Avoiding Email from Your Site Being Treated as Spam or Rejected

LegalServer allows users to send email messages from your site. For example when adding a case note.

These emails are sent by our server, but have a "From:" that is the user's email address (we do this so the recipients will know who created the message). These emails often run afoul of anti-spoofing and other spam/junk email rules because the message from janesmith@abclegal.org did not come from abclegal.org's server, but our server.

To avoid email sent to your staff from being tagged as spam, your incoming mail server should provide an exception for our server. Your staff or vendor who administers your email service can do this. Let them know that you want to exempt mail coming from this source:


IPv4 address:

IPv6 address: 2600:1f16:c7d:ab00:ec2:ea57:2c:9a7e

To avoid email sent to your clients, pro bono users, or others from being tagged as spam or blocked, your organization's SPF record should have an "include" for "legalserver.org".

Microsoft Mail Servers

One of our clients struggled to stop getting email from LS tagged as spam/junk. This is the final chapter in his story. Your mileage may vary, don't run with scissors, etc.:

"[Microsoft person] escalated it to a subject matter expert who recommended that I remove the advanced filter and change my Tenant Allow Spoof rule from “external” to “internal”, which I did last night. I started testing in the wee hours of this morning and so far everything is looking good. I’m actively monitoring mail flow, and everything is being delivered to Inboxes.

Honestly the fix is counterintuitive to me, because the sender is external to my domain. But apparently by marking it as internal, we’re actually telling exchange online protection that it is an internal server and can be trusted. It’s weird, but it works."

Weird indeed. But maybe helpful to others.