diff --git a/WINDOWS.md b/WINDOWS.md
index 4780e64b1..9d0414ddc 100644
--- a/WINDOWS.md
+++ b/WINDOWS.md
@@ -29,3 +29,155 @@ Surprisingly: most guides in fact recommend running everything in an Admin Power
 - Install NVM: Restart PowerShell (still as Admin) and run `choco install nvm -y`
 - Install Node: Restart PowerShell (still as Admin) and run `nvm install node`
 - Install Codebuff: Run `npm i -g codebuff`
+
+---
+
+## Common Windows Issues & Troubleshooting
+
+Running into problems? Here are solutions to the most common Windows-specific issues.
+
+### Issue: "Failed to determine latest version" on First Run
+
+**Symptom**:
+```powershell
+PS C:\> codebuff
+❌ Failed to determine latest version
+Please check your internet connection and try again
+```
+
+**Cause**:
+Codebuff checks GitHub for the latest release on first run. This fails when:
+- Corporate firewall blocks `github.com`
+- Proxy settings not configured
+- Network connectivity issues
+- VPN required for external access
+
+**Solutions**:
+
+1. **Verify GitHub access**:
+   ```powershell
+   curl https://github.com/CodebuffAI/codebuff/releases.atom
+   ```
+   If this fails, you have a network/firewall issue.
+
+2. **Configure npm proxy** (if behind corporate proxy):
+   ```powershell
+   npm config set proxy http://your-proxy-server:port
+   npm config set https-proxy http://your-proxy-server:port
+   ```
+
+3. **Disable VPN temporarily** or whitelist GitHub in your firewall
+
+4. **Clear npm cache and reinstall**:
+   ```powershell
+   npm cache clean --force
+   npm uninstall -g codebuff
+   npm install -g codebuff
+   ```
+
+**Reference**: Issue [#294](https://github.com/CodebuffAI/codebuff/issues/294)
+
+---
+
+### Issue: Git Commands Fail on Windows
+
+**Symptom**:
+Git operations (commit, rebase, complex commands) fail with syntax errors or unexpected behavior.
+
+**Cause**:
+Codebuff uses Windows `cmd.exe` for command execution, which:
+- Does not support bash syntax (HEREDOC, process substitution)
+- Has limited quote escaping compared to bash
+- Cannot execute complex git commands that work in Git Bash
+
+**Solutions**:
+
+1. **Install Git for Windows** (if not already installed):
+   - Download from https://git-scm.com/download/win
+   - Ensures git commands are available in PATH
+
+2. **Use Git Bash terminal** instead of PowerShell:
+   - Git Bash provides better compatibility with bash-style commands
+   - Launch Git Bash and run `codebuff` from there
+
+3. **Or use WSL (Windows Subsystem for Linux)**:
+   - Provides full Linux environment with native bash
+   - Install: `wsl --install` in PowerShell (Admin)
+   - Run codebuff inside WSL for best compatibility
+
+**Note**: Even when running in Git Bash, Codebuff spawns commands using `cmd.exe`. Using WSL provides the most reliable experience for git operations.
+
+**Reference**: Issue [#274](https://github.com/CodebuffAI/codebuff/issues/274)
+
+---
+
+### Issue: Login Browser Window Fails to Open
+
+**Symptom**:
+```
+Press ENTER to open your browser and finish logging in...
+
+Caught exception: Error: Executable not found in $PATH: "start"
+Error: Executable not found in $PATH: "start"
+TLCWeb > Unable to login. Please try again by typing "login" in the terminal.
+```
+
+**Cause**:
+When running Codebuff in Git Bash (MINGW64), the `start` command is not available in PATH. The browser auto-open feature fails.
+
+**Solutions**:
+
+1. **Manually open the login URL** (easiest):
+   - Codebuff displays the login URL after the error
+   - Copy the full URL starting with `https://codebuff.com/login?auth_code=...`
+   - Paste into your browser
+   - Complete login in browser
+   - Return to terminal - login will succeed
+
+2. **Use native Windows terminals**:
+   - PowerShell: `powershell`
+   - Command Prompt: `cmd`
+   - These have `start` command available
+
+3. **Clear cache if login still fails** (per issue #299):
+   ```powershell
+   npm cache clean --force
+   npm uninstall -g codebuff
+   npm install -g codebuff
+   ```
+
+**Reference**: Issue [#299](https://github.com/CodebuffAI/codebuff/issues/299)
+
+---
+
+### Message: "Update available: error → [version]"
+
+**What it means**:
+This is **not an error** - it's an informational message indicating:
+- Your local binary needs to be downloaded/updated
+- "error" is a placeholder version (not a real error state)
+- Codebuff will automatically download the correct version
+
+**What to do**:
+- Wait for the download to complete: "Download complete! Starting Codebuff..."
+- If download fails, check your internet connection
+- If it persists, try the solutions in "Failed to determine latest version" above
+
+**Reference**: Issue [#299](https://github.com/CodebuffAI/codebuff/issues/299)
+
+---
+
+### Still Having Issues?
+
+If these solutions don't resolve your problem:
+
+1. **Search existing issues**: https://github.com/CodebuffAI/codebuff/issues
+2. **Open a new issue**: https://github.com/CodebuffAI/codebuff/issues/new
+3. **Join Discord community**: https://codebuff.com/discord
+
+When reporting issues, please include:
+- Windows version: `winver` command
+- PowerShell/Git Bash/CMD
+- Node version: `node --version`
+- Full error message
+- Steps to reproduce