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Initial commit - 611 cybersecurity skills across all subdomains
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---
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name: deploying-osquery-for-endpoint-monitoring
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description: >
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Deploys and configures osquery for real-time endpoint monitoring using SQL-based queries to
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inspect running processes, open ports, installed software, and system configuration. Use when
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building visibility into endpoint state, threat hunting across fleet, or implementing
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compliance monitoring. Activates for requests involving osquery deployment, endpoint visibility,
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fleet management, or SQL-based endpoint querying.
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domain: cybersecurity
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subdomain: endpoint-security
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tags: [endpoint, osquery, endpoint-monitoring, threat-hunting, fleet-management]
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version: 1.0.0
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author: mahipal
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license: MIT
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---
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# Deploying Osquery for Endpoint Monitoring
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## When to Use
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Use this skill when:
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- Deploying osquery across Windows, macOS, and Linux endpoints for fleet-wide visibility
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- Building threat hunting queries using osquery's SQL interface
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- Monitoring endpoint compliance (installed software, open ports, running services)
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- Integrating osquery data with SIEM or Kolide/Fleet for centralized management
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**Do not use** for real-time alerting (osquery is periodic/on-demand; use EDR for real-time).
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## Prerequisites
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- Osquery package for target OS (https://osquery.io/downloads)
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- Fleet management server (Kolide Fleet or FleetDM) for enterprise deployment
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- TLS certificates for secure agent-to-server communication
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- Log aggregation pipeline (Filebeat, Fluentd) for osquery result logs
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## Workflow
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### Step 1: Install Osquery
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```bash
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# Ubuntu/Debian
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export OSQUERY_KEY=1484120AC4E9F8A1A577AEEE97A80C63C9D8B80B
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apt-key adv --keyserver hkp://keyserver.ubuntu.com:80 --recv-keys $OSQUERY_KEY
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add-apt-repository 'deb [arch=amd64] https://pkg.osquery.io/deb deb main'
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apt-get update && apt-get install osquery -y
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# Windows (MSI)
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# Download from https://osquery.io/downloads/official
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msiexec /i osquery-5.12.1.msi /quiet
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# macOS
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brew install osquery
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```
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### Step 2: Configure Osquery
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```json
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// /etc/osquery/osquery.conf (Linux/macOS) or C:\ProgramData\osquery\osquery.conf
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{
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"options": {
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"config_plugin": "filesystem",
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"logger_plugin": "filesystem",
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"logger_path": "/var/log/osquery",
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"disable_logging": "false",
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"schedule_splay_percent": "10",
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"events_expiry": "3600",
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"verbose": "false",
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"worker_threads": "2",
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"enable_monitor": "true",
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"disable_events": "false",
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"disable_audit": "false",
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"audit_allow_config": "true",
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"host_identifier": "hostname",
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"enable_syslog": "true"
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},
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"schedule": {
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"process_monitor": {
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"query": "SELECT pid, name, path, cmdline, uid, parent FROM processes WHERE on_disk = 0;",
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"interval": 300,
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"description": "Detect processes running without on-disk binary (fileless)"
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},
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"listening_ports": {
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"query": "SELECT DISTINCT p.name, p.path, lp.port, lp.protocol, lp.address FROM listening_ports lp JOIN processes p ON lp.pid = p.pid WHERE lp.port != 0;",
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"interval": 600,
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"description": "Monitor listening network ports"
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},
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"persistence_check": {
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"query": "SELECT name, path, source FROM startup_items;",
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"interval": 3600,
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"description": "Monitor persistence mechanisms"
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},
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"installed_packages": {
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"query": "SELECT name, version, source FROM deb_packages;",
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"interval": 86400,
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"description": "Daily software inventory"
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},
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"users_and_groups": {
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"query": "SELECT u.username, u.uid, u.gid, u.shell, u.directory FROM users u WHERE u.uid >= 1000;",
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"interval": 3600
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},
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"crontab_monitor": {
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"query": "SELECT * FROM crontab;",
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"interval": 3600,
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"description": "Monitor scheduled tasks"
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},
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"suid_binaries": {
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"query": "SELECT path, username, permissions FROM suid_bin;",
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"interval": 86400,
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"description": "Detect SUID binaries"
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}
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},
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"packs": {
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"incident-response": "/usr/share/osquery/packs/incident-response.conf",
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"ossec-rootkit": "/usr/share/osquery/packs/ossec-rootkit.conf",
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"vuln-management": "/usr/share/osquery/packs/vuln-management.conf"
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}
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}
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```
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### Step 3: Threat Hunting Queries
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```sql
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-- Detect processes with no on-disk binary (potential fileless malware)
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SELECT pid, name, path, cmdline FROM processes WHERE on_disk = 0;
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-- Find listening ports not associated with known services
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SELECT lp.port, lp.protocol, p.name, p.path
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FROM listening_ports lp JOIN processes p ON lp.pid = p.pid
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WHERE lp.port NOT IN (22, 80, 443, 3306, 5432);
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-- Detect unauthorized SSH keys
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SELECT * FROM authorized_keys WHERE NOT key LIKE '%admin-team%';
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-- Find recently modified system binaries
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SELECT path, mtime, size FROM file
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WHERE path LIKE '/usr/bin/%' AND mtime > (strftime('%s', 'now') - 86400);
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-- Detect processes connecting to external IPs
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SELECT DISTINCT p.name, p.path, pn.remote_address, pn.remote_port
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FROM process_open_sockets pn JOIN processes p ON pn.pid = p.pid
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WHERE pn.remote_address NOT LIKE '10.%'
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AND pn.remote_address NOT LIKE '172.16.%'
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AND pn.remote_address NOT LIKE '192.168.%'
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AND pn.remote_address != '127.0.0.1'
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AND pn.remote_address != '0.0.0.0';
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-- Windows: Detect unsigned running executables
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SELECT p.name, p.path, a.result AS signature_status
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FROM processes p JOIN authenticode a ON p.path = a.path
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WHERE a.result != 'trusted';
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```
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### Step 4: Deploy FleetDM for Centralized Management
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```bash
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# FleetDM provides centralized osquery management
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# Deploy FleetDM server, configure agents to report to it
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# Agents use TLS enrollment and config from Fleet
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# Agent configuration for Fleet:
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# --tls_hostname=fleet.corp.com
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# --tls_server_certs=/etc/osquery/fleet.pem
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# --enroll_secret_path=/etc/osquery/enroll_secret
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```
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## Key Concepts
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| Term | Definition |
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|------|-----------|
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| **Osquery** | Open-source endpoint agent that exposes OS state as SQL tables for querying |
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| **Schedule** | Periodic queries that run at defined intervals and log results |
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| **Pack** | Collection of related queries grouped for specific use cases (IR, compliance) |
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| **FleetDM** | Open-source osquery fleet management platform |
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| **Differential Results** | Osquery logs only changes between query executions, reducing data volume |
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## Tools & Systems
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- **Osquery**: https://osquery.io/ - endpoint visibility agent
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- **FleetDM**: https://fleetdm.com/ - centralized fleet management
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- **Kolide**: Cloud-based osquery management with Slack integration
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- **osquery-go**: Go client library for osquery extensions
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## Common Pitfalls
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- **Query performance**: Complex queries with large table scans impact endpoint performance. Use WHERE clauses and test query cost with `EXPLAIN`.
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- **Schedule intervals too aggressive**: Running heavy queries every 60 seconds causes CPU spikes. Use 300-3600 second intervals for most queries.
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- **Not using differential mode**: Without differential logging, osquery logs all results every interval. Differential mode logs only changes.
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- **Missing event tables**: Some osquery tables require events framework enabled (process_events, socket_events). Enable with `--disable_events=false`.
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