From 51cec3751420fea1d9ae1c895b295d45e8c8f807 Mon Sep 17 00:00:00 2001
From: Zaki <zaki@iqlusion.io>
Date: Sat, 7 Mar 2026 17:32:18 -0800
Subject: [PATCH] fix(libsql): standardize timestamp storage to RFC 3339 with
 UTC offset (#663)

Replace all `datetime('now')` defaults in libsql_migrations.rs with
`strftime('%Y-%m-%dT%H:%M:%fZ', 'now')` so new rows get proper RFC 3339
timestamps (e.g. `2024-01-15T10:30:00.123Z`) instead of naive datetimes
(e.g. `2024-01-15 10:30:00`).

Add tracing::warn! to parse_timestamp() naive fallback paths so legacy
timestamps are still accepted but produce a visible deprecation signal.

Backward compatible: no data migration needed; existing naive timestamps
continue to parse correctly via the multi-format fallback.

Co-Authored-By: Claude Opus 4.6 <noreply@anthropic.com>
---
 src/db/libsql/mod.rs        | 102 +++++++++++++++++++++++++++++++++
 src/db/libsql_migrations.rs | 110 ++++++++++++++++++------------------
 2 files changed, 157 insertions(+), 55 deletions(-)

diff --git a/src/db/libsql/mod.rs b/src/db/libsql/mod.rs
index 6ff8ca6b..299c09cb 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,
+            "parsing naive timestamp without timezone; assuming UTC — consider re-running migrations"
+        );
         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,
+            "parsing naive timestamp without timezone; assuming UTC — consider re-running migrations"
+        );
         return Ok(ndt.and_utc());
     }
     Err(format!("unparseable timestamp: {:?}", s))
@@ -510,4 +518,98 @@ mod tests {
             );
         }
     }
+
+    #[test]
+    fn test_parse_timestamp_rfc3339() {
+        use super::parse_timestamp;
+
+        // Standard RFC 3339 with Z suffix
+        let dt = parse_timestamp("2024-01-15T10:30:00.123Z").unwrap();
+        assert_eq!(
+            dt.to_rfc3339_opts(chrono::SecondsFormat::Millis, true),
+            "2024-01-15T10:30:00.123Z"
+        );
+
+        // RFC 3339 with +00:00 offset
+        let dt = parse_timestamp("2024-01-15T10:30:00.000+00:00").unwrap();
+        assert_eq!(
+            dt.to_rfc3339_opts(chrono::SecondsFormat::Millis, true),
+            "2024-01-15T10:30:00.000Z"
+        );
+    }
+
+    #[test]
+    fn test_parse_timestamp_naive_fallback() {
+        use super::parse_timestamp;
+
+        // Naive with fractional seconds (legacy datetime('now') output)
+        let dt = parse_timestamp("2024-01-15 10:30:00.123").unwrap();
+        assert_eq!(
+            dt.to_rfc3339_opts(chrono::SecondsFormat::Millis, true),
+            "2024-01-15T10:30:00.123Z"
+        );
+
+        // Naive without fractional seconds
+        let dt = parse_timestamp("2024-01-15 10:30:00").unwrap();
+        assert_eq!(
+            dt.to_rfc3339_opts(chrono::SecondsFormat::Millis, true),
+            "2024-01-15T10:30:00.000Z"
+        );
+    }
+
+    #[test]
+    fn test_parse_timestamp_invalid() {
+        use super::parse_timestamp;
+
+        assert!(parse_timestamp("not-a-timestamp").is_err());
+        assert!(parse_timestamp("").is_err());
+    }
+
+    #[tokio::test]
+    async fn test_default_timestamps_are_rfc3339() {
+        // Verify that DEFAULT column values produce RFC 3339 timestamps
+        // after the migration change from datetime('now') to strftime.
+        // Use file-based DB because in-memory doesn't share schema across connections.
+        let dir = tempfile::tempdir().unwrap();
+        let db_path = dir.path().join("test_ts.db");
+        let backend = LibSqlBackend::new_local(&db_path).await.unwrap();
+        backend.run_migrations().await.unwrap();
+
+        let conn = backend.connect().await.unwrap();
+        let id = uuid::Uuid::new_v4().to_string();
+        conn.execute(
+            "INSERT INTO conversations (id, channel, user_id) VALUES (?1, ?2, ?3)",
+            libsql::params![id.clone(), "test", "user1"],
+        )
+        .await
+        .unwrap();
+
+        let mut rows = conn
+            .query(
+                "SELECT started_at, last_activity FROM conversations WHERE id = ?1",
+                libsql::params![id],
+            )
+            .await
+            .unwrap();
+        let row = rows.next().await.unwrap().unwrap();
+        let started_at: String = row.get(0).unwrap();
+        let last_activity: String = row.get(1).unwrap();
+
+        // Must end with 'Z' (RFC 3339 UTC) and contain 'T' separator
+        assert!(
+            started_at.ends_with('Z') && started_at.contains('T'),
+            "started_at should be RFC 3339, got: {started_at}"
+        );
+        assert!(
+            last_activity.ends_with('Z') && last_activity.contains('T'),
+            "last_activity should be RFC 3339, got: {last_activity}"
+        );
+
+        // Must be parseable by the RFC 3339 parser directly (not just naive fallback)
+        use chrono::DateTime;
+        assert!(
+            DateTime::parse_from_rfc3339(&started_at).is_ok(),
+            "started_at not valid RFC 3339: {started_at}"
+        );
+    }
 }
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)
 );