diff --git a/src/db/libsql/mod.rs b/src/db/libsql/mod.rs
index 6ff8ca6b..2845c757 100644
--- a/src/db/libsql/mod.rs
+++ b/src/db/libsql/mod.rs
@@ -169,10 +169,18 @@ pub(crate) fn parse_timestamp(s: &str) -> Result<DateTime<Utc>, String> {
     }
     // Naive with fractional seconds (legacy or SQLite datetime() output)
     if let Ok(ndt) = NaiveDateTime::parse_from_str(s, "%Y-%m-%d %H:%M:%S%.f") {
+        tracing::warn!(
+            timestamp = %s,
+            "parsed naive timestamp without timezone; assuming UTC for backward compatibility"
+        );
         return Ok(ndt.and_utc());
     }
     // Naive without fractional seconds (legacy format)
     if let Ok(ndt) = NaiveDateTime::parse_from_str(s, "%Y-%m-%d %H:%M:%S") {
+        tracing::warn!(
+            timestamp = %s,
+            "parsed naive timestamp without timezone; assuming UTC for backward compatibility"
+        );
         return Ok(ndt.and_utc());
     }
     Err(format!("unparseable timestamp: {:?}", s))
@@ -402,8 +410,47 @@ pub(crate) fn row_to_routine_run_libsql(row: &libsql::Row) -> Result<RoutineRun,
 
 #[cfg(test)]
 mod tests {
+    use chrono::{TimeZone, Utc};
+
     use crate::db::Database;
-    use crate::db::libsql::LibSqlBackend;
+    use crate::db::libsql::{LibSqlBackend, parse_timestamp};
+
+    #[test]
+    fn test_parse_timestamp_accepts_rfc3339_and_legacy_naive_formats() {
+        let expected = Utc.with_ymd_and_hms(2026, 3, 7, 12, 34, 56).unwrap();
+
+        let with_millis = parse_timestamp("2026-03-07T12:34:56.789Z").unwrap();
+        assert_eq!(with_millis, expected + chrono::Duration::milliseconds(789));
+
+        let naive_with_millis = parse_timestamp("2026-03-07 12:34:56.789").unwrap();
+        assert_eq!(
+            naive_with_millis,
+            expected + chrono::Duration::milliseconds(789)
+        );
+
+        let naive_without_millis = parse_timestamp("2026-03-07 12:34:56").unwrap();
+        assert_eq!(naive_without_millis, expected);
+    }
+
+    #[tokio::test]
+    async fn test_libsql_now_format_is_rfc3339_and_parseable() {
+        let backend = LibSqlBackend::new_memory().await.unwrap();
+        backend.run_migrations().await.unwrap();
+
+        let conn = backend.connect().await.unwrap();
+        let mut rows = conn
+            .query("SELECT strftime('%Y-%m-%dT%H:%M:%fZ', 'now')", ())
+            .await
+            .unwrap();
+        let row = rows.next().await.unwrap().unwrap();
+        let ts: String = row.get(0).unwrap();
+
+        let parsed = parse_timestamp(&ts).unwrap();
+        assert_eq!(
+            ts,
+            parsed.to_rfc3339_opts(chrono::SecondsFormat::Millis, true)
+        );
+    }
 
     #[tokio::test]
     async fn test_wal_mode_after_migrations() {
diff --git a/src/db/libsql_migrations.rs b/src/db/libsql_migrations.rs
index 084ae53d..63708235 100644
--- a/src/db/libsql_migrations.rs
+++ b/src/db/libsql_migrations.rs
@@ -26,7 +26,7 @@ pub const SCHEMA: &str = r#"
 CREATE TABLE IF NOT EXISTS _migrations (
     version INTEGER PRIMARY KEY,
     name TEXT NOT NULL,
-    applied_at TEXT NOT NULL DEFAULT (datetime('now'))
+    applied_at TEXT NOT NULL DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now'))
 );
 
 -- ==================== Conversations ====================
@@ -36,8 +36,8 @@ CREATE TABLE IF NOT EXISTS conversations (
     channel TEXT NOT NULL,
     user_id TEXT NOT NULL,
     thread_id TEXT,
-    started_at TEXT NOT NULL DEFAULT (datetime('now')),
-    last_activity TEXT NOT NULL DEFAULT (datetime('now')),
+    started_at TEXT NOT NULL DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
+    last_activity TEXT NOT NULL DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
     metadata TEXT NOT NULL DEFAULT '{}'
 );
 
@@ -59,7 +59,7 @@ CREATE TABLE IF NOT EXISTS conversation_messages (
     conversation_id TEXT NOT NULL REFERENCES conversations(id) ON DELETE CASCADE,
     role TEXT NOT NULL,
     content TEXT NOT NULL,
-    created_at TEXT NOT NULL DEFAULT (datetime('now'))
+    created_at TEXT NOT NULL DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now'))
 );
 
 CREATE INDEX IF NOT EXISTS idx_conversation_messages_conversation
@@ -91,7 +91,7 @@ CREATE TABLE IF NOT EXISTS agent_jobs (
     failure_reason TEXT,
     stuck_since TEXT,
     repair_attempts INTEGER NOT NULL DEFAULT 0,
-    created_at TEXT NOT NULL DEFAULT (datetime('now')),
+    created_at TEXT NOT NULL DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
     started_at TEXT,
     completed_at TEXT
 );
@@ -116,7 +116,7 @@ CREATE TABLE IF NOT EXISTS job_actions (
     duration_ms INTEGER,
     success INTEGER NOT NULL,
     error_message TEXT,
-    created_at TEXT NOT NULL DEFAULT (datetime('now')),
+    created_at TEXT NOT NULL DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
     UNIQUE(job_id, sequence_num)
 );
 
@@ -137,8 +137,8 @@ CREATE TABLE IF NOT EXISTS dynamic_tools (
     failure_count INTEGER NOT NULL DEFAULT 0,
     last_error TEXT,
     status TEXT NOT NULL DEFAULT 'active',
-    created_at TEXT NOT NULL DEFAULT (datetime('now')),
-    updated_at TEXT NOT NULL DEFAULT (datetime('now'))
+    created_at TEXT NOT NULL DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
+    updated_at TEXT NOT NULL DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now'))
 );
 
 CREATE INDEX IF NOT EXISTS idx_dynamic_tools_status ON dynamic_tools(status);
@@ -156,7 +156,7 @@ CREATE TABLE IF NOT EXISTS llm_calls (
     output_tokens INTEGER NOT NULL,
     cost TEXT NOT NULL,
     purpose TEXT,
-    created_at TEXT NOT NULL DEFAULT (datetime('now'))
+    created_at TEXT NOT NULL DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now'))
 );
 
 CREATE INDEX IF NOT EXISTS idx_llm_calls_job ON llm_calls(job_id);
@@ -176,7 +176,7 @@ CREATE TABLE IF NOT EXISTS estimation_snapshots (
     actual_time_secs INTEGER,
     estimated_value TEXT NOT NULL,
     actual_value TEXT,
-    created_at TEXT NOT NULL DEFAULT (datetime('now'))
+    created_at TEXT NOT NULL DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now'))
 );
 
 CREATE INDEX IF NOT EXISTS idx_estimation_category ON estimation_snapshots(category);
@@ -192,7 +192,7 @@ CREATE TABLE IF NOT EXISTS repair_attempts (
     action_taken TEXT NOT NULL,
     success INTEGER NOT NULL,
     error_message TEXT,
-    created_at TEXT NOT NULL DEFAULT (datetime('now'))
+    created_at TEXT NOT NULL DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now'))
 );
 
 CREATE INDEX IF NOT EXISTS idx_repair_attempts_target ON repair_attempts(target_type, target_id);
@@ -206,8 +206,8 @@ CREATE TABLE IF NOT EXISTS memory_documents (
     agent_id TEXT,
     path TEXT NOT NULL,
     content TEXT NOT NULL,
-    created_at TEXT NOT NULL DEFAULT (datetime('now')),
-    updated_at TEXT NOT NULL DEFAULT (datetime('now')),
+    created_at TEXT NOT NULL DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
+    updated_at TEXT NOT NULL DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
     metadata TEXT NOT NULL DEFAULT '{}',
     UNIQUE (user_id, agent_id, path)
 );
@@ -222,7 +222,7 @@ CREATE TRIGGER IF NOT EXISTS update_memory_documents_updated_at
     FOR EACH ROW
     WHEN NEW.updated_at = OLD.updated_at
     BEGIN
-        UPDATE memory_documents SET updated_at = datetime('now') WHERE id = NEW.id;
+        UPDATE memory_documents SET updated_at = strftime('%Y-%m-%dT%H:%M:%fZ', 'now') WHERE id = NEW.id;
     END;
 
 -- ==================== Workspace: Memory Chunks ====================
@@ -234,7 +234,7 @@ CREATE TABLE IF NOT EXISTS memory_chunks (
     chunk_index INTEGER NOT NULL,
     content TEXT NOT NULL,
     embedding BLOB,
-    created_at TEXT NOT NULL DEFAULT (datetime('now')),
+    created_at TEXT NOT NULL DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
     UNIQUE (document_id, chunk_index)
 );
 
@@ -296,8 +296,8 @@ CREATE TABLE IF NOT EXISTS secrets (
     expires_at TEXT,
     last_used_at TEXT,
     usage_count INTEGER NOT NULL DEFAULT 0,
-    created_at TEXT NOT NULL DEFAULT (datetime('now')),
-    updated_at TEXT NOT NULL DEFAULT (datetime('now')),
+    created_at TEXT NOT NULL DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
+    updated_at TEXT NOT NULL DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
     UNIQUE (user_id, name)
 );
 
@@ -318,8 +318,8 @@ CREATE TABLE IF NOT EXISTS wasm_tools (
     source_url TEXT,
     trust_level TEXT NOT NULL DEFAULT 'user',
     status TEXT NOT NULL DEFAULT 'active',
-    created_at TEXT NOT NULL DEFAULT (datetime('now')),
-    updated_at TEXT NOT NULL DEFAULT (datetime('now')),
+    created_at TEXT NOT NULL DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
+    updated_at TEXT NOT NULL DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
     UNIQUE (user_id, name, version)
 );
 
@@ -340,8 +340,8 @@ CREATE TABLE IF NOT EXISTS wasm_channels (
     binary_hash BLOB NOT NULL,
     capabilities_json TEXT NOT NULL DEFAULT '{}',
     status TEXT NOT NULL DEFAULT 'active',
-    created_at TEXT NOT NULL DEFAULT (datetime('now')),
-    updated_at TEXT NOT NULL DEFAULT (datetime('now')),
+    created_at TEXT NOT NULL DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
+    updated_at TEXT NOT NULL DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
     UNIQUE (user_id, name)
 );
 
@@ -359,8 +359,8 @@ CREATE TABLE IF NOT EXISTS tool_capabilities (
     max_response_body_bytes INTEGER NOT NULL DEFAULT 10485760,
     workspace_read_prefixes TEXT NOT NULL DEFAULT '[]',
     http_timeout_secs INTEGER NOT NULL DEFAULT 30,
-    created_at TEXT NOT NULL DEFAULT (datetime('now')),
-    updated_at TEXT NOT NULL DEFAULT (datetime('now')),
+    created_at TEXT NOT NULL DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
+    updated_at TEXT NOT NULL DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
     UNIQUE (wasm_tool_id)
 );
 
@@ -373,7 +373,7 @@ CREATE TABLE IF NOT EXISTS leak_detection_patterns (
     severity TEXT NOT NULL DEFAULT 'high',
     action TEXT NOT NULL DEFAULT 'block',
     enabled INTEGER NOT NULL DEFAULT 1,
-    created_at TEXT NOT NULL DEFAULT (datetime('now'))
+    created_at TEXT NOT NULL DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now'))
 );
 
 -- ==================== Rate Limit State ====================
@@ -382,9 +382,9 @@ CREATE TABLE IF NOT EXISTS tool_rate_limit_state (
     id TEXT PRIMARY KEY,
     wasm_tool_id TEXT NOT NULL REFERENCES wasm_tools(id) ON DELETE CASCADE,
     user_id TEXT NOT NULL,
-    minute_window_start TEXT NOT NULL DEFAULT (datetime('now')),
+    minute_window_start TEXT NOT NULL DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
     minute_count INTEGER NOT NULL DEFAULT 0,
-    hour_window_start TEXT NOT NULL DEFAULT (datetime('now')),
+    hour_window_start TEXT NOT NULL DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
     hour_count INTEGER NOT NULL DEFAULT 0,
     UNIQUE (wasm_tool_id, user_id)
 );
@@ -400,7 +400,7 @@ CREATE TABLE IF NOT EXISTS secret_usage_log (
     target_path TEXT,
     success INTEGER NOT NULL,
     error_message TEXT,
-    created_at TEXT NOT NULL DEFAULT (datetime('now'))
+    created_at TEXT NOT NULL DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now'))
 );
 
 CREATE INDEX IF NOT EXISTS idx_secret_usage_user ON secret_usage_log(user_id);
@@ -415,7 +415,7 @@ CREATE TABLE IF NOT EXISTS leak_detection_events (
     source TEXT NOT NULL,
     action_taken TEXT NOT NULL,
     context_preview TEXT,
-    created_at TEXT NOT NULL DEFAULT (datetime('now'))
+    created_at TEXT NOT NULL DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now'))
 );
 
 -- ==================== Tool Failures ====================
@@ -425,8 +425,8 @@ CREATE TABLE IF NOT EXISTS tool_failures (
     tool_name TEXT NOT NULL UNIQUE,
     error_message TEXT,
     error_count INTEGER DEFAULT 1,
-    first_failure TEXT DEFAULT (datetime('now')),
-    last_failure TEXT DEFAULT (datetime('now')),
+    first_failure TEXT DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
+    last_failure TEXT DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
     last_build_result TEXT,
     repaired_at TEXT,
     repair_attempts INTEGER DEFAULT 0
@@ -441,7 +441,7 @@ CREATE TABLE IF NOT EXISTS job_events (
     job_id TEXT NOT NULL REFERENCES agent_jobs(id),
     event_type TEXT NOT NULL,
     data TEXT NOT NULL,
-    created_at TEXT NOT NULL DEFAULT (datetime('now'))
+    created_at TEXT NOT NULL DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now'))
 );
 
 CREATE INDEX IF NOT EXISTS idx_job_events_job ON job_events(job_id, id);
@@ -471,8 +471,8 @@ CREATE TABLE IF NOT EXISTS routines (
     next_fire_at TEXT,
     run_count INTEGER NOT NULL DEFAULT 0,
     consecutive_failures INTEGER NOT NULL DEFAULT 0,
-    created_at TEXT NOT NULL DEFAULT (datetime('now')),
-    updated_at TEXT NOT NULL DEFAULT (datetime('now')),
+    created_at TEXT NOT NULL DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
+    updated_at TEXT NOT NULL DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
     UNIQUE (user_id, name)
 );
 
@@ -485,13 +485,13 @@ CREATE TABLE IF NOT EXISTS routine_runs (
     routine_id TEXT NOT NULL REFERENCES routines(id) ON DELETE CASCADE,
     trigger_type TEXT NOT NULL,
     trigger_detail TEXT,
-    started_at TEXT NOT NULL DEFAULT (datetime('now')),
+    started_at TEXT NOT NULL DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
     completed_at TEXT,
     status TEXT NOT NULL DEFAULT 'running',
     result_summary TEXT,
     tokens_used INTEGER,
     job_id TEXT REFERENCES agent_jobs(id),
-    created_at TEXT NOT NULL DEFAULT (datetime('now'))
+    created_at TEXT NOT NULL DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now'))
 );
 
 CREATE INDEX IF NOT EXISTS idx_routine_runs_routine ON routine_runs(routine_id);
@@ -502,7 +502,7 @@ CREATE TABLE IF NOT EXISTS settings (
     user_id TEXT NOT NULL,
     key TEXT NOT NULL,
     value TEXT NOT NULL,
-    updated_at TEXT NOT NULL DEFAULT (datetime('now')),
+    updated_at TEXT NOT NULL DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
     PRIMARY KEY (user_id, key)
 );
 
@@ -558,24 +558,24 @@ CREATE INDEX IF NOT EXISTS idx_heartbeat_next_run ON heartbeat_state(next_run);
 
 -- Pre-populate leak detection patterns (matches PostgreSQL V2 migration).
 INSERT OR IGNORE INTO leak_detection_patterns (id, name, pattern, severity, action, enabled, created_at) VALUES
-    ('550e8400-e29b-41d4-a716-446655440001', 'openai_api_key', 'sk-(?:proj-)?[a-zA-Z0-9]{20,}(?:T3BlbkFJ[a-zA-Z0-9_-]*)?', 'critical', 'block', 1, datetime('now')),
-    ('550e8400-e29b-41d4-a716-446655440002', 'anthropic_api_key', 'sk-ant-api[a-zA-Z0-9_-]{90,}', 'critical', 'block', 1, datetime('now')),
-    ('550e8400-e29b-41d4-a716-446655440003', 'aws_access_key', 'AKIA[0-9A-Z]{16}', 'critical', 'block', 1, datetime('now')),
-    ('550e8400-e29b-41d4-a716-446655440004', 'aws_secret_key', '(?<![A-Za-z0-9/+=])[A-Za-z0-9/+=]{40}(?![A-Za-z0-9/+=])', 'high', 'block', 1, datetime('now')),
-    ('550e8400-e29b-41d4-a716-446655440005', 'github_token', 'gh[pousr]_[A-Za-z0-9_]{36,}', 'critical', 'block', 1, datetime('now')),
-    ('550e8400-e29b-41d4-a716-446655440006', 'github_fine_grained_pat', 'github_pat_[a-zA-Z0-9]{22}_[a-zA-Z0-9]{59}', 'critical', 'block', 1, datetime('now')),
-    ('550e8400-e29b-41d4-a716-446655440007', 'stripe_api_key', 'sk_(?:live|test)_[a-zA-Z0-9]{24,}', 'critical', 'block', 1, datetime('now')),
-    ('550e8400-e29b-41d4-a716-446655440008', 'nearai_session', 'sess_[a-zA-Z0-9]{32,}', 'critical', 'block', 1, datetime('now')),
-    ('550e8400-e29b-41d4-a716-446655440009', 'bearer_token', 'Bearer\s+[a-zA-Z0-9_-]{20,}', 'high', 'redact', 1, datetime('now')),
-    ('550e8400-e29b-41d4-a716-44665544000a', 'pem_private_key', '-----BEGIN\s+(?:RSA\s+)?PRIVATE\s+KEY-----', 'critical', 'block', 1, datetime('now')),
-    ('550e8400-e29b-41d4-a716-44665544000b', 'ssh_private_key', '-----BEGIN\s+(?:OPENSSH|EC|DSA)\s+PRIVATE\s+KEY-----', 'critical', 'block', 1, datetime('now')),
-    ('550e8400-e29b-41d4-a716-44665544000c', 'google_api_key', 'AIza[0-9A-Za-z_-]{35}', 'high', 'block', 1, datetime('now')),
-    ('550e8400-e29b-41d4-a716-44665544000d', 'slack_token', 'xox[baprs]-[0-9a-zA-Z-]{10,}', 'high', 'block', 1, datetime('now')),
-    ('550e8400-e29b-41d4-a716-44665544000e', 'discord_token', '[MN][A-Za-z\d]{23,}\.[\w-]{6}\.[\w-]{27}', 'high', 'block', 1, datetime('now')),
-    ('550e8400-e29b-41d4-a716-44665544000f', 'twilio_api_key', 'SK[a-fA-F0-9]{32}', 'high', 'block', 1, datetime('now')),
-    ('550e8400-e29b-41d4-a716-446655440010', 'sendgrid_api_key', 'SG\.[a-zA-Z0-9_-]{22}\.[a-zA-Z0-9_-]{43}', 'high', 'block', 1, datetime('now')),
-    ('550e8400-e29b-41d4-a716-446655440011', 'mailchimp_api_key', '[a-f0-9]{32}-us[0-9]{1,2}', 'medium', 'block', 1, datetime('now')),
-    ('550e8400-e29b-41d4-a716-446655440012', 'high_entropy_hex', '(?<![a-fA-F0-9])[a-fA-F0-9]{64}(?![a-fA-F0-9])', 'medium', 'warn', 1, datetime('now'));
+    ('550e8400-e29b-41d4-a716-446655440001', 'openai_api_key', 'sk-(?:proj-)?[a-zA-Z0-9]{20,}(?:T3BlbkFJ[a-zA-Z0-9_-]*)?', 'critical', 'block', 1, strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
+    ('550e8400-e29b-41d4-a716-446655440002', 'anthropic_api_key', 'sk-ant-api[a-zA-Z0-9_-]{90,}', 'critical', 'block', 1, strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
+    ('550e8400-e29b-41d4-a716-446655440003', 'aws_access_key', 'AKIA[0-9A-Z]{16}', 'critical', 'block', 1, strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
+    ('550e8400-e29b-41d4-a716-446655440004', 'aws_secret_key', '(?<![A-Za-z0-9/+=])[A-Za-z0-9/+=]{40}(?![A-Za-z0-9/+=])', 'high', 'block', 1, strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
+    ('550e8400-e29b-41d4-a716-446655440005', 'github_token', 'gh[pousr]_[A-Za-z0-9_]{36,}', 'critical', 'block', 1, strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
+    ('550e8400-e29b-41d4-a716-446655440006', 'github_fine_grained_pat', 'github_pat_[a-zA-Z0-9]{22}_[a-zA-Z0-9]{59}', 'critical', 'block', 1, strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
+    ('550e8400-e29b-41d4-a716-446655440007', 'stripe_api_key', 'sk_(?:live|test)_[a-zA-Z0-9]{24,}', 'critical', 'block', 1, strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
+    ('550e8400-e29b-41d4-a716-446655440008', 'nearai_session', 'sess_[a-zA-Z0-9]{32,}', 'critical', 'block', 1, strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
+    ('550e8400-e29b-41d4-a716-446655440009', 'bearer_token', 'Bearer\s+[a-zA-Z0-9_-]{20,}', 'high', 'redact', 1, strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
+    ('550e8400-e29b-41d4-a716-44665544000a', 'pem_private_key', '-----BEGIN\s+(?:RSA\s+)?PRIVATE\s+KEY-----', 'critical', 'block', 1, strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
+    ('550e8400-e29b-41d4-a716-44665544000b', 'ssh_private_key', '-----BEGIN\s+(?:OPENSSH|EC|DSA)\s+PRIVATE\s+KEY-----', 'critical', 'block', 1, strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
+    ('550e8400-e29b-41d4-a716-44665544000c', 'google_api_key', 'AIza[0-9A-Za-z_-]{35}', 'high', 'block', 1, strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
+    ('550e8400-e29b-41d4-a716-44665544000d', 'slack_token', 'xox[baprs]-[0-9a-zA-Z-]{10,}', 'high', 'block', 1, strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
+    ('550e8400-e29b-41d4-a716-44665544000e', 'discord_token', '[MN][A-Za-z\d]{23,}\.[\w-]{6}\.[\w-]{27}', 'high', 'block', 1, strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
+    ('550e8400-e29b-41d4-a716-44665544000f', 'twilio_api_key', 'SK[a-fA-F0-9]{32}', 'high', 'block', 1, strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
+    ('550e8400-e29b-41d4-a716-446655440010', 'sendgrid_api_key', 'SG\.[a-zA-Z0-9_-]{22}\.[a-zA-Z0-9_-]{43}', 'high', 'block', 1, strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
+    ('550e8400-e29b-41d4-a716-446655440011', 'mailchimp_api_key', '[a-f0-9]{32}-us[0-9]{1,2}', 'medium', 'block', 1, strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
+    ('550e8400-e29b-41d4-a716-446655440012', 'high_entropy_hex', '(?<![a-fA-F0-9])[a-fA-F0-9]{64}(?![a-fA-F0-9])', 'medium', 'warn', 1, strftime('%Y-%m-%dT%H:%M:%fZ', 'now'));
 
 "#;
 
@@ -613,7 +613,7 @@ CREATE TABLE IF NOT EXISTS memory_chunks_new (
     chunk_index INTEGER NOT NULL,
     content TEXT NOT NULL,
     embedding BLOB,
-    created_at TEXT NOT NULL DEFAULT (datetime('now')),
+    created_at TEXT NOT NULL DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
     UNIQUE (document_id, chunk_index)
 );