Building an Auto-Generated Technical Blog System Across Four Domain Properties

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This session involved architecting and implementing a comprehensive technical documentation system that automatically captures development work across four independent properties: queenofsandiego.com, sailjada.com, dangerouscentaur.com, and burialsatseasandiego.com. Each property now has its own technical blog accessible at tech.[domain].com, with infrastructure provisioning, DNS routing, and automated post generation.

The Problem Statement

The challenge was to create a transparent, granular technical audit trail visible to stakeholders (particularly for stakeholder review) without manual effort. High-level summaries don't expose the architectural decisions, infrastructure changes, and technical depth of ongoing work. The system needed to be:

Fully automated — capture work from Claude Code sessions without manual intervention
Granular — include specific file paths, function names, infrastructure resource IDs, exact changes
Property-aware — separate tech blogs for each domain with independent infrastructure
Secure — never expose credentials, API keys, or sensitive data
Integrated — accessible from the main site navigation (Ship's Papers menu)

Infrastructure Architecture

Each tech blog uses an identical AWS infrastructure pattern but deployed independently:

S3 Origin Bucket: Static HTML blog content stored in tech-[domain]-blog bucket (e.g., tech-queenofsandiego-blog, tech-sailjada-blog, tech-dangerouscentaur-blog, tech-burialsatseasandiego-blog)
CloudFront Distribution: Global CDN with automatic GZIP compression, cache invalidation support, and custom domain CNAME routing
DNS Integration: Route53 CNAME records (for AWS-managed domains) or external DNS provider records (GoDaddy for burialsatseasandiego.com, Namecheap for dangerouscentaur.com)
SSL/TLS: Existing wildcard ACM certificates leveraged where available (*.queenofsandiego.com, *.sailjada.com); new certificates provisioned for dangerouscentaur and burialsatseasandiego with DNS validation

Technical Implementation Details

Infrastructure Provisioning Script

The core provisioning logic was implemented in /Users/cb/Documents/repos/tools/tech_blog_init.py. This script:

Reads domain configuration from environment and hardcoded mappings
Creates S3 buckets with appropriate naming conventions and public read permissions for CloudFront
Provisions CloudFront distributions with origin access control (OAC) to restrict direct S3 access
Handles DNS routing through two providers:
- Route53: For queenofsandiego.com and sailjada.com domains (AWS-managed)
- External DNS: GoDaddy API integration for burialsatseasadiego.com; Namecheap manual CNAME records for dangerouscentaur.com
Manages ACM certificate validation with DNS CNAME records automatically added to GoDaddy
Outputs infrastructure configuration to memory/tech_blogs_infrastructure.json for reference and idempotency

Blog Generator and Automation

Created /Users/cb/Documents/repos/tools/tech_blog_generator.py to convert Claude Code session transcripts into technical blog posts. The generator:

Reads JSONL-formatted session transcripts from Claude's session directory
Extracts file modification events, command execution history, and tool interactions
Filters sensitive data using regex patterns for credentials, API keys, tokens, and personal information
Generates HTML articles with semantic structure (<h2>, <h3>, <ul>, <code>, <pre>)
Publishes to the appropriate S3 bucket based on session context
Invalidates CloudFront cache to ensure immediate visibility

Stop Hook Integration

Integrated with Claude Code's session lifecycle by creating /Users/cb/.claude/hooks/tech_blog_stop.sh:

Executes when a coding session ends
Triggers the blog generator automatically without manual intervention
Routes output to the correct domain's tech blog based on session metadata
Logs all operations to ~/.claude/logs/tech_blog_generation.log for debugging

The hook was registered in /Users/cb/.claude/settings.json under the hooks configuration section.

Site Navigation Integration

Updated the Ship's Papers navigation menu in each domain's main navigation HTML to include links to the tech blog:

Modified /Users/cb/Documents/repos/sites/queenofsandiego.com/index.html to add "Technical Blog" link in the Ship's Papers dropdown
Used consistent URL pattern: https://tech.[domain].com/
Maintained existing navigation hierarchy and styling

Domain-Specific Configuration

Each domain has unique DNS and certificate considerations:

queenofsandiego.com: Route53 hosted zone with existing wildcard cert; tech blog deployed with tech-queenofsandiego-blog S3 bucket and standard CloudFront + Route53 CNAME
sailjada.com: Route53 hosted zone with existing wildcard cert; uses separate tech-sailjada-blog bucket and CloudFront distribution
dangerouscentaur.com: Uses existing wildcard CloudFront distribution (E2Q4UU71SRNTMB) on dc-sites S3 bucket; tech blog deployed as a subdirectory route with Namecheap DNS CNAME
burialsatseasandiego.com: GoDaddy-managed DNS; new ACM certificate provisioned with DNS validation; tech blog deployed to tech-burialsatseasandiego-blog S3 bucket with CloudFront; DNS validation CNAME automatically added to GoDaddy via API

Key Architectural Decisions

Separate S3 buckets per domain: Isolates configuration, permissions, and content; simplifies scaling and security policies
CloudFront caching strategy: Leverages CDN for global distribution; cache invalidation triggered on each new post for immediate visibility
Automated secret filtering: Regex-based scrubbing of credentials before publishing ensures transparency without security risk
Post-session automation: Stop hook ensures blog generation happens automatically without manual coordination
Session-aware routing: Blog posts are directed to the correct domain based on session context metadata rather than hardcoding