I was again “Successfully removed from all lists” at SPAM Eating Monkey, but, when I follow their confirmation link, I’m still on the SEM-URIRED list, which was (and still is) the only one I was on before and afterwards – and it’s also the one from where I clicked on the “Request Removal” link. I guess “SPAM Eating Monkey” and I speak different languages where “removed from all blacklists” means something different to them than it does to me. It’s like pulling hen’s teeth. I’m guessing there is no other way to contact this outfit, except via their links. On MXTools they show this is the only blacklist I’m on, but apparently that’s enough. (Just venting, sorry.)
This might give you some hope. When I set up on DO, gmail worked, and keeps working. Well, I had to fix some issues with the various configuration as it was being set to junk. But since then it works fine.
I had an issue with outlook blocking emails completely. I signed up to MS snds service and registered my IP. https://postmaster.live.com/snds/ Took a while, and then some days later I could send email to outlook again. Unfortunately it goes to junk now. But apparently, it takes time to build up a better reputation with them.
I did check the ip address on the spam lists first however. The first one DO gave me was on a list, and also the host was buggy. So I ditched that ‘droplet’, and got a new IP.
Also, I reported the issue to DO through support and got a cookie-cutter response saying it was too hard for them to deal with spam, but they try. Also, they recommended to use a third party service to send mail, and also to try snapshot-moving a droplet to get a new IP address.
My domain is old, so that probably helps. I’ve also seen advice to get a dedicated server from a company that is a bit more reputable, and verifies its customers more. But I’d prefer to wait for the moment, and see how it goes. Dedicated servers have taken too much administration time for me before. And I like the double backup that DO+mailinabox do by default.
I feel this is unfortunately just the administration cost of looking after a mail system. Not sure of a way to reduce that cost for good actors. Mailinabox definitely makes it a LOT less work than completely running a mail server yourself.
When I first fired up DigitalOcean instance of MIAB, I was also having problem with Gmail recipients filing to spam. Not sure if this is coincidental with my sending a request to Gmail to whitelist my ip, but I also had the recipient move the message out of the junk folder (or maybe there’s a button to indicate “not spam” - can’t remember). I did this for my test messages to my own gmail account also. Shortly afterwards the problems went away, not just for these recipients but others too.
Again, may be coincidental but worth a try.
Okay, thanks. I know we can move them out of SPAM and that email address works from then on – which doesn’t help much when writing to someone you don’t even know uses Gmail (my wife’s business is based on Gmail, but she uses her own domain name, for example). But it does give me some hope is that if we do this enough it might clear our name for all emails. Thanks.
Still, this is not something I can give to my Dad and say, “you’ll have to tell your Gmail users to pull your first email out of SPAM and then it should work.”
Well, SEM URIRED no longer has me blacklisted. (MxToolbox shows no blacklisting at all.) Let’s see if I can actually email to a GMail address. (I’m guessing not.) …
Nope, still goes to SPAM in GMail. I guess you just have to keep tilting at windmills.
It appears that GMail is finally working correctly (not automatically putting my email into SPAM) with my Mail-in-a-Box account, so I guess it IS just a matter of waiting. So I guess the way to do this is set up the account, make the certificate is working, get hold of Spam Eating Monkey and request to be taken off of all their lists and then … wait. (Looks like it takes about four months.)
Or you can enrol into their postmaster tools program. That kinda expedites the process.
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I’ve been in the Postmaster programme since 2018 with my domains and they still go to spam. 
Microsoft is the worst.
I have been using DO for my mail server for the past 5 years.
Every year or so they will just start flat out bouncing my emails because it is a digital ocean IP, not even getting to the spam box.
It does NOT matter if you are on no blacklists or if you are on whitelists.
Microsoft has their own internal lists.
Postmaster program will tell you nothing. JMRP will tell you nothing.
You have to email them repeatedly until you get YOUR IP off their bounce list. It will still go to spam box though.
Your emails coming from a DO IP will most likely never get out of the spam box on any microsoft domain.
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 can have a perfectly good email server running on DO, that is not the issue. The problem is how many places flat out block DO ip address.
I have encountered many bounce messages from domains that just block all DO ip addresses, email them and most say oh-well.
I was having a problem that at first appeared to be because of blacklisting, so contacted DigitalOcean. Their form of help was to discourage me from using their services…
Sorry to hear that the emails that you send are blocked due to a bad IP reputation. This is one of the reasons why we recommend not run your own mail server, rather utilize dedicated mail relay services such as SendGrid or MailChimp. I would recommend referring to this article which should provide some insights on why we say this: Why You May Not Want To Run Your Own Mail Server | DigitalOcean. Also, DigitalOcean is not a dedicated email host and does not have a postmaster to maintain our IP reputation. As a result, some DigitalOcean IP ranges are blacklisted.
So instead I set up MiaB on a Vultr Cloud Compute (25GB SSD, 1GB, 1 CPU, $5) instance. Now all seems to be well. Port 25 was available without asking - maybe because I established an account a couple years back? Google and Outlook accept tests directly into Inboxes. The IP Vultr gave me was not blacklisted anywhere (including UCEPROTECT).
For anyone else reading this, I largely following these Vultr MiaB install instructions (slightly different from my DO steps)…
How to Install Mail-in-a-box on Ubuntu 18.04
Notes…
- MiaB is skipping Ubuntu 20.04 (MiaB won’t install on 20.04). No problem because Vultr still offers v18.04 instances.
- Contrary to the instructions, MiaB prefers the Reverse DNS to not include the IP address. So simply use box.yourDomainName