diff --git a/src/api-proxy-config-validation.test.ts b/src/api-proxy-config-validation.test.ts
index 7f6d68e0d..8723459ac 100644
--- a/src/api-proxy-config-validation.test.ts
+++ b/src/api-proxy-config-validation.test.ts
@@ -74,6 +74,23 @@ describe('validateApiProxyConfig', () => {
     expect(result.debugMessages[3]).toContain('Gemini');
   });
 
+  it('should not warn when Anthropic WIF auth is configured (no static key)', () => {
+    const result = validateApiProxyConfig(true, false, false, false, false, true);
+    expect(result.enabled).toBe(true);
+    expect(result.warnings).toEqual([]);
+    expect(result.debugMessages).toHaveLength(1);
+    expect(result.debugMessages[0]).toContain('WIF');
+  });
+
+  it('should emit WIF debug message alongside static key debug message when both present', () => {
+    const result = validateApiProxyConfig(true, false, true, false, false, true);
+    expect(result.enabled).toBe(true);
+    expect(result.warnings).toEqual([]);
+    // Both Anthropic key and WIF debug messages appear
+    expect(result.debugMessages.some(m => m.includes('Anthropic API key'))).toBe(true);
+    expect(result.debugMessages.some(m => m.includes('WIF'))).toBe(true);
+  });
+
   it('should not warn when disabled even with keys', () => {
     const result = validateApiProxyConfig(false, true, true);
     expect(result.enabled).toBe(false);
diff --git a/src/api-proxy-config.ts b/src/api-proxy-config.ts
index 34f8d67f3..d67e6302c 100644
--- a/src/api-proxy-config.ts
+++ b/src/api-proxy-config.ts
@@ -26,6 +26,7 @@ interface ApiProxyValidationResult {
  * @param hasAnthropicKey - Whether an Anthropic API key is present
  * @param hasCopilotKey - Whether a GitHub Copilot API key is present
  * @param hasGeminiKey - Whether a Google Gemini API key is present
+ * @param hasAnthropicWif - Whether Anthropic WIF (GitHub OIDC) auth is configured
  * @returns ApiProxyValidationResult with warnings and debug messages
  */
 export function validateApiProxyConfig(
@@ -33,7 +34,8 @@ export function validateApiProxyConfig(
   hasOpenaiKey?: boolean,
   hasAnthropicKey?: boolean,
   hasCopilotKey?: boolean,
-  hasGeminiKey?: boolean
+  hasGeminiKey?: boolean,
+  hasAnthropicWif?: boolean,
 ): ApiProxyValidationResult {
   if (!enableApiProxy) {
     return { enabled: false, warnings: [], debugMessages: [] };
@@ -42,7 +44,7 @@ export function validateApiProxyConfig(
   const warnings: string[] = [];
   const debugMessages: string[] = [];
 
-  if (!hasOpenaiKey && !hasAnthropicKey && !hasCopilotKey && !hasGeminiKey) {
+  if (!hasOpenaiKey && !hasAnthropicKey && !hasCopilotKey && !hasGeminiKey && !hasAnthropicWif) {
     warnings.push('⚠️  API proxy enabled but no API keys found in environment');
     warnings.push('   Set OPENAI_API_KEY, ANTHROPIC_API_KEY, COPILOT_GITHUB_TOKEN, COPILOT_PROVIDER_API_KEY, or GEMINI_API_KEY to use the proxy');
   }
@@ -52,6 +54,9 @@ export function validateApiProxyConfig(
   if (hasAnthropicKey) {
     debugMessages.push('Anthropic API key detected - will be held securely in sidecar');
   }
+  if (hasAnthropicWif) {
+    debugMessages.push('Anthropic WIF (GitHub OIDC) auth configured - OIDC token exchange will be used in sidecar');
+  }
   if (hasCopilotKey) {
     debugMessages.push('GitHub Copilot API key detected - will be held securely in sidecar');
   }
diff --git a/src/commands/validators/config-assembly.ts b/src/commands/validators/config-assembly.ts
index d29f86167..3d0a0f0d4 100644
--- a/src/commands/validators/config-assembly.ts
+++ b/src/commands/validators/config-assembly.ts
@@ -18,6 +18,7 @@ import {
   applyHostServicePortsConfig,
   applyAgentTimeout,
 } from '../../option-parsers';
+import { getLowerCaseProcessEnvValue } from '../../env-utils';
 import { buildConfig } from '../build-config';
 import { LogAndLimitsResult } from './log-and-limits';
 import { NetworkOptionsResult } from './network-options';
@@ -231,12 +232,18 @@ export function assembleAndValidateConfig(
   // mode (Azure Foundry, OpenRouter, etc.) without a GitHub token; the sidecar still
   // routes through it, so for "is there a Copilot path?" purposes either signal counts.
   const copilotByokDirect = !!config.copilotProviderApiKey;
+  // Detect Anthropic WIF (GitHub OIDC) auth: the sidecar performs the OIDC token
+  // exchange so no static ANTHROPIC_API_KEY is required.
+  const hasAnthropicWif =
+    getLowerCaseProcessEnvValue('AWF_AUTH_TYPE') === 'github-oidc' &&
+    getLowerCaseProcessEnvValue('AWF_AUTH_PROVIDER') === 'anthropic';
   const apiProxyValidation = validateApiProxyConfig(
     config.enableApiProxy || false,
     !!config.openaiApiKey,
     !!config.anthropicApiKey,
     !!config.copilotGithubToken || copilotByokDirect,
     !!config.geminiApiKey,
+    hasAnthropicWif,
   );
 
   // Log API proxy status at info level for visibility
@@ -246,8 +253,13 @@ export function assembleAndValidateConfig(
       : copilotByokDirect
         ? 'true (byok-direct)'
         : 'false';
+    const anthropicStatus = config.anthropicApiKey
+      ? 'true'
+      : hasAnthropicWif
+        ? 'true (wif)'
+        : 'false';
     logger.info(
-      `API proxy enabled: OpenAI=${!!config.openaiApiKey}, Anthropic=${!!config.anthropicApiKey}, Copilot=${copilotStatus}, Gemini=${!!config.geminiApiKey}`,
+      `API proxy enabled: OpenAI=${!!config.openaiApiKey}, Anthropic=${anthropicStatus}, Copilot=${copilotStatus}, Gemini=${!!config.geminiApiKey}`,
     );
   }
 
diff --git a/src/services/api-proxy-credential-env.ts b/src/services/api-proxy-credential-env.ts
index e924c8fb9..18720cc38 100644
--- a/src/services/api-proxy-credential-env.ts
+++ b/src/services/api-proxy-credential-env.ts
@@ -67,9 +67,14 @@ export function buildAgentCredentialEnv(params: ApiProxyCredentialEnvParams): Re
       logger.debug(`Anthropic API base path set to: ${config.anthropicApiBasePath}`);
     }
 
-    // Set placeholder token for Claude Code CLI compatibility
-    // Real authentication happens via ANTHROPIC_BASE_URL pointing to api-proxy
-    // Use sk-ant- prefix so Claude Code's key-format validation passes
+    // Set placeholder credentials for Claude Code CLI credential isolation.
+    // Real authentication happens via ANTHROPIC_BASE_URL pointing to api-proxy.
+    // Use sk-ant- prefix so Claude Code's key-format validation passes.
+    //
+    // NOTE: ANTHROPIC_API_KEY is NOT set here — it is excluded from the agent env
+    // via excluded-vars.ts when enableApiProxy is active. Setting it (even as a
+    // placeholder) would cause Claude Code to attempt direct auth with it instead
+    // of routing through ANTHROPIC_BASE_URL.
     agentEnvAdditions.ANTHROPIC_AUTH_TOKEN = 'sk-ant-placeholder-key-for-credential-isolation';
     logger.debug('ANTHROPIC_AUTH_TOKEN set to placeholder value for credential isolation');
 
diff --git a/src/services/api-proxy-service-split.test.ts b/src/services/api-proxy-service-split.test.ts
index 885ebb481..ff56ce85f 100644
--- a/src/services/api-proxy-service-split.test.ts
+++ b/src/services/api-proxy-service-split.test.ts
@@ -95,4 +95,49 @@ describe('API proxy split builders', () => {
       networkConfig: networkConfigWithoutProxyIp,
     })).toThrow('buildAgentCredentialEnv: networkConfig.proxyIp is required');
   });
+
+  it('buildAgentCredentialEnv sets ANTHROPIC_AUTH_TOKEN placeholder when anthropicApiKey is present', () => {
+    const agentEnvAdditions = buildAgentCredentialEnv({
+      config: {
+        ...baseConfig,
+        workDir: '/tmp/awf-test',
+        enableApiProxy: true,
+        anthropicApiKey: 'sk-ant-real-key',
+      },
+      networkConfig,
+    });
+
+    expect(agentEnvAdditions.ANTHROPIC_BASE_URL).toBe('http://172.30.0.30:10001');
+    // ANTHROPIC_API_KEY must NOT be in agentEnvAdditions — it is excluded via excluded-vars.ts
+    expect(agentEnvAdditions.ANTHROPIC_API_KEY).toBeUndefined();
+    expect(agentEnvAdditions.ANTHROPIC_AUTH_TOKEN).toBe('sk-ant-placeholder-key-for-credential-isolation');
+    expect(agentEnvAdditions.CLAUDE_CODE_API_KEY_HELPER).toBe('/usr/local/bin/get-claude-key.sh');
+  });
+
+  it('buildAgentCredentialEnv sets ANTHROPIC_AUTH_TOKEN placeholder for WIF auth (no static key)', () => {
+    const originalEnv = process.env;
+    process.env = {
+      ...originalEnv,
+      AWF_AUTH_TYPE: 'github-oidc',
+      AWF_AUTH_PROVIDER: 'anthropic',
+    };
+    try {
+      const agentEnvAdditions = buildAgentCredentialEnv({
+        config: {
+          ...baseConfig,
+          workDir: '/tmp/awf-test',
+          enableApiProxy: true,
+          // No anthropicApiKey — WIF-only path
+        },
+        networkConfig,
+      });
+
+      expect(agentEnvAdditions.ANTHROPIC_BASE_URL).toBe('http://172.30.0.30:10001');
+      // ANTHROPIC_API_KEY must NOT be in agentEnvAdditions — excluded-vars.ts handles removal
+      expect(agentEnvAdditions.ANTHROPIC_API_KEY).toBeUndefined();
+      expect(agentEnvAdditions.ANTHROPIC_AUTH_TOKEN).toBe('sk-ant-placeholder-key-for-credential-isolation');
+    } finally {
+      process.env = originalEnv;
+    }
+  });
 });
diff --git a/src/squid-config.test.ts b/src/squid-config.test.ts
index 4f6d32918..45d0b4982 100644
--- a/src/squid-config.test.ts
+++ b/src/squid-config.test.ts
@@ -413,6 +413,22 @@ describe('generatePolicyManifest', () => {
       expect(allowPos).toBeLessThan(denyIpv4Pos);
     });
 
+    it('should insert from_api_proxy src rule before domain denyRule', () => {
+      const config: SquidConfig = {
+        domains: ['example.com'],
+        port: defaultPort,
+        apiProxyIp,
+        apiProxyPorts,
+      };
+      const result = generateSquidConfig(config);
+      expect(result).toContain(`acl from_api_proxy src ${apiProxyIp}/32`);
+      expect(result).toContain('http_access allow from_api_proxy');
+      // from_api_proxy allow rule must fire before the domain denyRule
+      const fromApiProxyPos = result.indexOf('http_access allow from_api_proxy');
+      const denyRulePos = result.indexOf('http_access deny !allowed_domains');
+      expect(fromApiProxyPos).toBeLessThan(denyRulePos);
+    });
+
     it('should not emit api-proxy rules when apiProxyIp is not set', () => {
       const config: SquidConfig = {
         domains: ['example.com'],
@@ -420,6 +436,7 @@ describe('generatePolicyManifest', () => {
       };
       const result = generateSquidConfig(config);
       expect(result).not.toContain('allow_api_proxy_ip');
+      expect(result).not.toContain('from_api_proxy');
     });
 
     it('should reject non-integer apiProxyPorts values', () => {
@@ -517,4 +534,35 @@ describe('generatePolicyManifest - Api-Proxy Rules', () => {
     const apiProxyRule = manifest.rules.find(r => r.id === 'allow-api-proxy-ip');
     expect(apiProxyRule).toBeUndefined();
   });
+
+  it('should include allow-from-api-proxy rule when apiProxyIp is set', () => {
+    const manifest = generatePolicyManifest({
+      domains: ['example.com'],
+      port: defaultPort,
+      apiProxyIp: '172.30.0.30',
+    });
+
+    const fromProxyRule = manifest.rules.find(r => r.id === 'allow-from-api-proxy');
+    expect(fromProxyRule).toBeDefined();
+    expect(fromProxyRule!.action).toBe('allow');
+    expect(fromProxyRule!.aclName).toBe('from_api_proxy');
+    expect(fromProxyRule!.domains).toContain('*');
+    expect(fromProxyRule!.description).toContain('unrestricted outbound from api-proxy');
+
+    // Must come after allow-api-proxy-ip and before deny-raw-ipv4
+    const apiProxyRule = manifest.rules.find(r => r.id === 'allow-api-proxy-ip');
+    const denyIpv4Rule = manifest.rules.find(r => r.id === 'deny-raw-ipv4');
+    expect(fromProxyRule!.order).toBeGreaterThan(apiProxyRule!.order);
+    expect(fromProxyRule!.order).toBeLessThan(denyIpv4Rule!.order);
+  });
+
+  it('should not include allow-from-api-proxy rule when apiProxyIp is not set', () => {
+    const manifest = generatePolicyManifest({
+      domains: ['example.com'],
+      port: defaultPort,
+    });
+
+    const fromProxyRule = manifest.rules.find(r => r.id === 'allow-from-api-proxy');
+    expect(fromProxyRule).toBeUndefined();
+  });
 });
diff --git a/src/squid/config-sections.ts b/src/squid/config-sections.ts
index c6fff88d7..8bcbbed68 100644
--- a/src/squid/config-sections.ts
+++ b/src/squid/config-sections.ts
@@ -129,6 +129,13 @@ function generateApiProxySection(apiProxyIp?: string): string {
 # This allow rule fires first for the known api-proxy IP.
 acl allow_api_proxy_ip dst ${apiProxyIp}
 http_access allow allow_api_proxy_ip
+
+# Allow the api-proxy sidecar unrestricted outbound through Squid.
+# The sidecar must reach upstream API endpoints (e.g. api.anthropic.com for
+# WIF/OIDC token exchange) that may not be in the agent's allow-list.
+# The api-proxy is a trusted AWF component (not the agent threat model).
+acl from_api_proxy src ${apiProxyIp}/32
+http_access allow from_api_proxy
 ` : '';
 }
 
diff --git a/src/squid/policy-manifest.ts b/src/squid/policy-manifest.ts
index 21320cf19..19746ed7d 100644
--- a/src/squid/policy-manifest.ts
+++ b/src/squid/policy-manifest.ts
@@ -83,6 +83,15 @@ export function generatePolicyManifest(config: SquidConfig): PolicyManifest {
       domains: [apiProxyIp],
       description: 'Allow connections to the AWF api-proxy sidecar IP before raw-IP deny rules',
     });
+    rules.push({
+      id: 'allow-from-api-proxy',
+      order: ++order,
+      action: 'allow',
+      aclName: 'from_api_proxy',
+      protocol: 'both',
+      domains: ['*'],
+      description: 'Allow unrestricted outbound from api-proxy sidecar (trusted AWF component, not subject to agent domain ACL)',
+    });
   }
 
   // --- Raw IP blocking ---