MiaB, Digital Ocean and Gmail

I know there’s been several threads on this topic, but I’m curious what the general consensus might be. I set up a mail server on Digital Ocean last week and it works beautifully. Yahoo accepts mail, AOL accepts mail, not sure yet about the Microsoft mail services. But Gmail just passes the mail to SPAM. There’s no flag, everything is “pass”, but it goes to SPAM. If I reply to the email, the next email from MiaB will go through to the Inbox (the answered mail “cures” it). But, of course that doesn’t work unless the the mail is answered and that would assume that people check their SPAM folder. Headers look exactly the same on email that goes to SPAM and email that doesn’t, so Gmail must have their own blacklist. I’m not blacklisted anywhere else – I get a 10/10 on mail-tester.com. All is green in System Check. I’ve done a couple different email fix requests with Google (haven’t heard back yet) but I’m guessing there’s a switch they have to turn “on.”

The “solutions” I’ve seen so far seem “iffy.” Don’t use Digital Ocean. Use an out-of-country server with Digital Ocean. Change your IP. Wait for two or three months and Google will start accepting the email. Send your email to a verifier of some sort. None of this appeals to me. I like a black and white problem/solution. For personal use, I can work around it. If it’s a matter of waiting. I can do that. (As a matter of fact, I will do that if I have no other choice.) Mostly (personally) I just would like to know “why,” or at least get an educated guess what’s going on.

My main problem is, I was planning on setting up a mail server for my father. I can’t very well say, “you can send mail to just about any address … except Gmail and maybe Microsoft.”

So, mostly just a little frustrated and looking for reasons, or at least hints to where to look. Thank you.

And thanks to MiaB. Incredibly easy to set up.

Oh, one more question. What happens when Ubuntu 14.04 reaches EOL?

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Gmail does not accept email from domains it does not recognize, you need to contact GMAIL and prove to them you will not send spam, then they will add your domain to their whitelists

I am having the same issues. I set up a server for my family to use on a Droplet from DO. I too found I could not send email to gmail users. I searched forums and reached out to gmail support. I jumped through their hoops made sure i had a good rating on mail-tester.com and put some sort of file in my webserver root directory but non of it helped. I was expending way too much time and energy toward the solution so i just gave up. I hope somebody comes back with a bonefied solution which will address this issue.

@B_DubHay Ready my other post about gmail.

Is this a universal problem?

I have not experienced it so far.

When I set up MIAB day one all my initial tests were to GMail accounts (all of the team here use a Gmail account. All of the test mails went out and their replies came back without filtering into SPAM. The second round of tests went out to our client admins which were pretty global and all over the place in terms of email servers. They also passed.

Perhaps the issue really is related to the DO IP. When we set up DO gave a blacklisted IP and we had to approach the blacklists and “prove” we were the new “owners” of the IP. DO support were of no help on the matter with the suggestion that we write off the droplet and chance our luck with the next one.

I can’t quite see how Gmail can be so picky without hitting all DO originating email (which they don’t appear to be). So the explanation has to come back to IP or domain related at Gmail.

There are a lot of blacklists out there and not al of them are public. It wouldn’t surprise me that Google has their own list they keep to themselves. A clean IP is something quite hard to come by as by now I suspect they have all needed to go through the wash a few times. Have a look to see what sort of domains and where they were previously used. You may well be a bit surprised and shocked.

Did you have email setup for your domain before MIAB? This is specific to new email servers & new domains.

(Gmail might also be filtering IP blocks as well)

I had to call and email google to get this working for myself.

No, in our case it was a new DO droplet with their assigned IP and a new domain name.

Okay. I’ve tried contacting them twice by filling out forms. Is there a more direct route? Or is a little patience the next step? :slight_smile:

Yeah, that’s what I was reading. I think that’s basically a “let’s close this trouble ticket” response. I’ve also read that by going to DO servers in Canada or the Netherlands some folks have cured the problem. I’ve also read that it’s not just a DO problem, that other virtual server suppliers have this problem (like Vultr). I guess with my father’s server I could try Vultr and see if that makes a difference. It’s so close to working.

For me, I bought the domain specifically for the mail server. I bought the DO droplet right after buying the domain name.

Have MIAB + DO for years without any issue. Advise like “Don’t use Digital Ocean” is moronic and shows ignorance, and close to “don’t use email”.

You should dive into the gmail headers if you have not done it to see if you get any clues of what is going on and what flags are set. Check whether dkim=pass, spf=pass, dmarc=pass, Received-SPF: pass (google.com: domain of bla@bli.com designates 2aXX:23XX::XXX:3eff:XXaX:eXXX as permitted sender). If any errors are references, look them up: https://support.google.com/a/answer/3726730?hl=en

Also, do NOT use mail-tester.com. They do not publish a ToC and harvest YOUR email addresses for their own gain. The only thing you need for the test is your pubic IP(s) of your MIAB box. Instead, use something like https://mxtoolbox.com/blacklists.aspx

Not sure why murgero suggests to call and email google, because Google uses aggregated results from RBLs (Realtime Blacklists) like the ones mxtoolbox checks against, and therefore Google Support doesn’t accept requests to delist blacklisted addresses. IF you want to give the Google route a try, use the dedicated form for that: https://support.google.com/mail/contact/msgdelivery

It could be that if you started using a new VPS you got a dedicated IP that was recycled by the hosting provider, or if there are other users on the same server/IP that abuse Google services in one way or another, your IP is blacklisted by an important RBL service. In that case the advise to request/create/use a new dedicated IP.


Okay, thanks. I ran the blacklist checker again at mxtoolbox and, out of the 103 lists, it showed that I was on one blacklist, SEM URIRED. So I looked that up on Google, went to SPAM Eating Monkey, and ran their check – I was okay on five of their six lists, but this one (SEM URIRED) showed “Domain has been seen in the first few message of a large spam campaign.” This domain was created a few days ago and, though I tried a group message to five people in my family, the domain has definitely NOT been used for SPAM. At any rate, they do have a request removal form and I’ve done that. Is this one blacklist sufficient for Gmail’s SPAM assignment?

Oh, should mention, dkim, spf and dmarc all pass in Google’s header. Also I’ve filled out the linked Google form but haven’t heard back from Google.

Thanks for the response. Hopefully I’ll get removed from SEM URIRED and Gmail will work.

IPs get reused so much - it is becoming impossible to get a totally clean IP.
It takes only a few minutes to spin up any cloud based server, add MIAB (others are available) and send out millions of spam emails with dubious content and then close it down, just walking away from the carnage caused.

BTW don’t forget domains are also reused.

Sadly it is what we all have to put up with :frowning: So in DO defense you will be unlikely to get a clean one from them (or any provider).

Good luck with it. All reputable blacklists are aware of this and also actively monitor the situation. Sometime you have to pay a fee for removal or go through a close monitoring period.

Okay, thanks. I’ll just have to try my best to ride it out and jump through whatever hoops they set up for me. For our personal use (my brother and I are the ones using the new domain) this can be worked around (even if it stays as is). But setting up a mail server for someone else, like my father, is probably out of the question.

Murgero, is this trough postmaster.google.com? I’ve verified all my domains trough this way, but stil one is having trouble

I’ve (personally) tried that link and the other one …

… and so far no luck. But it’s been less than a week, so it may be that I just need a little patience.

Hi Guys,

I’ve had a DO MiaB setup for nearly 2 years and it has always been fine. However as of about a month ago both Microsoft services and Gmail blacklisted it. I think off an IP Block. I contacted Microsoft through their form and request to be delisted, and that seemed to work. Having no luck with Gmail though. And the headers give no decent reason.

I’ve only set up a few private mail servers (On ISP static IPs and on Cloud VMs), but from my experience it is just a never ending battle. You get it all running well, then you find you start going into spam for no apparent reason.

It really sucks. Get on all the whitelists, get off all the blacklists, build a reputation over years, even pay money in some cases to get on a list recommended by whoever blocks you, then it doesn’t work anyway! Some faceless corp decides you are spam based off some algorithm, and you are the one that has to do all the work because they own half the internet and don’t care. Grrrr

I received a reply from Spam Eating Monkey that my mail server had been successfully removed from all its blacklists, with a link to confirm … but that link and mxtools both show that I’m still blacklisted on SEM URIRED. I’m guessing it takes time for the list to update?

Yeah. And, especially in Google’s case (they sell email addresses for $5.00 a month) it almost seems to be a conflict of interest. “Your private email server is being blacklisted by us? … You might want to sign up with Gmail, we won’t blacklist you.” I also understand that SPAM is a major issue, but it’s a little frustrating to think you’ve done everything right and still end up with a “non-functional” email server. Your post is one of the more depressing I’ve read, since you managed to jump through the hoops and now you have to jump through them again.