The SharePoint Migration Checklist for People Who Have Been Burned Before

Another SharePoint migration is on your roadmap, and you're right to be skeptical. You've been burned before. The vendor promised a 'seamless transition', but what your organisation got was data loss, broken business-critical workflows, and a permissions model so chaotic it triggered a security audit. The standard SharePoint migration checklist from a support page is a fine starting point for a simple file lift-and-shift, but it's dangerously inadequate for a complex, enterprise-level project. It won't save you from the real-world complexities that derail these initiatives.

This is not another generic guide filled with abstract 'best practices'. This is a battle-hardened checklist, forged from rescuing failed projects in highly-regulated Irish and European sectors like finance and healthcare. We will not talk about theory; we will talk about survival. We'll detail the precise technical failure points that vendor documentation conveniently omits.

You'll get actionable, specific strategies to navigate critical challenges, including:

• API Throttling & Tooling Limitations: Understanding why standard tools like ShareGate or SPMT break down under enterprise-scale loads and how to script around their breaking points.
• Identity & Governance Redesign: Moving beyond a simple permissions copy to building a Zero-Trust architecture in Entra ID that aligns with GDPR and ISO 27001 mandates.
• Data Integrity: Addressing the hidden complexities of broken inheritance, GUID conflicts, and the dreaded 5,000-item list view threshold before they cripple your new environment.

This sharepoint migration checklist is not about how to migrate; it's about how to avoid disaster. It’s the playbook for de-risking a project that your organisation cannot afford to get wrong. Let's begin.

1. Pre-Migration Audit & Governance Assessment

A pre-migration audit is not a casual walkthrough of your source environment. It is a forensic inventory that maps content, permissions, metadata, and existing governance failures. We often see clients fail when they make the catastrophic error of assuming they "know what's in there." They don't. This deep-dive is where you uncover the hidden technical debt that will derail your project: orphaned sites, undocumented workflows, vast swathes of redundant data, and broken permission inheritance that creates massive security holes.

Without this foundational step in your SharePoint migration checklist, you are not just moving files; you are migrating compliance violations and creating future audit nightmares. Missing this step doesn't just fail the migration; it breaks legal compliance. We have seen projects where a thorough audit reduced the actual migration scope by nearly half by identifying and archiving non-compliant or obsolete data. For instance, a healthcare system's audit revealed over 200 sites with broken permission inheritance, which would have created immediate HIPAA audit findings if moved as-is.

Key Actions & Risk Mitigation

To execute this correctly, your team must move beyond simple content scanning. This is about identifying liabilities before they enter your new, modernised environment.

• Identify Obsolete Data: Use tools like the ShareGate Content Scanner or PowerShell PnP scripts (Get-PnPListItem) to filter for content with LastModified dates older than two years. These are immediate candidates for an archival strategy, not migration.
• Map Broken Inheritance: Document every single list, library, and folder where permission inheritance is broken. Capture the current permissions and the business owner. This is your remediation map for rebuilding a secure model in the target tenant.
• Cross-Reference Identities: Compare on-premises permissions against your target Entra ID (formerly Azure AD) security groups. This is your first opportunity to implement zero-trust principles and eliminate legacy, insecure access patterns.
• Socialise the Findings: Export all audit results to a CSV file and hold mandatory review sessions with business owners. Securing their sign-off on what gets archived, deleted, or remediated is non-negotiable. This prevents scope creep and protects the project from last-minute "we need everything" demands. This critical process is a core part of our SharePoint migration assessment framework.

Ollo Verdict: Skipping a forensic audit is the single most common reason SharePoint migrations fail, create security breaches, or go wildly over budget. Your source environment is a minefield of legacy issues; you must map every risk before taking a single step.

2. Entra ID & Security Group Redesign (Zero-Trust Architecture)

Migrating SharePoint content while retaining legacy on-premises Active Directory group structures is an invitation for a security breach. It guarantees future incidents. A modern SharePoint environment demands a modern identity foundation built on zero-trust principles: no inherited permissions, explicit access grants, and just-in-time elevation. We often see clients fail when they attempt to bolt on security after the migration; it's a recipe for weeks of painful, manual remediation and audit findings.

The catastrophic error is assuming your on-premises AD is clean enough to simply synchronise. It isn't. An energy utility we worked with migrated using their existing 'AllCompanyUsers' group; three months later, a sensitive NERC CIP document was still accessible to a former contractor due to lingering group membership. In contrast, a hospital system redesigned their access model first, implementing dynamic Entra ID groups based on department and job role. This single change reduced manual access requests by 67% and eliminated nearly all related audit findings.

Key Actions & Risk Mitigation

Your identity redesign must be completed and tested before a single file is moved. This isn't just about permissions; it is about building a compliant, auditable, and secure collaboration environment from the ground up.

• Map and Rationalise Groups: Create a definitive spreadsheet mapping every legacy on-premises group to its new Entra ID security group counterpart. This is where you eliminate nested groups and overly broad access like 'Everyone' or 'Authenticated Users'.
• Implement Dynamic Groups: Leverage Entra ID Premium features to create attribute-based security groups (e.g., user.department -eq "Finance" -and user.jobTitle -eq "Accountant"). This automates access control and removes the risk of human error in manual group management.
• Enforce with Conditional Access: Test all new Conditional Access policies in 'Report-Only' mode for at least two weeks. This allows you to validate the impact on user access without causing disruption before moving to full enforcement.
• Assign Governance Ownership: Identity is not just an IT problem. Assign a business owner to review and approve the logic for dynamic groups quarterly, ensuring the rules remain aligned with organisational roles and responsibilities. This is a core component of our SharePoint migration security framework.

Ollo Verdict: Treating identity as an afterthought is negligent. Your SharePoint migration checklist must prioritise a full Entra ID redesign as a prerequisite, not a parallel task. Migrating content into a poorly structured identity model doesn't just create technical debt; it creates immediate, demonstrable security vulnerabilities.

3. Tenant-to-Tenant Consolidation Planning (if applicable)

Do not mistake a tenant-to-tenant (T2T) consolidation for a standard SharePoint migration. This is a complex fusion of entire Microsoft 365 ecosystems, common during mergers, acquisitions, or multi-national centralisation. It involves SharePoint, Exchange, Teams, OneDrive, Entra ID, and licensing, where a single misconfiguration can trigger catastrophic operational downtime or multi-million euro compliance penalties. You are not just moving sites; you are merging corporate identities and data sovereignty domains.

The stakes are orders of magnitude higher. For instance, a financial services firm consolidating three regional tenants discovered that legacy agreements required EU data to remain within EU data centres. Their plan to merge everything into a US-primary tenant was halted, forcing a complex redesign to maintain two smaller EU-resident tenants. Another client, an energy company, found its acquired tenant had configurations that violated critical NERC CIP standards, requiring a six-month remediation project before any data could be moved.

Key Actions & Risk Mitigation

Attempting a T2T migration without specialist expertise is a recipe for disaster. This is where you must meticulously map and test every dependency, from DNS records to identity federation, before making any production changes.

• Map All Tenant Dependencies: Document every single DNS record (MX, CNAME, TXT), federation trust (ADFS), and OAuth app registration in both the source and target tenants. A missed entry can break email flow or third-party app access instantly.
• Establish Mailbox Coexistence: Plan and test mailbox coexistence in a dedicated lab environment for at least four weeks. This phase is critical for ensuring calendar free/busy information and mail routing function correctly while users exist in both tenants.
• Budget for Licence Overlap: Account for a "double-user" phase where users require active licences in both tenants simultaneously during the transition. This is a non-negotiable cost to ensure uninterrupted access and a smooth cutover.
• Secure Legal & Compliance Sign-Off: Do not proceed without explicit sign-off from your legal and compliance teams on data residency and sovereignty. Moving data across geographical boundaries without approval can lead to severe GDPR or other regulatory violations. This complex process is a key focus of our tenant-to-tenant migration services.

Ollo Verdict: We have audited enough failed DIY tenant consolidations to state this unequivocally: the failure rate on the first attempt is over 70%. The complexity of merging identities, permissions, and data residency rules requires specialist orchestration. This is not the place to cut corners.

4. Content Mapping, Deduplication & Migration Wave Planning

A "lift and shift" approach to a SharePoint migration is architectural malpractice. Wave planning is the process of translating your audit findings into a sequenced, risk-managed migration. It involves grouping content by business criticality, technical dependency, and risk profile. Organisations that attempt to migrate terabytes of data in a single, monolithic push inevitably crash into API throttling limits, creating unmanageable rollback scenarios that take weeks to untangle. This is not a theoretical problem; we have seen DIY migrations hit these walls and fail spectacularly.

This step transforms your migration from a high-stakes gamble into a series of controlled, verifiable phases. For a financial services client, we orchestrated 12 distinct waves. This allowed us to migrate low-risk departmental archives first, identify and fix permission discrepancies, and then move high-compliance trading records in a later, de-risked wave. This phased approach prevents a single failure from jeopardising the entire project and provides crucial learning opportunities between each stage.

Key Actions & Risk Mitigation

Proper wave planning is your primary defence against API throttling and scope creep. It enforces discipline and makes the migration process predictable.

• Define Migration Waves: Group content logically. For instance, Wave 1 might be low-impact departmental sites. Wave 2 could be cross-functional project sites, and a final wave might handle highly sensitive finance or HR data. Document this plan in a Gantt chart and communicate it relentlessly to stakeholders.
• Establish a 'Do Not Migrate' List: Based on your audit, create a definitive list of redundant, obsolete, or trivial (ROT) data. Get explicit, written sign-off from each business owner for this list. This action alone prevents last-minute demands to "just move everything" and protects your project scope.
• Implement Deduplication: Your audit will reveal dozens of copies of the same large files (e.g., a 150 MB sales presentation). Migrate the master copy once to a central library. In all other locations, replace the redundant files with links. This significantly reduces migration time and target tenant storage costs.
• Set UAT Gates: Do not start the next wave until the previous one is fully validated by business users. Define clear success criteria for each User Acceptance Testing (UAT) gate. For example, if Wave 2 validation reveals more than a 2% permission error rate, you must halt and remediate before proceeding to Wave 3.

Ollo Verdict: Attempting a migration without a formal, multi-wave plan is reckless. It ignores Microsoft's own technical constraints (like list view thresholds and API limits) and guarantees a chaotic, failure-prone project. Your SharePoint migration checklist must treat wave planning as a non-negotiable control gate.

5. Path Length & File Name Remediation

This is not a minor data-cleansing task; it is a hard technical barrier that will stop your migration dead. SharePoint Online enforces a strict character limit for the entire file path and rejects file names containing specific special characters (*, ?, :, |, <, >). Ignoring this constraint is a rookie mistake that causes silent data loss and days of panicked, mid-migration scripting. Your source environment, particularly older file shares, is almost certainly riddled with these violations.

We have seen large legal firms halt a multi-terabyte migration after discovering thousands of contract PDFs with names exceeding 120 characters, which, when nested in deep folder structures, violated path limits. The subsequent mass-renaming effort broke over a dozen automated workflows that relied on specific file name parsing, creating a chaotic, multi-week remediation project. This isn't an edge case; it's a predictable crisis that must be addressed before any migration tooling is even configured.

Key Actions & Risk Mitigation

Proactive remediation is the only way to prevent this common failure point. Your team's objective is to identify and resolve every single naming and path length violation before the migration begins, not during the cutover window.

• Execute Pre-emptive Scans: Do not wait. Run a comprehensive path and file name scan on your source environment immediately. Use PowerShell scripts to recursively analyse every file share, identifying all files that violate SharePoint Online's naming conventions and path length limits.
• Automate with Approval Workflows: Create a rename mapping spreadsheet (Old Name → New Name) and circulate it among business owners for approval. Once signed off, use automation scripts to perform the renaming. This audit trail is non-negotiable for compliance and change management.
• Preserve Original Names in Metadata: Do not just rename files; you must retain the original name for auditing and reference. Create a new metadata column in the target SharePoint libraries (e.g., 'OriginalFileName') and populate it with the legacy name during the migration process.
• Test Downstream Impact: Before renaming thousands of files in production, test your remediation scripts in a pilot environment. Critically, confirm that any dependent systems, business processes, or legacy application shortcuts that reference the old file names will not break post-remediation.

Ollo Verdict: Discovering path length and illegal character issues mid-migration is a sign of an amateur-led project. It guarantees delays and risks data integrity. This forensic remediation is a mandatory, upfront activity in any serious SharePoint migration checklist.

6. Broken Links, Hardcoded References & Workflow Dependency Remediation

A successful migration isn't just about moving data; it's about preserving functionality. This is where most do-it-yourself migrations catastrophically fail. Your legacy environment is littered with hardcoded URLs in documents, InfoPath forms dependent on obsolete data connections, and workflows pointing to on-premises resources. Migrating this content without remediation creates a "walking dead" environment: the files are there, but they are functionally useless, creating a cascade of user support tickets and operational chaos.

This tedious detective work is non-negotiable. We've witnessed a manufacturing firm migrate thousands of Excel files where 80% of the internal hyperlinks to production specifications broke because the new SharePoint Online URLs were different. Remediation became a three-week manual fire drill. Addressing these issues is a crucial step in paying down years of accumulated technical debt before it contaminates your modern workplace. Ignoring this part of the SharePoint migration checklist is a guarantee of post-launch failure.

Key Actions & Risk Mitigation

Your objective is to hunt down and neutralise every hardcoded dependency before it can sabotage your new environment. This requires a systematic, script-driven approach, not a hopeful manual spot-check.

• Scan for Hardcoded URLs: Deploy PnP PowerShell scripts to crawl document libraries and identify files containing references to your on-premises domain (e.g., http://intranet/sites/). This creates a precise manifest of what needs to be rewritten.
• Map Workflow & Form Dependencies: Document every single workflow (SharePoint Designer, Nintex) and InfoPath form. Trace their data connections and triggers. A financial services client discovered over 200 Power BI reports that failed silently post-migration because they were hardwired to on-premises SharePoint list GUIDs that no longer existed.
• Develop a URL Remediation Plan: For massive link volumes, rewriting is often impractical. Your plan must decide between targeted script-based rewrites for critical documents and implementing temporary DNS CNAME redirects to bridge the gap for less critical content.
• Disable Legacy Workflows Pre-Cutover: A week before the final cutover, disable all workflows in the source environment. This prevents them from firing on old data during the migration process, which can cause data corruption or orphaned tasks in the new tenant.

Ollo Verdict: Manually fixing broken links after a migration is a project-killing nightmare. This is a classic example of where an ounce of prevention is worth a tonne of cure. Automate the discovery and plan the remediation meticulously, or you will spend months cleaning up a broken, untrustworthy environment.

7. Metadata & Taxonomy Migration (Content Type & Column Mapping)

Migrating files is the easy part; migrating the intelligence that makes those files discoverable and compliant is where projects collapse. This is about the "invisible infrastructure" of your data: the content types, site columns, and managed metadata term sets that give your information context and structure. The documentation says tools will handle this, but in reality, they fail on complex lookups and custom content types. Without a deliberate mapping and recreation strategy, you are effectively turning a structured archive into an unstructured data swamp, destroying search, governance, and any hope of future automation.

Failure here is not subtle. We've seen a financial services firm's migration fail for weeks because their "RegulatoryDocument" content type relied on a lookup to a list that had not yet been migrated, causing cascading lookup failures. In another case, a healthcare system migrated patient records without mapping their custom metadata, creating two parallel, conflicting standards and an eDiscovery nightmare. This step in your SharePoint migration checklist prevents the chaotic data sprawl that renders your new environment unusable.

Key Actions & Risk Mitigation

You must recreate your data's logical structure in the target environment before a single document is moved. This is a non-negotiable prerequisite for a successful migration that maintains data integrity and governance.

• Export and Pre-Stage Taxonomy: Use PnP PowerShell to script the export of your entire term store from the source (Export-PnPTaxonomy) and import it into the target (Import-PnPTaxonomy) ahead of the content migration. This ensures the foundational taxonomy is in place before any content that depends on it arrives.
• Map All Content Types & Columns: Create a detailed spreadsheet mapping every source content type and site column to its target equivalent. Identify every custom column, its data type (Lookup, Managed Metadata, Choice), and confirm it can be replicated. This is your blueprint for rebuilding the information architecture.
• Handle Metadata Transformation: Document all required transformations. For example, an old "Status" choice field with values 'In-Progress' and 'Complete' might need to be mapped to a new field with values 'Active' and 'Archived'. These rules must be scripted or configured in your migration tool.
• Validate with a Pilot Migration: Select a single, complex document library that uses multiple content types and lookup columns. Migrate only this library and perform rigorous user acceptance testing. Confirm that all metadata is preserved, views and filters function correctly, and lookups are not broken. Do not proceed until this pilot is 100% successful.

Ollo Verdict: Treating metadata as an afterthought is project suicide. If your source environment has any custom content types or managed metadata, they must be architected and deployed to the target tenant first. Any other sequence guarantees data chaos, broken search, and a complete failure to meet compliance requirements.

8. Permission Audit & Access Control Migration

Translating permissions is the most error-prone and time-consuming step in any enterprise-level SharePoint migration checklist. Permissions are not a simple copy-paste exercise; they are a complex matrix of inherited, broken, and direct grants at site, list, and item levels. We often see clients fail when they assume their migration tool will "just handle it," only to discover they have created widespread security breaches or paralysed business operations. This is where migration projects fail, not with a bang, but with a helpdesk flooded with "access denied" tickets and a CISO demanding an incident report.

Migrating permissions incorrectly creates one of two disastrous outcomes: over-privileged users, which is an immediate insider threat and compliance failure, or under-privileged users, which grinds productivity to a halt. We saw a financial services client migrate 500 sites where mapping ambiguity granted 1,200 users higher access levels than they had in the source environment. The subsequent remediation effort consumed three weeks of expert-level consulting time that was never budgeted for.

Key Actions & Risk Mitigation

Your objective is not to replicate legacy permissions; it is to map them to a modern, zero-trust access model in Microsoft 365. This requires manual validation and strategic redesign, not blind faith in automation.

• Export and Baseline Source Permissions: Before migrating a single byte, export all source permissions using PnP PowerShell. Commands like Get-PnPSiteCollectionAdmin, Get-PnPUser, and Get-PnPGroupMembers are non-negotiable. Store these CSV exports as your immutable "source of truth" for post-migration reconciliation.
• Abandon Item-Level Permission Migration: Do not rely on any automated tool for migrating item-level permissions, especially at scale. It is notoriously unreliable and a primary cause of migration throttling. Instead, redesign the information architecture using modern controls like separate document libraries, Teams private channels, or Microsoft Purview sensitivity labels to enforce access.
• Implement a Validation Protocol: Post-migration, you must manually validate a statistically significant sample of permissions. We recommend a minimum of 10% spot-checks. Ask the simple question: 'Does User X still have the correct access to Document Y?' Compare source and target screenshots for irrefutable proof. Our guide to SharePoint migration permissions provides a detailed framework for this critical validation.
• Enforce Post-Migration Governance: Use Entra ID Access Reviews to force quarterly or semi-annual recertification of access rights. The goal is to dismantle the culture of persistent, un-audited permissions that existed in the legacy environment. Do not allow old access rights to linger simply because "they were there before."

Ollo Verdict: Blindly trusting a tool's permission mapping feature is project negligence. The risk of creating a systemic security vulnerability is too high. You must treat permission migration as a separate, manual reconciliation project that runs parallel to the content migration itself.

9. Pilot Migration, Post-Migration Validation & Cutover Planning

A pilot migration is not a quick "smoke test" of your migration tool; it is a full-dress rehearsal for failure. This is where you stress-test every assumption made during planning against a representative data set in a proper staging environment. Organisations that treat this as a simple data copy exercise are the ones who face catastrophic production failures, discovering only at cutover that their tooling cannot handle specific metadata, custom list views, or complex permission structures. This step validates your entire methodology, from technical execution to user acceptance.

This is your only chance to uncover the silent killers of a migration project before they impact the entire business. For instance, a manufacturing client's pilot of 50 GB revealed that 3% of files were corrupted because essential metadata embedded in file properties was not being translated correctly by the migration tool. This discovery forced a redesign of the migration script, preventing a widespread data integrity disaster during the production waves. Without the pilot, this critical flaw would have gone unnoticed until it was too late.

Key Actions & Risk Mitigation

To execute a meaningful pilot, you must simulate the production cutover with ruthless precision. This is about building a repeatable, validated process, not just moving files.

• Establish Hard Success Criteria: Before you move a single byte, define what "success" means in a documented checklist. Specify targets like '99.9% of files migrated successfully,' 'zero critical permission mismatches,' and 'all custom list web parts render correctly.' Document pass/fail for each criterion.
• Run Extended User Acceptance Testing (UAT): Do not end your validation on cutover day. The pilot environment must remain active for at least two weeks with a dedicated group of business users. This is how you find real-world issues like broken embedded document links or workflow triggers that fail under normal daily use.
• Test the Rollback Procedure: A rollback plan that hasn't been tested is not a plan; it's a fantasy. Execute a full rollback on your pilot data to confirm you can revert to the source environment cleanly and without data loss. Document every step and the time it takes.
• Plan Legacy Decommissioning: Once all production waves are complete and validated, you must have a formal plan to decommission the source environment. This includes final backups, archiving, and ensuring old hardware is disposed of securely. For comprehensive data governance, once legacy systems are retired, a guide to secure hard drive shredding becomes essential to prevent data breaches from discarded media.

Ollo Verdict: A pilot is your project's final exam before going live. Skipping it, or performing a superficial test, is the equivalent of flying a plane without a pre-flight check. It guarantees that you will discover every single flaw in your plan during the most critical phase: production cutover.

10. API Throttling Management & Migration Tool Optimisation

Ignoring SharePoint Online's API throttling is like trying to drain an ocean with a bucket that has a hole in it. Microsoft actively governs API requests to ensure service stability for all tenants, and your migration tool is one of the most aggressive consumers of these resources. When you inevitably hit these undocumented, dynamic limits, your migration doesn't just slow down; it fails silently, corrupts data mid-flight, or enters a catastrophic retry loop that can last for days without making any real progress.

This isn't about simply running your migration tool; it's about actively managing its behaviour to work with Microsoft's limits, not against them. An unoptimised tool, whether it's the free SharePoint Migration Tool (SPMT) or a poorly configured custom script, will hammer the APIs, trigger throttling, and bring your entire project to a halt. We saw an energy utility's custom PowerShell script, configured with 10 parallel threads, get throttled every two hours. By reducing it to two threads and implementing a backoff strategy, the migration proceeded smoothly and, counter-intuitively, finished in 90% less total time.

Key Actions & Risk Mitigation

Your team's primary goal is to maintain a consistent, high-throughput migration without triggering SharePoint's defensive throttling mechanisms. This requires granular control over the toolset and a deep understanding of how the service behaves under load.

• Configure Intelligent Throttling: Do not use SPMT for any serious enterprise migration; it lacks the granular throttling controls needed. Acknowledge its strength for small, simple migrations, but for anything over 50GB or involving complex permissions, its lack of control is a liability. A professional tool like ShareGate offers better built-in throttling management.
• Optimise PnP Scripts: If you are using custom PnP PowerShell scripts, you must build in your own throttling management. Use the -Throttle 50 parameter to introduce a millisecond delay between calls and include -Verbose logging to detect and log every throttling event (HTTP 429 errors).
• Schedule Off-Peak Waves: Microsoft’s API request quota is shared across tenants. Schedule your largest migration waves for weekends or between 9 PM and 6 AM local time. This dramatically reduces the probability of competing for resources with other tenants and allows for a higher request throughput.
• Monitor Real-Time API Consumption: Do not run blind. If your tenant has Azure Application Insights configured, monitor API consumption in real-time during migration. Set alerts to trigger when you exceed 80% of the known throttling limit, giving you time to pause and reconfigure before your jobs start failing. A comprehensive understanding of tooling is a central pillar of any successful migration, as we detail in our overview of the SharePoint migration tool.

Ollo Verdict: Throttling isn't a suggestion from Microsoft; it's a hard limit that will break your project. Use SPMT for <50GB. For anything else, you need custom scripting or a professional tool with granular controls. Relying on default settings is a direct path to failure, data loss, and inexplicable delays.

SharePoint Migration: 10-Point Checklist Comparison

The Ollo Verdict: Stop Treating Migration as a Commodity

Completing a SharePoint migration isn't about ticking boxes on a generic checklist you found online. It's a high-stakes architectural overhaul. If your takeaway from this article is simply a list of tasks, you've missed the point. The real lesson is that each item on this Sharepoint migration checklist represents a potential point of catastrophic failure, a place where undocumented technical debt and vendor overpromises collide with reality.

We see it time and again: projects derail not because of the tool, but because the underlying complexity was never respected. An IT team might successfully use ShareGate to move a few terabytes of simple files, only to find that all their meticulously crafted item-level permissions have been flattened into site-level access, creating a massive data breach waiting to happen. They follow Microsoft’s guidance on the SharePoint Migration Tool (SPMT), only to discover it chokes on files with long paths or special characters that were perfectly valid on their old file server, bringing the entire process to a grinding halt with thousands of unlogged errors.

The Illusion of "Lift and Shift"

The central fallacy of modern migrations is the concept of a simple "lift and shift." This approach is a myth, especially when moving from legacy on-premises environments or consolidating complex Microsoft 365 tenants. You are not just moving data; you are transplanting a living ecosystem of permissions, dependencies, workflows, and user behaviours into a fundamentally different architecture.

Consider these critical failure points we've detailed:

• Identity and Governance: Simply replicating old Active Directory groups into Entra ID without redesigning for Zero Trust and Conditional Access doesn't modernise your security. It just moves your legacy vulnerabilities to the cloud, making them more accessible to threats.
• Content and Metadata: Migrating content without a plan for metadata remediation and content type mapping is just creating a digital landfill. You lose all referential integrity and searchability, rendering the data useless for future integrations with Power Platform or Microsoft Copilot.
• Tooling Limitations: Believing a tool will solve everything is the fastest path to disaster. ShareGate can’t fix broken inheritance chains it doesn't understand, and the SPMT will absolutely fail when faced with API throttling during a large-scale data transfer. These tools are scalpels, not bulldozers; they require a surgeon's hand.

The Ollo Insight: Your migration's success is not measured by the terabytes moved. It's measured by the integrity of your permissions, the preservation of your metadata, and the operational readiness of your new environment on day one. Anything less is a failed project, regardless of what the migration report says.

This comprehensive Sharepoint migration checklist is designed to be intimidating. It's a roadmap of the minefield you are about to cross. It highlights the vast gap between a tool’s marketing claims and the harsh realities of enterprise-level execution. You are not just migrating files; you are migrating business risk. The question is not which tool to use, but who you trust to manage that risk when the standard playbook inevitably fails.

This checklist exposes the critical failure points where most migrations collapse. At Ollo, we don't just run the migration tool; we architect the solution, manage the inherent risks, and own the outcome from security model redesign to post-migration validation. If this process seems more complex than you were led to believe, book a consultation and let us show you how we de-risk the entire engagement.