Adversaries may send spearphishing emails with a malicious attachment in an attempt to gain access to victim systems. Spearphishing attachment is a specific variant of spearphishing. Spearphishing attachment is different from other forms of spearphishing in that it employs the use of malware attached to an email. All forms of spearphishing are electronically delivered social engineering targeted at a specific individual, company, or industry. In this scenario, adversaries attach a file to the spearphishing email and usually rely upon User Execution to gain execution. Spearphishing may also involve social engineering techniques, such as posing as a trusted source.

There are many options for the attachment such as Microsoft Office documents, executables, PDFs, or archived files. Upon opening the attachment (and potentially clicking past protections), the adversary’s payload exploits a vulnerability or directly executes on the user’s system. The text of the spearphishing email usually tries to give a plausible reason why the file should be opened, and may explain how to bypass system protections in order to do so. The email may also contain instructions on how to decrypt an attachment, such as a zip file password, in order to evade email boundary defenses. Adversaries frequently manipulate file extensions and icons in order to make attached executables appear to be document files, or files exploiting one application appear to be a file for a different one.

Adversaries may send spearphishing emails with a malicious link in an attempt to gain access to victim systems. Spearphishing with a link is a specific variant of spearphishing. It is different from other forms of spearphishing in that it employs the use of links to download malware contained in email, instead of attaching malicious files to the email itself, to avoid defenses that may inspect email attachments. Spearphishing may also involve social engineering techniques, such as posing as a trusted source.

All forms of spearphishing are electronically delivered social engineering targeted at a specific individual, company, or industry. In this case, the malicious emails contain links. Generally, the links will be accompanied by social engineering text and require the user to actively click or copy and paste a URL into a browser, leveraging User Execution. The visited website may compromise the web browser using an exploit, or the user will be prompted to download applications, documents, zip files, or even executables depending on the pretext for the email in the first place.

Adversaries may also include links that are intended to interact directly with an email reader, including embedded images intended to exploit the end system directly. Additionally, adversaries may use seemingly benign links that abuse special characters to mimic legitimate websites (known as an “IDN homograph attack”).(Citation: CISA IDN ST05-016) URLs may also be obfuscated by taking advantage of quirks in the URL schema, such as the acceptance of integer- or hexadecimal-based hostname formats and the automatic discarding of text before an “@” symbol: for example, `hxxp://google.com@1157586937`.(Citation: Mandiant URL Obfuscation 2023)

Adversaries may also utilize links to perform consent phishing, typically with OAuth 2.0 request URLs that when accepted by the user provide permissions/access for malicious applications, allowing adversaries to Steal Application Access Tokens.(Citation: Trend Micro Pawn Storm OAuth 2017) These stolen access tokens allow the adversary to perform various actions on behalf of the user via API calls. (Citation: Microsoft OAuth 2.0 Consent Phishing 2021)

An adversary may rely upon a user clicking a malicious link in order to gain execution. Users may be subjected to social engineering to get them to click on a link that will lead to code execution. This user action will typically be observed as follow-on behavior from Spearphishing Link. Clicking on a link may also lead to other execution techniques such as exploitation of a browser or application vulnerability via Exploitation for Client Execution. Links may also lead users to download files that require execution via Malicious File.

An adversary may rely upon a user opening a malicious file in order to gain execution. Users may be subjected to social engineering to get them to open a file that will lead to code execution. This user action will typically be observed as follow-on behavior from Spearphishing Attachment. Adversaries may use several types of files that require a user to execute them, including .doc, .pdf, .xls, .rtf, .scr, .exe, .lnk, .pif, and .cpl.

Adversaries may employ various forms of Masquerading and Obfuscated Files or Information to increase the likelihood that a user will open and successfully execute a malicious file. These methods may include using a familiar naming convention and/or password protecting the file and supplying instructions to a user on how to open it.(Citation: Password Protected Word Docs)

While Malicious File frequently occurs shortly after Initial Access it may occur at other phases of an intrusion, such as when an adversary places a file in a shared directory or on a user’s desktop hoping that a user will click on it. This activity may also be seen shortly after Internal Spearphishing.

Adversaries may employ various system checks to detect and avoid virtualization and analysis environments. This may include changing behaviors based on the results of checks for the presence of artifacts indicative of a virtual machine environment (VME) or sandbox. If the adversary detects a VME, they may alter their malware to disengage from the victim or conceal the core functions of the implant. They may also search for VME artifacts before dropping secondary or additional payloads. Adversaries may use the information learned from Virtualization/Sandbox Evasion during automated discovery to shape follow-on behaviors.(Citation: Deloitte Environment Awareness)

Specific checks will vary based on the target and/or adversary, but may involve behaviors such as Windows Management Instrumentation, PowerShell, System Information Discovery, and Query Registry to obtain system information and search for VME artifacts. Adversaries may search for VME artifacts in memory, processes, file system, hardware, and/or the Registry. Adversaries may use scripting to automate these checks into one script and then have the program exit if it determines the system to be a virtual environment.

Checks could include generic system properties such as host/domain name and samples of network traffic. Adversaries may also check the network adapters addresses, CPU core count, and available memory/drive size.

Other common checks may enumerate services running that are unique to these applications, installed programs on the system, manufacturer/product fields for strings relating to virtual machine applications, and VME-specific hardware/processor instructions.(Citation: McAfee Virtual Jan 2017) In applications like VMWare, adversaries can also use a special I/O port to send commands and receive output.

Hardware checks, such as the presence of the fan, temperature, and audio devices, could also be used to gather evidence that can be indicative a virtual environment. Adversaries may also query for specific readings from these devices.(Citation: Unit 42 OilRig Sept 2018)

Adversaries may employ various system checks to detect and avoid virtualization and analysis environments. This may include changing behaviors based on the results of checks for the presence of artifacts indicative of a virtual machine environment (VME) or sandbox. If the adversary detects a VME, they may alter their malware to disengage from the victim or conceal the core functions of the implant. They may also search for VME artifacts before dropping secondary or additional payloads. Adversaries may use the information learned from Virtualization/Sandbox Evasion during automated discovery to shape follow-on behaviors.(Citation: Deloitte Environment Awareness)

Specific checks will vary based on the target and/or adversary, but may involve behaviors such as Windows Management Instrumentation, PowerShell, System Information Discovery, and Query Registry to obtain system information and search for VME artifacts. Adversaries may search for VME artifacts in memory, processes, file system, hardware, and/or the Registry. Adversaries may use scripting to automate these checks into one script and then have the program exit if it determines the system to be a virtual environment.

Checks could include generic system properties such as host/domain name and samples of network traffic. Adversaries may also check the network adapters addresses, CPU core count, and available memory/drive size.

Other common checks may enumerate services running that are unique to these applications, installed programs on the system, manufacturer/product fields for strings relating to virtual machine applications, and VME-specific hardware/processor instructions.(Citation: McAfee Virtual Jan 2017) In applications like VMWare, adversaries can also use a special I/O port to send commands and receive output.

Hardware checks, such as the presence of the fan, temperature, and audio devices, could also be used to gather evidence that can be indicative a virtual environment. Adversaries may also query for specific readings from these devices.(Citation: Unit 42 OilRig Sept 2018)

Adversaries may communicate using OSI application layer protocols to avoid detection/network filtering by blending in with existing traffic. Commands to the remote system, and often the results of those commands, will be embedded within the protocol traffic between the client and server.

Adversaries may utilize many different protocols, including those used for web browsing, transferring files, electronic mail, or DNS. For connections that occur internally within an enclave (such as those between a proxy or pivot node and other nodes), commonly used protocols are SMB, SSH, or RDP.

Adversaries may communicate using application layer protocols associated with web traffic to avoid detection/network filtering by blending in with existing traffic. Commands to the remote system, and often the results of those commands, will be embedded within the protocol traffic between the client and server.

Protocols such as HTTP/S(Citation: CrowdStrike Putter Panda) and WebSocket(Citation: Brazking-Websockets) that carry web traffic may be very common in environments. HTTP/S packets have many fields and headers in which data can be concealed. An adversary may abuse these protocols to communicate with systems under their control within a victim network while also mimicking normal, expected traffic.