diff --git a/README.md b/README.md
index cbd06f9..5e8b26b 100644
--- a/README.md
+++ b/README.md
@@ -46,7 +46,61 @@ Instead of running one test case, Flakestorm takes a single "Golden Prompt", gen
 
 ## Quick Start
 
-### Installation
+### Installation Order
+
+1. **Install Ollama first** (system-level service)
+2. **Create virtual environment** (for Python packages)
+3. **Install flakestorm** (Python package)
+4. **Start Ollama and pull model** (required for mutations)
+
+### Step 1: Install Ollama (System-Level)
+
+FlakeStorm uses [Ollama](https://ollama.ai) for local model inference. Install this first:
+
+**macOS Installation:**
+
+```bash
+# Option 1: Homebrew (recommended)
+brew install ollama
+
+# If you get permission errors, fix permissions first:
+sudo chown -R $(whoami) /Users/imac-frank/Library/Logs/Homebrew
+sudo chown -R $(whoami) /usr/local/Cellar
+sudo chown -R $(whoami) /usr/local/Homebrew
+brew install ollama
+
+# Option 2: Official Installer
+# Visit https://ollama.ai/download and download the macOS installer (.dmg)
+```
+
+**Windows Installation:**
+
+1. Visit https://ollama.com/download/windows
+2. Download `OllamaSetup.exe`
+3. Run the installer and follow the wizard
+4. Ollama will be installed and start automatically
+
+**Linux Installation:**
+
+```bash
+# Using the official install script
+curl -fsSL https://ollama.com/install.sh | sh
+
+# Or using package managers (Ubuntu/Debian example):
+sudo apt install ollama
+```
+
+**After installation, start Ollama and pull the model:**
+
+```bash
+# Start Ollama (macOS/Linux - Windows starts automatically)
+ollama serve
+
+# In another terminal, pull the model
+ollama pull qwen3:8b
+```
+
+### Step 2: Install flakestorm (Python Package)
 
 **Using a virtual environment (recommended):**
 
@@ -65,19 +119,7 @@ pip install flakestorm
 pipx install flakestorm
 ```
 
-**Note:** Requires Python 3.10 or higher. On macOS, Python environments are externally managed, so using a virtual environment is required.
-
-### Prerequisites
-
-Flakestorm uses [Ollama](https://ollama.ai) for local model inference:
-
-```bash
-# Install Ollama (macOS/Linux)
-curl -fsSL https://ollama.ai/install.sh | sh
-
-# Pull the default model
-ollama pull qwen3:8b
-```
+**Note:** Requires Python 3.10 or higher. On macOS, Python environments are externally managed, so using a virtual environment is required. Ollama runs independently and doesn't need to be in your virtual environment.
 
 ### Initialize Configuration
 
diff --git a/docs/CONTRIBUTING.md b/docs/CONTRIBUTING.md
index 557e9d6..1ad1e7e 100644
--- a/docs/CONTRIBUTING.md
+++ b/docs/CONTRIBUTING.md
@@ -29,8 +29,27 @@ Please be respectful and constructive in all interactions. We welcome contributo
    ```
 
 3. **Install Ollama** (for mutation generation)
+
+   **macOS:**
+   ```bash
+   # Option 1: Homebrew (recommended)
+   brew install ollama
+
+   # Option 2: Official installer
+   # Visit https://ollama.ai/download and download the .dmg file
+   ```
+
+   **Windows:**
+   - Visit https://ollama.com/download/windows
+   - Download and run `OllamaSetup.exe`
+
+   **Linux:**
+   ```bash
+   curl -fsSL https://ollama.com/install.sh | sh
+   ```
+
+   **Then pull the model:**
    ```bash
-   curl -fsSL https://ollama.ai/install.sh | sh
    ollama pull qwen3:8b
    ```
 
diff --git a/docs/USAGE_GUIDE.md b/docs/USAGE_GUIDE.md
index a1ce900..02d20a5 100644
--- a/docs/USAGE_GUIDE.md
+++ b/docs/USAGE_GUIDE.md
@@ -90,16 +90,78 @@ flakestorm is an **adversarial testing framework** for AI agents. It applies cha
 - **Ollama** (for local LLM mutation generation)
 - **Rust** (optional, for performance optimization)
 
-### Step 1: Install Ollama
+### Installation Order
+
+**Important:** Install Ollama first (it's a system-level service), then set up your Python virtual environment:
+
+1. **Install Ollama** (system-level, runs independently)
+2. **Create virtual environment** (for Python packages)
+3. **Install flakestorm** (Python package)
+4. **Start Ollama service** (if not already running)
+5. **Pull the model** (required for mutation generation)
+
+### Step 1: Install Ollama (System-Level)
+
+**macOS Installation:**
 
 ```bash
-# macOS
+# Option 1: Homebrew (recommended)
 brew install ollama
 
-# Linux
+# If you get permission errors, fix permissions first:
+sudo chown -R $(whoami) /Users/imac-frank/Library/Logs/Homebrew
+sudo chown -R $(whoami) /usr/local/Cellar
+sudo chown -R $(whoami) /usr/local/Homebrew
+brew install ollama
+
+# Option 2: Official Installer (if Homebrew doesn't work)
+# Visit https://ollama.ai/download and download the macOS installer
+# Double-click the .dmg file and follow the installation wizard
+```
+
+**Windows Installation:**
+
+1. **Download the Installer:**
+   - Visit https://ollama.com/download/windows
+   - Download `OllamaSetup.exe`
+
+2. **Run the Installer:**
+   - Double-click `OllamaSetup.exe`
+   - Follow the installation wizard
+   - Ollama will be installed and added to your PATH automatically
+
+3. **Verify Installation:**
+   ```powershell
+   ollama --version
+   ```
+
+**Linux Installation:**
+
+```bash
+# Install using the official script
 curl -fsSL https://ollama.com/install.sh | sh
 
-# Start Ollama service
+# Or using package managers:
+# Ubuntu/Debian
+sudo apt install ollama
+
+# Fedora/RHEL
+sudo dnf install ollama
+
+# Arch Linux
+sudo pacman -S ollama
+```
+
+**Start Ollama Service:**
+
+After installation, start Ollama:
+
+```bash
+# macOS/Linux - Start the service
+ollama serve
+
+# Windows - Ollama runs as a service automatically after installation
+# You can also start it manually from the Start menu or run:
 ollama serve
 ```
 
@@ -113,12 +175,12 @@ ollama pull qwen2.5-coder:7b
 ollama run qwen2.5-coder:7b "Hello, world!"
 ```
 
-### Step 3: Install flakestorm
+### Step 3: Create Virtual Environment and Install flakestorm
 
-**Important:** On macOS (and some Linux distributions), Python environments are externally managed. You should use a virtual environment:
+**Important:** On macOS (and some Linux distributions), Python environments are externally managed. You must use a virtual environment:
 
 ```bash
-# Create a virtual environment
+# Create a virtual environment (do this AFTER installing Ollama)
 python3 -m venv venv
 
 # Activate it (macOS/Linux)
@@ -137,6 +199,8 @@ cd flakestorm
 pip install -e ".[dev]"
 ```
 
+**Note:** Ollama is installed at the system level and doesn't need to be in your virtual environment. The virtual environment is only for Python packages (flakestorm and its dependencies).
+
 **Alternative: Using pipx (for CLI applications)**
 
 If you only want to use flakestorm as a CLI tool (not develop it), you can use `pipx`:
@@ -758,6 +822,32 @@ agent:
 3. Improve your agent's handling of those cases
 4. Re-run tests
 
+#### "Homebrew permission errors when installing Ollama"
+
+If you get `Operation not permitted` errors when running `brew install ollama`:
+
+```bash
+# Fix Homebrew permissions
+sudo chown -R $(whoami) /Users/imac-frank/Library/Logs/Homebrew
+sudo chown -R $(whoami) /usr/local/Cellar
+sudo chown -R $(whoami) /usr/local/Homebrew
+
+# Then try again
+brew install ollama
+
+# Or use the official installer from https://ollama.ai/download instead
+```
+
+#### "Ollama binary contains HTML or syntax errors"
+
+If you downloaded a file that contains HTML instead of the binary:
+
+1. **macOS:** Use Homebrew or download the official `.dmg` installer from https://ollama.ai/download
+2. **Windows:** Download `OllamaSetup.exe` from https://ollama.com/download/windows
+3. **Linux:** Use the official install script: `curl -fsSL https://ollama.com/install.sh | sh`
+
+Never download binaries directly via curl from the download page - always use the official installers or package managers.
+
 ### Debug Mode
 
 ```bash