Seven Roadblocks to Consider Before Migrating to PostgreSQL

Seven Roadblocks to Consider Before Migrating to PostgreSQL

By Brian Boback, Director of  Oracle & Open-Source Services

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As someone with direct experience dealing with numerous environments, I see a need for organizations to look to reduce costs and improve agility as we enter an unprecedented technological era. Many SMB’s are considering a shift from commercial database platforms like Oracle or SQL Server to open-source alternatives such as PostgreSQL. The appeal is clear; PostgreSQL offers a flexible, extensible environment with no licensing fees and a thriving ecosystem of tools.

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However, from a Principal Database Administrator’s (DBA) perspective, the move is far more complex than a traditional lift-and-shift. Migrating a mission-critical database to PostgreSQL is a strategic initiative that impacts development, operations, compliance, and business continuity. Success depends on the ability to identify and plan for key roadblocks, many of which are not immediately visible at the executive level. Below are seven of the most significant strategic challenges to prepare for as you evaluate and execute a PostgreSQL migration.

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1. Legacy Feature Dependencies

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Many legacy systems are deeply embedded with features that are proprietary to Oracle or SQL Server, features that PostgreSQL either doesn’t support or only partially replicates through community plugins. Examples include advanced partitioning schemes, sophisticated materialized view refresh options, bitmap indexing, and Oracle’s DBMS_SCHEDULER.

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These features often underpin performance, high availability, and scalability. Their absence in PostgreSQL doesn’t mean the migration can’t happen. However, it does mean these areas will need to be redesigned. In some cases, entire data flows or business processes must be refactored.

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This isn’t just a technical task. It requires cross-functional coordination, risk analysis, and deep domain knowledge of how these features are used across the enterprise. Without this, you risk functional regressions, broken workflows, or misaligned business logic. Plan for custom development and increased QA investment early in the lifecycle. Treat legacy feature remediation as a critical path item, not a post-migration cleanup.

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2. Business Logic Translation Overhead

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Many enterprise databases house complex business logic in the form of stored procedures, triggers, packages, and functions; often written in languages like PL/SQL or T-SQL. These procedural scripts are tightly coupled with specific database behaviors, exception handling models, and optimization mechanisms that are not portable to PostgreSQL.

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Automated translation tools exist but are rarely reliable for non-trivial logic. For example, conditional flows, nested cursor operations, dynamic SQL, and exception trapping in Oracle behave differently than in PostgreSQL’s PL/pgSQL. Moreover, some database logic interacts with external systems, APIs, or auditing mechanisms that cannot be lifted directly.

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Each translation introduces risk. Logic may be misunderstood, partially translated, or functionally inconsistent. This is especially true when timelines are tight and documentation is lacking. My advice to executives is to allocate time and talent to thoroughly review and revalidate business logic after translation. Treat this as an integration project, not just a syntax conversion.

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3. Shift in Performance Management Approach

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Performance tuning in PostgreSQL is fundamentally different from Oracle or SQL Server. Query planners behave differently, indexing strategies vary, and memory management settings require entirely new tuning profiles.

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For teams used to managing performance through Oracle hints or SQL Server’s execution plans, PostgreSQL will feel unfamiliar. The dynamic nature of PostgreSQL’s planner means performance issues may not appear immediately, but when they do, diagnosing them requires expertise.

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Additionally, PostgreSQL lacks a unified GUI like Oracle Enterprise Manager, making monitoring and root cause analysis more fragmented unless a robust observability strategy is in place. Don’t assume existing DBAs will adapt instantly. Invest in PostgreSQL-experienced engineering support during and after the migration to avoid performance degradation in production environments.

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4. Gaps in Monitoring and Tooling

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Oracle and SQL Server provide integrated tooling for monitoring, backups, replication, patching, and alerting. PostgreSQL, in contrast, is modular and relies heavily on external tools, many of which are open-source and maintained by the community.

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Assembling a reliable PostgreSQL observability stack involves selecting, integrating, and configuring components such as pgBackRest for backups, Patroni for high availability, pg_stat_statements for performance analysis, and tools like Prometheus or Grafana for monitoring.

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While this flexibility is powerful, it creates a hidden cost: operational complexity. Each tool has its own configuration model, upgrade path, and documentation. Without careful planning, the observability stack becomes fragile and difficult to manage at scale. Make sure to include tooling transition and integration in your cost and time estimates. Treat observability as a first-class component of your architecture.

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5. Security and Compliance Migration Risks

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Your current database likely supports finely tuned access controls, granular auditing, data masking, and compliance hooks designed for HIPAA, PCI, SOX, or GDPR. These controls are often deeply embedded in stored procedures, role hierarchies, and logging policies.

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PostgreSQL can support similar security goals, but the implementation mechanisms are different. Row-level security, custom role sets, and open-source auditing extensions like pgaudit require redesign, validation, and buy-in from your compliance stakeholders. Migration can unintentionally create gaps in audit coverage, overly permissive access roles, or misaligned encryption policies, especially if security planning is deferred until late in the process.

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For anyone on the executive side, make sure to engage compliance and infosec teams early in the planning process. Validate that PostgreSQL can meet your audit requirements before proceeding to system migration.

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6. Application-Level Refactoring

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Even if the database is successfully migrated, applications built around Oracle-specific syntax and behavior will often fail or degrade under PostgreSQL. Common problems include implicit data type casting, use of proprietary functions, reliance on Oracle error codes, and assumptions about result set behavior.

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In some cases, application-side SQL is embedded in legacy codebase or third-party applications that are no longer actively maintained. This makes identification and remediation more difficult. Applications must be refactored, retested, and re-certified to ensure business continuity, especially those that feed customer-facing portals, billing systems, or analytics dashboards.

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If you’re on the technical side of leadership, you should coordinate migration plans across dev, QA, and data engineering teams. Assign ownership to identify and remediate application-level dependencies as early as possible.

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7. Talent and Change Management Challenges

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A successful PostgreSQL migration requires more than technology, it demands a shift in mindset, skills, and team structure. Many organizations assume their existing DBAs and developers can "learn as they go," but this often leads to burnout, delays, and rework.

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PostgreSQL has a different operational philosophy, ecosystem, and community support model. Without structured training and internal change management, teams may resist adoption or struggle to achieve post-migration stability.

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Additionally, the open-source nature of PostgreSQL means your team will often need to act as the integrator, evaluating tools, managing dependencies, and supporting patch cycles that are no longer dictated by a single vendor. A piece of advice I would offer to executives is to make talent readiness a pillar of your migration plan. Invest in formal training, incentivize certification, and establish clear lines of ownership for PostgreSQL operations.

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Final Thoughts

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Migrating to PostgreSQL can deliver measurable benefits, reduced costs, vendor independence, and increased agility. But those outcomes are only realized when the migration is approached as a strategic initiative, not a tactical exercise.

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Success depends on more than technical capability. It hinges on organizational readiness, resource planning, and a willingness to confront complexity with clarity. Leadership must be prepared to support cross-functional collaboration, anticipate disruption, and align the migration with broader business goals.

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This is not a simple vendor swap. It’s a full-stack modernization initiative, on par with a cloud migration or ERP overhaul. Treat it with the same rigor, funding, and governance required for mission-critical transformation. If you’re serious about moving to PostgreSQL, make sure your organization is equally serious about preparing for the road ahead.

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How an MSP Like DataStrike Helps You Navigate These Roadblocks

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Migrating to PostgreSQL is challenging, and you have to rethink how your organization approaches data architecture, performance, and operational continuity. That’s where an experienced MSP like DataStrike becomes indispensable to you.

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At DataStrike, we bring battle-tested strategies and cross-functional expertise to address all seven of the roadblocks outlined above. Our PostgreSQL architects and migration engineers begin with a detailed system assessment to surface hidden dependencies and legacy feature usage. We translate business logic with precision, using a combination of automated tooling and manual review, ensuring workflows are preserved and performance is maintained.

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Where in-house teams may struggle to manage PostgreSQL tuning, observability, and security configuration, we step in with a proven tooling stack and operational playbooks. From implementing row-level security and role hierarchies to reengineering application-level SQL for compatibility, we build out a full-stack migration plan aligned to your compliance and uptime requirements.

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Perhaps most importantly, we can elevate your team. DataStrike provides structured onboarding, documentation, and training to bring your internal talent along for the journey, minimizing disruption and ushering in long-term ownership.

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About DataStrike

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DataStrike is the largest onshore provider of data infrastructure services for small and mid-sized businesses, specializing in database modernization, cloud migration, and managed services. With deep expertise in PostgreSQL, Oracle, SQL Server, and cloud-native architectures, we help organizations plan, execute, and support complex database transformations with confidence.

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Our team of U.S.-based engineers delivers white-glove service across every phase of the migration lifecycle, from strategic assessments and replatforming to performance tuning, observability, and ongoing support. Whether you're reducing technical debt, optimizing cost, or preparing for a cloud-first future, DataStrike equips your organization with the tools, talent, and roadmap to move forward, securely and at scale. Contact us today to learn more.

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