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by tradewarsonlyn 2211 days ago
As some who has suffered through managing a qmail smtp cluster and dealing with DNSBLs, allow me to say just one thing: Very. Underrated. Comment.
3 comments

As someone who has set up many SMTP servers even on very new domain names. Yhe only issue I've actually come across is outlook.com who happily will whitelist if you poke them via their support once you you have dkim and spf set up.

EDIT: if you are working from IPs that may not be clean (and in an IPv4 world thats prob true) many DNSBLs will work with you to remove your ip's from their lists if you are actually nice and polite with them. Just check your IP's before your set up your network so they have a heads up that someone will be on the other end of any complaints.

That has always works for me.

In my experience, ATT is the worst. They've been blocking me for well over a decade. They're the only provider who has ignored every contact attempt I've made.

I don't care, from my perspective they're irrelevant. The last person I communicated who used their MX died recently, and otherwise ATT can bite me. But in a fit of annoyance several years ago I did configure my servers to deliver a heartfelt custom 550 response to ATT MXes.

IIRC AT&T is handled by Yahoo so pester them at https://io.help.yahoo.com/contact/index?page=contactform&loc...

EDIT: https://www.att.com/esupport/postmaster/digital-signature/ checked the AT&T support about delievery. Seems like they do use Yahoo these days.

Yahoo made a deal with them to service the mail services SBC bought/built that were rolled up into att.net. That is one of several mail services associated with them, and not the one I'm talking about.

I'm talking about the ones managed by Synacor, formerly managed by an ATT spinoff with a bland name I can't remember. I still have my notebook logging my (lack of) progress, which happened over several years and involved a bunch of entities - partners and internal spinoffs.

Trust me, I know how to google "att email".

I wasn't saying you didn't know any googlefu. just when you said ATT my head went to "oh you are dealing with their consumers... should thought I would C+P the link thats helped me in the past.

EDIT: As a follow up. I used to have contacts with BlueYonder, Sky and BT All ISP's that used to manager their own email systems but outsourced them to gmail and yahoo so my peronsal contacts within those companies for email have died off. It wasn't a slight on you. just one geek to another trying to help.

I think that came off as a lot snippier than intended, apologies.

All I meant is that I spent entirely too much time researching the web of entities supporting the Death Star's SMTP needs through the last decade, who on Linkedin listing those companies might be attached to the production technical team, etc. At some point I started joking that I knew knew more about their corporate structure than anyone not suing them or working in their legal department.

outlook.com is indeed the worst. Got a pointer how to make this whitelist happen @outlook? Got SPF and DKIM setup since I started my personal mailserver, but still piggybacking of my old University's open relay (on campus) to get my mail to land in outlook inboxes...
https://support.microsoft.com/en-us/supportrequestform/8ad56...

And if you get rejected with your first request, pester them with a follow up saying something like "Hey, I'm, a cloud customer. I don't control the whole IP range. I ask you to reconsider the initial rejection."

That's always worked for me with outlook. Takes a few days (which is why I say do it as soon as you know what your IP range is)

Be nice and polite (from what I understand real humans read that request) be honest with what you have done as of time of writing the requyest and what you are planning to do.

But be persistent with them and they will basically grant you a whitelist unless you start fucking up.

What about Gmail.
Yep. Just send it from a residential IP.

I ended up subscribing to an SMTP service that explicitly masked my home IP as Google's sending service included it and was causing my emails to my bank to automatically get flagged as spam.

What even is the best way (reliably and free) these days to set up a website that occasionally sends email? I have a hobby site on a linode for creative writers to follow up to each other's chapters, and it's very low volume, but I don't want to sent it all through my gmail account, either.
Mailgun reduced their free tier drastically recently, I think to 625/month. If that fits your needs it's a decent choice.
Hmm, I can't find a free plan: https://www.mailgun.com/pricing
Looks like you're right, they abandoned the free plan altogether on March 1. The new deal is $0.80 per thousand messages with no minimum spend, which may be negligible for you, but there are likely free alternatives out there too.

HN discussion from when they downgraded the free tier, includes some discussion of alternatives: https://news.ycombinator.com/item?id=22192543

They eliminated the free tier, but as of June they won't be billing for <=1250 messages a month.

Link from the email they sent: https://help.mailgun.com/hc/en-us/articles/360048661093-How-...

Shameless plug for transactional mail , i got a little comparison site setup. https://bestsendmail.com/
No SparkPost, Mandrill, Postmark or Mailgun?
Something like sendgrid?
Unpopular opinion, but... set up your own e-mail server. I've been running my own off my home connection for quite a while with basically no spam problems.
Mails sent from dialup IPs are almost guaranteed to be classified as spam (probably to prevent spam sent by malware). Many servers won't even accept such mail at all.
Nah, I even do okay with gmail actually. I did do SPF, DKIM, and DMARC, so maybe that helped.
Wanted to comment the same. Initial setup is a bit bumpy - make sure reverse dns is ok, set up dkim, dmarc, spf - but once up, is should be fine, especially if it's only to send, and not receive.
Just an addition to that: Don't use the cheapest possible provider available if you get a VPS to use as an email server; chances are the spammers are doing the same thing and that your emails will be sent straight to spam.

DigitalOcean, OVH and Hetzner are especially difficult. It is possible to run an email server there, but getting the IP reputation up will be a tedious process and some providers will simply reject sent emails simply for using one of those hosts.

Thank you for sharing your experience on digitalocean and OVH hosting providers. I want to understand the issue a bit more because we have a plan to host email service on both the platforms. Your inputs will help us to decide to go with them or to choose any other service provider. Can you please let me know when you sent those emails using both service providers is your emails authenticated with SPF and DKIM or you have used any free email service provider like gmail or yahoo as a from email address. Thank you in advance.
I've had luck with digital ocean by sending friends emails (who have accounts at major providers) and having them mark it as not spam a few times over the course of a week or two. After that, it worked without issue.
It is definitely possible to get it up and running, but there's often problems due to entire ranges having bad reputation. There was a gigantic thread about it in the Mailop mailing list last year. If you have access to it's archives then it's definitely a worthwhile read (and entertaining too!).
I've used Linode VM's for my mail server as long as Linode have existed. No issues. In full disclosure, I do not send a lot of email.
It probably helped that you got an IP early on before they'd been rotated through various users.
Use an external SMTP and several of them have free tier that includes several hundreds emails a day.
Postmark, or sendgrid