Microsoft Entra & UPN Migration Expert

Microsoft Entra & UPN Migration Expert Job Title Microsoft Entra ID Expert – Domain Migration, Tenant Rename & UPN Conversion (M365 / Azure AD) Job Description We are executing a complex Microsoft 365 identity migration for a mid-size enterprise and are looking for a seasoned Microsoft Entra ID (formerly Azure AD) specialist to provide expert-level guidance, and technical oversight throughout the engagement. Most hands-on configuration will be performed by senior developers. The project involves three interconnected workstreams: • UPN suffix migration — converting all user accounts from a legacy domain (@olddomain.com) to a new primary domain (@newdomain.com), including app dependency remediation, service account handling, and mail flow validation • Identity Provider (IDP) transition — migrating from Okta as the primary IDP to Microsoft Entra ID, with Okta retained as a secondary token-passing relay during the transition period • Primary Domain/MS Tenant rename – migrating the primary Microsoft 365 domain from an old domain to a new domain. The old domain will still exist on the tenant. You will work alongside an existing internal project team and are expected to provide both advisory support and direct technical execution. Scope of Work Identity & UPN Migration • Audit and remediate all applications authenticating via the legacy UPN suffix (SAML, OAuth, OIDC, and legacy auth) • Execute bulk UPN suffix change via PowerShell / Microsoft Graph for all user accounts and applicable service accounts • Validate post-migration authentication across Microsoft 365 workloads (Exchange Online, SharePoint/OneDrive, Teams, OneNote), Okta-federated apps, and third-party SaaS applications • Advise on and assist with OneDrive URL transition, sharing link remediation strategy, and OneNote notebook reconnection • Ensure Proofpoint/mail flow continuity with new primary SMTP domain Entra ID / IDP Configuration • Configure Microsoft Entra ID as primary IDP with Okta as secondary/token-passing relay • Design and implement Conditional Access policy baseline (MFA enforcement, device compliance, location controls, sign-in risk) • Validate and remediate Workday-to-Entra attribute sync and writeback • Validate AWS, Intune, and other Entra-integrated service trust configurations post-UPN change Documentation & Knowledge Transfer • Produce or review runbooks for UPN cutover, IDP flip, and MS Tenant domain rename. • Document rollback procedures for each major phase • Provide a help desk runbook covering common post-cutover user issues (OneDrive sync, OneNote, Teams, shared links, Office Backstage) • Participate in a post-migration health check and lessons-learned review Required Qualifications • 5+ years of hands-on experience with Microsoft Entra ID / Azure Active Directory in enterprise environments • Demonstrated experience with UPN suffix migrations and/or Microsoft 365 tenant/domain renames at scale (500+ users) • Proficiency with PnP PowerShell, Microsoft Graph API, and SPO Management Shell for bulk operations • Experience with Okta-to-Entra IDP migration or Okta federation configuration • Familiarity with Workday-Entra integration (attribute mapping, writeback) is a strong plus • Experience with Windows LAPS, GPO management, and AD OU design • Excellent written English — able to produce clear technical runbooks and decision documentation Preferred Certifications (any of the following) • Microsoft Certified: Identity and Access Administrator Associate (SC-300) • Microsoft Certified: Azure Solutions Architect Expert (AZ-305) • Microsoft Certified: Security Operations Analyst Associate (SC-200) • Microsoft 365 Certified: Enterprise Administrator Expert (MS-102) Engagement Details Project type Ongoing / milestone-based Estimated duration 3–4 months Estimated hours 10–20 hours/week (flexible based on milestone cadence) Availability required Overlap with US Central time zone for weekly syncs Communication Microsoft Teams + email; weekly status call Work type Remote What to Include in Your Proposal To be considered, please address the following in your proposal: 1. Describe a comparable engagement — Detail a UPN suffix migration or IDP transition you led, including the scale (number of users), the tools/methods you used, and any complications you encountered and resolved. 2. Microsoft Tenant/Domain rename – Describe a domain migration project you worked on and lessons learned when converting the domain. 3. Okta + Entra coexistence — Have you worked in an environment where Okta and Entra ID ran simultaneously? How did you handle the token-passing configuration? 4. OneDrive/SharePoint post-UPN remediation — What is your approach to handling broken sharing links and OneNote sync issues after a bulk UPN change? 5. Your hourly rate and estimated availability over the next 90 days. Applications that do not address the proposal questions above will not be reviewed.