Building Automated Technical Documentation: Multi-Site Blog Infrastructure with Session Capture

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What Was Done

Implemented a comprehensive automated technical blog system across four domains (queenofsandiego.com, sailjada.com, dangerouscentaur.com, and burialsatseasandiego.com) that captures development session activity and publishes granular technical posts in real-time. This system integrates with Claude Code's session management to extract work artifacts and infrastructure changes, then publishes sanitized technical documentation to dedicated tech subdomains.

Technical Architecture

Core Components

tech_blog_generator.py — Main Python module that parses Claude Code JSONL session transcripts, extracts file modifications and command executions, filters sensitive data (credentials, API keys, tokens), and generates HTML blog posts with proper metadata.
tech_blog_init.py — Infrastructure provisioning script that creates S3 buckets (one per domain), CloudFront distributions for static delivery, Route53 DNS records with health checks, and ACM certificate management with DNS validation.
tech_blog_stop.sh — Claude Code Stop hook that executes automatically at session end, triggers the blog generator, and uploads new posts to the appropriate tech subdomain.
Claude Code Settings Integration — Registered stop hook in ~/.claude/settings.json pointing to the executable stop script, ensuring every development session generates documentation.

Infrastructure Topology

Each technical blog runs on identical infrastructure:

S3 Buckets: qos-tech-blog, jada-tech-blog, dc-sites-tech-blog, bats-tech-blog — Static HTML storage with versioning and lifecycle policies.
CloudFront Distributions — Origin set to respective S3 buckets with custom domain CNAMEs (e.g., tech.queenofsandiego.com), HTTP/2 enabled, gzip compression, cache behaviors for index.html (minimal TTL) and assets (24hr TTL).
Route53 / DNS — For sailjada.com and queenofsandiego.com domains (Route53 hosted zones), A records point to CloudFront distribution aliases. For dangerouscentaur.com (existing wildcard CF dist on Namecheap) and burialsatseasandiego.com (GoDaddy DNS), CNAME records added for tech subdomains.
ACM Certificates — Leveraged existing wildcard certs (*.queenofsandiego.com, *.sailjada.com) for the CloudFront distributions; created new cert for tech.dangerouscentaur.com and validated via GoDaddy DNS for burialsatseasandiego.com.

Session Capture Mechanism

JSONL Transcript Parsing

Claude Code stores session transcripts as JSON Lines format in ~/.claude/sessions/. Each line contains message metadata including:

{"type": "tool_use", "name": "bash", "input": {"command": "..."}, ...}
{"type": "tool_result", "output": "..."}

The blog generator extracts:

File write/edit operations from filesystem commands and tool outputs
Bash commands executed (except those matching credential patterns)
AWS CLI operations (showing resource names, not credentials)
Configuration changes with before/after snippets

Data Sanitization

Critical security step — the generator uses regex patterns to detect and redact:

AWS credentials, API keys, and tokens
Password strings in environment variables or configs
GoDaddy/Namecheap API credentials
Email addresses and phone numbers
Database connection strings
SSH keys and personal identifiers

Redacted sections appear as [REDACTED: credential type] in the published post.

Integration Points

Ship's Papers Navigation

Updated HTML navigation menus across all four sites to include "Technical Blog" links in the Ship's Papers section. This makes development activity visible to stakeholders (like Sergio) without exposing infrastructure details.

CloudFront Invalidation

The stop hook includes cache invalidation for /* on the tech blog CloudFront distribution, ensuring new posts appear immediately without waiting for TTL expiration.

Timestamped Posts

Each generated post includes:

Session start/end timestamps
Ordered list of file modifications with line counts changed
Chronological command execution list
Infrastructure resource changes with before/after state
Decision rationale for architectural changes

Key Technical Decisions

Stop Hook vs. Scheduled Job

Using Claude Code's Stop hook (execution at session end) rather than cron jobs ensures documentation is generated only when actual work occurs, eliminating empty posts and keeping the blog focused on real activity.

Per-Domain vs. Centralized Blog

Created separate tech blogs for each domain rather than a single centralized blog. This allows different stakeholders to view relevant documentation (Sergio sees queenofsandiego.com work; other crew sees their domain's activity) and isolates credential risk—if one domain's S3 is compromised, only that blog is affected.

Static HTML Generation

Rather than a dynamic backend, posts are generated as static HTML and pushed to S3. This provides:

No server management or authentication needed
CloudFront edge caching for instant delivery
Immutable post history (versioned in S3)
No database or runtime dependencies

Route53 vs. External DNS

For domains already in Route53 (queenofsandiego.com, sailjada.com), A records point directly to CloudFront aliases with health checks. For external DNS (dangerouscentaur at Namecheap, burialsatseasandiego at GoDaddy), CNAME records created, adding a small lookup overhead but avoiding DNS provider lock-in.

Infrastructure Provisioning Details

S3 Bucket Creation:

aws s3api create-bucket \
  --bucket qos-tech-blog \
  --region us-west-2 \
  --create-bucket-configuration LocationConstraint=us-west-2

aws s3api put-bucket-versioning \
  --bucket qos-tech-blog \
  --versioning-configuration Status=Enabled

aws s3api put-bucket-public-access-block \
  --bucket qos-tech-blog \
  --public-access-block-configuration \
  "BlockPublicAcls=true,IgnorePublicAcls=true,BlockPublicPolicy=false,RestrictPublicBuckets=false"

CloudFront Distribution:

Configured with S3 bucket as origin, origin access identity (OAI) for secure bucket access,