Your team finally kicks off the SharePoint migration. Three weeks in, nobody can find the Q3 compliance reports. HR’s permission structure is wide open. And the auditor’s visit is in six weeks.
This is not a worst-case scenario. This is what happens when organizations treat a SharePoint migration like a file transfer instead of a business transformation. It happens to 5-person firms and 5,000-person enterprises alike, because the mistakes are the same regardless of size.
Skip the assessment, copy a broken folder structure into the cloud, ignore governance, and you end up with an environment that is more expensive to fix than the one you left.
The pressure is real. SharePoint Server 2016 and 2019 support ends in July 2026. Leadership wants Copilot. Your data is not ready. And every month you delay is a month your competitors are pulling ahead with AI-driven workflows you have not even started building yet.
This blog covers the 8 SharePoint migration mistakes we see most often after 30 years of dealing with Microsoft Migration Planning and Strategy. We also include a self-assessment scorecard you can use with your team before you engage any migration partner.
The 8 SharePoint Migration Mistakes We See Again and Again
Before we go deep on each one, here is a snapshot of what to expect. The most common SharePoint migration mistakes are:
- Skipping the pre-migration assessment
- Using a “lift and shift” approach with no architecture redesign
- Ignoring permissions and security settings
- Migrating everything at once instead of in phases
- Underestimating user training and change management
- Choosing the wrong migration tool for your scenario
- Forgetting about broken links and URL structures
- Treating compliance and governance as an afterthought
Now let us look at what each one actually means for your organization.
Mistake 1: Skipping the Pre-Migration Assessment
What it costs you: Weeks of post-migration cleanup, storage fees for redundant data you should not have moved, and broken links that erode user trust in the new platform on day one.
Every migration that goes sideways can be traced back to this mistake. Teams skip the assessment because it feels like it slows things down. In reality, it is the single fastest way to prevent problems.
Without a pre-migration assessment, you do not know what you have. You do not know which files are duplicates, which permissions are broken, which workflows depend on third-party tools that will not work in SharePoint Online, or which sites have not been touched in three years.
What a proper assessment covers:
A full content inventory across every site, library, and list. An audit of permissions and security groups, mapped against Azure Active Directory. A dependency map showing which workflows, integrations, and custom solutions need to be rebuilt or replaced. An identification of redundant, outdated, and trivial (ROT) content that should be archived or deleted not migrated.
Our Complete SharePoint Migration Guide walks through the assessment phase step by step.
Industry consequence examples:
- Banking: A mid-sized bank that skips this step may discover, post-migration, that loan approval workflows depended on a legacy integration that does not exist in SharePoint Online. The workflow breaks. Loan processing stops. Compliance reporting falls behind. The audit team starts asking questions nobody has answers for.
- Healthcare: A clinic network migrates without inventorying where protected health information (PHI) is stored. After migration, PHI ends up in a document library with broad access permissions. That is a HIPAA violation, potentially reportable.
Mistake 2: Treating Migration as a “Pump and Dump”
What it costs you: An environment that is just as messy as the one you left. Except now it is in the cloud, harder to restructure, and actively undermining the collaboration features you are paying for.
The pump-and-dump approach treats SharePoint like a file server. It is not. SharePoint is a collaboration platform, and its value comes from metadata, content types, hub sites, managed navigation, and modern search. When you dump a messy folder structure into SharePoint Online, you bring every problem with you.
Wondering how M365 Migration “Pump and Dump” really works? Joel’s got you covered!
https://youtu.be/NxIOi8OKHU0?si=UTxjlSqAy2Pu8bsv
The main reason companies are organizing their data today is to get it ready for AI. If your SharePoint environment is not structured with proper metadata and governance, it is not just disorganized, it is actively blocking your path to Copilot and AI-driven productivity.
Signs of poor information architecture after migration:
Thousands of files buried in nested folders with no metadata. Search that returns irrelevant results because nothing is tagged. Duplicate documents across multiple sites because nobody knows where the “real” version lives. Users giving up on SharePoint and going back to email or local drives.
How to avoid it: Redesign before you migrate. Use migration as your opportunity to plan the information architecture you should have had all along. Define hub sites, set up metadata columns, create content types, and design your structure around how people actually work.
Mistake 3: Ignoring Permissions and Security Settings
What it costs you: Data exposure, access failures, and in regulated industries, compliance violations that carry real financial penalties.
Permissions are the most technically complex part of a SharePoint migration, and they are the part most teams get wrong. The instinct is to copy the existing permission model directly into the new environment. But that model was probably broken before migration: overly granular, inconsistent, with orphaned user accounts and years of ad-hoc access changes layered on top of each other.
Common permission mistakes:
- Overwriting granular permissions during bulk data moves.
- Giving broad, site-wide access instead of role-based controls.
- Not understanding the difference between inherited and explicit permissions.
- Failing to align permissions with Azure AD security groups.
- Not using SharePoint’s built-in security groups for layered, reusable access management.
How to avoid it: Map your entire permission structure before migration. Simplify inherited permissions wherever possible. Align content access with Azure AD groups. At Reality Tech, we restructure permissions during migration to reduce complexity and strengthen security and compliance from day one.
Industry consequence example:
Legal: A law firm migrates without auditing permissions. Client-privileged case files from one matter end up accessible to associates working on a competing matter. That is an ethical violation, a potential malpractice claim, and a client relationship destroyed.
Mistake 4: Migrating Everything at Once Instead of in Phases
What it costs you: Timeouts, failed transfers, corrupted metadata, and downtime for active teams, during the exact period when people are supposed to be doing their jobs.
A phased migration lets you test with a small, representative set of content, benchmark throughput, validate permissions and metadata in a sandbox, gather real user feedback, and scale up only after confirming that everything works. A big-bang migration gives you none of those safety nets.
How to avoid it: Break your migration into waves: by department, by site collection, or by business priority. Start with a low-risk area. Test thoroughly. Fix what breaks. Then move to the next wave. Our team always runs test migrations and throughput benchmarks before scaling to production. For a detailed phased approach, see our SharePoint Migration Checklist.
Industry consequence example:
Manufacturing: A manufacturing firm attempts a weekend migration to avoid production disruption. The migration hits SharePoint Online’s throttling limits on Saturday afternoon. By Monday morning, half the content had not been transferred. Quality assurance documents are missing. The production floor cannot access safety data sheets. Operations stop. Revenue lost.
Mistake 5: Underestimating User Training and Change Management
What it costs you: Low adoption, wasted licensing fees, and a workforce that reverts to email and shared drives, making your investment in SharePoint Online effectively worthless.
Studies from Forrester show that each user of Microsoft 365 saves an average of 1.5 hours per week thanks to better collaboration and file access. For a 150-person company, that adds up to over $519,000 over three years. But those savings only materialize if people actually use the platform. And they will not use it if nobody teaches them how.
What goes wrong when you skip training:
Teams recreate old folder structures manually, defeating the purpose of metadata. Users do not know how to use versioning, co-authoring, or check-in features. Adoption is slow, and people revert to email or old systems. Powerful collaboration features in Microsoft Teams and Power Platform go unused. IT help desk tickets spike in the weeks after go-live.
How to avoid it: Build training into your migration plan from the start. Provide role-based sessions: what a department manager needs is different from what a frontline worker needs. Create short how-to guides and videos. Designate “champions” in each department. And remember: change management is not a one-time event. It is ongoing.
Mistake 6: Choosing the Wrong Migration Tool for Your Scenario
What it costs you: Incomplete data transfers, lost metadata, manual rework, and if you discover the problem late, starting over with a different tool mid-project.
Microsoft’s free SharePoint Migration Tool (SPMT) works well for basic moves from recent on-premises versions to SharePoint Online. But it does not support older versions like SharePoint 2010, may not preserve all metadata fields, and is not built for complex scenarios involving multiple source platforms, large data volumes, or custom workflows.
Third-party tools like ShareGate, AvePoint, and Tzunami Deployer handle more complex scenarios but each has trade-offs in cost, capability, and learning curve.
How to avoid it: Match the tool to the job. Evaluate your source environment, data volume, metadata requirements, permission complexity, and budget before you commit. Our guide on how to choose the right SharePoint migration tool and service partner walks through the decision process.
Mistake 7: Forgetting About Broken Links and URL Structures
What it costs you: A wave of “this link doesn’t work” complaints the week after go-live, broken reports and dashboards, and a loss of user confidence in the new platform exactly when adoption matters most.
SharePoint documents, lists, and reports often contain internal links to other SharePoint content. When those files move to a new URL structure in SharePoint Online, those links break silently. Users discover the problem one at a time, over weeks, creating a slow drip of frustration.
How to avoid it: Run a link inventory before migration. Use tools that support URL redirection so old links resolve correctly in the new environment. After migration, test links across a representative sample of documents. Reality Tech includes link correction services in every SharePoint migration engagement.
Mistake 8: Treating Compliance and Governance as an Afterthought
What it costs you: Audit findings, regulatory penalties, data sprawl that makes AI adoption impossible, and an environment that becomes a liability instead of an asset.
This is the mistake that separates a technically successful migration from a business-successful migration. And it is the one that most migration guides skip — because most migration guides are written by IT consultants, not by teams that understand regulated industries.
Governance is not about restricting your teams. It is about building the rules that let SharePoint scale without becoming chaotic. Without governance:
Sites and libraries multiply without naming conventions or ownership. Sensitive data ends up in unsecured locations because there is no classification system. Retention policies are not set, so regulated documents are deleted too early or kept forever. The organization is unprepared for eDiscovery requests, compliance audits, or AI adoption.
Why this matters right now: Microsoft enlisted Cohasset Associates to assess whether SharePoint, OneDrive, Teams, Exchange, and Viva Engage meet SEC Rules 17a-4 and 18a-6 for recording, storing, and managing electronic records in a non-rewriteable, non-erasable format. The capabilities are there but only if your environment is configured correctly. A migration without governance means those capabilities sit unused.
How to avoid it: Define your governance framework before migration. Establish policies for site creation, naming conventions, content retention, and sensitivity labeling. Configure Microsoft Purview for data classification and retention. Set up records management rules aligned with your industry’s regulations. Build the foundation that makes your environment ready for Microsoft Copilot adoption.
Industry consequence examples:
- Banking: Without proper retention policies, a bank migrates seven years of loan documents to SharePoint Online but does not set retention labels. An examiner requests records for a specific audit period. The bank cannot demonstrate that documents were retained according to SEC and FINRA requirements.
- Healthcare: A multi-clinic network migrates to SharePoint Online without configuring sensitivity labels. Patient intake forms with PHI are stored in a general document library accessible to administrative staff who do not need access. That is a HIPAA violation with notification obligations and potential penalties.
The Reality Tech Migration Readiness Scorecard
Before you hire any migration partner use this scorecard to assess where you stand.
Score yourself 0 (not started), 1 (partially done), or 2 (complete) for each item.
Assessment & Planning
- We have a full inventory of content, sites, and libraries across all source environments
- We have identified and flagged redundant, outdated, and trivial (ROT) content for deletion or archival
- We have mapped all dependencies: workflows, integrations, custom solutions, and third-party tools
Architecture & Structure
- We have designed our target information architecture with hub sites, metadata, and content types
- We have a plan for restructuring (not just copying) our folder and site hierarchy
- We have defined how search will work in the new environment
Security & Permissions
- We have audited all existing permissions and mapped them to Azure AD groups
- We have a simplified, role-based permission model designed for the target environment
- We have identified sensitive data that requires restricted access or encryption
Compliance & Governance
- We have established retention policies aligned with our regulatory requirements
- We have configured sensitivity labels and data loss prevention (DLP) rules
- We have defined site creation, naming convention, and ownership policies
Migration Execution
- We have selected a migration tool that matches our source, volume, and complexity
- We have planned a phased migration with defined waves, rollback criteria, and success metrics
- We have run at least one test migration and validated structure, permissions, and metadata
People & Adoption
- We have a change management plan with role-based training, communications, and champions
- We have scheduled pre-migration, during-migration, and post-migration training sessions
- We have defined success metrics for user adoption (not just data transfer completion)
Scoring:
- 30-36: You are well-prepared. Migration risk is low.
- 20-29: You have gaps. Address them before starting migration to avoid costly rework.
- Below 20: You are at high risk of a failed or problematic migration. Get expert help before proceeding.
Your Next Step
If you are planning a SharePoint migration or recovering from one that went wrong, experts at Reality Tech can help! Contact us today for an assessment – https://reality-tech.com/contact-us
FAQs
Start with a complete inventory of every site, library, and document in your current environment. Identify duplicates, outdated files, and content that no longer needs to exist. Choose a migration tool that matches your source platform, data volume, and complexity. Run a test migration in a sandbox environment to catch errors before they affect your production data. Then migrate in phases: department by department or site by site — rather than all at once. For a full walkthrough, see Reality Tech’s Complete SharePoint Migration Guide.
Skipping the pre-migration assessment. Without a clear inventory of your content, permissions, dependencies, and custom solutions, you are migrating blind. This leads to broken workflows, misplaced data, permission errors, and weeks of post-migration cleanup that could have been prevented. The assessment phase feels like it slows the project down, but it is the single fastest way to prevent expensive problems. Learn more about how Reality Tech approaches assessments as part of our SharePoint Migration Services.
Yes, but the path depends on your starting point. Microsoft’s free SharePoint Migration Tool supports migration from SharePoint Server 2013, 2016, and 2019. Older versions may require intermediate upgrades or third-party tools like ShareGate or Tzunami Deployer. Custom workflows built in SharePoint Designer or InfoPath will need to be rebuilt using Power Automate or Power Apps, since those legacy tools are retired in SharePoint Online. Reality Tech’s guide on choosing the right migration tool helps you evaluate your options.
The best approach is prevention. Before migration, run a link inventory to identify all internal references between SharePoint documents, lists, and sites. Use migration tools that support URL redirection so legacy links resolve correctly in the new environment. After migration, test links across a representative sample of documents and fix any that are broken. Reality Tech includes link correction services in every migration project, learn more on our SharePoint Migration Services page.
Speakable
The most common SharePoint migration mistakes are skipping the pre-migration assessment, using a lift-and-shift approach without redesigning information architecture, ignoring permissions and security settings, migrating everything at once instead of in phases, underestimating user training, choosing the wrong migration tool, forgetting about broken links, and treating compliance and governance as an afterthought. Of these, skipping the assessment and ignoring governance cause the most expensive long-term damage.
To avoid data loss during a SharePoint migration, start with a full inventory of your content, permissions, and workflows. Remove outdated and duplicate files before migrating. Choose a migration tool that matches your source environment and data volume. Run a test migration in a sandbox to catch errors early. Then migrate in phases, moving content department by department rather than all at once. Companies that use a phased approach with dedicated migration experts report significantly higher on-time completion rates.
Governance is critical because a migration without clear policies for site creation, naming conventions, data retention, and access controls will create an environment that is just as disorganized as the one you left. For organizations in regulated industries like banking, healthcare, and legal, governance mistakes during migration can lead to audit failures, data exposure, and regulatory penalties. Governance is also the foundation for AI readiness — without structured, well-governed data, tools like Microsoft Copilot cannot function effectively.
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