Hacker News Board Hacker News, browsed like a classic message board
Live data from Hacker News

Troubleshooting Email Delivery to Microsoft Users

rozumem.xyz

Post reply on HN
Print view View original

11–20 of 28 posts

Re: Troubleshooting Email Delivery to Microsoft Users

#11

Post by butvacuum »

svieira wrote: post #5
whynotmaybe wrote: post #4

Earlier quoted context omitted.

How would I do that? Have "mycompany.com" and "marketing-mycompany.com"? How

You've got it - subdomains are sufficient (IIRC). Something like notifications.mycompany.com for the important stuff and news.mycompany.com for the more marketing stuff (and of course someone.else.entirely for the the cold email list "well, surely this one little list couldn't hurt" ... nah, who am I kidding, never use those)

subdomains are not sufficient, unfortunately. I think the instance I'm thinking of is technically web/https (chrome's site safety feature where you can specify a domain as 3rd party content- so when something gets flagged uour entire domain doesn't get blacklisted)- but it's much easier to just grab another domain

Re: Troubleshooting Email Delivery to Microsoft Users

#13

Post by gib444 »

butvacuum wrote: post #11
svieira wrote: post #5

Earlier quoted context omitted.

You've got it - subdomains are sufficient (IIRC). Something like notifications.mycompany.com for the important stuff and news.mycompany.com for the more marketing stuff (and of course someone.else.entirely for the the cold email list "well, surely this one little list couldn't hurt" ... nah, who am I kidding, never use those)

subdomains are not sufficient, unfortunately. I think the instance I'm thinking of is technically web/https (chrome's site safety feature where you can specify a domain as 3rd party content- so when something gets flagged uour entire domain doesn't get blacklisted)- but it's much easier to just grab another domain

The majority of my spam from established companies are on subdomains of their main domains. Are they doing it wrong?

Re: Troubleshooting Email Delivery to Microsoft Users

#14

Post by watsonL1F7 »

stackskipton wrote: post #3

As former email admin who has put up with this, you are breaking cardinal rule about mixing marketing and transactional emails. Marketing should be different IP/Domain from transaction emails.

Learned this the hard way. Sent maybe 50 outreach emails from the same domain handling transactional stuff (signup confirmations, notifications). Domain reputation tanked within a week and the transactional emails users actually needed started landing in spam.

The painful part is recovery. You can fix SPF/DKIM/DMARC in an hour but domain reputation takes weeks to rebuild. Microsoft's SNDS portal shows you almost nothing useful while you wait.

Set up the subdomain split from day one if you're a small SaaS. Costs nothing.

Re: Troubleshooting Email Delivery to Microsoft Users

#15

Post by rozumem »

stackskipton wrote: post #3

As former email admin who has put up with this, you are breaking cardinal rule about mixing marketing and transactional emails. Marketing should be different IP/Domain from transaction emails.

Is 40k tranasactional emails a month enough to keep a dedicated IP warm? That's my main concern for not using a dedicated IP for transactional emails.

Re: Troubleshooting Email Delivery to Microsoft Users

#16

Post by joostdecock »

Plenty of advice here, which I'm certain is well intended, but it feels like we're victim blaming here.

Things like "you cannot mix marketing and transactional email" are good advice, but they do nothing if you're using different subdomains but the same infrastructure (IP address) to send them out.

Microsoft is simply trying to squeeze smaller operators out of the market.

I run an open source project, we send out transaction emails from ome subdomain, and a newsletter to 50K+ subscribers once every 3 months.

I can't afford to pay for different/dedicated IO addresses for each. We use Scaleway for email delivery and it's constant trouble with two providers: qq.com who don't give a damn about non-chinese senders, and Microsoft, who are simply trying to break the ipen internet.

Before, we were on AWS SES. Guess what, we didn't even bother using different subdomains. We also didn't have dedicated IPs. Yet Microsoft did not block us because the sender IP was AWS.

It's pay to play, as simple as that.

Fortunately, we're an open source project, not a business. So when people reach out, I simply explain to them that they have chosen a mail provider that is openly hostile to small volunteer-run projects like us and that that choice has consequences. No emails for you.

IMHO we need to be more vocal about what's really going on here (the rent-seeking on the open internet by big tech), and less victim blaming (what about dns-sec).

Re: Troubleshooting Email Delivery to Microsoft Users

#17

Post by rozumem »

gerdesj wrote: post #7

When it comes to email you have to be completely ... enthusiastic: "I was following all the best practices with SPF, SKIM, and DMARC." DKIM. Obviously that was a typo on a forum but you cannot be complacent, ever. You have missed out DNSSEC (nearly optional), SMTP-TLS and MTA-STS. Does your SPF record end with -all? Does your DMARC record have reporting addresses, does it have: "p=reject; sp=reject; adkim=s; aspf=s"…

Thanks for the tips and catching the typo (fixed).

Re: Troubleshooting Email Delivery to Microsoft Users

#19

Post by goku12 »

joostdecock wrote: post #16

Plenty of advice here, which I'm certain is well intended, but it feels like we're victim blaming here. Things like "you cannot mix marketing and transactional email" are good advice, but they do nothing if you're using different subdomains but the same infrastructure (IP address) to send them out. Microsoft is simply trying to squeeze smaller operators out of the market. I run an open source project, we send out tra…

Absolutely agreed. These two big corporate players with the biggest market-share are actively ruining the email ecosystem for their profit. I wish people would drop them and stop choosing them. Hopefully, the EU may soon do so.

Re: Troubleshooting Email Delivery to Microsoft Users

#20

Post by [deleted] »

butvacuum wrote: post #11
svieira wrote: post #5

Earlier quoted context omitted.

You've got it - subdomains are sufficient (IIRC). Something like notifications.mycompany.com for the important stuff and news.mycompany.com for the more marketing stuff (and of course someone.else.entirely for the the cold email list "well, surely this one little list couldn't hurt" ... nah, who am I kidding, never use those)

subdomains are not sufficient, unfortunately. I think the instance I'm thinking of is technically web/https (chrome's site safety feature where you can specify a domain as 3rd party content- so when something gets flagged uour entire domain doesn't get blacklisted)- but it's much easier to just grab another domain

[deleted]
Post reply on HN