Using Classic Outlook on Windows for personal email, calendar, and contact management
There are 2 issues that I know at this time:
- Missing or incorrect DNS records (SPF, DMARC, DKIM) for customers who use their own domain name
- IP reputation (DNSBL)
You are responsible for #1. Microsoft can't fix the problem for you.
#2 (Microsoft IP addresses blacklisted on many DNSBL database) is Microsoft's responsibility.