Sending, receiving, and organizing email in Outlook.com
Bob,
Since the other sender is sending it via CRM, I am almost certain that they didn't have SPF, DKIM set up in the CRM to send email on their domain address's behalf.
These days, a single email address or domain is often used by several different sending services, which is very common for businesses. I am IT for my organization, and we have multiple services authorized to send on our behalf.
For example,
Salesforce (our CRM) sends sales follow-up emails,
Constant Contact sends newsletters, Square sends invoices and receipts,
and Microsoft handles our main email service.
When a business allows third-party services to send email using its domain, all of those services must be included in the SPF record in DNS and have DKIM set up correctly too. For example, if I include Salesforce and Constant Contact in SPF but forget to include Square, then any receipt sent from Square could be rejected because SPF would fail. From the recipient’s side, there is no obvious difference because every message still appears to come from @business.com. That is why people often describe it as “some emails arrive, some don’t,” when in reality the messages are being sent from different services and one of them is not properly authorized.
You would need to have your contact check with their Email admin/IT, have them review these records on their end. Microsoft will either flag their incoming emails as spam, or reject them entirely if these records are missing or wrong. And this is something that needs to be fixed on their end.