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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:<br>
<br>
<pre class="raw_message_text" id="raw_message_text">ARC-Authentication-Results: i=1; mx.google.com;
dkim=pass <a class="moz-txt-link-abbreviated" href="mailto:header.i=@gmail.com">header.i=@gmail.com</a> header.s=20230601 header.b=h7ADTRHh;
spf=pass (google.com: domain of <a class="moz-txt-link-abbreviated" href="mailto:XXXXXX@gmail.com">XXXXXX@gmail.com</a> designates 209.85.220.41 as permitted sender) <a class="moz-txt-link-abbreviated" href="mailto:smtp.mailfrom=XXXXXXX@gmail.com">smtp.mailfrom=XXXXXXX@gmail.com</a>;
dmarc=pass (p=NONE sp=QUARANTINE dis=NONE) header.from=gmail.com
</pre>
You may also see headers from spam scanners with scores, rules, etc.
Any failures would be something you should try to address.<br>
<br>
Microsoft provides a utility to analyze and improve readability:
<a class="moz-txt-link-freetext" href="https://mha.azurewebsites.net/">https://mha.azurewebsites.net/</a>. 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.<br>
<br>
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.<br>
<br>
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.<br>
<br>
Best of luck - curious to hear about your findings.<br>
<br>
- Jeff<br>
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