30 Common DevOps Challenges and How to Resolve Them

This article is based on insights originally published on techbeacon.com, compiled from a series of enterprise DevOps innovation and optimization workshops.

Why DevOps Adoption Is Still Hard

As DevOps moves from buzzword to standard practice, the questions enterprise teams ask most often are remarkably consistent: Where do I start? What challenges am I likely to face? How do I resolve them? These questions surfaced repeatedly across a series of focus groups and facilitated workshops run with enterprise executives and senior engineering leaders.

DevOps represents the logical endpoint of a progression that began with waterfall development, moved through iterative delivery, Agile, and Scaled Agile, and now culminates in a model that shifts focus from building software to delivering it continuously and reliably. That shift sounds straightforward but consistently proves difficult in practice.

The DevOps body of knowledge has matured significantly. Books such as The DevOps Handbook (Gene Kim, Jez Humble, Patrick Debois, and John Willis) and The DevOps Adoption Playbook (Sanjeev Sharma) now emphasize real-world case studies and actionable practice over abstract theory. Even so, the gap between knowing what good looks like and achieving it inside a real enterprise remains large.

The Top 30 DevOps Challenges

Data gathered from more than 100 DevOps workshops with enterprise teams surfaced a consistent set of recurring challenge areas. The 30 most common are listed below, ranked by frequency of occurrence across those sessions:

1. Environment provisioning
2. Manual testing
3. No DevOps center of excellence
4. Test data management
5. Manual deployments
6. Planning in a DevOps environment
7. DevOps and suppliers
8. DevOps and governance
9. No integrated tools architecture
10. Manual releases
11. No DevOps metrics
12. DevOps and team composition
13. DevOps and regulatory compliance
14. No service virtualization
15. DevOps and specialist skills
16. Traceability across the DevOps landscape
17. Large, infrequent releases
18. Inconsistent environments
19. Agile practices confined to developers only
20. Limited transparency
21. Pervasive manual processes
22. Collaboration between development and operations
23. No DevOps vision or strategy
24. No production-like environments
25. Waste in existing processes
26. Limited customer feedback loops
27. Elicitation of non-functional requirements
28. Collaboration across all IT disciplines
29. Collaboration between business and IT
30. No standard source control (SCM) repository

How to Read This List

The list is deliberately broad. A few things to keep in mind as you review it:

• There is intentional overlap. Manual testing, manual releases, and manual deployments are distinct problems even though all three fall under the umbrella of manual processes. Each has different root causes and requires different interventions.
• Challenges span the people–process–technology triad. Some (e.g., no DevOps center of excellence) are primarily organizational. Others (e.g., environment provisioning, no integrated tools architecture) are technical. Many (e.g., planning in a DevOps environment) are process-level concerns.
• Scale matters. Some challenges, such as DevOps and suppliers or DevOps and regulatory compliance, are predominantly enterprise-level concerns. Others, such as eliciting non-functional requirements, operate at the team level.
• This is not a universal checklist. Every organization’s situation is unique. Your most pressing challenge may not appear on this list at all.

A Practice-Based Approach to Resolving DevOps Challenges

Each of the 30 challenges above can be addressed through well-defined DevOps practices. The important insight is that every practice simultaneously addresses people, process, and technology—not just one dimension in isolation.

Worked Example: Replacing Manual Deployments with Automated Deployment

Consider challenge #5: manual deployments. The typical symptoms are low deployment frequency, high error rates, and long mean time to recovery (MTTR). The obvious resolution is to adopt automated deployment as a practice. But automation is not only a tooling exercise. A genuine practice-based resolution addresses all three dimensions:

• People: Redefine deployment roles. For example, developers can be empowered to promote a code package to the next environment once it passes relevant automated tests, while promotion to production still requires an explicit approval gate.
• Process: Map and streamline the existing deployment workflow. Identify and eliminate unnecessary control points, approval steps, and handoff delays that add lead time without adding value.
• Technology: Automate the streamlined process using appropriate tooling—CI/CD pipelines, infrastructure-as-code, configuration management—so that human error is removed from the critical path.

This three-dimensional view applies to every challenge on the list. Addressing only the technology layer while leaving role definitions and process steps unchanged is the most common reason DevOps tool investments fail to deliver the expected improvement.

Walking Through the Practice Library

One effective workshop technique is to review a library of DevOps practices as a team—understanding the intent of each practice, assessing its applicability to your current context, and agreeing on a priority order. This review process naturally surfaces the challenges that matter most to your organization and grounds the resulting roadmap in shared understanding rather than top-down mandate.

A day-long practice review session with senior engineering and operations stakeholders—similar to the approach used during an agile transformation at a major European bank described in the source material—can produce a prioritized adoption roadmap with clear owners and dependencies. The output is more durable than a tool selection exercise because it builds organizational consensus alongside the technical plan.

Develop Your Own DevOps Adoption Roadmap

DevOps practices do not exist in isolation. They are derived from underlying principles that themselves have roots in Lean manufacturing, Agile software development, ITSM, and continuous improvement disciplines. Understanding that heritage helps teams select practices that are philosophically consistent with one another—avoiding the common mistake of grafting incompatible practices onto an existing process.

When building your roadmap, consider the following structure:

1. Identify your current challenges. Run your own internal assessment against the 30 challenge areas above. Add any challenges unique to your organization, industry, or regulatory environment.
2. Map challenges to practices. For each prioritized challenge, identify the DevOps practice or practices most likely to resolve it. Consult your practice library.
3. Assess practice readiness. For each candidate practice, evaluate your current people, process, and technology maturity. Gaps in any dimension are implementation risks.
4. Sequence and commit. Build a phased roadmap that sequences practices logically—foundational practices (e.g., source control standardization, environment automation) before advanced ones (e.g., continuous deployment to production, chaos engineering).
5. Measure and adapt. Define DevOps metrics before you start—deployment frequency, lead time for changes, change failure rate, and MTTR are widely used starting points. Review progress regularly and adjust the roadmap as challenges are resolved and new ones emerge.

Key Takeaways

• The 30 challenges above are the most frequently cited across enterprise DevOps engagements, but they are not exhaustive—your organization may face additional or different ones.
• Every DevOps challenge has a people dimension, a process dimension, and a technology dimension. Sustainable resolution requires addressing all three.
• Practices are the bridge between DevOps principles and real-world outcomes. A shared understanding of which practices apply to your context—and why—is more valuable than a tool selection decision made in isolation.
• A practice-based roadmap built through facilitated team workshops tends to generate stronger organizational commitment than a roadmap handed down from leadership.
• DevOps adoption is iterative. Start with your highest-impact challenges, measure results, and refine your approach continuously.

Originally sourced from techbeacon.com. The workshops and enterprise case studies referenced in this article are attributed to the original author’s consulting and facilitation work with enterprise DevOps teams.