3 WireGuard VPN Mistakes That Broke Our Remote Server Access

Short summary

A team migrating from OpenVPN to WireGuard shares three real-world configuration mistakes that caused outages and security exposures. Key-pair reuse across peers silently kicks the older connection off without errors; AllowedIPs=0.0.0.0/0 without proper NAT masquerade rules breaks internet access while SSH still works; and lack of process gates means onboarding shortcuts recur. The core lesson is that WireGuard's silent failure mode demands enforced processes, not just good intentions.

• •Reusing key pairs across peers causes silent connection drops — WireGuard lets the most recent peer win with zero error messages
• •Setting AllowedIPs=0.0.0.0/0 without matching server-side NAT rules breaks general internet access while internal SSH keeps working
• •Process gates (scripts, enforced key generation) are essential because WireGuard config mistakes never throw errors

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