What to do when an important email bounces

Some emails are more important than others. I know, I know, all emails are important, but really, some are more important than others.
I’ve recently been decluttering by the simple expedient of enrolling in paperless statements for some of our accounts. We have a 1TB NAS, I’m not going to run out of storage space and I will have so much less paper to deal with. Plus, electronic searches are easier than digging through a file I’ve just shoved statements in for the whole year.
Some companies just let you sign up for statements online and don’t take any extra steps to verify your email address or tell you what happens if your email breaks. But at least one company has gone the extra mile to establish how they handle email bounces.
consentforpaperlessdocs
First, to sign up for paperless notifications I have to give my consent to receive docs. Even better, when I look at the important information it expressly details what happens if my email address bounces.

Keeping Your Email Address Current, and Actions We Will Take if there is a Problem
It is your responsibility to notify Schwab of any change in your email address by logging in to the Schwab site and going to Service > My Profile > Email Addresses or using the contact information above. If we receive any indication either that the email notification did not reach you successfully or there is a problem with your email address or service, we will take the following actions:

The actions are all variations on the theme of sending us snail mail copies of the email and un-enrolling that email address from future paperless documents.
It seems like a very simple statement and a very simple policy; and it is. Most places don’t even think about “what happens if an email fails.” Often the people writing the communications don’t even know that email isn’t always a 100% thing so they don’t know they have to think about it. Some places do have policies in place but don’t inform the customer of the issue.
Of course, delivery failure doesn’t matter for 95% of bulk mail. You get it, you don’t get it, it doesn’t really matter. But certain communications are just too important, or are legally mandated communications, to let recipients lose communications due to email delivery problems.

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Delivering to Gmail

Gmail is a challenge for even the best senders these days.
With the recent Gmail changes there isn’t any clear fix to getting open rates or inbox delivery back up. Some of it depends on what is causing Gmail to filter the mail. Changing subject lines, from name, from address may get mail back to the inbox in the short term, but it only works until the filters catch up.
What I am seeing, across a number of clients, is that Gmail is doing a lot of content reputation and that content reputation gets spread across senders of that content.  That means you want to look at who is sending any mail on your behalf (mentioning your domain or pointing at your website) and their practices. If they have poor practices, then it can reflect badly on you and result in filtering.
From what I’ve seen, these are very deliberate filtering decisions by Google. And it’s making mail a lot harder for many, many senders. But I think it is, unfortunately, the new reality.

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Ever changing filtering

One of the ongoing challenges sending email, and managing a high volume outbound mail server is dealing with the ongoing changes in filtering. Filters are not static, nor can they be. As ISPs and filtering companies identify new ways to separate out wanted email from unwanted email, spammers find new ways to make their mail look more like wanted mail.
This is one reason traps are useful to filtering companies. With traps there is no discussion about whether or not the mail was requested. No one with any connection to the email address opted in to receive mail. The mail was never requested. While it is possible for trap addresses to get on any list monitoring mail to spam traps is a way to monitor which senders don’t have good practices.
New filtering techniques are always evolving. I mentioned yesterday that Gmail was making filtering changes, and that this was causing a lot of delivery issues for senders. The other major challenge for Gmail is the personalized delivery they are doing. It’s harder and harder for senders to monitor their inbox delivery because almost every inbox is different at Gmail. I’ve seen different delivery in some of my own mailboxes at Gmail.
All of this makes email delivery an ongoing challenge.

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AHBL Wildcards the Internet

AHBL (Abusive Host Blocking List) is a DNSBL (Domain Name Service Blacklist) that has been available since 2003 and is used by administrators to crowd-source spam sources, open proxies, and open relays.  By collecting the data into a single list, an email system can check this blacklist to determine if a message should be accepted or rejected. AHBL is managed by The Summit Open Source Development Group and they have decided after 11 years they no longer wish to maintain the blacklist.
A DNSBL works like this, a mail server checks the sender’s IP address of every inbound email against a blacklist and the blacklist responses with either, yes that IP address is on the blacklist or no I did not find that IP address on the list.  If an IP address is found on the list, the email administrator, based on the policies setup on their server, can take a number of actions such as rejecting the message, quarantining the message, or increasing the spam score of the email.
The administrators of AHBL have chosen to list the world as their shutdown strategy. The DNSBL now answers ‘yes’ to every query. The theory behind this strategy is that users of the list will discover that their mail is all being blocked and stop querying the list causing this. In principle, this should work. But in practice it really does not because many people querying lists are not doing it as part of a pass/fail delivery system. Many lists are queried as part of a scoring system.
Maintaining a DNSBL is a lot of work and after years of providing a valuable service, you are thanked with the difficulties with decommissioning the list.  Popular DNSBLs like the AHBL list are used by thousands of administrators and it is a tough task to get them to all stop using the list.  RFC6471 has a number of recommendations such as increasing the delay in how long it takes to respond to a query but this does not stop people from using the list.  You could change the page responding to the site to advise people the list is no longer valid, but unlike when you surf the web and come across a 404 page, a computer does not mind checking the same 404 page over and over.
Many mailservers, particularly those only serving a small number of users, are running spam filters in fire-and-forget mode, unmaintained, unmonitored, and seldom upgraded until the hardware they are running on dies and is replaced. Unless they do proper liveness detection on the blacklists they are using (and they basically never do) they will keep querying a list forever, unless it breaks something so spectacularly that the admin notices it.
So spread the word,

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