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Environment And State

Session state, configuration, working directory, filesystem, network, and runtime environment.

Failure modes: 7 active  |  🟠 4 high · 🟡 3 medium


File Severity Summary
26-high-session-management.md 🟠 High Some CLIs maintain state between invocations (login sessions, active contexts, selected environments)
28-high-config-shadowing.md 🟠 High Most CLI tools load config from multiple locations in a priority order
31-high-network-proxy.md 🟠 High Agent execution environments frequently route traffic through proxies (corporate networks, CI systems, VPNs, transpar...
32-high-self-update.md 🟠 High Some CLI tools automatically check for updates, download new versions, or silently upgrade themselves
27-medium-platform-portability.md 🟡 Medium Agent environments vary: macOS, Linux, Docker containers, CI runners
29-medium-working-directory.md 🟡 Medium Many CLI tools resolve paths, find config files, or change behavior based on the current working directory
30-medium-filesystem-side-effects.md 🟡 Medium Tools write to locations the agent doesn't know about: caches, logs, lock files, temp dirs, credential stores

Detailed Metrics

Challenge Severity Frequency Detectability Token Spend Time Context
§26 🟠 High Common Hard Medium Medium Low
§28 🟠 High Common Hard High High Medium
§31 🟠 High Situational Hard Medium High Low
§32 🟠 High Situational Hard Medium High Low
§27 🟡 Medium Common Easy Medium Medium Low
§29 🟡 Medium Common Medium Medium Low Low
§30 🟡 Medium Common Hard Low Low Low