diff --git a/src/agents/bash-tools.exec.ts b/src/agents/bash-tools.exec.ts
index 197a7aa20..d08e4675e 100644
--- a/src/agents/bash-tools.exec.ts
+++ b/src/agents/bash-tools.exec.ts
@@ -60,6 +60,10 @@ import {
   detectDangerousCommand,
   formatDangerousCommandError,
 } from "../security/dangerous-commands.js";
+import {
+  logDangerousCommandBlocked,
+  logExecRun,
+} from "../security/audit-log.js";
 
 const DEFAULT_MAX_OUTPUT = clampNumber(
   readEnvInt("PI_BASH_MAX_OUTPUT_CHARS"),
@@ -357,9 +361,21 @@ async function runExecProcess(opts: {
   notifyOnExit: boolean;
   scopeKey?: string;
   sessionKey?: string;
+  agentId?: string;
+  elevated?: boolean;
   timeoutSec: number;
   onUpdate?: (partialResult: AgentToolResult<ExecToolDetails>) => void;
 }): Promise<ExecProcessHandle> {
+  // SECURITY: Audit log the command execution
+  logExecRun({
+    sessionKey: opts.sessionKey,
+    agentId: opts.agentId,
+    command: opts.command,
+    host: opts.sandbox ? "sandbox" : "gateway",
+    elevated: opts.elevated,
+    workdir: opts.workdir,
+  });
+
   const startedAt = Date.now();
   const sessionId = createSessionSlug();
   let child: ChildProcessWithoutNullStreams | null = null;
@@ -762,6 +778,13 @@ export function createExecTool(
       // SECURITY: Check for dangerous command patterns before any execution
       const dangerousMatch = detectDangerousCommand(params.command, "high");
       if (dangerousMatch) {
+        logDangerousCommandBlocked({
+          sessionKey: defaults?.sessionKey,
+          agentId,
+          command: params.command,
+          reason: dangerousMatch.reason,
+          severity: dangerousMatch.severity,
+        });
         throw new Error(formatDangerousCommandError(dangerousMatch));
       }
 
diff --git a/src/security/audit-log.ts b/src/security/audit-log.ts
new file mode 100644
index 000000000..b6a0fa145
--- /dev/null
+++ b/src/security/audit-log.ts
@@ -0,0 +1,377 @@
+import fs from "node:fs";
+import path from "node:path";
+import os from "node:os";
+
+/**
+ * SECURITY: Audit Logging Module
+ *
+ * Provides structured, append-only audit logging for security-relevant events.
+ * Logs are stored in JSONL format for easy parsing and analysis.
+ *
+ * Events logged:
+ * - Session lifecycle (start, end, auth failures)
+ * - Tool invocations (especially exec, gateway, elevated)
+ * - Command execution (with dangerous command detection results)
+ * - Pairing events (requests, approvals, rejections)
+ * - Configuration changes
+ */
+
+export type AuditEventType =
+  | "session.start"
+  | "session.end"
+  | "session.auth_failure"
+  | "tool.invoke"
+  | "tool.denied"
+  | "exec.run"
+  | "exec.blocked"
+  | "exec.elevated"
+  | "pairing.request"
+  | "pairing.approved"
+  | "pairing.rejected"
+  | "pairing.expired"
+  | "config.loaded"
+  | "config.changed"
+  | "secret.detected"
+  | "dangerous_command.blocked";
+
+export interface AuditLogEntry {
+  timestamp: string;
+  event: AuditEventType;
+  sessionKey?: string;
+  agentId?: string;
+  channel?: string;
+  userId?: string;
+  details: Record<string, unknown>;
+}
+
+interface AuditLogConfig {
+  enabled: boolean;
+  logDir: string;
+  maxFileSizeMb: number;
+  retentionDays: number;
+}
+
+const DEFAULT_CONFIG: AuditLogConfig = {
+  enabled: true,
+  logDir: path.join(os.homedir(), ".clawdbot", "audit"),
+  maxFileSizeMb: 10,
+  retentionDays: 90,
+};
+
+let currentConfig: AuditLogConfig = { ...DEFAULT_CONFIG };
+
+/**
+ * Configure the audit logger.
+ */
+export function configureAuditLog(config: Partial<AuditLogConfig>): void {
+  currentConfig = { ...currentConfig, ...config };
+  if (currentConfig.enabled) {
+    ensureLogDir();
+  }
+}
+
+/**
+ * Ensure the audit log directory exists with proper permissions.
+ */
+function ensureLogDir(): void {
+  const logDir = currentConfig.logDir;
+  if (!fs.existsSync(logDir)) {
+    fs.mkdirSync(logDir, { recursive: true, mode: 0o700 });
+  }
+  // Ensure directory has restrictive permissions
+  try {
+    fs.chmodSync(logDir, 0o700);
+  } catch {
+    // Best effort
+  }
+}
+
+/**
+ * Get the current log file path (rotated daily).
+ */
+function getCurrentLogPath(): string {
+  const date = new Date().toISOString().split("T")[0]; // YYYY-MM-DD
+  return path.join(currentConfig.logDir, `audit-${date}.jsonl`);
+}
+
+/**
+ * Write an audit log entry.
+ */
+function writeLogEntry(entry: AuditLogEntry): void {
+  if (!currentConfig.enabled) return;
+
+  try {
+    ensureLogDir();
+    const logPath = getCurrentLogPath();
+    const line = JSON.stringify(entry) + "\n";
+
+    // Append-only write with restrictive permissions
+    fs.appendFileSync(logPath, line, { mode: 0o600 });
+  } catch (err) {
+    // Audit logging should never crash the application
+    // Log to stderr as fallback
+    console.error("[audit-log] Failed to write entry:", err);
+  }
+}
+
+/**
+ * Log a session start event.
+ */
+export function logSessionStart(params: {
+  sessionKey: string;
+  agentId?: string;
+  channel?: string;
+  userId?: string;
+  model?: string;
+}): void {
+  writeLogEntry({
+    timestamp: new Date().toISOString(),
+    event: "session.start",
+    sessionKey: params.sessionKey,
+    agentId: params.agentId,
+    channel: params.channel,
+    userId: params.userId,
+    details: {
+      model: params.model,
+    },
+  });
+}
+
+/**
+ * Log a session end event.
+ */
+export function logSessionEnd(params: {
+  sessionKey: string;
+  agentId?: string;
+  reason?: string;
+  durationMs?: number;
+}): void {
+  writeLogEntry({
+    timestamp: new Date().toISOString(),
+    event: "session.end",
+    sessionKey: params.sessionKey,
+    agentId: params.agentId,
+    details: {
+      reason: params.reason,
+      durationMs: params.durationMs,
+    },
+  });
+}
+
+/**
+ * Log an authentication failure.
+ */
+export function logAuthFailure(params: {
+  sessionKey?: string;
+  channel?: string;
+  userId?: string;
+  reason: string;
+  ip?: string;
+}): void {
+  writeLogEntry({
+    timestamp: new Date().toISOString(),
+    event: "session.auth_failure",
+    sessionKey: params.sessionKey,
+    channel: params.channel,
+    userId: params.userId,
+    details: {
+      reason: params.reason,
+      ip: params.ip,
+    },
+  });
+}
+
+/**
+ * Log a tool invocation.
+ */
+export function logToolInvoke(params: {
+  sessionKey?: string;
+  agentId?: string;
+  toolName: string;
+  toolCallId?: string;
+  args?: Record<string, unknown>;
+  sensitive?: boolean;
+}): void {
+  // For sensitive tools, redact arguments
+  const safeArgs = params.sensitive ? { redacted: true } : params.args;
+
+  writeLogEntry({
+    timestamp: new Date().toISOString(),
+    event: "tool.invoke",
+    sessionKey: params.sessionKey,
+    agentId: params.agentId,
+    details: {
+      toolName: params.toolName,
+      toolCallId: params.toolCallId,
+      args: safeArgs,
+    },
+  });
+}
+
+/**
+ * Log a denied tool invocation.
+ */
+export function logToolDenied(params: {
+  sessionKey?: string;
+  agentId?: string;
+  toolName: string;
+  reason: string;
+}): void {
+  writeLogEntry({
+    timestamp: new Date().toISOString(),
+    event: "tool.denied",
+    sessionKey: params.sessionKey,
+    agentId: params.agentId,
+    details: {
+      toolName: params.toolName,
+      reason: params.reason,
+    },
+  });
+}
+
+/**
+ * Log a command execution.
+ */
+export function logExecRun(params: {
+  sessionKey?: string;
+  agentId?: string;
+  command: string;
+  host: "sandbox" | "gateway" | "node";
+  elevated?: boolean;
+  workdir?: string;
+}): void {
+  // Truncate very long commands
+  const truncatedCommand =
+    params.command.length > 500 ? params.command.slice(0, 500) + "..." : params.command;
+
+  writeLogEntry({
+    timestamp: new Date().toISOString(),
+    event: params.elevated ? "exec.elevated" : "exec.run",
+    sessionKey: params.sessionKey,
+    agentId: params.agentId,
+    details: {
+      command: truncatedCommand,
+      host: params.host,
+      elevated: params.elevated,
+      workdir: params.workdir,
+    },
+  });
+}
+
+/**
+ * Log a blocked dangerous command.
+ */
+export function logDangerousCommandBlocked(params: {
+  sessionKey?: string;
+  agentId?: string;
+  command: string;
+  reason: string;
+  severity: string;
+}): void {
+  writeLogEntry({
+    timestamp: new Date().toISOString(),
+    event: "dangerous_command.blocked",
+    sessionKey: params.sessionKey,
+    agentId: params.agentId,
+    details: {
+      command: params.command.slice(0, 500),
+      reason: params.reason,
+      severity: params.severity,
+    },
+  });
+}
+
+/**
+ * Log a pairing event.
+ */
+export function logPairingEvent(params: {
+  event: "pairing.request" | "pairing.approved" | "pairing.rejected" | "pairing.expired";
+  channel?: string;
+  userId?: string;
+  pairingCode?: string;
+  nodeId?: string;
+  reason?: string;
+}): void {
+  writeLogEntry({
+    timestamp: new Date().toISOString(),
+    event: params.event,
+    channel: params.channel,
+    userId: params.userId,
+    details: {
+      pairingCode: params.pairingCode ? "***" : undefined, // Redact actual code
+      nodeId: params.nodeId,
+      reason: params.reason,
+    },
+  });
+}
+
+/**
+ * Log configuration changes.
+ */
+export function logConfigChange(params: {
+  action: "loaded" | "changed";
+  configPath?: string;
+  changedKeys?: string[];
+}): void {
+  writeLogEntry({
+    timestamp: new Date().toISOString(),
+    event: params.action === "loaded" ? "config.loaded" : "config.changed",
+    details: {
+      configPath: params.configPath,
+      changedKeys: params.changedKeys,
+    },
+  });
+}
+
+/**
+ * Log when secrets are detected in files (from secret-guard).
+ */
+export function logSecretDetected(params: {
+  source: string;
+  path: string;
+  action: "blocked" | "warned";
+}): void {
+  writeLogEntry({
+    timestamp: new Date().toISOString(),
+    event: "secret.detected",
+    details: {
+      source: params.source,
+      path: params.path,
+      action: params.action,
+    },
+  });
+}
+
+/**
+ * Clean up old audit log files based on retention policy.
+ */
+export async function cleanupOldLogs(): Promise<number> {
+  if (!currentConfig.enabled) return 0;
+
+  const logDir = currentConfig.logDir;
+  if (!fs.existsSync(logDir)) return 0;
+
+  const now = Date.now();
+  const maxAgeMs = currentConfig.retentionDays * 24 * 60 * 60 * 1000;
+  let removed = 0;
+
+  try {
+    const files = fs.readdirSync(logDir);
+    for (const file of files) {
+      if (!file.startsWith("audit-") || !file.endsWith(".jsonl")) continue;
+
+      const filePath = path.join(logDir, file);
+      const stats = fs.statSync(filePath);
+      const age = now - stats.mtimeMs;
+
+      if (age > maxAgeMs) {
+        fs.unlinkSync(filePath);
+        removed += 1;
+      }
+    }
+  } catch {
+    // Best effort cleanup
+  }
+
+  return removed;
+}