Building Automated Technical Blog Infrastructure Across Four Sites with Session-Based Content Generation

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This session implemented a comprehensive automated technical documentation system for four distinct web properties: queenofsandiego.com, sailjada.com, dangerouscentaur.com, and burialsatseasandiego.com. Each site now has a dedicated tech blog subdomain that auto-generates detailed posts capturing every infrastructure change, code modification, and deployment action—providing complete transparency for stakeholders like Sergio who need to see the exact technical work being performed.

What Was Done

Created automated tech blog infrastructure at tech.queenofsandiego.com, tech.sailjada.com, tech.dangerouscentaur.com, and tech.burialsatseasandiego.com
Built session-aware blog post generator that captures file modifications, command executions, and infrastructure changes
Integrated Claude Code hooks to trigger post generation at session end
Added navigation links to Ship's Papers menus across all four properties
Set up S3 static hosting, CloudFront CDN distribution, and DNS routing for each tech blog
Implemented credential scrubbing to ensure no secrets appear in published posts

Technical Architecture

The system comprises three primary components:

1. Blog Generator Engine

The core generator (/Users/cb/Documents/repos/tools/tech_blog_generator.py) reads Claude Code session transcripts in JSONL format and extracts:

File Operations: Exact file paths modified, created, or edited with timestamps
Command Executions: Every CLI command run, with arguments visible but credentials redacted
Tool Use: AWS API calls, infrastructure changes, DNS modifications
Context: User requests that drove the work, reasoning from the agent

The generator parses session data to identify infrastructure changes by pattern-matching command outputs and tool invocations, then structures findings into semantic HTML sections. Sensitive data (API keys, passwords, credential strings) are detected via regex patterns and replaced with placeholder text like [REDACTED_AWS_KEY].

2. Infrastructure Initialization

The infrastructure script (/Users/cb/Documents/repos/tools/tech_blog_init.py) provisions identical AWS resources for each tech blog:

S3 Bucket Creation: One bucket per tech blog (e.g., qos-tech-blog, jada-tech-blog, dc-sites, bats-tech-blog) with static website hosting enabled and index.html/error.html routing configured
CloudFront Distribution: Each bucket gets a custom CDN distribution with:
- Origin pointing to S3 website endpoint
- Default root object set to index.html
- Compression enabled for HTML, CSS, JSON
- Cache behaviors with appropriate TTLs
SSL/TLS Certificates: Leveraging existing wildcard ACM certificates:
- *.queenofsandiego.com wildcard cert for tech.queenofsandiego.com
- *.sailjada.com wildcard cert for tech.sailjada.com
- New certificate request and DNS validation for tech.dangerouscentaur.com
- GoDaddy-managed certificate for tech.burialsatseasandiego.com
DNS Configuration: CNAME records pointing to CloudFront distributions:
- Route53 for queenofsandiego.com and sailjada.com properties
- Namecheap for dangerouscentaur.com (wildcard CF dist E2Q4UU71SRNTMB reused)
- GoDaddy for burialsatseasandiego.com

3. Claude Code Integration Hook

A bash script at /Users/cb/.claude/hooks/tech_blog_stop.sh runs automatically when a Claude Code session ends. The hook:

Locates the current session's transcript file in /Users/cb/.claude/projects
Determines which repository/site the work involved by parsing file paths
Routes the transcript to the appropriate blog generator
Uploads generated HTML to the corresponding S3 bucket
Invalidates the CloudFront distribution cache for immediate visibility
Logs all operations to /Users/cb/.claude/logs/tech_blog_hook.log

The hook is registered in Claude Code settings (/Users/cb/.claude/settings.json) under hooks.onSessionStop, ensuring it fires after every session completes.

Infrastructure Details

Each tech blog follows an identical deployment pattern. For example, queenofsandiego.com:

S3 Bucket: qos-tech-blog in us-west-2 region
CloudFront Distribution: Custom domain tech.queenofsandiego.com, distribution ID visible in CloudFront console
SSL Certificate: Wildcard cert *.queenofsandiego.com (existing, no validation needed)
DNS CNAME: tech.queenofsandiego.com → d[distribution-id].cloudfront.net in Route53 hosted zone

The dangerouscentaur tech blog reuses the existing wildcard CloudFront distribution (E2Q4UU71SRNTMB) already serving from the dc-sites S3 bucket, adding a tech-blog prefix path in the S3 key structure rather than creating a separate distribution.

For burialsatseasandiego.com (GoDaddy-managed DNS), the new ACM certificate required DNS validation. The validation CNAME record was programmatically added to GoDaddy's DNS via their API, confirmed active, then the certificate was issued.

Key Decisions

Why Session-Based Generation? Rather than post-by-feature or post-by-day, session-based generation captures the natural workflow boundary. Each Claude Code session represents a focused effort, and the transcript contains complete context (what was asked, what was tried, what succeeded). This provides chronological accountability and technical precision.

Why Pattern Matching for Infrastructure Detection? The generator uses regex patterns to identify infrastructure changes from command output and tool use entries. Examples include detecting CloudFront distribution creation from AWS CLI JSON responses, S3 bucket names from tool invocations, and DNS records from Route53 API calls. This approach is resilient to tool output variations and requires no external state tracking.

Why Wildcard Certificates? Existing *.queenofsandiego.com and *.sailjada.com wildcards already covered these tech subdomains, eliminating certificate provisioning overhead. For dangerouscentaur.com (which didn't have a wildcard), a new certificate was requested. GoD