Confusing the engineers

We went camping last weekend with a bunch of friends. Had a great time relaxing on the banks of the Tuolumne River, eating way too much and visiting.
On Saturday I was wearing a somewhat geeky t-shirt. It said 554: abort mission. (Thank you MessageSystems). At some point on Saturday every engineer came up to me, read my shirt and then looked at me and said “That’s not HTTP.”
That lead to various discussions about how their junior engineers don’t actually know SMTP at all. Why? Because the SMTP libraries just work. Apparently the HTTP libraries aren’t that great, so folks have to learn more about HTTP to troubleshoot and use them.
I’m sure there’s a joke in there somewhere: A Kindle engineer, an Android engineer and a robot engineer walk into a campsite…
EmailFilters_boxes_forblogIt did leave me thinking, though, about how it’s not that easy to run your own mail server these days. Gone are the days when running your own server was cost effective and easy. These days, there is just too much spam coming in. Crafting filters is a skilled job. It’s not that hard to run good filters. But to run good filters takes time to do well.
There are also a lot of challenges to sending mail. One of the discussions I had at the campsite was how hard it was to configure outbound mail. The engineer was helping a friend set up a website and trying to get the website to send notifications to the friend. But without setting up authentication the mail kept silently failing.
Of course, we do run our own mail server. But it’s our job and, in many ways, it keeps us honest. We don’t run many filters meaning we see what spammers are doing and can use our own experiences to better understand what commercial filters are dealing with.
For most people, though, I really think using a service is the right solution. Find one with filters that meet your needs and just pay them to deal with the headache.
 

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June 2015: the Month in Email

Happy July! We are back from another wonderful M3AAWG conference and enjoyed seeing many of you in Dublin. It’s always so great for us to connect with our friends, colleagues, and readers in person. I took a few notes on Michel van Eeten’s keynote on botnets, and congratulated our friend Rodney Joffe on winning the prestigious Mary Litynski Award.
In anti-spam news, June brought announcements of three ISP-initiated CAN-SPAM cases, as well as a significant fine leveled by the Canadian Radio-television and Telecommunications Commission (CRTC) against Porter Airlines. In other legal news, a UK case against Spamhaus has been settled, which continues the precedent we’ve observed that documenting a company’s practice of sending unsolicited email does not constitute libel.
In industry news, AOL started using Sender Score Certification, and Yahoo announced (and then implemented) a change to how they handle their Complaint Feedback Loop (CFL). Anyone have anything to report on how that’s working? We also noted that Google has discontinued the Google Apps for ISPs program, so we expect we might see some migration challenges along the way. I wrote a bit about some trends I’m seeing in how email programs are starting to use filtering technologies for email organization as well as fighting spam.
Steve, Josh and I all contributed some “best practices” posts this month on both technical issues and program management issues. Steve reminded us that what might seem like a universal celebration might not be a happy time for everyone, and marketers should consider more thoughtful strategies to respect that. I wrote a bit about privacy protection (and pointed to Al Iverson’s post on the topic), and Josh wrote about when senders should include a physical address, what PTR (or Reverse DNS) records are and how to use them, testing your opt-out process (do it regularly!), and advice on how to use images when many recipients view email with images blocked.

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IPv6 and authentication

I just saw a post over on the mailop mailing list where someone had been bitten by some of the IPv6 email issues I discussed a couple of months ago.
They have dual-stack smarthosts – meaning that their smarthosts have both IPv4 and IPv6 addresses, and will choose one or the other to send mail over. Some domains they send to use Office 365 and opted-in to receiving mail over IPv6, so their smarthosts decided to send that mail preferentially over IPv6.
The mail wasn’t authenticated, so it started bouncing. This is probably going to happen more and more over the next year or so as domain owners increasingly accept mail over IPv6.
If your smarthosts are dual stack, make sure that your workflow authenticates all the mail you send to avoid this sort of delivery issue.
One mistake I’ve seen several companies make is to have solid SPF authentication for all the domains they send – but not for their IPv6 address space. Check that all your SPF records include your IPv6 ranges. While you’re doing that keep in mind that having too many DNS records for SPF can cause problems, and try not too bloat the SPF records you have your customers include.

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Filtering more than spam

The obvious application of machine learning for email is to send spam to the junk/bulk folder. Most services use some level of machine learning for filters. Places like Gmail have extensive machine learning filters to filter spam and unwanted mail away from their users.
Some organizations are taking the filtering process a step further. Almost every mail client more advanced than PINE has the ability for users to create rules to sort mail into folders.  Late last year, Office 365 rolled out a feature, Clutter that tracks how a user interacts with mail and filters unimportant mail. This allows each user to have their own filters, but without the overhead of having to create the filters.
The Clutter engine looks at both how the user interacts with mail and things it knows about the organization. For example, if Exchange is tied into Active Directory, then mail from a manager will be prioritized while mail from a co-worker may end up in the clutter folder.
Email is a critical business tool. A significant number of companies rely on email for internal and external communication. Many users treat their inbox as a todo list, prioritizing what they work on based on what’s in their mail box. Despite the needs of users, the mail client hasn’t really changed.
Over the last few years, we’ve seen different online services attempt to build a more effective email client. Some of these features were things like tabs and priority inbox at Gmail. Microsoft created the “sweep” feature for Outlook/Hotmail users to manage inbox clutter. Third parties have created services to try and improve the mailbox experience for their users. 
Many of the email filters, up to this point, have really been focused on protecting users from spam and malicious emails. Applying that filtering knowledge to more than just spam, but to the different kinds of emails makes sense to me. I’ve always had a fairly extensive set of filters, initially procmail but now sieve, to process and organize incoming mail. But I kinda like the idea that my mail client learns how I filter messages and do the right thing on its own.
I’d love to see some improvements in the mail client, that make it easier to manage and organize incoming email. It remains to be seen if this is a feature that takes off and makes its way to other clients or not.
 
 

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