6 ms·

Yeah I stopped running my own. I kept getting blocked by Microsoft in particular (mainly consumer recipients at live.com and outlook.com, strange enough not cor

by _abox 5y ago

Yeah I stopped running my own. I kept getting blocked by Microsoft in particular (mainly consumer recipients at live.com and outlook.com, strange enough not corporate O365 users!). I'm 100% sure I did not send any spam, the only emails going to those addresses were legit from a family member. DMARC and SPF were all set perfectly, relays blocked, I was not on any spamlist and I never have been either. Literally every month I got blocked again because my server did not have enough reputation. Kept logging tickets to get it unblocked and then a month later it was back. One time I did manage to get a personal email back from a guy in India. Said that it was because my mailserver did not send enough legitimate mail for their algorithm to trust it. So the lack of spam is not enough anymore to be blocked. You actually have to send a load of legit traffic to build up 'reputation'. Now just being a small time sender is a problem. This way the big players can just carve out a bigger market for themselves. They basically break the decentralised concept of email by doing this. In the end I moved to O365, which felt bad because I didn't want to reward them for their behaviour. But we moved to it at work too and I wanted an instance with full admin rights to explore. My contract is up next year so I may change then if I can find a party that does it well and ideally cheaper.

jacob019 5y ago
You can configure postfix to relay emails to certain domains through a 3rd party SMTP service like SES. The MS domains give all of us the same problems, there is no other solution.
- GekkePrutser 5y ago
  Thanks I wasn't aware of this option. I'll consider it. Thanks for the tip! At least I'm not the only one but I'm sorry you're experiencing this too.
ssl232 5y ago
You may just have been unlucky with your IP block having spammers. How were you hosting it - own ISP or another provider? I have not had deliverability issues for years with my Kimsufi (OVH France) server. While I am confident my server is well configured using best practices, I suspect some of it is also just luck not to be in the same IP block as a spammer.
- GekkePrutser 5y ago
  I was using a colocation hoster in Belgium. They actually moved me to another netblock to test (they were a really nice small company). But the same happened. I heard Kimsufi is indeed pretty bad as it's so cheap people tend to use it for 'throwaway' purposes. It's basically the white label budget brand of OVH :)
  - ssl232 5y ago
    I've had 2 kimsufi email servers and both were fine. It shares the same data centres as OVH so I guess IP ranges are similar. No problems with blacklisting based on anything other than my own misconfiguration so far, and it's been maybe 8 years.
mcbits 5y ago
> Said that it was because my mailserver did not send enough legitimate mail for their algorithm to trust it. In other words, a small self-hosted email server will be considered a spammer until it starts sending out large amounts of email? Maybe that can be automated...
- bijant 5y ago
  In theory it would be simple to provide a "cloudworkers cooperative" kind of service that just bundles the outbound mail so that traffic is sufficiently large to be whitelisted by the big providers. The two biggest problems are A. Scaling up sufficiently without attracting Spammers. Because even a single Spammer can ruin your reputation forever. So ideally you'd have a tight knit group of friends or similar. Even then you could hardly assure than no one ever gets hacked. B. Edge Cases. Even if your US or West European Traffic is sufficient to be whitelisted by all major Providers, how do you ensure that the occasional Email to a customer of an Indonesian ISP does not get blocked by their provider...
  - southerntofu 5y ago
    Yeah SMTP relaying is quite common. The problem is due to email architecture, to my knowledge, that same relay is going to be able to read your incoming emails because remote servers will block emails from user@endserver.org sent from relay.net unless endserver.org has MX entries pointing to relay.net.
    - EvanAnderson 5y ago
      That is less the case today. Back before SPF, absolutely. Today, with properly configured SPF records, not so much.
- judge2020 5y ago
  'large amounts' is also pretty relative, I'm sure if you had a small team of 10-25 employees on a self-hosted mail server (preferably with a static IP via the ISP) you'd be taken seriously pretty quickly versus only you sending an email once a week or less.
bijant 5y ago
I had a very similar experience. Is there any cheaper option than just using aws SES nowadays ? (for outbound only! don't understand why people would pay the same rate for inbound) My concern is what happens when aws decides to massively increase rates...
- mhitza 5y ago
  If you send from an ec2 instance is "always free" (tm) for the first 62k outbound emails each month and 1k inbound.
davidhyde 5y ago
I tried office 365 for email this year but couldn’t get the marketing emails from Microsoft under control. No matter how much time I spent trawling through the settings menus. Almost every email I got was about some security update or promotion from some ms product I did not use and had no intention of using. And I was paying for O365 too!
- GekkePrutser 5y ago
  It is possible. I managed to stop them in the end. One of the many admin sites if I recall correctly (seriously, they have an office admin portal, exchange online admin, Azure Ad portal and everything is spread out across those)
southerntofu 5y ago
I'm sorry this happened to you, but it's a shame. You end up giving money to your perpetrators and leaving the rest of us in the same situation you were in previously. Maybe a hosting coop could be an option? Large enough for reputation but ethical enough to still federate with smaller hosts?
- GekkePrutser 5y ago
  Agreed. But I did learn a lot from it. I needed that because in our large organisation at work the admin rights are highly compartmentalized. And this way I was able to understand what other admins were and weren't able to do. You can actually get a free test tenant from MS for 3 months but setting up a real production environment is much better than doing some tests. But yeah I feel lousy about it.
kiklion 5y ago
> This way the big players can just carve out a bigger market for themselves. Or it’s because there is a near infinite number of domains so it’s relatively simple for spammers to avoid bad rep blocks by grabbing new domains and starting fresh.
- GekkePrutser 5y ago
  Yeah but then why keep putting me on the Blacklist every month? After I've been in touch so many times.
andix 5y ago
If you use hotmail.com a lot of legitimate email goes to spam. I see it as a problem of the hotmail users, not mine as a sender.
feanaro 5y ago
I host my own email and I have the same problem with MS. Perhaps this is something for the new Digital Markets Act and interoperability laws in the EU to handle.
judge2020 5y ago
Moved away from outlook.com hosting a while ago since so much legitimate transactional email went to spam whilst actual spam easily got through. Now, when outlook forwards to gmail, gmail catch it before it hits the inbox.
emteycz 5y ago
Corporate O365 users often have their own Exchange server (cloud or self-hosted) with custom configuration.

by _abox 5y ago

jacob019 5y ago

You can configure postfix to relay emails to certain domains through a 3rd party SMTP service like SES. The MS domains give all of us the same problems, there is no other solution.

GekkePrutser 5y ago
Thanks I wasn't aware of this option. I'll consider it. Thanks for the tip! At least I'm not the only one but I'm sorry you're experiencing this too.

ssl232 5y ago

You may just have been unlucky with your IP block having spammers. How were you hosting it - own ISP or another provider? I have not had deliverability issues for years with my Kimsufi (OVH France) server. While I am confident my server is well configured using best practices, I suspect some of it is also just luck not to be in the same IP block as a spammer.

GekkePrutser 5y ago
I was using a colocation hoster in Belgium. They actually moved me to another netblock to test (they were a really nice small company). But the same happened. I heard Kimsufi is indeed pretty bad as it's so cheap people tend to use it for 'throwaway' purposes. It's basically the white label budget brand of OVH :)
- ssl232 5y ago
  I've had 2 kimsufi email servers and both were fine. It shares the same data centres as OVH so I guess IP ranges are similar. No problems with blacklisting based on anything other than my own misconfiguration so far, and it's been maybe 8 years.

mcbits 5y ago

> Said that it was because my mailserver did not send enough legitimate mail for their algorithm to trust it. In other words, a small self-hosted email server will be considered a spammer until it starts sending out large amounts of email? Maybe that can be automated...

bijant 5y ago
In theory it would be simple to provide a "cloudworkers cooperative" kind of service that just bundles the outbound mail so that traffic is sufficiently large to be whitelisted by the big providers. The two biggest problems are A. Scaling up sufficiently without attracting Spammers. Because even a single Spammer can ruin your reputation forever. So ideally you'd have a tight knit group of friends or similar. Even then you could hardly assure than no one ever gets hacked. B. Edge Cases. Even if your US or West European Traffic is sufficient to be whitelisted by all major Providers, how do you ensure that the occasional Email to a customer of an Indonesian ISP does not get blocked by their provider...
- southerntofu 5y ago
  Yeah SMTP relaying is quite common. The problem is due to email architecture, to my knowledge, that same relay is going to be able to read your incoming emails because remote servers will block emails from user@endserver.org sent from relay.net unless endserver.org has MX entries pointing to relay.net.
  - EvanAnderson 5y ago
    That is less the case today. Back before SPF, absolutely. Today, with properly configured SPF records, not so much.
judge2020 5y ago
'large amounts' is also pretty relative, I'm sure if you had a small team of 10-25 employees on a self-hosted mail server (preferably with a static IP via the ISP) you'd be taken seriously pretty quickly versus only you sending an email once a week or less.

bijant 5y ago

I had a very similar experience. Is there any cheaper option than just using aws SES nowadays ? (for outbound only! don't understand why people would pay the same rate for inbound) My concern is what happens when aws decides to massively increase rates...

mhitza 5y ago
If you send from an ec2 instance is "always free" (tm) for the first 62k outbound emails each month and 1k inbound.

davidhyde 5y ago

I tried office 365 for email this year but couldn’t get the marketing emails from Microsoft under control. No matter how much time I spent trawling through the settings menus. Almost every email I got was about some security update or promotion from some ms product I did not use and had no intention of using. And I was paying for O365 too!

GekkePrutser 5y ago
It is possible. I managed to stop them in the end. One of the many admin sites if I recall correctly (seriously, they have an office admin portal, exchange online admin, Azure Ad portal and everything is spread out across those)

southerntofu 5y ago

I'm sorry this happened to you, but it's a shame. You end up giving money to your perpetrators and leaving the rest of us in the same situation you were in previously. Maybe a hosting coop could be an option? Large enough for reputation but ethical enough to still federate with smaller hosts?

GekkePrutser 5y ago
Agreed. But I did learn a lot from it. I needed that because in our large organisation at work the admin rights are highly compartmentalized. And this way I was able to understand what other admins were and weren't able to do. You can actually get a free test tenant from MS for 3 months but setting up a real production environment is much better than doing some tests. But yeah I feel lousy about it.

kiklion 5y ago

> This way the big players can just carve out a bigger market for themselves. Or it’s because there is a near infinite number of domains so it’s relatively simple for spammers to avoid bad rep blocks by grabbing new domains and starting fresh.

GekkePrutser 5y ago
Yeah but then why keep putting me on the Blacklist every month? After I've been in touch so many times.

andix 5y ago

If you use hotmail.com a lot of legitimate email goes to spam. I see it as a problem of the hotmail users, not mine as a sender.

feanaro 5y ago

I host my own email and I have the same problem with MS. Perhaps this is something for the new Digital Markets Act and interoperability laws in the EU to handle.

judge2020 5y ago

Moved away from outlook.com hosting a while ago since so much legitimate transactional email went to spam whilst actual spam easily got through. Now, when outlook forwards to gmail, gmail catch it before it hits the inbox.

emteycz 5y ago

Corporate O365 users often have their own Exchange server (cloud or self-hosted) with custom configuration.