Why This Migration Deadline Matters More Than Previous Ones

I've guided organizations through every major SharePoint migration since 2007. This one is different. Here's why:

The on-premises era is over. Microsoft isn't building another traditional SharePoint Server release after Subscription Edition. The strategic path forward is SharePoint Online within Microsoft 365. Organizations delaying this decision are choosing technical debt over competitive advantage.

After July 2026, your SharePoint 2019 environment becomes a liability, not an asset. No security patches. No bug fixes. No technical support. And here's what your auditors and cyber insurance carriers will tell you: you're now operating negligently.

The Real Costs: What Your Consultant Won't Tell You Up Front

Let me be direct about enterprise SharePoint migration costs for 10K+ users. I've personally led migrations for healthcare systems with 25,000 users and financial institutions with 50,000 users. The industry averages you see online? They're usually wrong.

Typical Cost Breakdown (10,000 User Organization)

• Migration Tools & Licenses: $50,000 - $150,000 (ShareGate, AvePoint, Quest, or custom solutions)
• Consulting Services: $300,000 - $1,000,000 (assessment, architecture, execution, testing)
• Microsoft 365 Licensing: $150,000 - $300,000 annually (E3 or E5 plans, depends on features needed)
• Custom Development: $100,000 - $500,000 (workflow conversion, web part redesign, integration updates)
• User Training: $50,000 - $200,000 (change management, adoption programs, documentation)
• Contingency Buffer: 15-25% of total budget (you'll need it)

Total realistic range: $650,000 - $2,150,000

The organizations that exceed these budgets share one common mistake: they underestimate customization complexity. You think you have 20 workflows. You actually have 200, many undocumented and maintained by someone who left three years ago.

The Hidden Cost: Custom Code Nobody Remembers

Here's the conversation I have with every CTO about 4 weeks into discovery:

"We just found another 40 custom web parts we didn't know existed. They're all using deprecated APIs. We need to completely rewrite them or find replacements."

Technical debt accumulates silently in SharePoint environments. Solutions built in 2012 using SharePoint 2010 workflows. InfoPath forms processing business-critical approvals. Custom master pages breaking modern authentication. Event receivers triggering undocumented business logic.

Budget 12+ months for discovery and assessment if you're an enterprise. Rush this phase and you'll pay triple later.

Compliance Requirements: HIPAA, SOC 2, and FedRAMP Considerations

If you're in healthcare, finance, or government, compliance isn't optional—it's the primary constraint driving your architecture decisions.

HIPAA-Regulated Healthcare Organizations

Microsoft 365 supports HIPAA compliance, but it's not automatic. You need:

• Business Associate Agreement (BAA) with Microsoft (available for E3/E5 plans)
• Data Loss Prevention (DLP) policies configured to detect and block PHI sharing
• Encryption at rest and in transit (enabled by default, but verify)
• Audit logging retention for minimum 6 years (HIPAA requirement)
• Access controls and conditional access preventing unauthorized PHI access
• Guest access restrictions (most healthcare orgs should disable completely)

The configuration matters as much as the platform. I've seen organizations deploy Microsoft 365 and still fail HIPAA audits because they left guest sharing enabled or didn't configure DLP properly.

SOC 2 Compliance for Financial Services

Financial institutions need SOC 2 Type II attestation. Microsoft provides this for Microsoft 365, but your implementation also requires controls:

• Multi-factor authentication (MFA) for all users accessing financial data
• Privileged access management (PAM) for SharePoint administrators
• Document versioning and retention policies aligned with regulatory requirements
• Segregation of duties for administrative functions
• Continuous monitoring and alerting for suspicious access patterns

FedRAMP for Government Contractors

If you support federal agencies, you need Microsoft 365 Government GCC High or DoD environments. These are separate tenants with FedRAMP High authorization. You cannot simply migrate from commercial Microsoft 365 to GCC High—it's a complete tenant-to-tenant migration.

Budget an additional 30-40% for GCC High migrations due to stricter requirements and limited tooling support.

Your 6-Month Migration Roadmap (Starting Today)

You have 188 days until SharePoint 2019 end of support. Here's your survival timeline:

Month 1-2: Emergency Assessment & Executive Alignment

• Week 1-2: Inventory all SharePoint farms, content databases, site collections, and customizations
• Week 3-4: Identify compliance requirements and data classification (HIPAA, SOC 2, FedRAMP)
• Week 5-6: Document custom workflows, InfoPath forms, web parts, and third-party solutions
• Week 7-8: Calculate realistic budget and present to executive leadership with risk assessment

Month 3-4: Architecture & Pilot Preparation

• Week 9-10: Design Microsoft 365 tenant architecture (information architecture, security model, compliance policies)
• Week 11-12: Select migration tools and establish migration factory process
• Week 13-14: Convert highest-priority workflows from SharePoint Designer to Power Automate
• Week 15-16: Execute pilot migration with 500-1,000 users from non-critical department

Month 5-6: Production Migration & Cutover

• Week 17-20: Phased migration of production site collections (prioritize by business criticality)
• Week 21-22: User training and change management rollout
• Week 23-24: Final cutover, decommission on-premises farms, post-migration validation

This timeline is aggressive. Most enterprise migrations take 9-12 months. If you're starting now for a July 2026 deadline, you need executive commitment to move faster than normal.

Strategic Decision: SharePoint Online vs. Subscription Edition

Should you migrate to SharePoint Online (cloud) or SharePoint Server Subscription Edition (on-premises)? For 95% of organizations, the answer is SharePoint Online. Here's why:

Choose SharePoint Online If:

• Your organization values continuous feature updates without maintenance windows
• You want to reduce infrastructure costs (no more server hardware, patching, database maintenance)
• Your compliance requirements permit cloud-based data storage (most do with proper configuration)
• You plan to adopt Microsoft Teams, Copilot, and other modern collaboration tools
• You want to scale user capacity without buying more hardware

Choose Subscription Edition Only If:

• You have regulatory requirements explicitly mandating on-premises data residency (rare but real)
• You operate air-gapped networks with no internet connectivity (defense, intelligence)
• You've calculated that your hybrid architecture legitimately costs less than cloud (almost never true)

I've had clients argue for Subscription Edition because "we've always been on-premises." That's not a technical justification—it's organizational inertia. Challenge that assumption with TCO modeling.

Workflow Conversion: Your Biggest Technical Challenge

SharePoint 2010 and 2013 workflows do not work in SharePoint Online. Period. You must convert them to Power Automate.

This isn't a simple lift-and-shift. Power Automate uses a different architecture, different connectors, and different logic patterns. A complex approval workflow that took 2 hours to build in SharePoint Designer might take 40 hours to redesign, test, and validate in Power Automate.

Workflow Conversion Strategy

1. Document existing workflows exhaustively (business logic, approval chains, error handling, email notifications)
2. Prioritize by business impact (which workflows are mission-critical vs. nice-to-have?)
3. Identify workflows to retire (surprising number haven't been used in years)
4. Rebuild in Power Automate with modern patterns (approvals, parallel branches, error handling)
5. Test with actual business users (not just IT testing)

Budget 40-80 hours per complex workflow for complete conversion. If you have 50+ workflows, this becomes a $200K+ line item.

Risk Management: What Happens If You Miss the Deadline?

Let's be realistic. Some organizations will not complete migration by July 2026. Here's what happens:

Security Risks

• Zero-day vulnerabilities discovered after July 2026 will never be patched
• Your environment becomes an attractive target for ransomware operators who know you're unpatched
• Cyber insurance carriers may deny claims or cancel policies for running unsupported infrastructure

Compliance Risks

• HIPAA, SOC 2, and FedRAMP audits will cite unsupported platforms as control failures
• You cannot pass security questionnaires from enterprise customers asking about platform currency
• Legal liability if breach occurs and plaintiff attorneys discover you were running unsupported systems

Mitigation Options (If You're Truly Stuck)

If you absolutely cannot complete migration by July 2026:

• Purchase Microsoft Extended Security Updates (ESU) if available (provides critical security patches for additional fee)
• Implement network segmentation to isolate SharePoint environment from broader network
• Deploy third-party security tools (web application firewalls, intrusion detection, endpoint protection)
• Accelerate timeline with external consultants (yes, this means calling firms like ours)

But understand: these are band-aids. The strategic answer is migration, not indefinite delay.

Why Hire Enterprise Migration Specialists vs. DIY

I'm biased—I run a consulting firm that does these migrations. But let me explain the decision calculus:

DIY Migration Makes Sense If:

• You have fewer than 1,000 users
• You have minimal customizations (out-of-box SharePoint features only)
• Your IT team has 6+ months of dedicated time (not 10% allocation, full-time dedication)
• You can tolerate mistakes and learning curves

Hire Specialists If:

• You're migrating 10,000+ users across multiple business units
• You have extensive customizations, workflows, and integrations
• You're in a regulated industry requiring compliance validation (HIPAA, SOC 2, FedRAMP)
• You need this done in 6-9 months and can't afford failures
• Your IT team is already underwater with operational demands

The value we bring isn't just technical execution—it's pattern recognition from doing this 100+ times. We know which tools actually work at scale. We know which migration sequences minimize user disruption. We know how to negotiate with Microsoft licensing when issues arise.

That pattern recognition is worth the consulting fees when you're risking a $2M project.

FAQ: SharePoint 2016/2019 End of Support

Next Steps: How to Start Your Migration Today

If you're reading this in January 2026 and haven't started your SharePoint migration, you need to move immediately. Here's your action plan:

1. This week: Schedule emergency meeting with CIO, CISO, and compliance leadership to acknowledge the July deadline
2. Next 2 weeks: Engage a migration assessment firm (or allocate internal resources) to inventory your current environment
3. Next 4 weeks: Develop high-level migration roadmap with timeline, budget, and resource requirements
4. Next 8 weeks: Execute pilot migration with small user group to identify hidden complexity
5. Next 24 weeks: Full production migration in phased waves

The organizations that succeed in this migration share one trait: they acknowledged the problem early and committed resources to solve it properly.

The organizations that fail? They spent months debating whether they really needed to migrate.

Don't be the latter.