claude-home/networking/examples/ssh-troubleshooting.md

---
title: "SSH Troubleshooting Reference"
description: "Solutions for common SSH issues including UseKeychain errors, key deployment failures, permission denied, port conflicts, emergency access, and key rotation."
type: troubleshooting
domain: networking
tags: [ssh, troubleshooting, keys, authentication, emergency-access]
---

# SSH Troubleshooting Reference

## Common Configuration Issues

### UseKeychain Compatibility Error
**Error:** `Bad configuration option: usekeychain`

**Cause:** `UseKeychain yes` is macOS-specific and not supported on Linux

**Solution:** Remove or comment out the line from SSH config
```bash
# UseKeychain yes  # macOS only - remove on Linux
```

### Port Forwarding Conflicts
**Error:** `bind [127.0.0.1]:8080: Address already in use`

**Cause:** Local port already in use by another service

**Solutions:**
1. Remove LocalForward line from SSH config
2. Change to different port: `LocalForward 8081 localhost:80`
3. Find conflicting service: `sudo netstat -tulpn | grep :8080`

### Host Key Verification Loops
**Issue:** Asked to verify host key on every connection

**Cause:** SSH config discarding host keys with `UserKnownHostsFile /dev/null`

**Solution:** Change StrictHostKeyChecking policy
```bash
# Instead of:
StrictHostKeyChecking no
UserKnownHostsFile /dev/null

# Use:
StrictHostKeyChecking accept-new
```

## Key Deployment Issues

### ssh-copy-id False Warnings
**Warning:** `All keys were skipped because they already exist on the remote system`

**Issue:** Warning appears even when keys aren't actually deployed

**Solution:** Force deployment with `-f` flag
```bash
ssh-copy-id -f -i ~/.ssh/emergency_homelab_rsa.pub cal@10.10.0.42
```

### Permission Denied After Key Deployment
**Error:** `Permission denied (publickey)`

**Troubleshooting Steps:**
1. Check key permissions locally:
   ```bash
   ls -la ~/.ssh/
   # Private keys should be 600, public keys 644
   ```

2. Check authorized_keys on remote server:
   ```bash
   ssh user@server "ls -la ~/.ssh/authorized_keys"
   # Should be 600 with correct ownership
   ```

3. Verify key is actually deployed:
   ```bash
   ssh user@server "cat ~/.ssh/authorized_keys"
   ```

4. Test specific key file:
   ```bash
   ssh -i ~/.ssh/specific_key user@server
   ```

### Key Authentication Not Working
**Debug connection issues:**
```bash
# Verbose SSH connection for debugging
ssh -v user@server

# Super verbose for detailed debugging
ssh -vvv user@server

# Test specific identity file
ssh -i ~/.ssh/homelab_rsa -v cal@10.10.0.42
```

## Server-Side Issues

### SSH Service Not Running
**Check SSH service status:**
```bash
sudo systemctl status sshd
sudo systemctl start sshd
sudo systemctl enable sshd
```

### Firewall Blocking SSH
**Check firewall rules:**
```bash
# Ubuntu/Debian
sudo ufw status
sudo ufw allow ssh

# CentOS/RHEL
sudo firewall-cmd --list-services
sudo firewall-cmd --add-service=ssh --permanent
sudo firewall-cmd --reload
```

### Wrong SSH Port
**Check SSH configuration:**
```bash
sudo grep "^Port" /etc/ssh/sshd_config
# Update SSH client config accordingly
```

## Emergency Access Procedures

### Primary Keys Lost/Corrupted
1. **Use emergency keys:**
   ```bash
   ssh -i ~/.ssh/emergency_homelab_rsa cal@10.10.0.16
   ```

2. **Restore from NAS backup:**
   ```bash
   cp /mnt/NV2/ssh-keys/backup-*/homelab_rsa* ~/.ssh/
   chmod 600 ~/.ssh/homelab_rsa
   chmod 644 ~/.ssh/homelab_rsa.pub
   ```

3. **Generate new keys if needed:**
   ```bash
   ssh-keygen -t rsa -b 4096 -f ~/.ssh/new_homelab_rsa
   ssh-copy-id -i ~/.ssh/new_homelab_rsa.pub user@server
   ```

### Complete SSH Access Lost
1. **Physical/console access** (home servers)
2. **Cloud provider web console** (cloud servers)
3. **Recovery mode** if available
4. **Manual authorized_keys editing:**
   ```bash
   # On the server via console:
   echo "your-public-key-here" >> ~/.ssh/authorized_keys
   chmod 600 ~/.ssh/authorized_keys
   ```

## Network Connectivity Issues

### Connection Timeouts
**Check network connectivity:**
```bash
# Basic connectivity test
ping 10.10.0.42

# Check if SSH port is open
telnet 10.10.0.42 22
# Or using nc
nc -zv 10.10.0.42 22
```

### DNS Resolution Issues
**Bypass DNS with IP addresses:**
```bash
# Instead of hostname
ssh server.local

# Use IP directly
ssh 10.10.0.42
```

### VPN/Network Routing
**Check routing to server:**
```bash
traceroute 10.10.0.42
ip route | grep 10.10.0.0
```

## Configuration Validation

### SSH Config Syntax Check
```bash
# Test SSH config syntax
ssh -F ~/.ssh/config -T git@github.com 2>&1 | head
```

### Key Fingerprint Verification
```bash
# Local key fingerprint
ssh-keygen -lf ~/.ssh/homelab_rsa.pub

# Remote server's authorized keys fingerprints
ssh user@server "ssh-keygen -lf ~/.ssh/authorized_keys"
```

### Connection Test Script
```bash
#!/bin/bash
# Test all configured SSH hosts
for host in strat-database pihole docker-home akamai vultr; do
    echo "Testing $host..."
    if ssh -o ConnectTimeout=5 -o BatchMode=yes "$host" 'echo "OK"' 2>/dev/null; then
        echo "✅ $host: Connected successfully"
    else
        echo "❌ $host: Connection failed"
    fi
done
```

## Maintenance Commands

### Clean Up Known Hosts
```bash
# Remove specific host key
ssh-keygen -R 10.10.0.42

# Remove hostname and IP
ssh-keygen -R server.local
ssh-keygen -R 10.10.0.42
```

### Key Rotation Process
```bash
# Generate new key
ssh-keygen -t rsa -b 4096 -f ~/.ssh/homelab_rsa_new

# Deploy new key alongside old one
ssh-copy-id -i ~/.ssh/homelab_rsa_new.pub user@server

# Test new key works
ssh -i ~/.ssh/homelab_rsa_new user@server

# Update SSH config to use new key
# Remove old public key from server authorized_keys
# Archive old key pair
```

## Server-Specific Troubleshooting

### Home Lab Servers (10.10.0.x)
- **Physical access available** for recovery
- **Container hosts** may need different user contexts
- **Shared credentials** historically used (security risk)

### Cloud Servers
- **Provider console access** as fallback
- **Root user** typically used (create non-root users)
- **Different security contexts** than home network

## Related Documentation

- Patterns: `patterns/networking/ssh-key-management.md`
- Complete setup: `examples/networking/ssh-homelab-setup.md`