SMTP server, specified in the settings for a Fastmail sending identity, will work to avert the 'lots of messages from messagingengine.com have been flagged as spam' alert in Gmail? Thank you.

[evfrson]

Originally Posted by TenFour

Microsoft 365 filters have a mind of their own.

Microsoft very often classifies its own marketing emails as spam.

[FredOnline]

Has anyone mentioned the rotation of the DKIM keys?

Does anyone know if Fastmail automates this, or do they change manually, depending on circumstances?

Taking as an example of one of my domains, there are 4 x records for DKIM (mesmtp, fm1, fm2, fm3). I believe that the mesmtp record is no longer required (but it's still there). I've checked the records in MXToolBox, and all except fm3 are valid - the fm3 record errors and is shown as:

v=DKIM1; k=rsa; n=Intentionally_Left_Blank_As_Per_DKIM_Rotation_BCP; p=

Perhaps someone with a better understanding of DKIM could comment on the above?

[PON]

I've just discovered this has happened twice more with emails to Gmail users. I'm concerned not to see a report here that the problem has been resolved.

Update:

Not sure now long this has been in place but I've discovered that Fastmail's Settings for Domains now includes DKIM and SPF instructions and a warning in my case that current values are wrong. I have changed them per instructions but have yet to see any green checkmark. I'm using DNSmadeEasy as my DNS provider. It's not in the list of providers for which specific instructions are available, but I've followed the generic instructions. I've emailed Fastmail Support but ... what are the chances the email is discarded??

Update 2:

Fastmail support did get my email and responded with a solution. I used cut and paste to enter domain key values and inadvertently had duplicated one!

[bbbc]

I also recently sent an email that ended up in the recipient's spam folder (Gmail). This party has gotten emails from me before.

Per Fastmail's warning banner, I fixed the SPF and DKIM for my domain that's with Cloudflare. mail-tester reported that I was missing a DMARC policy, so I added that to the mix.