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Old 14 Sep 2019, 01:51 PM   #1
benaboo
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Emails sent through Fastmail never reach recipients

I'm opening a new thread because I had a similar issue to another user here, and didn't want to hijack their thread.

Initial post on other thread: Having the same issue as of a couple days ago. Using a custom domain and suddenly everything from Fastmail is being snagged by a couple email providers as spam. Even simple messages.

Only way I was able to find out was to send an email to my work address (I'm the email admin there), and sure enough, Microsoft grabbed it before it even got to my inbox. Fastmail is saying contact Microsoft (because their spam codes are proprietary), Microsoft says contact Fastmail. Grrrrr.

Course, it's not just happening with MS recipients. It's happening with a bunch of different recipients. MS was just an example.

Update for this thread, after I was asked more details: I have a custom domain where Fastmail manages the DNS and sends mail directly as my domain. My wife and I were set up as a "family" with that domain. As of a couple days ago, a number of email systems started snagging any emails either of us sent as spam.

She uses the Fastmail app on her phone, I generally use the Fastmail web app on a computer.

My wife was the first one who noticed it. A few people were not getting her emails. With the start of the school year, this was an urgent matter. I tried sending an email from my own account. It didn't get through either to the recipients. Tried sending to my work (where I administer our Office365) and that's how I noticed it was getting snagged by MS and put into quarantine. I figured that's what was happening on other systems as well.

I sent a copy of the headers to Fastmail to see if they could figure out why the emails were being seen as spam. They said contact Microsoft because only they could make sense of the spam headers MS put in the message. I contacted MS. They said it had nothing to do with them (sure, sure). I've escalated it, but not hopeful.

In the meantime, I have moved off Fastmail after 15-20 years, and moved to my web hosting account's web service for this domain.

Surprise, surprise, suddenly any emails I send get through just fine to my work email, where ALL of them were getting snagged before - simple emails, complex emails. ALL snagged before. Now ALL are going through now that I've moved my DNS and custom domain over to my web hosting service (MDD Hosting).

Had to have been something with Fastmail, unfortunately. It was a good run, but if they can't go the extra half mile to help look a little deeper, I guess it's time to move on. Not sure to what. I loved the web aggregation of all my email accounts and not sure what to do now.

My wife was only using the custom domain, no other accounts. So I've set her up with Outlook app connected via IMAP to the new mail server. For me, I'm not looking forward to going back to IMAP access for all my accounts (three custom domains + gmail), although I do have fewer than I used to so maybe it won't be quite as painful.

Last edited by benaboo : 14 Sep 2019 at 01:58 PM.
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Old 14 Sep 2019, 01:54 PM   #2
benaboo
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Quote:
Originally Posted by n5bb View Post
If the problem is only when sending from your own domain through Fastmail outgoing servers, I would check that your DKIM and SPF setup is correct and if you are using DMARC try loosening up your policy.
It was the first thing I checked - DKIM and SPF were fine. The Fastmail support rep said "DNS looked fine." I wasn't using DMARC.
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Old 14 Sep 2019, 04:27 PM   #3
Terry
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Quote:
Originally Posted by benaboo View Post
It was the first thing I checked - DKIM and SPF were fine. The Fastmail support rep said "DNS looked fine." I wasn't using DMARC.
I have that trouble using my domain....in most cases we have to get people to add us the their address book, but in saying that it is not always possible.

I think possibly it is customers who use MS outlook that has the problem but us using our own domain.
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Old 15 Sep 2019, 05:22 AM   #4
benaboo
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Originally Posted by Terry View Post
I have that trouble using my domain....in most cases we have to get people to add us the their address book, but in saying that it is not always possible.

I think possibly it is customers who use MS outlook that has the problem but us using our own domain.
I didn't know this was an issue. I'm just wondering why, as soon as I switched to my own mail server (using the same domain), the messages are all getting through fine now? What is it about Fastmail that causes other mail servers to snag mail as spam? No answer from either MS or Fastmail yet. Still waiting on both of them.

Asking people to whitelist is unacceptable, especially since I now know it can be prevented. I have to be able to rely on my email to get through to people when I need it to, you know? So infuriating.
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Old 15 Sep 2019, 07:11 AM   #5
Terry
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Yea its strange, perhaps something in the headers.
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Old 15 Sep 2019, 08:56 AM   #6
benaboo
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Originally Posted by Terry View Post
Yea its strange, perhaps something in the headers.
Whatever it is, Fastmail seems ultimately uninterested in trying to determine what the issue is. In an ideal world, MS would be able to tell me what specific things caused the message to be flagged, but we're going on 48 hours now with no answer from them. You'd think Fastmail would be concerned that a legitimate email sender sending a legitimate email through their system isn't being delivered to its designated recipients, but they don't seem to care either.
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Old 15 Sep 2019, 09:00 AM   #7
benaboo
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I don't know enough to know if this is relevant. When I did an mxtoolbox check at the time I was configured to use Fastmail, there were a few warnings about DMARC, which I don't think is an issue, but there was this:

smtp - in1-smtp.messagingengine.com - Reverse DNS does not match SMTP Banner
smtp - in1-smtp-messagingengine.com - Warning - Does not support TLS
smtp - in1-smtp-messagingengine.com - 15.578 seconds - Not good! on Transaction time

Is the first warning relevant? I know the second two might not be.

EDIT: Did a little more digging. I wonder if that could be the cause?
https://blog.mxtoolbox.com/2010/03/2...agnostic-tool/

Quote:
This is only a warning, and in some cases you may have no control over this. However, if you have the ability to make these match, you should. Some mail servers look for this and use it to mark messages you send as questionable. Most mail systems will not reject your messages outright, but this may effect your spam score increasing the likelihood your messages will be marked as spam.
Keep in mind I was using Fastmail's DNS, the support rep said all the settings were fine, I was sending THROUGH their app using a domain that was set up to work directly through Fastmail.

Now that I've moved to my own email hosting and off Fastmail, I do not see any of these errors... and my email is once again being delivered properly.

Last edited by benaboo : 15 Sep 2019 at 11:45 AM. Reason: clarity
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Old 15 Sep 2019, 10:08 AM   #8
Berenburger
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Quote:
Originally Posted by benaboo View Post
smtp - is1-smtp.messagingengine.com - Reverse DNS does not match SMTP Banner
smtp - is1-smtp-messagingengine.com - Warning - Does not support TLS
smtp - is1-smtp-messagingengine.com - 15.578 seconds - Not good! on Transaction time
Is there a typo here?
Isn't it in1-smtp.messagingengine.com?
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Old 15 Sep 2019, 11:45 AM   #9
benaboo
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Originally Posted by Berenburger View Post
Is there a typo here?
Isn't it in1-smtp.messagingengine.com?
Sorry, yes. I was going off a low-res image that I captured at the time. Will fix.
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Old 15 Sep 2019, 01:40 PM   #10
TenFour
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Maybe try it not using FM's DNS? Just set up using the DNS of your domain host and give it a try.
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Old 15 Sep 2019, 01:43 PM   #11
benaboo
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Maybe try it not using FM's DNS? Just set up using the DNS of your domain host and give it a try.
Thanks for the suggestion, but not sure I want to play with DNS again right now, especially since it's working on my own server. It's been a disruptive weekend already, but I'll probably try that next if I decide to go back to Fastmail. Right now, I'm just too irritated at the time I've wasted on this issue.
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Old 15 Sep 2019, 01:54 PM   #12
TenFour
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Just curious. Is the domain extension something other than .com .org or .net?
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Old 15 Sep 2019, 02:15 PM   #13
benaboo
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Originally Posted by TenFour View Post
Just curious. Is the domain extension something other than .com .org or .net?
It's tiserves.com. Guess I don't need to be cagey about it.

After my cloud webmail with multiple POP3 account quest came up short, I went looking for an email client that could just do IMAP on my family's phones. Found AquaMail which seems pretty decent, and very customizable. Gotta find a friendly desktop IMAP app now. Thunderbird is pretty powerful, but I've gotten used to friendly colors and large fonts.

https://www.tiserves.com/images/AquaMail.png

Last edited by benaboo : 16 Sep 2019 at 08:19 AM.
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Old 15 Sep 2019, 03:12 PM   #14
Terry
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Originally Posted by benaboo View Post
It's tiserves.com. Guess I don't need to be cagey about it.


https://www.tiserves.com/images/AquaMail.jpg
The above dont work...
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Old 15 Sep 2019, 09:07 PM   #15
TenFour
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In my experience as the admin on a business Office 365 account for a small nonprofit I have experienced the same problem receiving emails, even from domains I had regularly been receiving email from. I have made it my routine to regularly look at the Junk folder in order to find important emails I want. Some of these emails are from major companies that should be considered safe senders. Gmail and G Suite filtering is much better, but rather humorously they frequently put Microsoft marketing emails in Spam.
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