Email Deliverability Specialist – Fix Microsoft (Outlook/Hotmail) Spam Filtering Issues

We are Finance Lobby (financelobby.com), a commercial real estate lending marketplace. We send deal alert emails to lenders from multiple sending domains via Mailgun. THE PROBLEM: We have a critical and persistent email deliverability issue exclusively with Microsoft's email ecosystem. Across 4 recent inbox placement tests (June 20-24, 2026), every single Microsoft-controlled inbox routes our emails to spam: - outlook.com: 0% inbox, 100% spam (all 4 tests) - hotmail.com: 0% inbox, 100% spam (all 4 tests) - Office 365: averaging ~80% spam across tests Meanwhile, all other major providers deliver to inbox: - Gmail: 100% inbox - Yahoo: 100% inbox - Google Workspace: 100% inbox - iCloud: 100% inbox - AOL, Comcast, AT&T, and all others: 100% inbox OUR TECHNICAL SETUP: - Email platform: Mailgun - SPF: Passing (100% of tested seeds) - DKIM: Passing (100% of tested seeds) - DMARC: Passing (100% of tested seeds) - SpamAssassin Score: 1 (well within acceptable range) - Bulk Complaint Level (BCL): Ranges from 0.00 to 6.33 depending on the sending domain (one domain showed BCL of 6.33, which is very concerning) - Spam Confidence Level (SCL): Consistently 5.0-5.67 across all domains (Microsoft considers 5+ as likely spam) The SCL of 5.67 is the key indicator -- Microsoft's engine rates our emails as borderline spam even though authentication is perfect and SpamAssassin is clean. WHAT WE NEED: We need an expert who specializes in Microsoft email deliverability (Outlook, Hotmail, Live, Office 365) to: 1. Diagnose why Microsoft is flagging our emails (SCL ~5.67, BCL up to 6.33) 2. Analyze our sending domains and IP reputation via Microsoft SNDS and JMRP 3. Review our email content, headers, and sending patterns for Microsoft-specific triggers 4. Check if our sending IPs are on Microsoft-specific blocklists 5. Guide us through Microsoft Sender Support / SNDS mitigation request process if needed 6. Recommend and implement concrete fixes to get SCL below 4 and achieve inbox placement on Outlook/Hotmail 7. Advise on separate sending infrastructure for Microsoft vs. other ISPs if needed 8. Help reduce the elevated BCL on one of our sending domains (currently 6.33) IDEAL CANDIDATE: - Proven track record resolving Microsoft-specific email deliverability issues - Deep understanding of Microsoft's filtering: SCL, BCL, Microsoft 365 Defender, EOP (Exchange Online Protection) - Experience with Mailgun or similar transactional email platforms - Familiarity with Microsoft SNDS portal and sender reputation tools - Experience submitting Microsoft Sender Support escalation tickets - B2B email environment experience is a plus Please include in your proposal: - Specific examples of Microsoft deliverability issues you have resolved - Your diagnostic approach for SCL 5.67 / BCL 6.33 situations - Estimated timeline to achieve inbox placement improvement on Outlook/Hotmail