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SharePoint Migration Guide 2026

The Definitive Enterprise Playbook for SharePoint Online Migration

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Errin O'ConnorJanuary 15, 202618 min read

SharePoint Migration Guide 2026: The Complete Enterprise Playbook for SharePoint Online Migration

After leading 5,200+ SharePoint migrations over 28 years, including environments with 50,000+ users and petabyte-scale data, EPC Group has distilled everything we know about successful SharePoint Online migration into this comprehensive guide. Whether you are migrating from SharePoint Server 2016, 2019, or Subscription Edition, consolidating file shares, or moving from competing platforms, this guide covers the strategy, tactics, and hard-won lessons that separate successful migrations from costly failures.

5,200+
Migrations Completed
28+
Years Experience
99.7%
Data Integrity Rate
50K+
Largest User Migration

In This Guide

  1. Why Migrate to SharePoint Online in 2026
  2. Migration Assessment: Where Every Successful Project Begins
  3. Migration Planning Phases
  4. SharePoint Online vs. On-Premises: The 2026 Comparison
  5. Data Mapping Strategies for Complex Environments
  6. User Adoption: The Make-or-Break Factor
  7. Post-Migration Optimization
  8. Common Pitfalls and How to Avoid Them
  9. Compliance Considerations: HIPAA, GDPR, and Beyond
  10. Real Migration Scenarios from the Field
  11. Frequently Asked Questions

Why Migrate to SharePoint Online in 2026

The case for SharePoint Online migration has never been more compelling. Microsoft continues to invest heavily in cloud-first capabilities while the on-premises roadmap narrows. SharePoint Server Subscription Edition receives feature updates, but the pace and scope of innovation in SharePoint Online far outstrips what is available on-premises. Organizations that delay migration face compounding technical debt, increasing security risk from aging infrastructure, and a widening gap between their collaboration capabilities and those of competitors already operating in the cloud.

In 2026, several factors make migration particularly urgent. Microsoft Copilot integration, which delivers AI-powered content creation, search, and summarization across SharePoint, is exclusively available in SharePoint Online. The new SharePoint Premium features, including advanced content processing, document understanding through AI Builder, and enhanced eSignature capabilities, require a cloud foundation. Organizations still running SharePoint 2016 face end-of-extended-support in July 2026, creating a hard deadline for migration planning.

Beyond feature parity, the economics have shifted decisively. Managing on-premises SharePoint farms requires dedicated infrastructure, SQL Server licensing, patching cycles, disaster recovery configurations, and specialized administrator headcount. For a 10,000-user SharePoint farm, the fully loaded annual cost of on-premises operations typically runs between $400,000 and $750,000 when you account for hardware refresh cycles, software licensing, and personnel. A comparable SharePoint Online environment within Microsoft 365 E3 licensing costs approximately $216,000 per year for the SharePoint component, with infrastructure, patching, and disaster recovery fully managed by Microsoft.

Key Insight

Organizations that completed their SharePoint Online migration before deploying Microsoft Copilot saw a 34% higher Copilot adoption rate compared to those attempting to deploy Copilot while still operating hybrid on-premises environments. The cloud foundation is not just a migration target; it is an AI readiness prerequisite.

Migration Assessment: Where Every Successful Project Begins

The single most common reason SharePoint migrations fail or exceed budget is inadequate assessment. After 5,200+ migrations, EPC Group has found that organizations which invest 10 to 15 percent of their total migration budget in a thorough discovery phase reduce the overall project cost by 25 to 40 percent and cut the timeline by 30 percent on average. The assessment phase is not overhead; it is the highest-ROI investment in the entire project.

A comprehensive migration assessment must cover six critical dimensions. Skipping any one of these creates blind spots that surface as costly surprises during execution.

1

Content Inventory

Catalog every site collection, subsite, document library, and list across all farms. Document total data volume at the site collection level. Identify the largest individual files (SharePoint Online has a 250GB file size limit, increased from 15GB in 2024). Flag content with special characters, excessively long file paths (SharePoint Online supports 400 characters in the full URL), and files with blocked extensions. For a 15,000-user environment we assessed for a healthcare system in 2025, this inventory identified 12TB of content across 340 site collections, with 2.1TB of content that had not been accessed in over 4 years.

2

Custom Solutions Audit

Document every farm solution, sandbox solution, SharePoint Designer workflow, InfoPath form, and custom web part. Classify each solution as migrate-as-is, rebuild, replace with out-of-the-box, or retire. Farm solutions cannot run in SharePoint Online and must be rebuilt as SharePoint Framework (SPFx) solutions, Power Platform applications, or Azure-hosted services. This is consistently the most underestimated area of migration projects. A Fortune 500 financial institution we worked with had 87 active SharePoint Designer workflows, 23 InfoPath forms, and 14 farm solutions that collectively required 1,400 hours of remediation effort.

3

Permissions and Security Analysis

Map all Active Directory groups, SharePoint groups, and individual permission assignments. Identify sites with broken inheritance, which create migration complexity and ongoing governance challenges. Document external sharing configurations and guest access patterns. For HIPAA and GDPR regulated environments, classify all content containing sensitive data and map current access controls to planned sensitivity labels and DLP policies in Microsoft Purview.

4

Integration Dependency Mapping

Identify every system that reads from or writes to SharePoint: line-of-business applications, reporting tools, ERP connectors, and third-party integrations. These integrations often use legacy APIs (SOAP, CSOM) that may need to be updated to Microsoft Graph API for SharePoint Online. Missing an integration dependency can cause business process disruptions that are far more impactful than a delayed migration timeline.

5

Network and Bandwidth Assessment

Calculate migration throughput requirements based on data volume and timeline. For multi-terabyte migrations, network bandwidth can become the bottleneck. A 20TB migration over a 100Mbps connection would take approximately 19 days of continuous transfer at maximum throughput, which is unrealistic. Factor in throttling limits imposed by Microsoft (which vary by tenant), business hours usage contention, and the need for incremental sync passes. Organizations with multiple geographic locations must plan migration streams per location to avoid saturating WAN links.

6

User and Stakeholder Analysis

Identify content owners, power users, and executive sponsors for every major site collection. Document current usage patterns, user pain points with the existing system, and feature requests for the new environment. This data shapes your information architecture design, training curriculum, and change management communications. It also identifies the champions who will drive adoption within their teams.

EPC Group delivers assessment findings in a detailed Migration Readiness Report that includes data volume breakdowns, risk-scored custom solutions, a remediation backlog with effort estimates, a recommended migration sequence, and a preliminary timeline and budget. This document becomes the foundation for all subsequent planning. Learn more about our SharePoint assessment services.

Migration Planning Phases: Building a Bulletproof Execution Strategy

With assessment data in hand, the planning phase translates findings into an actionable migration program. For enterprise migrations involving 10,000+ users, EPC Group structures planning into four overlapping workstreams that run in parallel to compress the overall timeline.

Phase 1: Information Architecture Design (Weeks 1-3)

The target information architecture defines how content will be organized in SharePoint Online. This is not a one-to-one recreation of your on-premises structure. Migration is the opportunity to rationalize years of organic growth, consolidate redundant sites, and implement a modern hub-and-spoke topology that aligns with how your organization actually works today.

  • Design hub site topology aligned to business units, regions, or functions
  • Define site provisioning templates and naming conventions
  • Establish managed metadata term sets for enterprise taxonomy
  • Plan Microsoft Teams integration (each Team creates a SharePoint site)

Phase 2: Governance Framework (Weeks 2-4)

Governance must be established before migration, not after. Migrating content into an ungoverned environment simply recreates the sprawl problems of the legacy system in a new location. Your governance framework defines who can create sites, how content is classified, what retention policies apply, and how compliance requirements are enforced.

  • Configure sensitivity labels and auto-labeling policies in Microsoft Purview
  • Define data loss prevention (DLP) policies for regulated content
  • Establish retention policies and disposition workflows
  • Create a site lifecycle management policy with provisioning and decommissioning processes

Phase 3: Technical Migration Plan (Weeks 3-5)

The technical migration plan defines the exact sequence, tooling, and procedures for moving content. For large enterprises, this includes defining migration waves (which sites move when), configuring migration tools and agents, establishing quality gates between waves, and creating detailed runbooks for each wave with step-by-step procedures and rollback criteria.

  • Define migration waves sequenced by complexity (simple first, complex later)
  • Configure migration tools with optimal throttling and scheduling settings
  • Build validation checklists for post-wave quality assurance
  • Plan incremental sync windows and cutover procedures with defined rollback triggers

Phase 4: Change Management and Training (Weeks 2-6)

Change management runs parallel to technical planning because user readiness must align with migration execution. The change management workstream handles communications, training development, champion identification, and feedback mechanisms. For organizations with 10,000+ users, this requires a structured communication cadence, localized training for different business units, and escalation paths for adoption issues.

  • Develop a communication plan with executive messaging and department-specific details
  • Create role-based training curriculum (executive, power user, general user)
  • Identify and train 1 champion per 50 users before go-live
  • Establish feedback channels and a rapid response process for post-migration issues

SharePoint Online vs. On-Premises: The 2026 Decision Framework

While this guide focuses on migrating to SharePoint Online, some organizations, particularly in government and defense with strict data sovereignty requirements, evaluate hybrid or continued on-premises scenarios. Here is how the platforms compare in 2026 across the dimensions that matter most to enterprise decision-makers.

CapabilitySharePoint OnlineSharePoint On-Premises
AI and CopilotFull Microsoft Copilot, AI Builder, SharePoint PremiumNot available
Feature UpdatesContinuous monthly releasesFeature packs every 6-12 months
Storage1TB base + 10GB per user, expandableLimited by your SQL Server infrastructure
Infrastructure CostIncluded in M365 license, no hardwareServers, SQL licensing, networking, DR
Patching and UpdatesManaged by Microsoft, zero downtimeManual, requires maintenance windows
Compliance Certifications80+ certifications including HIPAA, SOC 2, FedRAMPYour responsibility to achieve and maintain
Data SovereigntyMulti-geo, data residency controlsFull control of data location
CustomizationSPFx, Power Platform, Graph APIFull trust solutions, farm solutions, full API surface
Mobile ExperienceNative apps, responsive modern sitesLimited mobile support
Disaster RecoveryBuilt-in geo-redundancy, 93-day recycle binYour responsibility to architect and maintain

For the vast majority of enterprises, SharePoint Online is the clear strategic choice. The exceptions are highly classified government environments where FedRAMP High or Impact Level 5 requirements are not yet met, organizations with regulatory mandates that explicitly require on-premises data custody (which are becoming increasingly rare as cloud compliance certifications expand), and scenarios where legacy custom code dependencies are so extensive that the remediation cost exceeds the 5-year value of cloud migration. Even in these cases, most organizations pursue a hybrid strategy where new workloads go to SharePoint Online while legacy systems are maintained on-premises during a transition period.

Data Mapping Strategies for Complex Environments

Data mapping is the bridge between your current environment and your target architecture. For enterprises with hundreds of site collections, thousands of document libraries, and complex metadata schemas, data mapping is a discipline unto itself. A poorly executed data mapping leads to broken links, orphaned content, confused users, and a new environment that replicates the organizational dysfunction of the old one.

EPC Group uses a three-tier data mapping methodology refined across thousands of migrations.

Structural Mapping

Structural mapping defines how source site collections, subsites, and libraries correspond to target SharePoint Online sites, hub associations, and document libraries. This is where information architecture decisions become concrete. A single on-premises site collection with 15 subsites might map to a hub site with 15 associated sites in SharePoint Online, or it might consolidate into 3 sites based on actual usage patterns.

For a multi-national manufacturing client with 22,000 users, EPC Group mapped 180 on-premises site collections to 45 SharePoint Online sites organized under 6 hub sites aligned to their business divisions. This 75 percent reduction in site count was possible because many on-premises sites were created for organizational reasons that no longer existed, and duplicate sites had proliferated across regions for the same business function.

Metadata Mapping

Metadata mapping translates source content types, site columns, and managed metadata term sets to the target environment. SharePoint Online supports the same metadata constructs as on-premises, but migration is the opportunity to rationalize your taxonomy. Most enterprises accumulate redundant and conflicting content types over years of organic growth. A single concept like “project status” might exist as 12 different site columns with inconsistent value sets across different site collections.

During metadata mapping, consolidate duplicate term sets, standardize content types across the enterprise, and establish a managed metadata service that serves as the single source of truth. This effort pays dividends in search quality, compliance reporting, and AI capabilities, since Microsoft Copilot and SharePoint Premium both leverage structured metadata to deliver more accurate results.

Permissions Mapping

Permissions mapping translates on-premises Active Directory groups, SharePoint groups, and individual permission assignments to Azure AD security groups and SharePoint Online permission levels. This is the most error-prone aspect of migration because on-premises environments frequently have broken inheritance, directly assigned user permissions (rather than group-based), and orphaned permissions for accounts that no longer exist. EPC Group audits the permissions model during assessment and recommends a simplified group-based permissions model for the target environment. For regulated industries, this is also where we map current access controls to Microsoft Purview sensitivity labels to ensure that content classified as confidential, PHI, or PII receives appropriate protection labels during migration.

User Adoption: The Make-or-Break Factor in Migration Success

A technically flawless migration that users refuse to adopt is a failed migration. EPC Group has observed that organizations which allocate less than 10 percent of their migration budget to change management and training consistently report lower satisfaction scores, higher support ticket volumes, and longer time-to-productivity after go-live. Conversely, organizations that invest 15 to 20 percent in adoption programs typically see full user productivity restored within 4 weeks of cutover compared to 10 to 12 weeks for underinvested programs.

Effective adoption strategy operates on three levels, each targeting different user behaviors and motivations.

Executive Sponsorship

Visible executive commitment signals organizational priority. The C-suite sponsor should communicate the business case in town halls, use the new platform visibly, and allocate budget for adoption resources. In our experience, migrations with an active executive sponsor achieve 2.5 times higher adoption rates in the first 30 days.

Champion Network

Recruit and train 1 champion per 50 users, selected for their influence and willingness to help peers. Champions receive advanced training 4 weeks before go-live, serve as first-line support within their teams, and provide ground-level feedback to the project team. Equip them with quick-reference cards, FAQ documents, and a dedicated Teams channel for champion collaboration.

Role-Based Training

Executives need a 15-minute overview of how to find their content and use the mobile app. Power users need deep training on document management, metadata, and Power Automate workflows. General users need a 45-minute session covering navigation, file management, and search. Tailor content to each audience and provide on-demand video recordings for just-in-time learning.

Adoption Warning

Do not schedule user training more than 2 weeks before their content is migrated. Users who are trained too early forget what they learned before they can apply it. Align training delivery with your migration wave schedule so users are trained the week before their content moves.

Post-Migration Optimization

Migration completion is not the finish line; it is the starting point for optimization. The first 90 days after migration are critical for identifying issues, tuning performance, and building on the foundation you have established. EPC Group structures post-migration support into three phases that progressively shift from reactive issue resolution to proactive optimization.

1

Hypercare (Days 1-30)

Dedicated support team available during business hours to resolve user-reported issues within 4-hour SLA. Daily monitoring of migration logs for delayed items, permission errors, and content integrity issues. Weekly adoption analytics review tracking active users, page views, file activity, and search usage. Rapid remediation of any content gaps identified during user acceptance testing. This phase typically requires 40 to 60 support hours per week for a 10,000-user migration.

2

Stabilization (Days 31-60)

Transition from reactive support to proactive optimization. Tune search configuration based on actual usage patterns and user feedback. Refine information architecture based on real navigation data. Implement advanced features like custom search verticals, news and communication sites, and Power Automate workflows that were deferred during migration. Address training gaps identified through support ticket analysis. Decommission source systems that have been fully validated.

3

Optimization (Days 61-90)

Conduct a formal post-migration review with stakeholders covering success metrics, lessons learned, and outstanding items. Evaluate Microsoft Copilot readiness now that your cloud foundation is in place. Plan phase-2 improvements including SharePoint Premium features, advanced compliance configurations, and Power Platform integrations. Establish ongoing governance operations including quarterly site reviews, storage management, and compliance audits.

Common Pitfalls and How to Avoid Them

After 28 years and 5,200+ migrations, EPC Group has cataloged the patterns that consistently derail projects. These are not theoretical risks; they are failures we have witnessed firsthand and, in our early years, occasionally experienced ourselves. Every one of these pitfalls is preventable with proper planning and expertise.

Underestimating Custom Solution Remediation

Organizations regularly underestimate the effort required to rebuild SharePoint Designer workflows, InfoPath forms, and farm solutions by 50 to 70 percent. Every custom solution must be individually assessed, and many require complete rewrites using Power Automate, Power Apps, or SPFx. Budget 30 percent more time for this workstream than your initial estimate.

Migrating Everything Without Content Rationalization

The impulse to migrate everything and sort it out later creates an expensive mess. Stale content inflates migration costs, extends timelines, degrades search quality, and creates governance problems. Invest in content rationalization before migration. In our experience, 20 to 35 percent of content in a typical on-premises environment can be archived or deleted without any business impact.

Ignoring Network Bandwidth Constraints

Multi-terabyte migrations over standard business internet connections take far longer than expected when you factor in Microsoft throttling, business-hours contention, and the need for incremental sync passes. Failing to plan for bandwidth constraints leads to missed deadlines and extended periods of dual-system operation that confuse users and increase support costs.

Treating Migration as a Purely Technical Exercise

The technology of moving bits from point A to point B is the easier part. The hard part is organizational change. Migrations that invest less than 10 percent of budget in change management, training, and adoption consistently underperform on user satisfaction, time-to-productivity, and business value realization. Treat migration as a business transformation program, not an IT project.

Skipping the Pilot Migration

Organizations under time pressure sometimes skip the pilot and go directly to production migration. This eliminates your opportunity to validate the migration runbook, identify tooling issues, measure actual throughput, and train your migration team on error resolution. A 2-week pilot with 2 to 3 representative site collections saves weeks of troubleshooting during production waves.

Insufficient Post-Migration Validation

Declaring migration complete based on tool reports without thorough manual validation is a recipe for silent data loss and broken functionality. Automated validation catches content counts and basic permission checks, but manual validation must cover search accuracy, metadata integrity, workflow functionality, and user-reported experience. Budget at least 1 week of validation per migration wave.

Neglecting to Plan for Cutover Logistics

The cutover window between running the final incremental sync, switching DNS or redirect rules, and communicating the go-live to users is operationally complex. Without a detailed cutover runbook with assigned roles, communication templates pre-approved, and rollback criteria clearly defined, cutover weekends frequently overrun and cause Monday-morning disruptions for the entire organization.

Compliance Considerations: HIPAA, GDPR, and Beyond

For organizations in regulated industries, compliance is not a migration afterthought; it is a prerequisite that shapes every decision from architecture design to tool selection to validation procedures. EPC Group has led SharePoint migrations for healthcare systems, financial institutions, government agencies, and educational institutions where compliance failure carries legal liability, financial penalties, and reputational damage. Here is how compliance requirements intersect with your migration program.

HIPAA Compliance

Healthcare organizations migrating SharePoint content that contains Protected Health Information (PHI) must satisfy HIPAA Security Rule requirements throughout the migration process, not just in the target environment.

  • Ensure Microsoft BAA covers all M365 services in scope
  • Encrypt all PHI data in transit during migration (TLS 1.2+)
  • Configure sensitivity labels for PHI before migration begins
  • Enable audit logging for all PHI-containing site collections
  • Validate access controls post-migration to prevent unauthorized PHI exposure
  • Document chain of custody for all migrated health records
  • Conduct HIPAA risk assessment specific to the migration project

GDPR Compliance

Organizations that process personal data of EU residents must ensure GDPR compliance throughout migration, with particular attention to data residency, lawful basis for processing, and data subject rights.

  • Configure multi-geo to ensure EU data remains in EU data centers
  • Update your Record of Processing Activities to reflect new data flows
  • Implement content search for data subject access requests (DSARs)
  • Configure DLP policies for personal data classification (PII, financial)
  • Enable retention labels with disposition review for right-to-erasure compliance
  • Conduct Data Protection Impact Assessment (DPIA) for the migration program
  • Ensure third-party migration tools have appropriate Data Processing Agreements

Additional Regulatory Frameworks

Beyond HIPAA and GDPR, EPC Group has managed SharePoint migrations under SOC 2 Type II audit requirements (financial services), FedRAMP (federal government), ITAR/EAR (defense contractors), FERPA (higher education), and PCI DSS (payment card industry). Each framework imposes specific data handling, access control, and audit requirements that must be integrated into the migration plan from day one. Our compliance team reviews the applicable regulatory landscape during assessment and builds a compliance validation checklist tailored to your specific obligations.

Contact our compliance-focused migration team to discuss your specific regulatory requirements.

Real Migration Scenarios from the Field

Theory informs strategy, but experience builds confidence. Here are three representative migration scenarios from EPC Group engagements that illustrate how the principles in this guide apply to real enterprise environments.

Healthcare System

15,000 Users, 18TB, HIPAA-Regulated

A regional health system with 15,000 employees across 12 hospitals and 40 clinics needed to migrate from SharePoint 2016 to SharePoint Online. The environment contained 18TB of content across 340 site collections, including clinical documentation, research data, and administrative records containing PHI. The organization was simultaneously deploying Microsoft Teams and needed the SharePoint migration to serve as the foundation for a unified collaboration platform.

Challenges:

  • - 47 SharePoint Designer workflows processing clinical forms
  • - HIPAA chain-of-custody requirements for all PHI content
  • - 24/7 operations requiring zero-downtime cutover
  • - 6 different EHR system integrations with SharePoint

Results:

  • - Completed in 16 weeks with zero PHI exposure incidents
  • - Content rationalization reduced scope from 18TB to 11.5TB
  • - All 47 workflows rebuilt in Power Automate
  • - 92% user satisfaction score at 30-day post-migration survey
Financial Services

35,000 Users, 45TB, Multi-Region SOC 2

A global financial services firm needed to consolidate SharePoint environments from 4 acquired companies, each running different SharePoint versions (2013, 2016, and 2019), into a single SharePoint Online tenant. The combined environment spanned 45TB of content across 720 site collections serving 35,000 users in 14 countries. SOC 2 Type II audit requirements mandated full chain of custody, access logging, and data integrity verification for all financial records.

Challenges:

  • - 4 separate Active Directory forests requiring identity consolidation
  • - 130+ custom solutions across the 4 environments
  • - Multi-geo data residency requirements for EU, APAC, and Americas
  • - SOC 2 auditor observing migration process

Results:

  • - Completed in 24 weeks across 8 migration waves
  • - 720 site collections consolidated to 180 modern sites
  • - Passed SOC 2 Type II audit with zero findings related to migration
  • - Estimated $1.8M annual cost savings from infrastructure consolidation
Government Agency

50,000+ Users, Hybrid File Share + SharePoint 2019

A federal agency with 50,000+ users needed to migrate a hybrid environment consisting of SharePoint 2019 farms and 200TB of network file shares to SharePoint Online and OneDrive for Business within Microsoft 365 Government (GCC High). The environment included classified and controlled unclassified information (CUI) subject to NIST 800-171 and CMMC requirements, along with records subject to federal retention schedules.

Challenges:

  • - 200TB of file shares with inconsistent folder structures
  • - Federal records management and NARA retention requirements
  • - GCC High environment with limited migration tool compatibility
  • - Union requirements for employee training and change notification

Results:

  • - Completed in 9 months across 12 regional waves
  • - File shares reduced from 200TB to 85TB through rationalization
  • - Federal records properly classified with retention labels
  • - 88% adoption rate within 60 days of regional go-live

View more enterprise migration case studies to see how EPC Group has delivered successful outcomes across industries and scales.

Frequently Asked Questions About SharePoint Migration

How long does a SharePoint Online migration take for a large enterprise?

For enterprises with 10,000+ users and multi-terabyte data volumes, a full SharePoint Online migration typically takes 3 to 6 months. This includes 4 to 6 weeks for assessment and planning, 2 to 4 weeks for environment preparation, 6 to 12 weeks for phased data migration, and 2 to 4 weeks for validation, user acceptance testing, and hypercare. The timeline depends heavily on data volume, the number of custom solutions that need to be remediated, and the complexity of your permissions model. EPC Group has completed migrations for organizations with over 50TB of content within a 4-month window using parallel migration streams and off-hours scheduling.

What is the average cost of a SharePoint migration?

SharePoint migration costs vary significantly based on scope. Small organizations (under 500 users) typically spend between $15,000 and $50,000. Mid-size enterprises (500 to 5,000 users) range from $50,000 to $200,000. Large enterprises (5,000 to 50,000+ users) can expect $200,000 to $750,000 or more, depending on the complexity of custom solutions, compliance requirements, and third-party integrations. The primary cost drivers are data volume, the number of custom workflows and web parts that require remediation, compliance validation (HIPAA and GDPR add 15 to 25 percent to project cost), and the extent of user training needed. EPC Group provides fixed-price engagements after a thorough discovery phase to eliminate budget surprises.

Can I migrate SharePoint Server 2016 or 2019 directly to SharePoint Online?

Yes, both SharePoint Server 2016 and 2019 can be migrated directly to SharePoint Online, but the approach differs. SharePoint 2019 migrations are more straightforward because the platform already shares many modern features with SharePoint Online. SharePoint 2016 migrations require additional remediation for deprecated features, classic web parts, and InfoPath forms. In both cases, you cannot perform a simple database-attach migration. You need to use content migration tools such as Microsoft Migration Manager, ShareGate, or AvePoint to move content. Custom code, workflows, and InfoPath forms must be assessed individually and rebuilt using Power Automate, Power Apps, or SharePoint Framework (SPFx) solutions.

What happens to our existing SharePoint workflows during migration?

SharePoint Designer workflows and SharePoint 2010-style workflows cannot run in SharePoint Online and must be rebuilt. Microsoft officially retired SharePoint 2010 workflows in 2024 and SharePoint 2013 workflows follow. The recommended approach is to audit all existing workflows, classify them by business criticality, and rebuild them using Power Automate (for simple approval and notification flows) or Azure Logic Apps (for complex integrations). For organizations with hundreds of workflows, EPC Group uses an automated discovery tool that catalogs every workflow, identifies its trigger conditions and actions, and generates a Power Automate migration blueprint. This reduces the manual effort of workflow migration by up to 60 percent.

How do we handle HIPAA compliance during a SharePoint migration?

HIPAA compliance during SharePoint migration requires a signed Business Associate Agreement (BAA) with Microsoft, which covers SharePoint Online under Microsoft 365 enterprise plans. During migration, all data containing Protected Health Information (PHI) must be encrypted in transit and at rest. Your migration plan must include sensitivity label classification for all PHI content, data loss prevention (DLP) policies configured before migration begins, audit logging enabled for all PHI-containing site collections, access controls validated post-migration to prevent unauthorized PHI exposure, and a documented chain of custody for all migrated health records. EPC Group maintains a HIPAA migration checklist with over 140 validation points that we execute for every healthcare client engagement.

Should we clean up content before or during migration?

Content cleanup should happen before migration. Migrating stale, duplicate, or obsolete content wastes time, increases costs, and creates governance problems in your new environment. EPC Group recommends a content rationalization phase where you identify and archive content older than 3 years with no recent access, remove duplicate files (which typically account for 15 to 30 percent of total content), delete orphaned sites with no active owners, and consolidate redundant document libraries. In a recent 25TB migration for a financial services client, content rationalization reduced the migration scope to 16TB, saving 5 weeks of migration time and $85,000 in project costs.

What migration tools does Microsoft recommend for SharePoint Online?

Microsoft provides several first-party migration tools. Migration Manager in the SharePoint Admin Center handles file share and on-premises SharePoint migrations at scale with centralized reporting. The SharePoint Migration Tool (SPMT) is a free downloadable client for smaller migrations. Mover handles cloud-to-cloud migrations from Google Drive, Box, and Dropbox. For enterprise migrations, third-party tools like ShareGate, AvePoint, and Metalogix provide advanced features including pre-migration reporting, incremental migration, scheduling, and detailed error resolution. EPC Group evaluates and recommends tools based on your specific environment. For most enterprises with 10K+ users, we use a combination of Migration Manager for bulk content and ShareGate for complex site collections with custom configurations.

How do we ensure user adoption after migrating to SharePoint Online?

User adoption is the single biggest factor in migration ROI and the most commonly underinvested area. EPC Group implements a structured adoption framework that begins 6 weeks before migration and continues 12 weeks after. Key elements include executive sponsorship with visible leadership engagement, champion network of 1 early adopter per 50 users trained 4 weeks before go-live, role-based training tailored to different user groups (executives, power users, casual users), quick-reference guides and short video tutorials embedded in the new SharePoint intranet, a dedicated support channel in Microsoft Teams for the first 90 days, and usage analytics dashboards tracking adoption metrics weekly. Organizations that invest in structured adoption programs see 3 times higher satisfaction scores and reach full productivity 40 percent faster than those that rely on self-service learning alone.

Ready to Plan Your SharePoint Migration?

EPC Group has guided 5,200+ organizations through successful SharePoint migrations. From initial assessment through post-migration optimization, our team of Microsoft-certified architects ensures your migration is on time, on budget, and fully compliant with your industry regulations.

Schedule a Migration AssessmentExplore SharePoint Services

Or call us directly: 888-381-9725

About the Author

Errin O'Connor, Founder & CEO, EPC Group

Errin O'Connor is a bestselling Microsoft Press author of 4 books covering SharePoint, Power BI, Azure, and large-scale enterprise migrations. With 28+ years of experience leading Microsoft platform implementations for Fortune 500 companies, healthcare systems, financial institutions, and government agencies, Errin has personally overseen more than 5,200 SharePoint migrations. He is recognized as one of the foremost authorities on enterprise SharePoint architecture, compliance-focused migration strategies, and Microsoft 365 governance frameworks.

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