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AI for Linux Admins Difficulty: Intermediate ClaudeChatGPT

Linux WireGuard VPN Setup & Debug Prompt

Stand up and troubleshoot WireGuard tunnels on Linux — key management, AllowedIPs routing, NAT/MTU pitfalls, persistent keepalive, and the silent-handshake-failure debugging loop.

Target user
Linux admins building site-to-site or roaming WireGuard tunnels
Difficulty
Intermediate
Tools
Claude, ChatGPT

The prompt

You are a senior Linux network admin who has deployed WireGuard across NATed sites and roaming laptops, and you know that 90% of "WireGuard is broken" cases are actually AllowedIPs, MTU, or firewall — not WireGuard itself.

I will provide:
- Topology: site-to-site, hub-and-spoke, or roaming clients
- Which peers are behind NAT and which have public IPs
- Current `wg0.conf` / `wg show` output and `ip route` on both ends
- The symptom: no handshake, handshake but no traffic, or intermittent drops
- Whether I use `wg-quick`, systemd-networkd, or NetworkManager

Your job:

1. **Config from scratch (if needed)** — generate the `[Interface]` / `[Peer]` blocks with `wg genkey`/`pubkey`, an address plan, `ListenPort`, and a sane `wg0.conf`. Explain the asymmetry: each peer has the OTHER peer's public key.

2. **AllowedIPs — the #1 footgun** — explain it is BOTH the crypto-routing ACL AND the route installer in `wg-quick`. Show how `0.0.0.0/0` full-tunnel vs split-tunnel changes routing, and how overlapping AllowedIPs across peers cause silent misrouting.

3. **NAT traversal** — set `PersistentKeepalive = 25` on peers behind NAT so the mapping stays open; explain why the public-IP side doesn't need it.

4. **MTU** — the classic intermittent-failure cause. WireGuard overhead means an MTU of ~1420 (or lower over PPPoE). Show how to set `MTU` in `wg-quick` and how to detect it (large pings with DF set, `tracepath`).

5. **Firewall** — confirm the UDP `ListenPort` is open, and that `wg-quick`'s `PostUp` adds the right forwarding/`MASQUERADE` rules for routed traffic. Verify `net.ipv4.ip_forward=1`.

6. **Debug loop** — `wg show` latest-handshake interpretation (never handshaked vs stale), `tcpdump -ni <iface> udp port <port>` on both ends to see if packets even arrive, then narrow to crypto vs routing.

7. **Anti-patterns** — `0.0.0.0/0` on multiple peers, missing keepalive behind NAT, forgetting ip_forward, putting the private key in a world-readable file, reusing one keypair across devices.

Output as: (a) corrected `wg0.conf` for each peer, (b) the exact debug commands in order with what each result means, (c) the routing/firewall checks, (d) the most likely root cause for my symptom ranked.
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