Is your organization moving from Box to OneDrive? You’re not alone—and while the benefits are huge (cost savings, tighter Microsoft 365 integration, enhanced collaboration), the migration journey isn’t always smooth sailing. Since our last take in 2020, the migration landscape has evolved dramatically. Let’s walk through the top Box to OneDrive migration challenges—and how to tackle them with confidence, clarity, and as few headaches as possible.
1. Scale, Speed & Data Volume Overwhelm
Challenge: Cloud migrations now often involve massive volumes—multiple terabytes (or more)—and the need to move quickly to avoid vendor lock-ins or expiring contracts.
Solution: Intelligent migration tools now support continuous synchronization (“continuous copy”) that preserves fidelity while keeping files live during the transition. That means cutovers can happen with minimal disruption. Indiana University moved more than 3 PB and 140,000 users this way.
2. Preserving File Fidelity: Metadata, Versions, Sharing & Structure
Challenge: Moving files isn’t just about the bytes—it’s about preserving metadata, timestamps, version history, sharing links, folder hierarchies, and Box-specific features like Box Notes. Manual migrations often lose this fidelity.
Solution: Platforms like DryvIQ automatically migrate those granular details—and even convert Box Notes into Word documents—so nothing important gets left behind.
3. Filename & Path Constraints
Challenge: Box allows special characters and very long paths that OneDrive doesn’t support (e.g. “*”, “<”, or path length over 400 characters).
Solution: Migration tools pre-remediate naming conflicts—truncating paths, replacing illegal characters, and flagging unresolvable cases—so the migration doesn’t fail unexpectedly.
4. Permissions & Account Mapping Complexity
Challenge: Box and OneDrive (plus SharePoint/Microsoft 365) have fundamentally different permissions models. Mapping users, groups, and permission levels manually is prone to error—and often unsustainable at enterprise scale.
Solution: Migration platforms can map and transform permissions across platforms intelligently, at scale, helping preserve access while aligning with Microsoft 365’s structures.
5. Unstructured Data & “Dark Data” Discovery
Challenge: The real migration challenge often isn’t just moving data but understanding what needs to move—what’s stale, redundant, sensitive, or obsolete (often called “dark data”).
Solution: AI-driven platforms now scan across environments to classify, discover, and surface these insights—empowering you to make smarter migration decisions and reduce unnecessary transfers and risk.
6. Integration with Microsoft’s Native Migration Tools
Challenge: Microsoft’s own Migration Manager has improved—but it still requires manual mapping, planning, and preparation to properly migrate data and permissions from Box to OneDrive, SharePoint, or Teams.
Solution: While it’s viable, many enterprises opt for dedicated third-party solutions to avoid labor-intensive prep work. Microsoft’s tool does scan, identity map, review paths, and migrate—but it still requires thorough oversight.
7. Cost Estimation & Planning Accuracy
Challenge: Migration costs vary wildly—depending on data size, user count, timelines, security/compliance needs, vendor pricing, and remediation workload. Underestimating can be costly; overestimating may delay your project.
Solution: Build your plan around real-world drivers: corpus size, version counts, path complexity, known risk factors, rate limits, and available automation. Many providers now offer simulation tools or trial runs to help set realistic migration expectations.
8. Organizational Change & Stakeholder Communication
Challenge: Migrations aren’t just a tech project—they’re an organizational shift. If only IT owns it, end-users get left behind. That can cause miscommunication, confusion, and resistance.
Solution: Form a cross-functional migration committee with representatives from IT, HR, Finance, Legal, and business units. Build change management and communications plans—including early user training, emails, documentation, and phased onboarding—to ensure smooth adoption.
| Challenge | 2025-Ready Solution |
|---|---|
| Scale & speed | Continuous sync with minimal disruption |
| Fidelity & file attributes | Full metadata/version preservation + format conversion |
| Path & filename constraints | Automated remediation and alerting |
| Permissions & user mapping | Scale-aware mapping and identity transformation |
| Dark/unstructured data discovery | AI-driven scanning and classification |
| Native tool limitations | Simulation + workflows, or third-party alternatives |
| Cost & timeline estimation | Simulation tools and corpus-based planning |
| Organizational change | Cross-functional team + communications strategy |
[Webinar] Box to OneDrive Migrations Made Easy
Our own migration experts Shihan Wijeyeratne and Russ Houberg (DryvIQ) shared important information about how you can take advantage of Office 365 and avoid a costly renewal on a redundant cloud storage platform. From planning your migration project and analyzing your content, to managing user permissions and avoiding campus disruption, they’ve provided expert insights every step of the way. If you’re interested, you can watch the recording here.
Webinar Highlights:
- Learn how to assess your current source environment
- Understand potential issues faced during migration
- Learn best practices and strategies for a better migration
- Gather insight on the ROI of moving from a third-party storage solution (Box) to the all-up Office 365 platform
