Alpha Cyber

Vintage Malice: Unmasking APT29’s Wine-Tasting Trap

APT29 a notorious Russian cyber espionage group has recently targeted European diplomats using GRAPELOADER malware.

Alpha Cyber Research4 min readupdated 1 Apr 2026
APT-29 Grapeloader cover Photo

APT29 Targets Diplomats with GRAPELOADER Malware: Uncovering the Threat with Graph Analysis

APT29 a notorious Russian cyber espionage group has recently targeted European diplomats using GRAPELOADER malware. The attackers used a seemingly innocuous wine-tasting invitation as a lure, drawing in unsuspecting victims. But what’s lurking behind this social engineering attack?

Let’s take a deep dive into this sophisticated campaign and explore how a comprehensive infrastructure mapping approach can help identify, mitigate, and prevent future breaches.

The GRAPELOADER Malware: An Overview

VirusTotal Grapeloader Graph

GRAPELOADER is a sophisticated piece of malware that has been associated with APT29 (also known as Cozy Bear), a group with ties to Russian state-sponsored cyber activities. This malware is distributed using well-crafted phishing campaigns that convince targets to open malicious attachments disguised as documents related to wine-tasting events.

The file of interest, identified by its name d931078b63d94726d4be5dc1a00324275b53b935b77d3eed1712461f0c180164.exe, is a PE64 executable designed to run on Windows (Vista or newer). Below are key findings from an investigation of this malware using forensic tools like Pestudio:

Key Malware Indicators

  1. VirusTotal Score: The file achieved a 46/70 malicious detection score. This indicates that 46 out of 70 security vendors flagged the file as malicious. While the score is high, it’s not perfect, making it difficult for traditional antivirus solutions to catch every instance of the malware.

VirusTotal Grapeloader Detection

  1. Malicious Imports: The malicious imports observed include several system calls like GetCurrentProcessId, WriteFile, and GetCurrentThreadId. These functions are commonly used in malware to manipulate system processes and execute malicious tasks. Detection of these imports often signals that a file is trying to access or manipulate key system functions.

PEStudio Grapeloader Imports 10

  1. PE File Structure:

    • Compiler: Microsoft Visual C/C++ (19.36.33808)

    • Linker: Microsoft Linker (14.36.34123)

    • Language: C++ (likely used for efficient, low-level system manipulation)

    • Operating System: Windows (Vista, AMD64 64-bit)

DIE GrapeLoader APT-29

  1. File Hash:

    • MD5: e025fa8354968f298af3f6ef2f22d7d3

    • SHA-1: b4221c83a3fffe7bc358dfc613c3e58fcc522a23

    • SHA-256: d931078b63d94726d4be5dc1a00324275b53b935b77d3eed1712461f0c180164

    These cryptographic hash values help security researchers uniquely identify the malware sample.

Detailed Analysis

  • Operating System Compatibility:
    GRAPELOADER has been developed for Windows (Vista or later) operating systems and compiled using Microsoft Visual Studio 2022.

  • Malicious Behavior:
    Upon execution, the malware opens a backdoor, communicates with remote command and control servers, and downloads additional payloads, often leading to data exfiltration and espionage.

  • File Structure:
    The malware’s DLL (Dynamic-Link Library) format allows it to interact directly with other applications and system resources. The PE64 header suggests it is designed to target 64-bit Windows environments, making it effective against more recent systems.

CAPA Analysis: A Deeper Dive into GRAPELOADER’s Capabilities

Capa GrapeLoader

By running CAPA on the sample d931078b63d94726d4be5dc1a00324275b53b935b77d3eed1712461f0c180164.exe, we can get a more detailed understanding of its behavior. Here’s a summary of the findings from the CAPA analysis:

File Metadata:

AttributeValue
MD5e025fa8354968f298af3f6ef2f22d7d3
SHA1b4221c83a3fffe7bc358dfc613c3e58fcc522a23
SHA256d931078b63d94726d4be5dc1a00324275b53b935b77d3eed1712461f0c180164
AnalysisStatic
OSWindows
FormatPE (Portable Executable)
ArchAMD64 (64-bit architecture)
PathC:/Users/lorenzo10/Desktop/stuff/Malware Samples/Cozy Bear – AKA APT-29/d931078b63d94726d4be5dc1a00324275b53b935b77d3eed1712461f0c180164.exe

ATT&CK Tactics and Techniques:

TacticTechnique
Defense EvasionObfuscated Files or Information [T1027]
DiscoveryFile and Directory Discovery [T1083]
System Information Discovery [T1082]
ExecutionShared Modules [T1129]

MBC Objectives and Behaviors:

MBC ObjectiveMBC Behavior
CommunicationHTTP Communication::Read Header [C0002.014]
CryptographyEncrypt Data::RC4 [C0027.009]
Generate Pseudo-random Sequence::RC4 PRGA [C0021.004]
DiscoveryFile and Directory Discovery [E1083]
System Information Discovery [E1082]
File SystemWrites File [C0052]
ProcessTerminate Process [C0018]

Detailed Capabilities:

CapabilityNamespace
Check HTTP status codecommunication/http/client
Encrypt data using RC4 PRGA (23 matches)data-manipulation/encryption/rc4
Query environment variablehost-interaction/environment-variable
Enumerate files on Windowshost-interaction/file-system/files/list
Write file on Windows (2 matches)host-interaction/file-system/write
Terminate processhost-interaction/process/terminate
Get kernel32 base addresslinking/runtime-linking
Link function at runtime on Windows (3 matches)linking/runtime-linking
Parse PE header (2 matches)load-code/pe
Resolve function by parsing PE exports (2 matches)load-code/pe

These findings show how GRAPELOADER employs various techniques to evade detection and establish persistence within the target system. By utilizing RC4 encryption, the malware ensures secure communication with its command and control servers. It also performs file system enumeration and process termination, allowing it to maintain control of the system while hiding its presence.

A Closer Look at the Infrastructure: Mapping APT29’s Attack

To fully understand the extent of this threat, we can map out its infrastructure. The attack seems to involve a multi-layered approach, starting with malicious email attachments and progressing to complex server interactions for data exfiltration. The malware is also capable of leveraging bundled files and ZIP archives, which increase the attack’s effectiveness by evading basic security filters.

Key Infrastructure Elements to Monitor:

  • IP addresses:

    • 87.121.61.238

  • Domains:

    • bakenhof.com

    • bravecup.com

    • ophibre.com

    • silry.com

VirusTotal Grapeloader Relations

Indicators of Compromise (IOCs) to Block

To raise awareness and help organizations block the threat, here’s a table of IOCs (Indicators of Compromise) related to GRAPELOADER malware. Blocking these IOCs can help prevent the malware from infiltrating your network.

TypeIOC Value
FileHash-MD5a89b9bdf5f28f4380f383ee199401bdc
FileHash-MD5e025fa8354968f298af3f6ef2f22d7d3
FileHash-MD5e06fbace9c2297e47e6bf991f2681b2b
FileHash-MD5f474f6cd156e53a994ae3d25dcecb50c
FileHash-SHA13a7b4a507db8ac2aa59c83a59dcf1242411d14f5
FileHash-SHA156248469a7c079c4174f6c8351b48294bd7a57e0
FileHash-SHA15a3bd2f12875098bd06b9f5a5a9405d9cf3af837
FileHash-SHA1b4221c83a3fffe7bc358dfc613c3e58fcc522a23
FileHash-SHA25624c079b24851a5cc8f61565176bbf1157b9d5559c642e31139ab8d76bbb320f8
FileHash-SHA256420d20cddfaada4e96824a9184ac695800764961bad7654a6a6c3fe9b1b74b9a
FileHash-SHA256653db3b63bb0e8c2db675cd047b737cefebb1c955bd99e7a93899e2144d34358
FileHash-SHA25678a810e47e288a6aff7ffbaf1f20144d2b317a1618bba840d42405cddc4cff41
FileHash-SHA25685484716a369b0bc2391b5f20cf11e4bd65497a34e7a275532b729573d6ef15e
FileHash-SHA256adfe0ef4ef181c4b19437100153e9fe7aed119f5049e5489a36692757460b9f8
FileHash-SHA256d931078b63d94726d4be5dc1a00324275b53b935b77d3eed1712461f0c180164
URLhttps://bakenhof.com/invb.php
URLhttps://silry.com/inva.php
Domainbakenhof.com
Domainbravecup.com
Domainophibre.com
Domainsilry.com

Conclusion: Securing Against APT29’s GRAPELOADER Malware

The APT29 GRAPELOADER malware is a clear and present threat to organizations, particularly in diplomatic and government sectors. Using graph analysis tools to map the attack’s infrastructure allows organizations to gain valuable insights into how these attacks unfold and how they can defend against them.

By blocking the indicators mentioned above, security teams can strengthen their defenses and reduce the risk of successful exploitation. Staying vigilant and continually updating security measures are key to mitigating the evolving threat landscape presented by APT29 and other sophisticated adversaries.

Stay secure and keep your defenses strong!

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