Hey, you need to white list yourself personally on Microsoft's network for your servers IP's.

It's a sneaky bastard of a link to find but I dug it up for you: https://support.microsoft.com/en-us/getsupport?oaspworkflow=...

Look at that address... I bookmarked it for when we had to do it for GamerDating.com a while back.

Anyway that will sort you out for MSN/Hotmail/Outlook etc.

AOL I have no clue.

Good luck.

I used to have delivery problems (throttling errors caused by another customer) sending messages to Microsoft related domains (hotmail, msn, live, etc.) when using MailGun.

There was no progress at all when discussing this topic with MailGun's support so I created another account at PostMark [1] to choose provider depending on recipient's domain. No more problems when sending messages to Microsoft related domains.

Anyway, "silently discarded" sounds like you need to put in place DMARC reports [2] to troubleshoot what is going on there.

PS: I chose PostMark because I like its online documentation. Currently a happy customer, not affiliate at all.

[1] https://postmarkapp.com/ [2] https://dmarc.postmarkapp.com/faq/

Make sure you have your DMARC, SPF, DKIM all correctly setup. Then test some emails with this tool: https://www.mail-tester.com/

Go through the issues one by one and you should be all good.

I've used Mailgun for years with hardly any issues.

Thanks, that will be a useful tool.

Quick thought I had, you're right those services should be charging for rep management, the fact your emails aren't getting through is a sign that perhaps the IP Mailgun are using to send those mails from isn't exactly white listed. If you're sending legit traffic it's way easier and cheaper to setup a mass mailer on a server of your own with a dedicated IP and then build the reputation slowly. It doesn't take very long if your emails are legit and you have unsubscribe etc inside so people don't flag you as spammy once they get bored of you.

For AOL deliverability issues, postmaster.aol.com has some tools for diagnosing the issue along with the ability to open a trouble ticket or whitelisting request.