Master Cloud Migration with Expert Insights on Intune & Entra ID AMA 2025

The coming week will see a significant opportunity for IT professionals working with Microsoft technologies to get unfiltered, real-world insights on two of the most complex and consequential cloud migration topics of the day: Intune and Entra ID migrations. Timed to align with Microsoft’s recent series of June events and the highly anticipated Windows 11 24H2 update, Devicie—an established leader in automated Intune deployment—has announced an open Reddit “Ask Me Anything” (AMA) to be helmed by Sean Ollerton, its Head of Solutions. With over 25 years in technical engineering and direct involvement in more than 50 major migration projects, Ollerton’s rare perspective is poised to offer clarity (and perhaps some hard truths) to administrators grappling with the daunting details of cloud modernization.

Context: Why This AMA Matters Now​

Rarely has the Microsoft ecosystem moved as rapidly or as disruptively as it is now. In the span of mere weeks, the landscape for device and identity management has shifted:

• June 3-6: The Microsoft Tech Partner Summit generated a wave of AI-infused solution announcements, many with direct impact on Intune and Entra ID roadmap strategies.
• June 10-12: Microsoft’s internal briefing spotlighted Intune’s evolving AI features, raising expectations for smarter automation and compliance monitoring.
• Upcoming: The rollout of Windows 11 24H2—featuring fresh policy controls, identity enhancements, and stricter compliance configurations—has left enterprise, MSP, and midmarket IT teams working overtime to update playbooks or scramble for external guidance.

In this turbulent climate, Devicie’s decision to put their head of solutions on the public stage, fielding unfiltered questions via Reddit’s r/Intune community, is both timely and bold. It signals a shift: rather than learning hard lessons in isolation, IT pros can now directly interrogate an expert with deep, firsthand context across industries, from regulated enterprises to lean MSPs.

Sean Ollerton: Bringing Real-World Lessons to the Forefront​

Sean Ollerton’s experience is not merely theoretical. With more than fifty successful Intune and Entra ID migrations under his belt, his expertise encompasses:

• Hands-on handling of Group Policy Object (GPO) conversions—critical as organizations shift from classic, on-premises controls to agile, cloud-driven policies using Intune and Entra ID.
• Navigating the thorniest issues, like legacy application compatibility, hybrid join infrastructure, and modern challenges stemming from cloud printing requirements.
• Extensive work around Conditional Access—one of the most misunderstood (and risk-prone) areas in the modern Microsoft identity stack.

As Ollerton himself puts it, “Too many migration projects fall apart over avoidable issues, like tech debt, policy misalignment and unrealistic timelines. This AMA is a chance to share what actually works, and what to watch out for, based on what I’ve seen happen in the last 50+ migrations.”
This degree of candor and specificity is rare in an industry that often communicates in generic best practices. For organizations googling after the fact—“why did policy X break my device fleet?”—direct interaction with someone who has tackled precisely those issues can be transformational.

Unpacking the Discussion Topics: What IT Pros Need to Know​

Migrating from GPOs to Cloud-Based Policies​

For many enterprises, Group Policy has been the backbone of endpoint configuration for decades. Moving these carefully tuned settings into Intune’s cloud-native policy framework is fraught with risk:

• Full Feature Parity Is a Myth: Not every on-prem GPO setting has a direct equivalent in Intune. Device configuration profiles continue to expand, but niche or legacy GPOs (often used for granular security or app control) remain unsupported, requiring case-by-case analysis and, sometimes, uncomfortable trade-offs.
• Policy Precedence Pitfalls: While Intune introduces the concept of policy layering and ordering, it isn’t always transparent how settings interact when delivered via the cloud. Seemingly innocuous defaults can override business-critical policies if not mapped carefully.
• Troubleshooting Complexity: When GPO overlap occurs during hybrid coexistence, tracking which setting “won” for a given endpoint can be maddening even for seasoned admins, particularly as devices move in and out of network or cloud reach.

Ollerton’s real-world playbooks—gleaned from migrations for MSPs and highly regulated organizations—are expected to demystify some of these challenges, and, crucially, provide workaround strategies for partial or staged migrations.

Tackling Legacy Apps, Hybrid Join, and Cloud Printing​

The march toward “modern management” often collides with reality:

• Legacy Application Maze: Many business-critical apps lack modern installers or depend on deprecated protocols, forcing organizations into creative packaging, sequenced deployments, or even last-resort VM solutions.
• Hybrid Join Confusion: Balancing devices enrolled both in on-premises Active Directory and cloud-based Azure AD (now Entra ID) is notoriously complex, and mistakes here can undermine both security posture and device authentication.
• Cloud Printing’s Double-Edged Sword: While Microsoft’s Universal Print is lauded as the future, many organizations still rely on legacy print servers or bespoke print devices. Modern management tools can sometimes break these by default, requiring intensive remediation.

Participants in the AMA can expect nuanced guidance that moves beyond “just patch the app” or “migrate your printers.” Instead, Ollerton will likely highlight concrete examples of remediation tactics as well as warning signs that a given environment may not be ready for full-blown cloud enablement.

Avoiding Conditional Access Misfires​

Conditional Access (CA) in Entra ID is a double-edged sword: done right, it is the core of a mature Zero Trust security strategy. Done wrong, it can lock out fleets of users, break business workflows, or inadvertently expose sensitive data.

• Policy Bloat and Blind Spots: Many organizations, in attempts to keep up with security guidance, accumulate dozens of CA policies, often conflicting or redundant. Overlapping conditions and exclusions create “holes” in the security perimeter and can leave attackers with unexpected pathways.
• Deployment Disasters: Applying a broad CA policy without piloting has, on more than one occasion, resulted in company-wide lockouts or loss of access to essential resources. Recovery from these misfires is never as easy as “just roll back”—especially if break-glass accounts weren’t set up correctly.
• Compliance and Audit Headaches: With regulatory environments tightening, organizations must demonstrate not only that policies exist, but that they are applied consistently and monitored in real time.

Ollerton’s session is likely to surface best-practice approaches—including pilot phasing, comprehensive documentation, and alerting mechanisms—to ensure that Conditional Access is an enabler instead of a catastrophe.

What Breaks During Rollout—and How to Prevent It​

Perhaps the most valuable aspect of the AMA will be its willingness to dwell on practical failures and near-misses. In highly orchestrated migration projects, the devil is always in the details:

• Ad hoc policies lingering in test environments suddenly affecting production after a batch migration.
• Policy misalignment between security and endpoint management leading to endless cycling, duplication, or even policy “tug-of-war.”
• Inherited technical debt from previous IT generations, requiring deep audits and, in some cases, hard resets.

Devicie’s visibility across dozens of unique migrations gives the company (and Ollerton) an unusually wide-angle lens on both common pitfalls and edge-case emergencies. For organizations amid or about to embark on migration projects, first-hand warnings can translate directly into risk mitigation.

The Broader State of Intune and Entra ID in 2025​

Microsoft’s Modern Management Trajectory​

Underpinning this AMA is a larger story about how Microsoft is reshaping the ecosystem for endpoint and identity management:

• AI Assistants and Automation: Announcements at the Tech Partner Summit suggest that Intune’s next phase will be tightly coupled with AI-driven policy recommendations, remediation, and compliance mapping. While these capabilities promise efficiency, they also amplify risk if automation acts on incomplete or misconfigured policies.
• Security and Compliance at the Forefront: Windows 11 24H2 and the evolving Entra ID (formerly Azure AD) stack are increasingly being positioned as the “operating system” of compliance-first organizations. Device trust, policy provenance, and continuous monitoring are not additive—they’re foundational.
• Rapid Release Cycles: With features shipping faster, organizations have less time for methodical pilots. This increases the value of practitioner insight—such as that shared in AMAs—over vendor whitepapers alone.

Devicie’s Differentiated Approach​

According to Devicie, their unique selling proposition rests on a few key pillars:

• Zero-Touch Configuration: Automated workflows eliminate repetitive, manual endpoint tasks, reducing strain on IT teams even as endpoints scale.
• Advanced Security and Compliance: Out-of-the-box compliance configurations (aligned to industry and regulatory standards) can be deployed en masse while still allowing for tailored exception handling.
• Synergy Between Security and IT Operations: Rather than forcing organizational silos, Devicie claims its model enhances collaboration between security teams (focused on risk minimization) and endpoint administrators (focused on productivity and experience).
• Enterprise Distribution Partnerships: Relationships with global distributors like TD SYNNEX, Microsoft, and Crayon make Devicie solutions accessible to both direct buyers and MSPs, improving market penetration and support responsiveness.

These strengths position Devicie well for organizations looking to accelerate their Intune and Entra ID deployments without incurring the technical debt that often accompanies poorly planned migrations. However, it’s worth noting that some of these claims—such as “always-optimized deployment”—should be weighed against real-world results, which the AMA may spotlight through direct user testimonies or challenging scenarios.

Critical Analysis: Strengths, Risks, and the Unwritten Rules​

Notable Strengths​

• Unfiltered Interaction: By placing a senior engineer in a live Reddit AMA, Devicie demonstrates a commitment to transparency rarely seen among SaaS or security vendors.
• Breadth and Depth of Experience: With over fifty real-world migrations as a basis, the advice offered is far more tailored and actionable than that found in general documentation.
• Market Alignment: The AMA is directly tuned to the questions practitioners are actually asking, rather than a vendor-selected agenda.
• Ecosystem Engagement: Utilizing platforms like Reddit’s r/Intune brings together a community known for peer accountability and the willingness to dissect both success and failure.

Potential Risks and Challenges​

• Oversaturation of “Best Practices”: Even the most experienced experts cannot address every nuance live. Some edge cases may be oversimplified, and practitioners should exercise caution before generalizing AMA guidance to unique or highly regulated environments.
• Commercial Motives: While educational, there is an inherent marketing angle. Claims that Devicie can optimize any migration “without additional workload” should be corroborated with independent case studies or peer reviews.
• Security and Privacy Sensitivities: Given the regulatory environments of many users (healthcare, finance, government), advice given in a public forum may occasionally be too generic to meet compliance mandates without additional legal or privacy review.
• AMA Format Limitations: Reddit AMAs are time-bound and rely on upvotes to surface questions. Complex, nuanced technical scenarios may not receive the depth of answer they require, or may be missed altogether.

Cross-Referencing and Cautionary Notes​

While Ollerton’s and Devicie’s credentials are easily validated—Ollerton’s LinkedIn and Devicie’s case study corpus underline their practical expertise—some of the more ambitious claims around “automated, always-optimized” cloud migration should be considered with measured skepticism. IT administrators are well-advised to seek out peer commentary post-AMA, as well as to review independent audits or recommendations from trusted MSP forums or regulatory guidance before adopting wholesale workflows.
It is noteworthy that user feedback, available through Reddit threads and Microsoft Tech Community discussions, often highlight both the transformative potential and the unexpected pain points of Intune and Entra ID migrations, echoing many of the topics Ollerton is prepared to address. Practitioners should make use of r/Intune’s rich archive, as many “gotchas” surface there sooner than in official documentation.

Final Thoughts: Why This AMA Sets a New Bar​

The decision by Devicie, and Ollerton specifically, to engage with the practitioner community on a platform known for tough questions and peer skepticism should be viewed as a high-water mark in transparency. As the Microsoft ecosystem shifts more aggressively to cloud-native management—accelerated by every Windows 11 update and each new wave of security guidance—learning from those who have already traversed the migration minefield is invaluable.
For IT professionals, MSP partners, and even DevOps teams considering or in the midst of a GPO-to-Intune or hybrid-to-cloud migration, participating in (or at least reviewing the transcript of) this AMA is likely to provide actionable advice, relevant warning flags, and the kind of candid technical honesty too rare in vendor marketing or official documentation.
In the era of rapid cloud transformation, making the right decisions hinges not just on understanding the roadmap, but on learning from those who have already weathered the journey. Devicie’s Reddit AMA—anchored in real-world experience, and sharpened by direct community scrutiny—offers a pragmatic, forward-looking resource for those striving to build a robust, agile, and secure Microsoft environment.

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Source: The Manila Times Devicie's Head of Solutions to Host Reddit AMA on Intune and Entra ID Migrations