I recently decided to give my 8 year old Hugo website a serious refresh. The trigger was simple: I still used the first Hugo theme I picked up 8 years ago, some content menu options didn’t actually do anything or were no longer relevant. Then I also had screenshots and other image files all over the place (5 different folder locations, duplicate image file names and alike).

Instead of doing this modernization and cleanup manually over a few weekends, I used GitHub Copilot as an active engineering partner to accelerate the full modernization journey.

Where it started: search was broken in production

The first issue looked small, but it exposed deeper reliability problems:

• The search JSON endpoint existed
• The /search/ page in production was effectively empty
• The pipeline still reported success

So this wasn’t a single typo. It was a classic “green pipeline, broken runtime behavior” scenario.

With Copilot, I moved from guessing to structured troubleshooting:

1. Validate generated Hugo output
2. Compare source routing/content metadata with deployed artifacts
3. Harden the pipeline to fail fast when critical pages are missing

That immediately changed the workflow from reactive debugging to proactive validation.

Copilot helped me modernize beyond just the bug

Once search was fixed, I used the same momentum to clean up years of accumulated content and asset drift.

1) Build and deployment reliability

I updated the Azure Static Web Apps pipeline to be more explicit and defensive:

• Build validation checks for critical output files
• Safer prebuilt artifact deployment behavior
• Better guardrails so partial site generation doesn’t silently pass

Result: deployment confidence went up significantly.

1) Build and deployment reliability

I updated the Azure Static Web Apps pipeline to be more explicit and defensive:

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trigger:
    - main

pool:
    vmImage: 'ubuntu-latest'

steps:
    - task: UseHugoExtended@1
        inputs:
            version: 'latest'
    
    - script: hugo --minify
        displayName: 'Build Hugo site'
    
    # 🛡️ GUARDRAIL: Validate critical output files exist
    - script: |
            if [ ! -f "public/search/index.json" ]; then
                echo "ERROR: Search JSON endpoint missing!"
                exit 1
            fi
            if [ ! -f "public/index.html" ]; then
                echo "ERROR: Homepage not generated!"
                exit 1
            fi
        displayName: 'Validate critical pages exist'
    
    # 🛡️ GUARDRAIL: Check for empty or malformed search index
    - script: |
            SIZE=$(wc -c < public/search/index.json)
            if [ $SIZE -lt 100 ]; then
                echo "ERROR: Search index is suspiciously small ($SIZE bytes)!"
                exit 1
            fi
        displayName: 'Validate search index integrity'
    
    # 🛡️ GUARDRAIL: Verify content pages were generated
    - script: |
            COUNT=$(find public -name "index.html" -type f | wc -l)
            if [ $COUNT -lt 10 ]; then
                echo "WARNING: Only $COUNT pages generated (expected more)"
                exit 1
            fi
        displayName: 'Verify minimum content threshold'
    
    - task: PublishBuildArtifacts@1
        inputs:
            pathToPublish: 'public'
            artifactName: 'hugo-site'
        displayName: 'Publish build artifacts'
    
    - task: AzureStaticWebApp@0
        inputs:
            azure_static_web_apps_api_token: $(AZURE_STATIC_WEB_APPS_TOKEN)
            repo_token: $(GITHUB_TOKEN)
            action: 'upload'
            app_location: 'public'
        displayName: 'Deploy to Azure Static Web Apps'

Key safety improvements:

• ✅ Explicit validation that search index exists and has realistic content
• ✅ Minimum page count check to catch silent generation failures
• ✅ Pipeline fails fast instead of deploying broken output
• ✅ Clear error messages for debugging

Result: deployment confidence went up significantly.

2) Content architecture cleanup

Over time, I had duplicate and legacy routes (especially around books and videos). Copilot helped audit what was truly used versus what was just historical baggage.

I then:

• Redesigned the Books page into a cleaner 2-column layout (cover + title/description)
• Removed duplicate publications pages where canonical pages already existed
• Reviewed and cleaned aliases to keep routing intentional

Result: fewer moving parts and clearer content ownership.

3) Image and asset governance

This was the biggest hidden technical debt.

I had images spread across multiple legacy folders with overlapping filenames. That made reference checks noisy and risky. Copilot helped me run source-scoped audits, identify true usage, and avoid false positives from generated output.

I used that to:

• Move post-related images into content/post/images
• Rewrite Markdown links in affected posts
• Handle filename collisions safely
• Remove unused files/folders only after reference validation

Result: cleaner repository, fewer dead assets, and lower risk of accidental content breakage.

What I liked most about using Copilot on an older codebase

The biggest value wasn’t “AI wrote code for me.” It was this:

• Faster root-cause analysis
• Safer bulk refactoring with validation checkpoints
• Less context switching for repetitive search/update tasks
• Better confidence to remove legacy clutter without fear

For old websites, this matters a lot. Most of the work is not feature development — it’s careful archaeology.

Practical lessons if you want to modernize your own Hugo site

If your site is aging and you don’t know where to start, this sequence worked very well for me:

1. Fix one visible production issue first (high leverage)
2. Add pipeline checks for critical pages/artifacts
3. Identify canonical routes and remove duplicates
4. Consolidate assets by usage domain (e.g., post images)
5. Delete only after source-level reference validation

Small, verified steps beat one giant risky migration every time.

Final thoughts

This modernization started as a broken search page after switching to a new Hugo theme and ended as a full site health upgrade and removal of technical debt.

GitHub Copilot didn’t replace engineering judgment — it amplified it. For me, that was the real win: I could move faster and be more careful at the same time.

If you have an older Hugo site (or any long-running static site), this is absolutely worth doing.

By the way, this whole process took less than 2 hours, and about 20 prompts in a continuous conversational approach. Are you a fan of GitHub Copilot? Let me know what your coolest use case has been so far!

Cheers!!

/Peter