Setting Up a Chirpy Jekyll Blog - Part 1: Local Development

Series Overview

This is Part 1 of a series on setting up and deploying a Chirpy Jekyll blog:

1. Part 1: Local Development (this post)
2. Part 2: Deploying to Production (InMotion/VPS) - Coming Soon
3. Part 3: Custom Domain & SSL - Coming Soon

What is Chirpy?

Chirpy is a minimal, responsive Jekyll theme designed for technical writing. It’s perfect for:

• Security research blogs
• HackTheBox/TryHackMe writeups
• Development documentation
• Personal portfolios

Local Setup

Prerequisites

# Install Ruby and Jekyll (Kali Linux)
sudo apt install ruby-full build-essential zlib1g-dev
gem install jekyll bundler

Installation

1. Clone the Chirpy starter:

   git clone https://github.com/cotes2020/chirpy-starter.git ranger-chirpy
   cd ranger-chirpy
   bundle install
   

2. Run locally:

   bundle exec jekyll serve
   # Or create an alias:
   alias jchirpy='cd /path/to/blog && bundle exec jekyll serve'
   

3. Access at: http://127.0.0.1:4000/

Configuration

Basic Site Settings

Edit _config.yml:

title: Ranger                              # Site name
tagline: Security Research & HTB Writeups # Subtitle
social:
  name: Ranger                             # Author name in footer
avatar: /assets/img/profile.png           # Sidebar profile picture

Adding Profile Picture

# Copy image to assets
cp ~/images/profile.png assets/img/profile.png

# Update _config.yml
avatar: /assets/img/profile.png

Creating Posts

File Naming Convention

Posts must follow: YYYY-MM-DD-title-with-dashes.md

_posts/
├── 2025-11-17-jerry-hackthebox-walkthrough.md
├── 2025-11-17-building-python-pentest-tool.md
└── 2025-11-17-setting-up-chirpy-part-1.md

Front Matter Template

---
title: "Your Post Title"
date: 2025-11-17 00:00:00 +0000
categories: [Primary, Secondary]
tags: [tag1, tag2, tag3]
pin: false
math: false
mermaid: false
---

Category Strategy

I organize posts by purpose:

Category	Use Case
[HackTheBox, Easy]	HTB writeups by difficulty
[TryHackMe, Medium]	THM writeups
[Security, Tools]	Custom tool development
[Blogging, Chirpy]	Meta posts about the blog

Chirpy auto-generates category pages at /categories/hackthebox/, etc.

Common Issues

Posts Not Showing - Future Date

Problem: Jekyll skips posts with future timestamps

Skipping: _posts/2025-11-17-post.md has a future date

Solution: Use past/current time in front matter:

# BAD - might be in future depending on timezone
date: 2025-11-17 23:00:00 +0000

# GOOD - safe past time
date: 2025-11-17 00:00:00 +0000

Changes Not Appearing

1. Check Jekyll output for errors/warnings
2. Restart server after _config.yml changes
3. Clear cache: Delete .jekyll-cache/ folder

Current Blog Structure

ranger-chirpy/
├── _config.yml           # Site configuration
├── _posts/               # All blog posts
│   ├── HTB writeups
│   ├── Tool documentation
│   └── Setup guides
├── _tabs/                # Sidebar navigation
├── assets/
│   └── img/              # Profile pic, post images
└── _site/                # Generated static site

What’s Next

In Part 2, I’ll cover:

• Choosing a hosting provider (InMotion, DigitalOcean, GitHub Pages)
• Deploying the static site
• Setting up CI/CD for automatic builds
• Custom domain configuration
• SSL/HTTPS setup

Why Jekyll + Chirpy?

• Fast: Static HTML = no database queries
• Secure: No PHP/dynamic code to exploit
• Free hosting: GitHub Pages support
• Markdown: Write posts in familiar format
• Version control: Git-based workflow
• Offline writing: No internet required for drafts

Resources

• Chirpy Theme Demo
• Chirpy Documentation
• Jekyll Docs
• Markdown Guide

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This is a living document. As I add more features to the blog, I’ll update this series.

Series: Setting Up Chirpy Jekyll Blog Part 1 of 3