7 Common Challenges When Migrating WordPress to Contentful (and How to Fix Them)

When enterprises decide to migrate from WordPress to Contentful, it’s rarely about features. It’s about scale.

As organizations grow, WordPress can start to feel restrictive — whether it’s the increasing plugin maintenance, performance inconsistencies, or the difficulty of managing content across multiple regions and brands. Teams begin to look for faster publishing cycles, developers seek modern workflows, and leadership starts prioritizing governance and scalability.

But here’s the catch: while Contentful solves many of those problems, the migration itself introduces a whole new set of challenges — from mapping content models to ensuring SEO continuity and stakeholder alignment.

For global organizations with complex sites, migrating isn’t just a technical project. It’s a strategic transformation that touches marketing operations, development workflows, and governance.

This definitive guide will unpack the seven most common challenges when migrating WordPress to Contentful — and how to overcome each one, step by step.

Why Migrating from WordPress to Contentful Matters

Enterprises often start on WordPress because it’s fast to launch and easy to use. But as the business scales, so does the complexity:

• Multiple regional sites and language variants
• Plugins that create functional conflicts with each other or cause unpredictable page load times.
• CMS workflows that depend too much on developers
• Security and compliance limitations in open-source environments

At this stage, WordPress becomes a bottleneck, not an enabler.

To move beyond those limits, many enterprises turn to Contentful — a composable content platform built on an API-first structure. It allows teams to organize content into reusable components, manage access through defined roles and environments, and integrate more easily with modern development frameworks.

It allows teams to:

• Reuse structured content across channels
• Integrate seamlessly with APIs and CDNs
• Manage multi-brand or multi-region architectures
• Empower marketers through a decoupled front-end

However, this flexibility comes at a cost — you must rebuild your content foundation from scratch. Unlike a simple CMS swap, migrating from WordPress to Contentful means rethinking how content is modeled, stored, and delivered.

The Stakes for Enterprise Teams

A poorly managed migration can lead to:

• Broken SEO rankings
• Data loss or formatting inconsistencies
• Increased project costs
• Frustrated stakeholders who lose confidence in the new platform

These risks make it crucial for enterprise web teams to plan migrations strategically — aligning stakeholders, processes, and technology early on.

7 Common Challenges When Migrating WordPress to Contentful (and How to Fix Them)

1. Rebuilding Content Models from Scratch

Unlike WordPress, which structures content around posts and pages, Contentful relies on content models — modular components representing reusable content types (e.g., hero banners, testimonials, blog articles).

The challenge?
Most WordPress sites don’t have clearly defined models. They rely on custom fields, shortcodes, or plugins like ACF (Advanced Custom Fields) — none of which translate directly into Contentful.

Fix:
Start with a content model audit.

1. Identify all content types currently used (pages, posts, landing pages, resources).
2. Define reusable patterns and atomic components.
3. Map these to Contentful content types.

Tip: Treat this as an opportunity to simplify and standardize. Overly complex models slow down editors and increase API payloads.

 2. Preserving SEO Equity

A common mistake during migration is losing search engine visibility due to broken URLs, missing metadata, or inconsistent redirects.

Fix:

• Maintain a URL redirect matrix mapping all old URLs to new ones.
• Audit and migrate meta titles, descriptions, and structured data.
• Use Contentful’s API to automate metadata fields.
• Keep your WordPress site live temporarily for reference and validation.

3. Handling Media Assets and Image Optimization

WordPress typically stores images in /wp-content/uploads/ directories — often unmanaged and bloated. Migrating these to Contentful requires careful planning.

Fix:

• Audit image usage and remove duplicates or unused assets.
• Use Contentful’s Media API or bulk upload tools for large imports.
• Implement dynamic image resizing through services like Cloudinary or Imgix.

4. Ensuring Editorial Workflow Alignment

In WordPress, editors rely on plugins like Yoast or Gutenberg. In Contentful, workflows are custom-configured — meaning teams must define roles, permissions, and stages from scratch.

Fix:

• Define roles (Author, Editor, Approver, Developer).
• Create content lifecycle workflows that mimic or improve current processes.
• Integrate Contentful with project management tools (e.g., Jira, Airtable).

5. Integrating Plugins and Rebuilding Features

WordPress’s plugin ecosystem is vast, but those shortcuts disappear in Contentful. Every functionality — forms, analytics, schema, etc. — must be re-implemented.

Fix:

• Create an inventory of existing plugins and their purpose.
• Replace them with API-based integrations (e.g., HubSpot, Google Tag Manager, Segment).
• Plan for custom middleware if no direct equivalent exists.

6. Managing Multi-Environment Deployments

In WordPress, staging and production often live on the same server. In Contentful, you’re managing multiple environments and delivery tokens.

Fix:

• Set up separate environments for development, staging, and production.
• Use Contentful’s migration CLI for version-controlled model changes.
• Automate deployments with CI/CD tools (e.g., GitHub Actions, Netlify).

7. Aligning Stakeholders Across Marketing, Dev, and IT

Migration isn’t just technical — it’s organizational.
Marketers want simplicity. Developers want flexibility. IT wants governance.

Without clear alignment, projects stall or result in frustration on all sides.

Fix:

• Kick off with cross-functional discovery workshops.
• Create shared definitions for success: uptime, speed, editorial usability.
• Use prototypes and demos to get buy-in early.

Common Pitfalls in WordPress to Contentful Migrations (and Their Implications)

Pitfall	What Goes Wrong	Implications for Enterprise Teams
Over-modeling content structures	Teams create overly granular content types that slow down publishing workflows and increase API complexity.	Overly complex models can frustrate editors and slow localization for many enterprise teams.
Broken SEO continuity	Failure to map old URLs to new ones or migrate metadata properly.	Organic traffic drops, rankings plummet, and the brand loses visibility during the transition period. Recovery may take months.
Unoptimized media migration	Media files are bulk uploaded without compression, naming standards, or CDN optimization.	Bloated assets slow page load, hurt Core Web Vitals, and increase hosting costs. This impacts UX and SEO performance.
Undefined editorial roles and workflows	Teams neglect to define publishing roles and approval flows in the new CMS.	Editors either lack the access they need or override controls. This leads to delays, inconsistent publishing, and audit trail issues.
Assuming plugin functionality will transfer	Features provided by WordPress plugins aren’t rebuilt in Contentful (e.g., form builders, SEO helpers).	Core site functionality is lost, resulting in launch delays, broken UX, or surprise dev work post-migration.
Skipping cross-functional alignment	Migration is treated as an IT-only initiative, leaving marketing, SEO, or legal teams out of the process.	Misaligned expectations lead to rework, missed requirements, and friction between departments.
Lack of staging/testing environments	Deployments are made directly to production without sandboxing or QA environments.	Bugs go live, redirects fail, and content is exposed prematurely. Fixing in production increases risk and stress.
Poor redirect strategy	Redirects are managed manually or inconsistently across environments.	Broken links and crawl errors reduce SEO value and confuse users. Analytics data becomes fragmented.
Inconsistent localization approach	Content types don’t account for locale variations or language-specific fields.	Global teams are blocked from publishing, and regional campaigns stall. Workarounds create long-term governance issues.
Underestimating the change management effort	The transition to a structured, headless CMS is assumed to be a simple platform switch.	Editors are overwhelmed, adoption suffers, and leadership loses confidence in the investment.

Actionable Takeaways

• Audit before you migrate — understand every dependency.
• Standardize your content model — keep it simple and scalable.
• Automate SEO tasks — don’t rely on manual redirects.
• Train your editorial teams early — adoption is half the battle.
• Align marketing and IT goals — success depends on both sides.
• Test migrations incrementally — not all content types need to move at once.
• Partner with experienced CMS experts — it’s not just about moving data, but transforming systems.

Migrating from WordPress to Contentful is more than a CMS upgrade — it’s a foundational investment in scalability, security, and speed. Handled strategically, it can transform how your teams collaborate, publish, and grow.

About eight25

eight25 is a global digital agency that delivers high-performing web experiences for enterprise companies. Established in 2011, we’ve grown to 150 employees across three offices worldwide and have served over 500 customers including global leaders such as Google, Samsung, Hyundai, and Qlik. Ranked by Clutch as a top Silicon Valley web design agency, we continue to drive growth through innovative, customer-first digital strategies.

We bridge strategy, design, and technology to create seamless digital journeys. From CX and UX/UI to CMS, personalization, and integrations, we bring every element together. With deep expertise in content, SEO, CRO, analytics, and AI, we deliver digital experiences that not only engage but also drive measurable growth.