[Hidden-tech] email deliverability issue

[Jeff Brand]

For messages that arrive in the spam folder, you can learn a lot about 
why from checking the headers. Finding the headers varies from mail 
client to client. On Gmail, click the 3 dots next to the Reply icon and 
select "Show Original". Once you have that, it'll take some time to weed 
through the headers to look for useful data. This is a good example of a 
successful delivery:

ARC-Authentication-Results: i=1; mx.google.com;
        dkim=passheader.i=@gmail.com  header.s=20230601 header.b=h7ADTRHh;
        spf=pass (google.com: domain ofXXXXXX at gmail.com  designates 209.85.220.41 as permitted sender)smtp.mailfrom=XXXXXXX at gmail.com;
        dmarc=pass (p=NONE sp=QUARANTINE dis=NONE) header.from=gmail.com


You may also see headers from spam scanners with scores, rules, etc. Any 
failures would be something you should try to address.

Microsoft provides a utility to analyze and improve readability: 
https://mha.azurewebsites.net/. Paste the header from the "Show 
Original" page, which is everything from the top of the message up to 
the first blank line. That will often be just after the "Subject:" line.

Microsoft (Outlook 365, live.com, etc) is notoriously strict about 
certain spammy behaviors but others are ratcheting up their policies. 
I'm currently helping a client navigate this with their Constant Contact 
account.

If the link shortener is the cause, you will probably see a spam filter 
rule mentioned in the headers. Tracking redirects are so pervasive these 
days that I don't think that would be the reason unless you're using a 
service known for malicious content.

Best of luck - curious to hear about your findings.

  - Jeff
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