github
diff --git a/‎.github/workflows/smoke-claude.lock.yml‎
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diff --git a/‎.github/workflows/smoke-claude.md‎
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diff --git a/‎.github/workflows/smoke-codex.lock.yml‎
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diff --git a/‎README.md‎
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diff --git a/‎containers/agent/Dockerfile‎
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diff --git a/‎containers/agent/api-proxy-health-check.sh‎
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diff --git a/‎containers/agent/entrypoint.sh‎
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diff --git a/‎containers/agent/get-claude-key.sh‎
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diff --git a/‎containers/api-proxy/Dockerfile‎
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diff --git a/‎containers/api-proxy/server.js‎
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@@ -49,6 +49,23 @@ safe-outputs:
       run-failure: "💫 **TO BE CONTINUED...** [{workflow_name}]({run_url}) {status}! Our hero faces unexpected challenges..."
 timeout-minutes: 10
 post-steps:
+  - name: Show final Claude Code config
+    if: always()
+    run: |
+      echo "=== Final Claude Code Config ==="
+      if [ -f ~/.claude.json ]; then
+        echo "File: ~/.claude.json"
+        cat ~/.claude.json
+      else
+        echo "~/.claude.json not found"
+      fi
+      if [ -f ~/.claude/config.json ]; then
+        echo ""
+        echo "File: ~/.claude/config.json (legacy)"
+        cat ~/.claude/config.json
+      else
+        echo "~/.claude/config.json not found"
+      fi
   - name: Validate safe outputs were invoked
     run: |
       OUTPUTS_FILE="${GH_AW_SAFE_OUTPUTS:-/opt/gh-aw/safeoutputs/outputs.jsonl}"
 
@@ -35,6 +35,7 @@ The `--` separator divides firewall options from the command to run.
 - [Usage guide](docs/usage.md) — CLI flags, domain allowlists, examples
 - [Chroot mode](docs/chroot-mode.md) — use host binaries with network isolation
 - [API proxy sidecar](docs/api-proxy-sidecar.md) — secure credential management for LLM APIs
+- [Authentication architecture](docs/authentication-architecture.md) — deep dive into token handling and credential isolation
 - [SSL Bump](docs/ssl-bump.md) — HTTPS content inspection for URL path filtering
 - [GitHub Actions](docs/github_actions.md) — CI/CD integration and MCP server setup
 - [Environment variables](docs/environment.md) — passing environment variables to containers
 
@@ -62,11 +62,13 @@ RUN if ! getent group awfuser >/dev/null 2>&1; then \
     mkdir -p /home/awfuser/.copilot/logs && \
     chown -R awfuser:awfuser /home/awfuser
 
-# Copy iptables setup script and PID logger
+# Copy iptables setup script, PID logger, API proxy health check, and Claude key helper
 COPY setup-iptables.sh /usr/local/bin/setup-iptables.sh
 COPY entrypoint.sh /usr/local/bin/entrypoint.sh
 COPY pid-logger.sh /usr/local/bin/pid-logger.sh
-RUN chmod +x /usr/local/bin/setup-iptables.sh /usr/local/bin/entrypoint.sh /usr/local/bin/pid-logger.sh
+COPY api-proxy-health-check.sh /usr/local/bin/api-proxy-health-check.sh
+COPY get-claude-key.sh /usr/local/bin/get-claude-key.sh
+RUN chmod +x /usr/local/bin/setup-iptables.sh /usr/local/bin/entrypoint.sh /usr/local/bin/pid-logger.sh /usr/local/bin/api-proxy-health-check.sh /usr/local/bin/get-claude-key.sh
 
 # Copy pre-built one-shot-token library from rust-builder stage
 # This prevents tokens from being read multiple times (e.g., by malicious code)
 
@@ -0,0 +1,108 @@
+#!/bin/bash
+# api-proxy-health-check.sh
+# Pre-flight health check to verify API proxy credential isolation
+# This script ensures:
+# 1. API keys are NOT present in agent environment (credential isolation working)
+# 2. API proxy is reachable and healthy (connectivity established)
+#
+# Usage: source this script before running agent commands
+# Returns: 0 if checks pass, 1 if checks fail (prevents agent from running)
+
+set -e
+
+echo "[health-check] API Proxy Pre-flight Check"
+echo "[health-check] =========================================="
+
+# Track if any API proxy is configured
+API_PROXY_CONFIGURED=false
+
+# Check Claude/Anthropic configuration
+if [ -n "$ANTHROPIC_BASE_URL" ]; then
+  API_PROXY_CONFIGURED=true
+  echo "[health-check] Checking Anthropic API proxy configuration..."
+
+  # Verify credentials are NOT in agent environment
+  if [ -n "$ANTHROPIC_API_KEY" ] || [ -n "$CLAUDE_API_KEY" ]; then
+    echo "[health-check][ERROR] Anthropic API key found in agent environment!"
+    echo "[health-check][ERROR] Credential isolation failed - keys should only be in api-proxy container"
+    echo "[health-check][ERROR] ANTHROPIC_API_KEY=${ANTHROPIC_API_KEY:+<present>}"
+    echo "[health-check][ERROR] CLAUDE_API_KEY=${CLAUDE_API_KEY:+<present>}"
+    exit 1
+  fi
+  echo "[health-check] ✓ Anthropic credentials NOT in agent environment (correct)"
+
+  # Verify ANTHROPIC_AUTH_TOKEN is placeholder (if present)
+  if [ -n "$ANTHROPIC_AUTH_TOKEN" ]; then
+    if [ "$ANTHROPIC_AUTH_TOKEN" != "placeholder-token-for-credential-isolation" ]; then
+      echo "[health-check][ERROR] ANTHROPIC_AUTH_TOKEN contains non-placeholder value!"
+      echo "[health-check][ERROR] Token should be 'placeholder-token-for-credential-isolation'"
+      exit 1
+    fi
+    echo "[health-check] ✓ ANTHROPIC_AUTH_TOKEN is placeholder value (correct)"
+  fi
+
+  # Perform health check using BASE_URL
+  echo "[health-check] Testing connectivity to Anthropic API proxy at $ANTHROPIC_BASE_URL..."
+
+  # Extract host and port from BASE_URL (format: http://IP:PORT)
+  PROXY_HOST=$(echo "$ANTHROPIC_BASE_URL" | sed -E 's|^https?://([^:]+):.*|\1|')
+  PROXY_PORT=$(echo "$ANTHROPIC_BASE_URL" | sed -E 's|^https?://[^:]+:([0-9]+).*|\1|')
+
+  # Test TCP connectivity with timeout
+  if timeout 5 bash -c "cat < /dev/null > /dev/tcp/$PROXY_HOST/$PROXY_PORT" 2>/dev/null; then
+    echo "[health-check] ✓ Anthropic API proxy is reachable at $ANTHROPIC_BASE_URL"
+  else
+    echo "[health-check][ERROR] Cannot connect to Anthropic API proxy at $ANTHROPIC_BASE_URL"
+    echo "[health-check][ERROR] Proxy may not be running or network is blocked"
+    exit 1
+  fi
+fi
+
+# Check OpenAI/Codex configuration
+if [ -n "$OPENAI_BASE_URL" ]; then
+  API_PROXY_CONFIGURED=true
+  echo "[health-check] Checking OpenAI API proxy configuration..."
+
+  # Verify credentials are NOT in agent environment
+  # Note: CODEX_API_KEY check is temporarily disabled - Codex receives credentials directly
+  if [ -n "$OPENAI_API_KEY" ] || [ -n "$OPENAI_KEY" ]; then
+    echo "[health-check][ERROR] OpenAI API key found in agent environment!"
+    echo "[health-check][ERROR] Credential isolation failed - keys should only be in api-proxy container"
+    echo "[health-check][ERROR] OPENAI_API_KEY=${OPENAI_API_KEY:+<present>}"
+    # echo "[health-check][ERROR] CODEX_API_KEY=${CODEX_API_KEY:+<present>}"  # Temporarily disabled - Codex uses direct credentials
+    echo "[health-check][ERROR] OPENAI_KEY=${OPENAI_KEY:+<present>}"
+    exit 1
+  fi
+  echo "[health-check] ✓ OpenAI credentials NOT in agent environment (correct)"
+  # Note: CODEX_API_KEY is intentionally passed through for Codex agent compatibility
+
+  # Perform health check using BASE_URL
+  echo "[health-check] Testing connectivity to OpenAI API proxy at $OPENAI_BASE_URL..."
+
+  # Extract host and port from BASE_URL (format: http://IP:PORT)
+  PROXY_HOST=$(echo "$OPENAI_BASE_URL" | sed -E 's|^https?://([^:]+):.*|\1|')
+  PROXY_PORT=$(echo "$OPENAI_BASE_URL" | sed -E 's|^https?://[^:]+:([0-9]+).*|\1|')
+
+  # Test TCP connectivity with timeout
+  if timeout 5 bash -c "cat < /dev/null > /dev/tcp/$PROXY_HOST/$PROXY_PORT" 2>/dev/null; then
+    echo "[health-check] ✓ OpenAI API proxy is reachable at $OPENAI_BASE_URL"
+  else
+    echo "[health-check][ERROR] Cannot connect to OpenAI API proxy at $OPENAI_BASE_URL"
+    echo "[health-check][ERROR] Proxy may not be running or network is blocked"
+    exit 1
+  fi
+fi
+
+# Summary
+if [ "$API_PROXY_CONFIGURED" = "true" ]; then
+  echo "[health-check] =========================================="
+  echo "[health-check] ✓ All API proxy health checks passed"
+  echo "[health-check] ✓ Credential isolation verified"
+  echo "[health-check] ✓ Connectivity established"
+  echo "[health-check] =========================================="
+else
+  echo "[health-check] No API proxy configured (ANTHROPIC_BASE_URL and OPENAI_BASE_URL not set)"
+  echo "[health-check] Skipping health checks"
+fi
+
+exit 0
@@ -114,6 +114,54 @@ fi
 # Setup iptables rules
 /usr/local/bin/setup-iptables.sh
 
+# Run API proxy health checks (verifies credential isolation and connectivity)
+# This must run AFTER iptables setup (which allows api-proxy traffic) but BEFORE user command
+# If health check fails, the script exits with non-zero code and prevents agent from running
+/usr/local/bin/api-proxy-health-check.sh || exit 1
+
+# Configure Claude Code API key helper
+# This ensures the apiKeyHelper is properly configured in the config file
+# The config file must exist before Claude Code starts for authentication to work
+# In chroot mode, we write to /host$HOME/.claude.json so it's accessible after chroot
+if [ -n "$CLAUDE_CODE_API_KEY_HELPER" ]; then
+  echo "[entrypoint] Claude Code API key helper configured: $CLAUDE_CODE_API_KEY_HELPER"
+
+  # In chroot mode, write to /host path so file is accessible after chroot transition
+  if [ "${AWF_CHROOT_ENABLED}" = "true" ]; then
+    CONFIG_FILE="/host$HOME/.claude.json"
+  else
+    CONFIG_FILE="$HOME/.claude.json"
+  fi
+
+  if [ -f "$CONFIG_FILE" ]; then
+    # File exists - check if it has apiKeyHelper
+    if grep -q '"apiKeyHelper"' "$CONFIG_FILE"; then
+      # apiKeyHelper exists - validate it matches the environment variable
+      echo "[entrypoint] Claude Code config file exists with apiKeyHelper, validating..."
+      CONFIGURED_HELPER=$(grep -o '"apiKeyHelper":"[^"]*"' "$CONFIG_FILE" | cut -d'"' -f4)
+      if [ "$CONFIGURED_HELPER" != "$CLAUDE_CODE_API_KEY_HELPER" ]; then
+        echo "[entrypoint][ERROR] apiKeyHelper mismatch:"
+        echo "[entrypoint][ERROR]   Environment variable: $CLAUDE_CODE_API_KEY_HELPER"
+        echo "[entrypoint][ERROR]   Config file value: $CONFIGURED_HELPER"
+        exit 1
+      fi
+      echo "[entrypoint] ✓ Claude Code API key helper validated: $CLAUDE_CODE_API_KEY_HELPER"
+    else
+      # File exists but no apiKeyHelper - write it (overwrites empty {} created by docker-manager)
+      echo "[entrypoint] Claude Code config file exists but missing apiKeyHelper, writing..."
+      echo "{\"apiKeyHelper\":\"$CLAUDE_CODE_API_KEY_HELPER\"}" > "$CONFIG_FILE"
+      chmod 666 "$CONFIG_FILE"
+      echo "[entrypoint] ✓ Wrote apiKeyHelper to $CONFIG_FILE"
+    fi
+  else
+    # File doesn't exist - create it
+    echo "[entrypoint] Creating Claude Code config file with apiKeyHelper..."
+    echo "{\"apiKeyHelper\":\"$CLAUDE_CODE_API_KEY_HELPER\"}" > "$CONFIG_FILE"
+    chmod 666 "$CONFIG_FILE"
+    echo "[entrypoint] ✓ Created $CONFIG_FILE with apiKeyHelper: $CLAUDE_CODE_API_KEY_HELPER"
+  fi
+fi
+
 # Print proxy environment
 echo "[entrypoint] Proxy configuration:"
 echo "[entrypoint]   HTTP_PROXY=$HTTP_PROXY"
 
@@ -0,0 +1,20 @@
+#!/bin/bash
+# API Key Helper for Claude Code
+# This script outputs a placeholder API key since the real key is held
+# exclusively in the api-proxy sidecar container for credential isolation.
+#
+# The api-proxy intercepts requests and injects the real ANTHROPIC_API_KEY,
+# so this placeholder key will never reach the actual Anthropic API.
+#
+# This approach ensures:
+# 1. Claude Code agent never has access to the real API key
+# 2. Only api-proxy container holds the real credentials
+# 3. Health checks verify keys are NOT in agent environment
+
+# Log helper invocation to stderr (stdout is reserved for the API key)
+echo "[get-claude-key.sh] API key helper invoked at $(date -Iseconds)" >&2
+echo "[get-claude-key.sh] Returning placeholder key for credential isolation" >&2
+echo "[get-claude-key.sh] Real authentication via ANTHROPIC_BASE_URL=${ANTHROPIC_BASE_URL:-not set}" >&2
+
+# Output a placeholder key (will be replaced by api-proxy)
+echo "sk-ant-placeholder-key-for-credential-isolation"
@@ -28,5 +28,6 @@ USER apiproxy
 # 10001 - Anthropic API proxy
 EXPOSE 10000 10001
 
-# Start the proxy server
-CMD ["node", "server.js"]
+# Redirect stdout/stderr to log file for persistence
+# Use shell form to enable redirection and tee for both file and console
+CMD node server.js 2>&1 | tee -a /var/log/api-proxy/api-proxy.log
@@ -175,6 +175,7 @@ if (OPENAI_API_KEY) {
     }
 
     console.log(`[OpenAI Proxy] ${sanitizeForLog(req.method)} ${sanitizeForLog(req.url)}`);
+    console.log(`[OpenAI Proxy] Injecting Authorization header with OPENAI_API_KEY`);
     proxyRequest(req, res, 'api.openai.com', {
       'Authorization': `Bearer ${OPENAI_API_KEY}`,
     });
@@ -216,6 +217,7 @@ if (ANTHROPIC_API_KEY) {
     }
 
     console.log(`[Anthropic Proxy] ${sanitizeForLog(req.method)} ${sanitizeForLog(req.url)}`);
+    console.log(`[Anthropic Proxy] Injecting x-api-key header with ANTHROPIC_API_KEY`);
     // Only set anthropic-version as default; preserve agent-provided version
     const anthropicHeaders = { 'x-api-key': ANTHROPIC_API_KEY };
     if (!req.headers['anthropic-version']) {
Original file line number	Diff line number	Diff line change
`@@ -175,6 +175,7 @@ if (OPENAI_API_KEY) {`
`175`	`175`	`}`
`176`	`176`
`177`	`177`	console.log(`[OpenAI Proxy] ${sanitizeForLog(req.method)} ${sanitizeForLog(req.url)}`);
	`178`	+ console.log(`[OpenAI Proxy] Injecting Authorization header with OPENAI_API_KEY`);
`178`	`179`	`proxyRequest(req, res, 'api.openai.com', {`
`179`	`180`	'Authorization': `Bearer ${OPENAI_API_KEY}`,
`180`	`181`	`});`
`@@ -216,6 +217,7 @@ if (ANTHROPIC_API_KEY) {`
`216`	`217`	`}`
`217`	`218`
`218`	`219`	console.log(`[Anthropic Proxy] ${sanitizeForLog(req.method)} ${sanitizeForLog(req.url)}`);
	`220`	+ console.log(`[Anthropic Proxy] Injecting x-api-key header with ANTHROPIC_API_KEY`);
`219`	`221`	`// Only set anthropic-version as default; preserve agent-provided version`
`220`	`222`	`const anthropicHeaders = { 'x-api-key': ANTHROPIC_API_KEY };`
`221`	`223`	`if (!req.headers['anthropic-version']) {`