Davey Winder: Emails to Gmail vanishing?


Davey Winder writing for Forbes recently shared a tale of woe brought to his attention wherein an email sender points out that email messages they're sending to Gmail subscribers seem to be vanishing without a trace. It's a difficult issue to troubleshoot, and the exact underlying cause can seem unclear.

Wondering how to troubleshoot a scenario like this? Here's what I would do:

  1. Check SMTP server logs and confirm proof of handoff. Outbound mail servers (MTAs) usually log this. You really need this to prove that messages are vanishing (because you're handing them off successfully, and then the mailbox provider somehow loses them), and not actually being rejected (which would also be reflected in the logs). You can't really claim that a mailbox provider is silently discarding messages unless you can prove that you're handing them off successfully.
  2. Make sure you're handling bounces properly. If mail is being rejected, but the envelope sender (return-path/bounce) address doesn't actually route back to the person sending the email (if a 1:1 email) or if the rejection is not getting logged properly by the sending platform (if an ESP, CRM or marketing automation platform), you're going to assume that the message "disappeared" when, in fact, it was rejected, but the sender set themselves up to send in a way that they're not able to see when permanent rejections (bounces) are happening.
  3. Check the recipient's spam and trash folder. Yep, it does actually happen that sometimes people forget to look in the spam folder, or they've got a Gmail filter rule set up to discard certain messages. Never rule this out until you can see for yourself.
  4. Check the outbound MTA (mail server) queue. Gmail has made significant improvements in spam filtering and moved to a greater reliance on sending domain reputation, especially over the past year or so. And they declined to accept -- either deferring or rejecting -- more mail nowadays than in years prior. Your mail could still be sitting in the outbound mail server's queue, stuck there due to receiving a 4xx deferral whenever handoff is being attempted, due to a poor sending reputation or technical misconfiguration.
  5. Make sure you're complying with modern sender requirements. That's how you prevent delivery issues caused by technical misconfigurations and/or a poor sending reputation. Make sure you've implemented SPF, DKIM and DMARC. Make sure you've got a list-unsubscribe (if it's marketing mail). Make sure your mail is wanted. Read my Yahoo Mail/Gmail 2024 Sender Compliance Guide and make sure you're following all of the requirements and recommendations found there.

It is just absolutely so rare for Gmail to silently discard email messages. I haven't seen proof of it happening in years. I see people saying this happens periodically, but the ones who come to me for help, it invariably ends up being something else. Messages are bouncing and nobody's noticing, or messages are stuck in an MTA queue with endless 4xx deferrals.

Following the steps above will help you figure out what's actually happening and that's something you'll need to know before you can begin to determine how to fix the issue. Good luck!

2 Comments

Comments

  1. I work at an ESP. Say a sender sends to their whole list (40k recipients), is properly authenticated, and has signs of low Gmail reputation (seedlist has low inbox placement, open rates are sub 10%, etc). We see same metrics as usual from that send - low opens, low seedlist placement data - but there are 0 transients, 5 expired and normal bounce rates (say .2 soft, .01 hard). MTA shows 99% handoff for Gmail within a few minutes.
    Would this be a sign of Gmail simply not delivering the email, or more a sign that those emails ARE being delivered but to the spam folder? With low reputation and not following best practices, I guess I thought Gmail would simply not deliver (even to spam folder) a lot of these messages, aligning with the “vanished” thinking.

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