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Comment by gingerlime | Hacker News Reader

Sending email out is a royal pain. Trying to deal with a Microsoft ban on my IP even though it’s sparkling clean for several years. DKIM, DMARC, SPF etc all ser up, reverse dns, you name it. Looks like Linode is being blocked as a whole pretty much?

Hate the level of centralization, particularly since there’s still a shit ton of spam still around. Sorry for the rant.

https://docs.microsoft.com/en-us/answers/questions/674558/55...

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I've been running a private mailserver for myself and a couple of friends since 2002. I hit a similar issue with Microsoft last year.

I route outgoing mail to hotmail.com, live.com, outlook.com and msn.com domains via email-smtp.us-east-2.amazonaws.com. I started doing this when I noticed a large portion of e-commerce email I was receiving originated from amazon vms and they clearly had no deliverability issues.

The ability to do this is a paid-for service, and needs to be configured appropriately. I was expecting to have to pay for a VM when I set out to do this. However, it turns out you do not need that - you can just configure the SMTP forwarding without needing to purchase any other products, and the cost for this is a few cents per 10k emails, which I can see would be significant for commercial services and/or spammers, but for a private mail server essentially means I will never have to pay. Amazon go to great pains to maintain deliverability for those servers, so you don't have to.

I don't really see a problem with adding one extra SMTP hop to outgoing emails tbh, but as no-one other than Microsoft has (to date) a permanent IP block ban with no recourse whatsoever policy, while I've had transient issues with most other big providers at one time or another, those four Microsoft domains remain the only destination I have to route this way.

office 365 hosts a bunch of domains though. My bounce was to a .berlin domain hosted there. Yes, I could route all smtp via a ESP and pay for it, but that’s centralization.

Interesting - whatever permaban it is that my IP block got didn't affect office 365 hosted services (verified with several different domains at the time) - just literally the domains I mention. Guess I've lucked out so far.

File a complaint request, they will fix it, they did for me.

Wouldn't surprise me if Linode were entirely blocked. Also anything in M247 Ltd's ASN. They host a lot of VPN endpoints, including Mullvad's.

Step 1, I'd move off Linode. Find a local DC or business you can support by hosting a VPS or dedi box with them. LowEndBox might be an interesting place to search but avoid anything too famous.

Step 2, join this https://sendersupport.olc.protection.outlook.com/pm/services.... They don't actually email me when they block my IP, but at least when I contact them I can argue I'm already in their program and they didn't actually notify me of any sending issues. I've got myself unblocked relatively quickly this way.

IMO, any low-cost VPS provider is going to have a poor reputation. I've even had trouble running websites on some of them, as some "endpoint security" products have their IP addresses blacklisted, causing users to get alarming warnings if they try to visit sites hosted there.

You'll run into the same issues with the "free/trial" tiers of bulk email services like Mailgun.

I agree with OP, you pretty much have to at least send your outgoing email via an established, widely-accepted SMTP service provider, or in some other way pay a lot for a "clean" reputation.

I'd still say it depends. I've used memset (www.memset.com) in the UK in the past without issue. They have low end VPS offerings, but they're not as well known as say Linode.

It isn't so easy to categorise such a service by pure ASN, as they also offer dedicated and colocation services, so you might be blocking a licensed 'on prem' exchange box for a local UK council.

"Wouldn't surprise me if Linode were entirely blocked."

I'd be very surprised. I hosted email on Linode for years without issue.

I have my personal e-mail on linode for probably 15 years or so and haven't had any issues with e-mail delivery (knock on wood). Had the same two static IPs there for years, and have always had things locked down so I couldn't be used as a relay for spammers.

mine is maybe 10 years? I don’t recall. No issues so far, but started seeing those Microsoft blocks when I moved my brother’s domain over to my server. I hardly send email out, so it could be unrelated to his domain, just that he sends much more email out.

> Trying to deal with a Microsoft ban on my IP

https://sendersupport.olc.protection.outlook.com/snds/index....

Thanks I’ll check it out. The bounce link was to an office 365 spam delist portal. My request was auromatically rejected and my only option was to escalate it to support (one click luckily). I’m yet to hear back, but from the stories on the link I shared, I doubt it will do anything.

Wow that is a wonderful link, they really seem to be improving on interacting with the public in these matters.

The link used to be <https://postmaster.live.com/snds/index.aspx>, and has existed since at least 2018.

I vaguely recall seeing in Linode docs that Linode itself blocks outgoing mail, unless you contact them to arrange for them not to.

I had that issue with them once in the past, I found a form on their site, filled it out and they had it fixed in a week or so. No issues since then.

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