Spamfighting: Bulk sending

In parts 1 and 2 of this series, I’ve explored the current best practices for authenticating outbound email, validating inbound email, and my own system configurations for such.

When not busy with my day job, I also serve on the board of our neighborhood youth basketball league as registrar and co-webmaster. As part of these roles, I maintain the email infrastructure, and send most of the announcement emails.

I had made a point of “warming up” the IP address for this server. I’ve been using this same IP for several months, and it has a returnpath.com Sender Score of 99, so I thought I’d be in the clear.

We have about 1500 parent email addresses on our announcement mailing list, with over 160 of them going to a single domain – austin.rr.com. No surprise there – Roadrunner is a very popular ISP. The problem is this: Roadrunner’s mail servers don’t appreciate when my mail server sends an email, via this mailing list, to their inbound MX mail server. Even after mailman splits the message up so there are only 10 recepients per message. The first few messages get through, the rest get put on hold (SMTP 4.x.x try again later), allowing only a trickle of messages per hour from my one IP address.

During the Austin Snowpocalypse last week, we needed to get an announcement out to our parents, that, because schools were closed, and because we rent all our court space from the area schools, our practices and games had to be cancelled for the night. I sent that note around noon. It took until 6pm before all the @austin.rr.com emails were allowed through – just in time to get notice of a cancelled 6pm event. Note – my message came from a valid SPF mail server, had a valid DKIM key attached, and the DMARC policy is “none”, so it wasn’t blocked at that level. It was blocked because my mail server’s IP address isn’t allowed to send more than a few messages to Roadrunner subscribers each hour.

Roadrunner does provide a way for you to request relaxed rate limits for your IP. I followed their process, which uses Return Path’s Feedback Loop Management service, but my request was denied, no explaination given. Perhaps they know it’s a cloud service IP, which in theory could be given to another customer at any moment. I’ll file a request with my ISP to see if they’ll sign up with ReturnPath to be responsible for their netblocks on behalf of their customers. Not sure how well that’ll go over – it could make a lot of work for the ISP mail technicians.

One other alternative is to use an outbound mail service such as Amazon Simple Email Service, Mailchimp or SendGrid, in order to get my mails out to our player’s families in a timely manner. Mailchimp appears to have the disadvantage of needing to migrate all my mailing lists to them, instead of my existing GNU Mailman setup. SendGrid has better pure SMTP integration, and with some sendmail smarttable hacking, I could probably make that work. All three involve some increased cost to us, in the months I send a lot of announcements.

Do you send bulk mail from a cloud service? How do you ensure your mails get through? Leave your comments below.

2 thoughts on “Spamfighting: Bulk sending

  1. I use both Sendgrid (at work) and Mailchimp (volunteering) and if you asked me which I’d use for your situation, I’d go with Mailchimp. Their free version just adds a Mailchimp logo to the footer of the email. So, if that’s not a big deal, you have a really nice out-of-the-box mass email setup without jumping through all the hoops of maintaining your own mass email server. If you want to stay with hosting it yourself, you’ll have to move to an IP address block that your local ISP likes. No short way around that. Good luck!

  2. I have filed a ticket with my server’s ISP – they’re looking into it. That’s the easiest path for me to follow. And upon review, it was just a couple hour delay, not 6, so I may be able to tolerate it anyhow as-is.

    I’m not sure how to categorize “mailing lists” (e.g. announcements to everyone, conversations among coaches of each division, conversations from a coach with their team…). Mailchimp might consider them marketing, not transactional. I don’t really consider them marketing though, which is what steered me away from Mailchimp, and I don’t consider them transactional either, which would steer me away from Mailchimp’s Mandrill service.

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