Building a Multi-Site Automated Technical Blog Generator with AWS Infrastructure

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This session focused on creating a comprehensive technical documentation system that automatically publishes detailed engineering notes from development sessions across four separate domain tech blogs. The goal was to provide complete transparency into technical work being performed on Queen of San Diego, Sail Jada, Dangerous Centaur, and Burials at Sea San Diego properties.

Architecture Overview

The system consists of three main components:

Tech Blog Generator: Parses Claude Code session transcripts and generates granular HTML blog posts
Infrastructure Init: Provisions S3 buckets, CloudFront distributions, and DNS records for each tech blog domain
Stop Hook: Automatically invokes the generator at the end of each development session

Technical Implementation Details

Blog Generator Script

Created /Users/cb/Documents/repos/tools/tech_blog_generator.py to extract session data and convert it into structured blog posts. The generator:

Reads Claude Code session transcripts in JSONL format from the Claude projects directory
Extracts file modifications, commands executed, and reasoning from agent notes
Filters out sensitive data (credentials, API keys, tokens) using regex patterns
Groups changes by domain (queenofsandiego.com, sailjada.com, dangerouscentaur.com, burialsatseasandiego.com)
Generates HTML posts with sections for What Was Done, Technical Details, Infrastructure Changes, and Key Decisions
Uploads posts to the appropriate S3 bucket and invalidates the CloudFront distribution

The script uses environment variables to determine which AWS profile and S3 bucket to target based on extracted domain context. It maintains a manifest file in each bucket to track published posts and prevent duplicates.

Infrastructure Initialization Script

Created /Users/cb/Documents/repos/tools/tech_blog_init.py to provision cloud resources for all four tech blog domains:

S3 Buckets: Created qos-tech-blog, jada-tech-blog, dc-sites (shared), and bats-tech-blog buckets with versioning enabled and public read access configured
CloudFront Distributions: Deployed distributions for each domain using existing wildcard ACM certificates where available
DNS Records: Configured Route53 aliases for queenofsandiego.com and sailjada.com; added CNAME records via Namecheap for dangerouscentaur.com; configured GoDaddy DNS for burialsatseasandiego.com

The script handles domain-specific DNS providers:

Route53: Used for zones under AWS management with hosted zone IDs Z2M2Z7XYYX2ZQJ and Z1BK3GN8Z0OQYT
Namecheap: CNAME pointing to dangerouscentaur wildcard CloudFront distribution (E2Q4UU71SRNTMB)
GoDaddy: REST API integration for burialsatseasandiego.com DNS management with ACM certificate validation

Claude Code Integration

Created /Users/cb/.claude/hooks/tech_blog_stop.sh and registered it in Claude Code settings to execute automatically when sessions end. The hook:

Sources environment variables from repos.env
Identifies which domain the session was working on
Invokes the blog generator with appropriate parameters
Logs output to ~/.claude/logs/tech_blog_generation.log
Ensures generated posts are published within seconds of session completion

Infrastructure Details

S3 Bucket Configuration

Each tech blog bucket is configured with:

Versioning enabled for content history and rollback capability
Block public access disabled with explicit bucket policies allowing CloudFront origin access
Default index.html for root path requests
Error document configuration for 404 handling

CloudFront Distributions

Distributions created with:

Origin configuration pointing to S3 bucket REST endpoints
Cache behaviors with TTL of 300 seconds for HTML, longer for static assets
ACM certificates: wildcard certificates for *.queenofsandiego.com and *.sailjada.com; domain-specific for dangerouscentaur and burialsatseasandiego
HTTP/2 and HTTP/3 support enabled
HTTPS redirect configured to ensure secure access

DNS Configuration

DNS records established across three providers:

tech.queenofsandiego.com: Route53 alias to CloudFront distribution
tech.sailjada.com: Route53 alias to CloudFront distribution
tech.dangerouscentaur.com: Namecheap CNAME to shared wildcard CloudFront distribution
tech.burialsatseasandiego.com: GoDaddy DNS CNAME with ACM certificate validation records

Additional Work: Site Content Updates

During this session, also addressed:

Updated queenofsandiego.com/index.html and other site files to add Ship's Papers navigation menu entries linking to the tech blogs
Fixed event and promotion pages (events.html, mothersday.html) with corrected minimum guest counts
Created email templates for upcoming 2026 events (Gipsy Kings, Birthday Sail, Kool Gang) with validation tooling
Created email_template_validator.py to validate email HTML structure and compliance
Created jada_unsubscribe_monitor.py to track unsubscribe trends and identify potential list health issues
Updated blast scheduling system in jada_blast.py with refined event email handling

Key Decisions and Rationale

Multi-Provider DNS Approach: Rather than migrating all domains to a single DNS provider, leveraged existing infrastructure (Route53, Namecheap, GoDaddy) to minimize disruption while establishing tech blogs across all four properties.

Automated Session-Based Publishing: The hook-based approach ensures posts are generated immediately after work completes, with no manual intervention. This provides real-time visibility into engineering activities without requiring developers to write documentation.

Credential Filtering: The generator actively scrubs sensitive data using multiple regex patterns to prevent accidental exposure of API keys, passwords, or tokens in published posts.

Granular Documentation: Posts capture exact file paths, function names, AWS resource identifiers, and command examples to provide engineers (particularly stakeholders like Sergio) with detailed visibility into what was built and why