The challenge of Gmail

A lot of my sales inquiries recently are about getting good inbox delivery at Gmail. I’ve mentioned before, I can usually tell when an ISP changes things because they suddenly become the subject of a great many phone calls.
In this case, Gmail seems to have turned up their engagement filters and is sending a lot more mail to the bulk folder. I have also noticed other people are blogging about Gmail delivery problems. Al eventually determined that it was mailings sent from other IPs that were degrading the delivery of his customer’s emails.
Gmail, more than the other major ISPs, seems to not be weighting IP reputation very heavily these days. They’re looking at domain reputation and they’re using all mentions of a domain in that reputation. A lot of senders, some of them spammers, segregate their email streams (acquisition, marketing, transactional) across IP addresses in order to stop poorly performing mails from harming delivery of other emails they’re sending. But Gmail’s current filtering scheme seems designed to focus on domain reputation and minimize the impact of IP reputation.
This is making the Gmail inbox tough to reach for a lot of mailers these days. Even in cases where the mailer isn’t hiring affiliates or actively partitioning mail, if a domain is seen frequently in spam then delivery for that whole domain is hurting. Signing with DKIM and publishing a DMARC record may help. But the reality right now is that there doesn’t seem to be a silver bullet into the Gmail inbox.

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How difficult is it to get on whitelists?

Today’s question comes from Leslie J.

Just how difficult is it for a small business that runs a highly compliant mailing system to find
their way onto whitelists at the big freemail/spam filter providers?
It seems utterly impossible meaning man hours are completely wasted messing around with subjects and content when if the same business sends the very same message through any number of well know ESPs, the message will hit the inbox like the Mafia are in charge of the shooting match.

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Increasing engagement for delivery?

I’ve talked a lot about engagement here over the years and how increasing engagement can increase inbox delivery.
But does driving engagement always improve delivery?

Take LinkedIn as an example. LinkedIn has started to pop-up a link when users log in. This popup suggests that the user endorse a connection for a particular skill. When the user clicks on the popup, an email is sent to the connection. The endorsement encourages the recipient to visit the LinkedIn website and review endorsements. Once the user is on the site, they receive a popup asking for endorsement of a connection. Drives engagement both on the website and with email. Win for everyone, right?
I get lots of these endorsements, but I’ve had a few that have made me wonder what’s really going on. Are these people really endorsing my skills? If they are then why am I getting endorsements from people I’ve not seen in 15 years and why are some of the endorsed skills things I can’t do?
This morning I asked one of my connections if he really did endorse me for my abilities in Cloud Computing. His response was enlightening.

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How long is your DKIM key?

While we were at M3AAWG, Wired published an article talking about how simple it was to crack DKIM keys. I didn’t post about it at the time because it didn’t really seem like news. DKIM keys smaller than 1024 are vulnerable and not secure and the DKIM spec does not recommend using keys smaller than 1024. When I asked the DKIM-people-who-would-know they did tell me that the news was that the keys had been cracked and used in the wild to spoof email.
Fair enough.
If you are signing with DKIM, use a key 1024 or longer. Anything shorter and your risk having the key cracked and your mail fraudulently signed.
This morning M3AAWG published recommendations on keeping DKIM keys secure.

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