Microsoft 365 Migration Hidden Steps That Delay Go-Live
Cutover weekend that went sideways—why
Many Montréal businesses have lived this nightmare: everything is planned for a Friday night cutover to Microsoft 365, but by Monday morning users still can’t sign in, email is delayed, or Teams meetings disappear. The real issue? It’s usually not the migration tool or Microsoft itself, but the hidden pre-work that was missed before the cutover.
Discovery: domains, tenants, licensing, shared resources
A smooth migration begins with discovery. That means mapping out:
- Domains: Verify ownership, DNS records, and SPF/DKIM alignment.
- Tenants: Are you consolidating multiple tenants, or migrating from another provider?
- Licensing: Matching the right M365 SKUs to current and future needs.
- Shared resources: Distribution lists, shared mailboxes, public folders—often overlooked.
Identity & security: Entra ID, MFA, conditional access
Identity is the backbone of Microsoft 365. Before migrating, ensure:
- Azure Entra ID sync or cloud-only identity is configured properly.
- MFA is enforced without breaking service accounts.
- Conditional access rules won’t lock out remote staff during go-live.
Data mapping: mailboxes, SharePoint, OneDrive, Teams
Data rarely lives in one place. Beyond email, migrations must account for:
- User mailboxes and archives (PSTs, on-prem Exchange, or Gmail exports).
- SharePoint sites and permissions.
- OneDrive storage quotas and ownership transfer.
- Teams channels, private chats, and meeting history.
Coexistence vs. big-bang: how to choose
Should you move everyone at once, or run a coexistence phase? Big-bang cutovers reduce complexity but require intense prep. Coexistence allows staged moves but needs hybrid connectors, directory sync, and clear rules of engagement.
Communication plan & rollback
No migration is risk-free. Success depends on:
- Clear communication with staff about timelines and login changes.
- Training resources before and after migration.
- A tested rollback plan in case DNS changes or identity syncs fail.
Post-migration hardening: DLP, retention, backups
Going live is only the start. Secure the new tenant with:
- Data Loss Prevention (DLP) policies to prevent accidental leaks.
- Retention and compliance rules for industry regulations.
- Third-party backups—Microsoft protects infrastructure, not your accidental deletions.
FAQ: Microsoft 365 Migration Montréal
How much does an M365 migration cost?
Costs vary by tenant size and data complexity. Small Montréal businesses often budget between $3,000 and $10,000 for a cutover, while multi-tenant or hybrid projects can be higher.
How long does it take?
A simple cutover can be completed in a weekend, but proper discovery and pre-flight checks take 2–4 weeks. Complex tenant consolidations may take months.
Do staff need training?
Yes. Even if they’ve used Outlook and Teams before, every migration changes sign-in behavior, MFA, and file paths. A short training reduces helpdesk calls by 40%.
Next steps
Ready to move without downtime? Book a Microsoft 365 migration consult today. As part of our Managed IT Services and Cybersecurity solutions, we help Montréal SMBs migrate securely and efficiently.