Diagnose why Sam@demandsam.com bounced and verify kylawoffice.com to demandsam.com address parity.
Session objective: Diagnose why Sam@demandsam.com bounced and verify whether kylawoffice.com recipients have matching demandsam.com addresses.
What was accomplished: Public DNS was checked for demandsam.com and kylawoffice.com. Both domains point MX to Microsoft 365 and include Microsoft SPF. Microsoft Graph app-only access was used read-only to verify both domains are present, verified, and support Email in the tenant. Sam@kylawoffice.com was inspected directly. Current proxyAddresses are only smtp:sam@kylawoffice.onmicrosoft.com and SMTP:Sam@kylawoffice.com. No sam@demandsam.com recipient object or alias exists. Sam's mailbox contains a fresh NDR from 2026-05-29 13:07:12 UTC saying the message to sam@demandsam.com could not be delivered because sam was not found at demandsam.com. Older NDRs for website intake leads also show recipients not found at demandsam.com.
Scanned 183 Graph recipient objects. Found 116 kylawoffice.com addresses, 42 demandsam.com addresses, 18 exact local-part matches, and 98 missing counterparts.
Local report: /Users/samaguiar/Documents/Projects/admin/outlook-audits/demandsam-alias-diagnosis-20260529T131134Z.md JSON evidence: /Users/samaguiar/Documents/Projects/admin/outlook-audits/demandsam-alias-diagnosis-20260529T131134Z.json
Diagnostic complete. No live aliases changed. Importance High. Repair pending.
Use Exchange Online PowerShell 3.9.2, already installed locally, or another admin-safe Exchange path to add secondary SMTP aliases. Start with sam@demandsam.com on Sam Aguiar if Sam approves immediate repair. Then create a staged plan for enabled user mailboxes first, followed by shared/service mailboxes and groups after reviewing whether every group should accept public demandsam.com mail. Preserve rollback by exporting current EmailAddresses for every changed recipient before Set-Mailbox or Set-DistributionGroup updates. After each change, verify with Get-Recipient and a controlled test email.
Handoff note: The Outlook and Notion MCP connectors failed at startup during this session, so direct Graph and direct Notion API were used. Do not assume connector access is healthy just because API credentials worked. The local report is the strongest evidence packet for continuation.