During most red team engagements, after compromising a target, pentester’s will often find they need to learn as much about the device and its network surroundings as possible. This is commonly referred to as “situational awareness.” This is the act of gathering hardware, software, and network information about the target. This information can be used to further compromise the target, their online accounts, and pivot to other devices and services within the network.
Our goal as penetration testers is to learn as much about our newly compromised macOS device as possible without alerting the target to our presence. Generally, using tools built into the operating system to perform information gathering will help us evade detection. There are many tools in macOS that we can use to fingerprint the device, the network, and Wi-Fi networks it’s connected to. The first (and possibly the most important) tool we’ll be talking about is system_profiler.
The system_profiler tool was designed to print system hardware and software configurations. It features the ability to export information in XML format and supports several degrees of output verbosity.
In most cases, system_profiler will produce over 55,000 lines of data pertaining to the target macOS device. This data includes very specific hardware details, firewall settings, Wi-Fi adapter details, startup items, and detailed application info, to name just a few.
System_profiler can be used without root privileges and is, therefore, an attacker’s greatest tool for quickly discovering hardware and software specifications.
The following system_profiler commands can be executed using a Terminal or from a Netcat backdoor. Use the –help argument to view the available options.
system_profiler --help Usage: system_profiler [-listDataTypes] system_profiler [-xml] [-timeout n] [-detailLevel n] system_profiler [-xml] [-timeout n] [dataType1 ... dataTypeN] -detailLevel n specifies the level of detail for the report mini = short report (contains no identifying or personal information) basic = basic hardware and network information full = all available information -listDataTypes lists all the available datatypes -xml generates xml output instead of plain text if redirected to a file with the extension ".spx" the file can be opened in System Profiler.app -timeout specifies the maximum time to spend gathering information the default is 180 seconds, 0 means no timeout Redirect stderr to /dev/null to suppress progress and error messages.
The system_profiler “Datatypes” represent different components of the macOS system. For example, using the SPFirewallDataType argument will print the device’s firewall configuration.
system_profiler SPFirewallDataType Firewall: Firewall Settings: Mode: Block all incoming connections Firewall Logging: Yes Stealth Mode: No/Yes (As Per Need)
We’ve now learned the device has the firewall enabled and is blocking all incoming connections. This small bit of information is critical to an attacker planning their next move and trying to establish persistence.
There’s a -listDataTypes argument that can be used to view all of the available Datatypes.
system_profiler -listDataTypes Available Datatypes: SPParallelATADataType SPUniversalAccessDataType SPApplicationsDataType SPAudioDataType SPBluetoothDataType SPCameraDataType SPCardReaderDataType SPComponentDataType SPiBridgeDataType SPDeveloperToolsDataType SPDiagnosticsDataType SPDisabledSoftwareDataType SPDiscBurningDataType SPEthernetDataType SPExtensionsDataType SPFibreChannelDataType SPFireWireDataType SPFirewallDataType SPFontsDataType SPFrameworksDataType SPDisplaysDataType SPHardwareDataType SPHardwareRAIDDataType SPInstallHistoryDataType SPNetworkLocationDataType SPLogsDataType SPManagedClientDataType SPMemoryDataType SPNVMeDataType SPNetworkDataType SPPCIDataType SPParallelSCSIDataType SPPowerDataType SPPrefPaneDataType SPPrintersSoftwareDataType SPPrintersDataType SPConfigurationProfileDataType SPRawCameraDataType SPSASDataType SPSerialATADataType SPSPIDataType SPSmartCardsDataType SPSoftwareDataType SPStartupItemDataType SPStorageDataType SPSyncServicesDataType SPThunderboltDataType SPUSBDataType SPNetworkVolumeDataType SPWWANDataType SPAirPortDataType
Multiple Datatypes can be used simultaneously. Below, I’m printing the MacBook’s OS version and network info.
system_profiler SPSoftwareDataType SPNetworkDataType Software: System Software Overview: System Version: macOS 10.13.6 (17G65) Kernel Version: Darwin 17.7.0 Boot Volume: macOS Boot Mode: Normal Computer Name: tokyoneon’s MacBook Air User Name: tokyoneon (tokyoneon) Secure Virtual Memory: Enabled System Integrity Protection: Enabled Time since boot: 1:27 Network: Wi-Fi: Type: AirPort Hardware: AirPort BSD Device Name: en0 IPv4 Addresses: 192.168.1.98 IPv4: AdditionalRoutes: DestinationAddress: 192.168.1.98 SubnetMask: 255.255.255.255 DestinationAddress: 169.254.0.0 SubnetMask: 255.255.0.0 Addresses: 192.168.1.98 ARPResolvedHardwareAddress: xx:xx:xx:xx:xx:xx ARPResolvedIPAddress: 192.168.1.1 Configuration Method: DHCP ConfirmedInterfaceName: en0 Interface Name: en0 Network Signature: IPv4.Router=192.168.1.1;IPv4.RouterHardwareAddress=xx:xx:xx:xx:xx:xx Router: 192.168.1.1 Subnet Masks: 255.255.255.0 IPv6: Configuration Method: Automatic DNS: Server Addresses: 192.168.1.1 DHCP Server Responses: Domain Name Servers: 192.168.1.1 Lease Duration (seconds): 0 DHCP Message Type: 0x05 Routers: 192.168.1.1 Server Identifier: 192.168.1.1 Subnet Mask: 255.255.255.0 Ethernet: MAC Address: xx:xx:xx:xx:xx:xx Media Options: Media Subtype: Auto Select Proxies: Exceptions List: *.local, 169.254/16 FTP Passive Mode: Yes Service Order: 0 Bluetooth PAN: Type: Ethernet Hardware: Ethernet BSD Device Name: en2 IPv4: Configuration Method: DHCP IPv6: Configuration Method: Automatic Proxies: Exceptions List: *.local, 169.254/16 FTP Passive Mode: Yes Service Order: 1 Thunderbolt Bridge: Type: Ethernet Hardware: Ethernet BSD Device Name: bridge0 IPv4: Configuration Method: DHCP IPv6: Configuration Method: Automatic Proxies: Exceptions List: *.local, 169.254/16 FTP Passive Mode: Yes Service Order: 2
When using the system_profiler without any arguments, it will use all of the available Datatypes. This will produce an enormous amount of data and can take several minutes to complete.
Identify Devices on the Network
The Address Resolution Protocol, known commonly as ARP, translates physical (MAC) addresses into IP addresses. Computers cache ARP information in “ARP tables,” which aid routers and devices on the network in quickly locating each other.
The arp command can be used to print the macOS device’s ARP table and discover devices on the network without performing a single Nmap scan.
arp -i en0 -l -a Neighbor Linklayer Address Expire(O) Expire(I) Netif Refs Prbs 192.168.1.1 xx:xx:xx:xx:xx:xx 1m36s 1m36s en0 1 192.168.1.79 xx:xx:xx:xx:xx:xx expired 1m18s en0 1 192.168.1.102 xx:xx:xx:xx:xx:xx expired 1m20s en0 1
There’s still so much that can be done to gain awareness of the compromised device and other devices on the network. Stay tuned for more on extracting sensitive information from a target’s Terminal history, locating interesting and recently edited documents on the device, enumerating external hard drives and USB-connected drives, and much more.