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Comment by timthelion | Hacker News Reader

The real story here, is that if you try to set up your mail server so that you can send mail to a microsoft email server such as live or hotmail, you eventually end up here where they ask for a bribe: https://returnpath.com/solutions/email-deliverability-optimi...

Nomx may be terrible, but it's not their fault you can't send mail to hotmail.com

Edit: here is the price list for sending mail to hotmail.com https://returnpath.com/wp-content/uploads/2015/06/Return-Pat...

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For Microsoft/Hotmail, you'll want to register your IP with their feedback loop (Junk Mail Reporting Program):

https://postmaster.live.com/snds/JMRP.aspx

It's free. A bonus of this is that you get reports about emails from your IP that their users mark as spam.

Thanks Mike!

I know you work on a lot of email tools. What is your go-to resource when someone asks about deliverability? If you're written something up yourself I'd appreciate a link!

I don't really have a go-to resource, or anything written down. It's all in my head. I should probably write up a blog post about it at some point.

Just wanted to say that building a site around this info would draw a lot of traffic - perhaps much of it coming from the spammers! A solid amount of legit info in one place would probably lead the big webmail providers to have to change their tactics, so it owuld be a commitment to keep it updated.

That's strange: I have my own hosted mail server (on a static home IP) and I haven't had a problem with hotmail (but I've got DKIM, reverse DNS, and SPF configured)

I have it all configured and I still cannot send mail to my parents. Though maybe having a Czech domain name doesn't help. The strange thing, is that the bounce emails directly link to the website asking for the bribe.

That's exactly what make this kind of home mail server box impossible on dynamic IP and even on most of ISP providing static IP. As long as you can't set the reverse DNS for your IP, mails will be rejected.

Can you prove this? I've also set up DKIM, reverse DNS, and SPF, but Microsoft places mail sent from my AWS box straight into the spam folder. Every other email provider that I've tried has been able to receive my email correctly. Microsoft is the only one asking for a bribe to do so.

I've even tried to contact them by phone and their support forum. On the phone they told me that this is a "feature": all mail goes to spam folder until the client whitelists the sending address. This is false, and on their support forums I was told that my static IP from Amazon "is not eligible for appeasement" or something like that.

When you look at what Microsoft has done with Skype and Windows, it's fairly obvious that they don't care about security. Even so, I find it especially egregious that they are offering a "pay to spam" service while at the same time knowingly blocking legitimate email.

Are you sending from AWS SES?

You should not be able to originate any mail from EC2.

I'm sending from EC2. Why do you say that?

A LOT of spam originates from EC2, to the point that many major email providers have blocked all of EC2.

This is not true. I can mail everywhere except Microsoft.

That's not a bribe. E-mail has become a real tragedy of the commons.

It is a bribe, given that you are allowed to send SPAM if you pay up. This isn't an attempt to prevent SPAM, it is actually a policy that allows you to do so if you pay.

It's an additional hurdle - spammers would need to invest at least $400 up-front, which would put off a good many of them.

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