Malware descriptions

Dissecting TriangleDB, a Triangulation spyware implant

Over the years, there have been multiple cases when iOS devices were infected with targeted spyware such as Pegasus, Predator, Reign and others. Often, the process of infecting a device involves launching a chain of different exploits, e.g. for escaping the iMessage sandbox while processing a malicious attachment, and for getting root privileges through a vulnerability in the kernel. Due to this granularity, discovering one exploit in the chain often does not result in retrieving the rest of the chain and obtaining the final spyware payload. For example, in 2021, analysis of iTunes backups helped to discover an attachment containing the FORCEDENTRY exploit. However, during post-exploitation, the malicious code downloaded a payload from a remote server that was not accessible at the time of analysis. Consequently, the analysts lost “the ability to follow the exploit.”

In researching Operation Triangulation, we set ourselves the goal to retrieve as many parts of the exploitation chain as possible. It took about half a year to accomplish that goal, and, after the collection of the chain had been completed, we started an in-depth analysis of the discovered stages. As of now, we have finished analyzing the spyware implant and are ready to share the details.

The Operation Triangulation infection chain

The implant, which we dubbed TriangleDB, is deployed after the attackers obtain root privileges on the target iOS device by exploiting a kernel vulnerability. It is deployed in memory, meaning that all traces of the implant are lost when the device gets rebooted. Therefore, if the victim reboots their device, the attackers have to reinfect it by sending an iMessage with a malicious attachment, thus launching the whole exploitation chain again. In case no reboot occurs, the implant uninstalls itself after 30 days, unless this period is extended by the attackers.

Meet TriangleDB

The TriangleDB implant is coded using Objective-C, a programming language that preserves names of members and methods assigned by the developer. In the implant’s binary, method names are not obfuscated; however, names of class members are uninformative acronyms, which makes it difficult to guess their meaning:

Class method examples

Class member examples

-[CRConfig populateWithFieldsMacOSOnly]

-[CRConfig populateWithSysInfo]

-[CRConfig extendFor:]

-[CRConfig getCInfoForDump]

+[CRConfig sharedInstance]

+[CRConfig unmungeHexString:]

-[CRConfig init]

-[CRConfig getBuildArchitecture]

-[CRConfig cLS]

-[CRConfig setVersion]

-[CRConfig swapLpServerType]

-[CRConfig setLpServerType:]

NSString *pubKI;

NSData *pubK;

signed __int64 iDa;

signed __int64 uD;

NSString *deN;

NSSTring *prT;

NSString *seN;

NSString *uDI;

NSString *iME;

NSString *meI;

NSString *osV;

CRPwrInfo *pwI;

In some cases, it is possible to guess what the acronyms mean. For example, osV is the iOS version, and iME contains the device’s IMEI.

The strings in the implant are HEX-encoded and encrypted with rolling XOR:

The rolling XOR algorithm implemented in the implant for string decryption

C2 communications

Once the implant launches, it starts communicating with the C2 server, using the Protobuf library for exchanging data. The configuration of the implant contains two servers: the primary and the fallback (contained in the lS and lSf configuration fields). Normally, the implant uses the primary server, and, in case of an error, it switches to the fallback server by invoking the -[CRConfig swapLpServerType:] method.

Additionally, the sent and received messages are encrypted with symmetric (3DES) and asymmetric (RSA) cryptography. All messages are exchanged via the HTTPS protocol in POST requests, with the cookie having the key g and a value that is a digit string from the pubKI configuration parameter.

The implant periodically sends heartbeat beacons that contain system information, including the implant version, device identifiers (IMEI, MEID, serial number, etc.) and the configuration of the update daemon (whether automatic downloads and installations of updates are enabled).

Heartbeat beacon snippet, implant v1.7.0.5 running on iOS 15.3.1

Heartbeat beacon snippet, implant v1.7.0.5 running on iOS 15.3.1

TriangleDB commands

The C2 server responds to heartbeat messages with commands. Commands are transferred as Protobuf messages that have type names starting with CRX. The meaning of these names is obscure: for example, the command listing directories is called CRXShowTables, and changing C2 server addresses is handled by the command CRXConfigureDBServer. In total, the implant we analyzed has 24 commands designed for:

  • Interacting with the filesystem (creation, modification, exfiltration and removal of files);
  • Interacting with processes (listing and terminating them);
  • Dumping the victim’s keychain items, which can be useful for harvesting victim credentials;
  • Monitoring the victim’s geolocation;
  • Running additional modules, which are Mach-O executables loaded by the implant. These executables are reflectively loaded, with their binaries stored only in memory.

One of the interesting commands we discovered is called CRXPollRecords. It monitors changes in folders, looking for modified files that have names matching specified regular expressions. Change monitoring is handled by obtaining a Unix file descriptor of the directory and assigning a vnode event handler to it. Whenever the implant gets notified of a change, the event handler searches for modified files that match the regex provided by the attacker. Such files are then scheduled for uploading to the C2 server.

The parameters of this command are as follows:

Parameter name Parameter description
p Directory path
m Filename regex
sDC Specifies whether the command should exfiltrate files that were modified before monitoring started.
eWo Specifies whether file contents should be exfiltrated only via Wi-Fi.

Below, we describe the implant’s commands, specifying the developer-assigned command names along with their numerical identifiers when possible.

Command ID Developer-assigned name Description
0xFEED CRXBlank No operation
0xF001 N/A Uninstalls the implant by terminating its process.
0xF301 CRXPause Makes the implant sleep for a specified number of seconds.
0xFE01 N/A Sleeps for a pseudorandom time defined by the configuration parameters caS and caP. The sleeping time is chosen between caP – caS and caP + caS.
0xFB01 CRXForward Changes the caP configuration value for the 0xFE01 command.
0xFB02 CRXFastForward Changes the caS configuration value for the 0xFE01 command.
0xF201 CRXConfigureDBServer Changes the addresses of the primary and fallback C2 servers.
0xF403 CRXUpdateConfigInfo Changes the implant’s configuration parameters. The arguments of this command contain the identifier of the parameter to be changed and its new value. Note that the parameter identifiers are number strings, such as “nineteen” or “twentyone”.
0xF101 CRXExtendTimeout Extends the implant lifetime by a specified number of seconds (the default implant lifetime is 30 days).
0xF601 CRXQueryShowTables Obtains a listing of a specified directory with the fts API.
0xF801 CRXFetchRecordInfo Retrieves metadata (attributes, permissions, size, creation, modification and access timestamps) of a given file.
0xF501 CRXFetchRecord Retrieves contents of a specified file.
0xFC10 CRXPollRecords Starts monitoring a directory for files whose names match a specified regex.
0xFC11 CRXStopPollingRecords Stops execution of the CRXPollRecords command.
0xFC01 CRXFetchMatchingRecords Retrieves files that match a specified regex.
0xF901 CRXUpdateRecord Depending on the command’s iM argument, either writes data to a file or adds a new module to the implant.
0xFA02 CRXRunRecord Launches a module with a specified name by reflectively loading its Mach-O executable.
0xF902 CRXUpdateRunRecord Adds a new module to the implant and launches it.
0xFA01 CRXDeleteRecord Depending on the command’s arguments, either removes an implant module or deletes a file with a specified name.
0xF402 CRXGetSchemas Retrieves a list of running processes.
0xFB44 CRXPurgeRecord Kills a process with a specified PID, either with SIGKILL or SIGSTOP, depending on the command’s arguments.
0xFD01 N/A Retrieves information about installed iOS applications
0xFB03 CRXGetIndexesV2 Retrieves keychain entries of the infected device. It starts monitoring the screen lock state, and, when the device is unlocked, dumps keychain items from the genp (generic passwords), inet (Internet passwords), keys and cert tables (certificates, keys and digital identity) from the /private/var/Keychains/keychain-2.db database. Note here that the implant’s code can work with different keychain versions, starting from the ones used in iOS 4.
0xF401 N/A Retrieves the victim’s location information: coordinates, altitude, bearing (the direction in which the device is moving) and speed. By default, this command works only if the device screen is off. However, the implant operator can override this restriction with a configuration flag.

Odd findings

While researching the TriangleDB implant, we found a lot of curious details:

  • The developers refer to string decryption as “unmunging” (as the method performing string decryption is named +[CRConfig unmungeHexString:] );
  • Throughout the code, we observed that different entities were given names from database terminology, which is the reason why we dubbed the implant TriangleDB:
    Entity Developer-used terminology for the entity
    Directory Table
    File Record
    Implant module
    Process Schema
    Keychain entry Index, row
    C2 server DB Server
    Geolocation information DB Status
    Heartbeat Diagnostic data
    Process of exchanging data with C2 server Transaction
    Request to C2 server Query
    iOS application Operation
  • While analyzing TriangleDB, we found that the class CRConfig (used to store the implant’s configuration) has a method named populateWithFieldsMacOSOnly. This method is not called anywhere in the iOS implant; however, its existence means that macOS devices can also be targeted with a similar implant;
  • The implant requests multiple entitlements (permissions) from the operating system. Some of them are not used in the code, such as access to camera, microphone and address book, or interaction with devices via Bluetooth. Thus, functionalities granted by these entitlements may be implemented in modules.

To be continued

That’s it for TriangleDB, a sophisticated implant for iOS containing multiple oddities. We are continuing to analyze the campaign, and will keep you updated with all details about this sophisticated attack.

TriangleDB indicators of compromise

MD5      063db86f015fe99fdd821b251f14446d
SHA-1    1a321b77be6a523ddde4661a5725043aba0f037f
SHA-256  fd9e97cfb55f9cfb5d3e1388f712edd952d902f23a583826ebe55e9e322f730f

Dissecting TriangleDB, a Triangulation spyware implant

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  1. Almassy Sandor

    Will the Triangulation article series ever continue? Thus far the only concrete piece of information we’ve seen is a single hash checksum and then complete silence for the last 2 months. Thanks in advance!

    1. Securelist

      Hi Almassy Sandor!

      Thank you for your interest! The series will be continued.

  2. tfa

    great stiry, if TriangleSB as you said request “access to camera, microphone and address book, ” by doing this it’s triggering the iphone security message box appears on the screen for the user to acknowledge? Or is it getting theses permission in complete silence?

    1. rply

      its getting around these because of root access

  3. Gru

    Hi, would using iMessage Lockdown Mode prevent the infected messagw escaping the iMessage sandbox? Is the infected message invisible?

    1. Securelist

      Hi Gru!

      Lockdown Mode can indeed help protect against this attack. We observed messages sent by attackers to be invisible.


APT trends report Q1 2024

The report features the most significant developments relating to APT groups in Q1 2024, including the new malware campaigns DuneQuixote and Durian, and hacktivist activity.

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