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How to Debug AI Agent Connectivity Failures Behind Corporate Firewalls

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AI agents deployed inside corporate networks often fail silently due to firewall and NAT restrictions, not code errors. Enterprise environments typically block all outbound traffic except TCP on ports 80, 443, and sometimes 22, breaking most peer-to-peer agent communication frameworks. Developers can diagnose the issue by systematically testing UDP reachability, DNS resolution, transparent proxy interception, and open egress ports using command-line tools. Corporate firewalls frequently intercept TLS connections via transparent proxies, which can break certificate pinning and WebSocket upgrades that many AI frameworks rely on. Understanding the exact network constraints — such as whether only TCP/443 is available — helps developers choose appropriate fallback strategies like TLS tunneling or relay-based connectivity.

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