mail going to spam from gmail to multiple domains

I have lots of stuff to try and digest. Thanks everyone. Does it seem odd that mxtoolbox does not have the domain flagged, yet they are having issues?
No. Many email servers will bounce mail if it does not have proper SPF, etc setup. Especially if the mail appears to have multiple recipients. BCC exists for a reason as does Mass mailout services. It's not the year 2001 anymore.
 
And even the BCC field is monitored for the "too many recipients" check where that checking is done. Spamming via BCC was once very, very common before the "too many recipients" checking came into being.
And some email servers will even promptly drop an email if no "To", if "To" matches "From" and there are "BCC". I've seen one where more than one BCC on an email will just dump the email.

That said
I have lots of stuff to try and digest. Thanks everyone. Does it seem odd that mxtoolbox does not have the domain flagged, yet they are having issues?
mxtoolbox does not show the whole story. It only shows the public listings. We got to discussing this yesterday, and another angle is if the destination has you "tagged" as high risk for spamming them, and in some instances, they don't want you figuring out how to bypass their spam listing so they remove it so you can't use their public reporting to "See" if your new spam technique is working.

I would also evaluate their outbound email practices. I have a feeling even if your headers don't show it, the domain/server has ended up on some quiet black list.
 
I would also evaluate their outbound email practices. I have a feeling even if your headers don't show it, the domain/server has ended up on some quiet black list.
This can happen if an Office 365 or Gmail user marks the email as spam. This is noted inside the system and marks all mail moving through them with more suspect. Get enough people marking the item as spam and you get bounced no matter what you do. It's why Constant Contact and Mailchimp are so valuable as services. They are recognized as such by Microsoft and Google and are given more latitude in exchange for the fact that they have required unsubscribe links in the mail. And if you mark such an email as spam it can generate a bounce that will trigger an auto unsubscribe. Microsoft and Google usually do not bounce spam messages but they do for known mail services to aid in this function.
 
SPF:NEUTRAL with IP ***.85.220.41
DKIM:'PASS' with domain c***-org.2****112.g****smtp.com
Have you logged into the DNS provider to actually look at the entry? You can publish a SPF record that doesn't work the way it should. And does the IP return the proper MX server? What about DMARC?

 
Have you logged into the DNS provider to actually look at the entry? You can publish a SPF record that doesn't work the way it should. And does the IP return the proper MX server? What about DMARC?

Pcpete contacted me via PM and told me the fqdn. It doesn’t have SPF, DKIM, or Dmarc. It does have Google Workspaces generic DKIM signature which I didn’t know was a thing until now. But that should moderately improve the email reputation.

Test emails to my Office 365 domain and a gmail account both were NOT classified as spam. IMO it is the mass mailings and some recipient flagging the mail as spam. The client is a non profit and is likely sending out appeals for donations which is as spammy as it gets. Simply put by modern usage she IS a spammer just an unintentional one.
 
Pcpete contacted me via PM and told me the fqdn. It doesn’t have SPF, DKIM, or Dmarc. It does have Google Workspaces generic DKIM signature which I didn’t know was a thing until now. But that should moderately improve the email reputation.

Test emails to my Office 365 domain and a gmail account both were NOT classified as spam. IMO it is the mass mailings and some recipient flagging the mail as spam. The client is a non profit and is likely sending out appeals for donations which is as spammy as it gets. Simply put by modern usage she IS a spammer just an unintentional one.
I've had a couple of customers over the years doing mass mailing on their own so I've dealt with this as well. Content and sentence construction do play a part. But that doesn't change SPF, DKIM, and DMARC. If it was my customer there would be no discussion. All three are required as we all know the email system will just continue to tighten things up. Even though it's Google Business they should not rely on that as a sole solution. Why? Simple. When processing the troubleshooting tree those three will be check boxes that need to be cleared before an L2 or L3 will do anything more advanced.
 
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