Twenty microservices. Seven engineering days each to fix. That’s 140 days of engineering time—not including testing, QA, reviews, or releases.
The cause? A tech lead’s decision to “just upgrade everything and see what happens.”
I’ve seen this pattern repeatedly over my 10 years as a consultant. Teams treat dependency updates like a lottery ticket: click update, hope for the best, deal with the fallout later. It’s surprisingly common, devastatingly expensive, and completely preventable.
The Real Cost of Blind Upgrades
Let’s break down what actually happened at this client:
The team received security alerts about outdated packages. Under pressure to “fix it quickly,” they ran their package manager’s update command across all services, committed the changes and pushed out to their environments. No research. No planning. No understanding of what would break.
The result:
- 140 engineering days for initial fixes
- 60+ additional days for testing and QA
- 3 months of delayed features
- Immeasurable impact on team morale
- One very unhappy business leadership team
The tragedy? With proper planning, this could have been a 20-day effort with minimal disruption.
The Antidote: Strategic Upgrade Planning
After witnessing this pattern too many times, I’ve developed a systematic approach that transforms upgrades from Russian roulette into predictable, manageable projects.
Step 1: Know Your Dependencies
Before touching that update button, you need intelligence:
Create a Software Bill of Materials (SBOM): Document every dependency, its current version, and—critically—how your code actually uses it. Are you using 5% or 50% of that framework’s features? This matters immensely for upgrade complexity.
ℹ️ Note
For those who don’t have an SBOM or know what they are, give the following blog post a read: The 5-Minute Investment That Could Save Your Company Millions: A Developer’s Guide to SBOMs
Set Up Continuous Monitoring: Tools like Dependabot (available for both GitHub and Azure DevOps) automatically scan repositories and alert you to updates. But don’t let these tools make decisions for you—they’re scouts, not generals.
Subscribe to Change Notifications: Join mailing lists, watch repositories, follow key maintainers on social media. When a major framework plans breaking changes, you want to know months in advance, not days after.
Case in point: .NET 10 releases in a few weeks. Teams who’ve been following the development blogs, preview releases, and migration guides are ready. They know about the breaking changes in minimal APIs, the new collection expressions, and the performance improvements they can leverage. Teams who discover .NET 10’s existence when Dependabot creates a PR? They’re in for surprises.
Step 2: Analyze Before You Act
When updates appear, resist the urge to immediately apply them. Instead:
Read the Changelogs (Yes, All of Them):
- Breaking changes
- Deprecation notices
- Migration guides
- Performance implications
- New prerequisites
Map Your Usage Patterns: Compare your SBOM against the changelog. If a breaking change affects an API you use extensively, that’s a red flag. If it’s in a feature you don’t touch, it might be trivial.
Check the Dependency Chain: That innocent-looking minor update might trigger a cascade of other updates. Understand the full impact before proceeding.
Step 3: Create a Real Upgrade Plan
This is where most teams fail. A real plan isn’t “we’ll upgrade next sprint.” It’s:
Proof of Concept First: Choose your simplest service as a canary. Document every issue, every workaround, every surprise. This becomes your playbook for the remaining services.
Time Estimates Based on Reality:
- Research and planning: X days
- Implementation per service: Y days
- Testing and validation: Z days
- Buffer for unknowns: 30% minimum
Resource Allocation: Who’s doing this work? When? What features get delayed? Be honest about the trade-offs.
Rollback Strategy: What’s your escape plan if things go wrong? Feature flags? Blue-green deployments? Hope is not a strategy.
Step 4: Execute with Discipline
Incremental Progress: Upgrade one service, fully test it, deploy it, monitor it. Only then move to the next. Resist the temptation to parallelize too aggressively.
Document Everything: Every issue encountered, every solution found. Your future self (and team) will thank you.
Communicate Constantly: Daily updates to stakeholders. No surprises. Bad news early is infinitely better than bad news late.
ℹ️ Note
This step requires adopting the ideas behind Extreme Ownership. To learn about what that is, and how it applies to what we do read my notes on the subject here: Leading with Ownership: Lessons from Extreme Ownership for the Modern Workplace
The DevEx Dividend
Most teams miss the fact that well-executed upgrades actually improve Developer Experience:
- Modern language features that make code cleaner
- Better debugging tools and error messages
- Performance improvements that make builds faster
- Security patches that let everyone sleep better
- Active community support for current versions
But this only happens when upgrades are planned, not panicked.
The Learning Investment
There’s an uncomfortable truth we need to address: staying current requires continuous learning. If your team doesn’t know what’s new in your dependencies, how can they plan upgrades effectively?
This is especially prescient right now. With .NET 10 releasing in the coming weeks, thousands of teams will face upgrade decisions. Those who’ve been following the preview releases, reading the migration guides, and understanding the breaking changes will execute smooth transitions. Those who haven’t? They’ll join the “upgrade and pray” statistics.
Successful teams invest in:
- Conference attendance (virtual or in-person)
- Time to read documentation and changelogs
- Access to online courses and training
- Regular “learning Fridays”, “lunch and learns” or similar programs
- Internal knowledge sharing sessions
This isn’t overhead—it’s preventive maintenance. A team that understands their tools deeply can upgrade them safely.
Making the Business Case
Need to convince leadership? Here’s your formula:
Cost of Planned Upgrade:
- Planning time: 5 days
- Implementation: 20 days
- Testing: 10 days
- Total: 35 engineering days
Cost of “Upgrade and Pray”:
- Fixing breaks: 140 days
- Testing/QA: 60 days
- Opportunity cost: Immeasurable
- Team morale: Devastating
ROI of Proper Planning: 400%+
Your Upgrade Checklist
Before your next upgrade:
- Document all dependencies and usage patterns (SBOM)
- Set up automated monitoring (Dependabot or similar)
- Read all relevant changelogs and migration guides
- Create proof of concept with simplest service
- Develop realistic time estimates with buffer
- Get stakeholder buy-in with clear trade-offs
- Plan incremental rollout with rollback strategy
- Allocate time for team learning and research
The Bottom Line
Blind upgrades are technical malpractice. They waste time, destroy morale, and damage your credibility with business stakeholders. But with proper planning, upgrades become predictable projects that actually improve your codebase and developer experience.
The choice is yours: 140 days of emergency fixes or 35 days of controlled progress. I know which one I’d choose.
ℹ️ Note
Having trouble getting buy-in for proper upgrade planning? Share this companion piece with your business leaders: Why Your ‘Stable’ Software Is a Ticking Time Bomb
Need help creating a strategic upgrade plan or improving your team’s Developer Experience? I offer DevEx assessments and strategic technology consulting specifically designed for teams facing these challenges. Simply use the contact form below, and I’ll be in touch as soon as possible to arrange a free 30-minute discovery session at your convenience.