Mike Baptiste

While I understand that - my point in sending the headers I did is that it probably is NOT due to GMail connector and possibly due to the way the emails are encoded, etc that are triggering Spam filters. We don't have any trouble reaching people directly via GMail on Yahoo and AOL. We use GMail connector precisely because we've had pristine SPF/DKIM/DMARC setup and rely on deliverability of it that way. But Zendesk emails are consistently marked SPAM, even though SPF, DKIM, and DMARC are all passing on Yahoo's side, as the headers show. 

So please don't do the 'oh some other company is involved so it's definitely their problem' bit. It's clearly not a GMail issue given Yahoo verifies every anti-spam setting/feature and marks it passed (See above). I send email directly from the same address to the same Yahoo address and it delivers fine.

Is there any way for Zendesk to reach out to Yahoo to enquire as to why emails like this are being flagged? Clearly a number of users are experiencing it. Is it the [] prefix in the subject? The ## Please reply above this line ##. The keyword Zendesk? I checked the headers between successful and marked emails - they are almost identical in terms of which headers are included - as you'd expect. Hopefully you all can help us troubleshoot this to get our ticket emails reliably delivered. We're having to waste so much time following up with users by phone now, or hoping SMS alerts on ticket resolution get through because this is breaking communication with a significant segment of our customers that still use these email services.

We're seeing this as well. It seems to have gotten much worse recently. We use the GMail connector for outgoing emails and can confirm we have valid SPF, DKIM *AND* DMARC settings. And it STILL goes directly to Yahoo's spam folder (AOL about the same). This is the header in a Zendesk email sent to my Yahoo test account.

Received-SPF: pass (domain of itxpress.biz designates X.X.X.X as permitted sender)
Authentication-Results: atlas212.free.mail.bf1.yahoo.com;
 dkim=pass header.i=@itxpress.biz header.s=ussems;
 spf=pass smtp.mailfrom=itxpress.biz;
 dmarc=pass(p=NONE) header.from=itxpress.biz;

I completely understand this is somewhat out of Zendesk's hands - despite everything passing, they still mark is as Spam. But we never had this much trouble with our ticket emails getting seen before (thankfully we send SMS texts when a ticket is solved, so we often get a call asking if the problem is solved). 

Is it possible something in the way emails are getting composed is causing this? Yahoo even alerts that it has disabled links in the email (though helpfully provides a link to activate them and suggests clicking 'Not Spam').