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Insights into Iranian Cyber Espionage: APT33 Targets Aerospace and
Energy Sectors and has Ties to Destructive Malware


When discussing suspected Middle Eastern hacker groups with
  destructive capabilities, many automatically think of the     href="/content/fireeye-www/en_US/blog/threat-research/2016/11/fireeye_respondsto.html">suspected
    Iranian group that previously used SHAMOON – aka   href="https://www.microsoft.com/security/portal/threat/encyclopedia/entry.aspx?Name=Trojan%3AWin32%2FWipMBR.B">Disttrack
  – to target organizations in the Persian Gulf. However, over the past
  few years, we have been tracking a separate, less widely known
  suspected Iranian group with potential destructive capabilities, whom
  we call APT33. Our analysis reveals that APT33 is a capable group that
  has carried out cyber espionage operations since at least 2013. We
  assess APT33 works at the behest of the Iranian government.


 

Recent investigations by FireEye’s     href="/content/fireeye-www/en_US/services.html">Mandiant incident
  response consultants combined with FireEye iSIGHT Threat
  Intelligence analysis have given us a more complete picture of APT33’s
  operations, capabilities, and potential motivations. This blog
  highlights some of our analysis. Our detailed report on     href="/content/fireeye-www/en_US/products/isight-cyber-threat-intelligence-subscriptions.html">FireEye
  MySIGHT contains a more thorough review of our supporting evidence
  and analysis. We will also be discussing this threat group further
  during our   href="https://www.brighttalk.com/webcast/10703/275683?utm_source=FireEye_blog">webinar
  on Sept. 21 at 8 a.m. ET.


 

Targeting


 

APT33 has targeted organizations – spanning multiple industries –
  headquartered in the United States, Saudi Arabia and South Korea.
  APT33 has shown particular interest in organizations in the aviation
  sector involved in both military and commercial capacities, as well as
  organizations in the energy sector with ties to petrochemical production.


 

From mid-2016 through early 2017, APT33 compromised a U.S.
  organization in the aerospace sector and targeted a business
  conglomerate located in Saudi Arabia with aviation holdings.


 

During the same time period, APT33 also targeted a South Korean
  company involved in oil refining and petrochemicals. More recently, in
  May 2017, APT33 appeared to target a Saudi organization and a South
  Korean business conglomerate using a malicious file that attempted to
  entice victims with job vacancies for a Saudi Arabian petrochemical company.


 

We assess the targeting of multiple companies with aviation-related
  partnerships to Saudi Arabia indicates that APT33 may possibly be
  looking to gain insights on Saudi Arabia’s military aviation
  capabilities to enhance Iran’s domestic aviation capabilities or to
  support Iran’s military and strategic decision making vis a vis Saudi Arabia.


 

We believe the targeting of the Saudi organization may have been an
  attempt to gain insight into regional rivals, while the targeting of
  South Korean companies may be due to South Korea’s recent partnerships
  with Iran’s petrochemical industry as well as South Korea’s
  relationships with Saudi petrochemical companies. Iran has     href="https://financialtribune.com/articles/energy/41665/call-for-restoring-past-petrochemical-status">expressed
  interest in growing their petrochemical industry and often posited
  this expansion in competition to Saudi petrochemical companies. APT33
  may have targeted these organizations as a result of Iran’s desire to
  expand its own petrochemical production and improve its
  competitiveness within the region. 


 

The generalized targeting of organizations involved in energy and
  petrochemicals mirrors previously observed targeting by other
  suspected Iranian threat groups, indicating a common interest in the
  sectors across Iranian actors.


 

Figure 1 shows the global scope of APT33 targeting.


 


 
 
 Figure 1: Scope of APT33 Targeting


 

Spear Phishing


 

APT33 sent spear phishing emails to employees whose jobs related to
  the aviation industry. These emails included recruitment themed lures
  and contained links to malicious HTML application (.hta) files. The
  .hta files contained job descriptions and links to legitimate job
  postings on popular employment websites that would be relevant to the
  targeted individuals.


 

An example .hta file excerpt is provided in Figure 2. To the user,
  the file would appear as benign references to legitimate job postings;
  however, unbeknownst to the user, the .hta file also contained
  embedded code that automatically downloaded a custom APT33 backdoor.


 


 
 
 Figure 2: Excerpt of an APT33 malicious
    .hta file


 

We assess APT33 used a built-in phishing module within the publicly
  available ALFA TEaM Shell (aka ALFASHELL) to send hundreds of spear
  phishing emails to targeted individuals in 2016. Many of the phishing
  emails appeared legitimate – they referenced a specific job
  opportunity and salary, provided a link to the spoofed company’s
  employment website, and even included the spoofed company’s Equal
  Opportunity hiring statement. However, in a few cases, APT33 operators
  left in the default values of the shell’s phishing module. These
  appear to be mistakes, as minutes after sending the emails with the
  default values, APT33 sent emails to the same recipients with the
  default values removed.


 

As shown in Figure 3, the “fake mail” phishing module in the ALFA
  Shell contains default values, including the sender email address
  (solevisible@gmail[.]com), subject line (“your site hacked by me”),
  and email body (“Hi Dear Admin”).


 


 
 
 Figure 3: ALFA TEaM Shell v2-Fake Mail (Default)


 

Figure 4 shows an example email containing the default values the shell.


 


 
 
 Figure 4: Example Email Generated by the
    ALFA Shell with Default Values


 

Domain Masquerading


 

APT33 registered multiple domains that masquerade as Saudi Arabian
  aviation companies and Western organizations that together have
  partnerships to provide training, maintenance and support for Saudi’s
  military and commercial fleet. Based on observed targeting patterns,
  APT33 likely used these domains in spear phishing emails to target
  victim organizations.    


 

The following domains masquerade as these organizations: Boeing,
  Alsalam Aircraft Company, Northrop Grumman Aviation Arabia (NGAAKSA),
  and Vinnell Arabia.


 
   
     
   
     
   
     
   
     
   
     

boeing.servehttp[.]com

alsalam.ddns[.]net

ngaaksa.ddns[.]net

ngaaksa.sytes[.]net

vinnellarabia.myftp[.]org


     

 

Boeing, Alsalam Aircraft company, and Saudia Aerospace Engineering
  Industries entered into a     href="http://boeing.mediaroom.com/2015-08-26-Boeing-Saudia-Aerospace-Engineering-Industries-and-Alsalam-Aircraft-Company-to-Establish-Saudi-Rotorcraft-Support-Center-in-Saudi-Arabia">joint
  venture to create the Saudi Rotorcraft Support Center in Saudi
  Arabia in 2015 with the goal of servicing Saudi Arabia’s     href="https://www.aerosociety.com/Assets/Docs/Publications/SpecialistPapers/Definition_of_a_Rotorcraft.pdf">rotorcraft
  fleet and building a self-sustaining workforce in the Saudi
  aerospace supply base.


 

Alsalam Aircraft Company also offers military and commercial
  maintenance, technical support, and interior design and refurbishment services.


 

Two of the domains appeared to mimic Northrop Grumman joint
  ventures. These     href="http://www.northropgrumman.com/Capabilities/RotaryWingAviation/Pages/default.aspxv">joint
  ventures – Vinnell Arabia and Northrop Grumman Aviation Arabia –
  provide aviation support in the Middle East, specifically in Saudi
  Arabia. Both Vinnell Arabia and Northrop Grumman Aviation Arabia have
  been involved in   href="http://www.prnewswire.com/news-releases/northrop-grumman-forms-industry-leading-team-for-ministry-of-national-guard-aviation-support-contract-saudi-arabia-234754491.html">contracts
  to train Saudi Arabia’s Ministry of National Guard.


 

Identified Persona Linked to Iranian Government


 

We identified APT33 malware tied to an Iranian persona who may have
  been employed by the Iranian government to conduct cyber threat
  activity against its adversaries.


 

We assess an actor using the handle “xman_1365_x” may have been
  involved in the development and potential use of APT33’s TURNEDUP
  backdoor due to the inclusion of the handle in the
  processing-debugging (PDB) paths of many of TURNEDUP samples. An
  example can be seen in Figure 5.


 


 
 
 Figure 5: “xman_1365_x" PDB String
    in TURNEDUP Sample


 

Xman_1365_x was also a community manager in the Barnamenevis Iranian
  programming and software engineering forum, and registered accounts in
  the well-known Iranian Shabgard and Ashiyane forums, though we did not
  find evidence to suggest that this actor was ever a formal member of
  the Shabgard or Ashiyane hacktivist groups.


 

Open source reporting links the “xman_1365_x” actor to the “Nasr
  Institute,” which is purported to be equivalent to Iran’s “cyber army”
  and controlled by the Iranian government. Separately, additional
  evidence ties the “Nasr Institute” to the 2011-2013 attacks on the
  financial industry, a series of denial of service attacks dubbed
  Operation Ababil. In March 2016, the U.S. Department of Justice
  unsealed an   href="https://www.justice.gov/usao-sdny/file/835061/download">indictment that
  named two individuals allegedly hired by the Iranian government to
  build attack infrastructure and conduct distributed denial of service
  attacks in support of Operation Ababil. While the individuals and the
  activity described in indictment are different than what is discussed
  in this report, it provides some evidence that individuals associated
  with the “Nasr Institute” may have ties to the Iranian government.


 

Potential Ties to Destructive Capabilities and Comparisons with SHAMOON


 

One of the droppers used by APT33, which we refer to as DROPSHOT,
  has been linked to the wiper malware SHAPESHIFT. Open source research
  indicates SHAPESHIFT may have been used to target organizations in
  Saudi Arabia.


 

Although we have only directly observed APT33 use DROPSHOT to
  deliver the TURNEDUP backdoor, we have identified multiple DROPSHOT
  samples in the wild that drop SHAPESHIFT. The SHAPESHIFT malware is
  capable of wiping disks, erasing volumes and deleting files, depending
  on its configuration. Both DROPSHOT and SHAPESHIFT contain Farsi
  language artifacts, which indicates they may have been developed by a
  Farsi language speaker (Farsi is the predominant and official language
  of Iran).


 

While we have not directly observed APT33 use SHAPESHIFT or
  otherwise carry out destructive operations, APT33 is the only group
  that we have observed use the DROPSHOT dropper. It is possible that
  DROPSHOT may be shared amongst Iran-based threat groups, but we do not
  have any evidence that this is the case.


 

In March 2017, Kasperksy released a report that compared DROPSHOT
  (which they call Stonedrill) with the most recent variant of SHAMOON
  (referred to as Shamoon 2.0). They stated that both wipers employ
  anti-emulation techniques and were used to target organizations in
  Saudi Arabia, but also mentioned several differences. For example,
  they stated DROPSHOT uses more advanced anti-emulation techniques,
  utilizes external scripts for self-deletion, and uses memory injection
  versus external drivers for deployment. Kaspersky also noted the
  difference in resource language sections: SHAMOON embeds Arabic-Yemen
  language resources while DROPSHOT embeds Farsi (Persian) language resources.


 

We have also observed differences in both targeting and tactics,
  techniques and procedures (TTPs) associated with the group using
  SHAMOON and APT33. For example, we have observed SHAMOON being used to
  target government organizations in the Middle East, whereas APT33 has
  targeted several commercial organizations both in the Middle East and
  globally. APT33 has also utilized a wide range of custom and publicly
  available tools during their operations. In contrast, we have not
  observed the full lifecycle of operations associated with SHAMOON, in
  part due to the wiper removing artifacts of the earlier stages of the
  attack lifecycle.


 

Regardless of whether DROPSHOT is exclusive to APT33, both the
  malware and the threat activity appear to be distinct from the group
  using SHAMOON. Therefore, we assess there may be multiple Iran-based
  threat groups capable of carrying out destructive operations.


 

Additional Ties Bolster Attribution to Iran


 

APT33’s targeting of organizations involved in aerospace and energy
  most closely aligns with nation-state interests, implying that the
  threat actor is most likely government sponsored. This coupled with
  the timing of operations – which coincides with Iranian working hours
  – and the use of multiple Iranian hacker tools and name servers
  bolsters our assessment that APT33 may have operated on behalf of the
  Iranian government.


 

The times of day that APT33 threat actors were active suggests that
  they were operating in a time zone close to 04:30 hours ahead of
  Coordinated Universal Time (UTC). The time of the observed attacker
  activity coincides with     href="https://www.timeanddate.com/time/zones/irdt">Iran’s Daylight
  Time, which is +0430 UTC.


 

APT33 largely operated on days that correspond to Iran’s workweek,
  Saturday to Wednesday. This is evident by the lack of attacker
  activity on Thursday, as shown in Figure 6. Public sources report that
  Iran works a Saturday to Wednesday or Saturday to Thursday work week,
  with government offices     href="https://financialtribune.com/articles/travel/59580/weekend-reform-proposal-rejected">closed
    on Thursday and some     href="http://www.irdiplomacy.ir/en/page/1959937/Will+Iran+Change+Weekends+to+Friday+and+Saturday.html">private
  businesses operating on a half day schedule on
  Thursday. Many other Middle East countries have   href="https://blogs.wsj.com/middleeast/2013/06/23/saudi-arabia-switches-its-weekend-pleasing-businesses">elected
  to have a Friday and Saturday weekend. Iran is one of few
  countries that subscribes to a Saturday to Wednesday workweek.


 

APT33 leverages popular Iranian hacker tools and DNS servers used by
  other suspected Iranian threat groups. The publicly available
  backdoors and tools utilized by APT33 – including NANOCORE, NETWIRE,
  and ALFA Shell – are all available on Iranian hacking websites,
  associated with Iranian hackers, and used by other suspected Iranian
  threat groups. While not conclusive by itself, the use of publicly
  available Iranian hacking tools and popular Iranian hosting companies
  may be a result of APT33’s familiarity with them and lends support to
  the assessment that APT33 may be based in Iran.


 


 
 
 Figure 6: APT33 Interactive Commands by
    Day of Week


 

Outlook and Implications


 

Based on observed targeting, we believe APT33 engages in strategic
  espionage by targeting geographically diverse organizations across
  multiple industries. Specifically, the targeting of organizations in
  the aerospace and energy sectors indicates that the threat group is
  likely in search of strategic intelligence capable of benefitting a
  government or military sponsor. APT33’s focus on aviation may indicate
  the group’s desire to gain insight into regional military aviation
  capabilities to enhance Iran’s aviation capabilities or to support
  Iran’s military and strategic decision making. Their targeting of
  multiple holding companies and organizations in the energy sectors
  align with Iranian national priorities for growth, especially as it
  relates to increasing petrochemical production. We expect APT33
  activity will continue to cover a broad scope of targeted entities,
  and may spread into other regions and sectors as Iranian interests dictate.


 

APT33’s use of multiple custom backdoors suggests that they have
  access to some of their own development resources, with which they can
  support their operations, while also making use of publicly available
  tools. The ties to SHAPESHIFT may suggest that APT33 engages in
  destructive operations or that they share tools or a developer with
  another Iran-based threat group that conducts destructive operations.


 

Appendix


 
Malware Family Descriptions

 
   
              width="331">

Description


   
     
       
   
     
   
     
   
     

Malware Family

        valign="bottom">

Availability

DROPSHOT

Dropper
          that has been observed dropping and launching the TURNEDUP
          backdoor, as well as the SHAPESHIFT wiper malware

Non-Public

NANOCORE

Publicly
          available remote access Trojan (RAT) available for purchase.
          It is a full-featured backdoor with a plugin framework


     

Public

NETWIRE

Backdoor
          that attempts to steal credentials from the local machine from
          a variety of sources and supports other standard backdoor
        features.

Public


     

TURNEDUP

Backdoor
          capable of uploading and downloading files, creating a reverse
          shell, taking screenshots, and gathering system
        information

Non-Public


 
Indicators of Compromise

 

APT33 Domains Likely Used in Initial Targeting


 
   
     
   
     
   
     
   
     
   
     
   
     

Domain

boeing.servehttp[.]com

alsalam.ddns[.]net

ngaaksa.ddns[.]net

ngaaksa.sytes[.]net

vinnellarabia.myftp[.]org


     

 

APT33 Domains / IPs Used for C2


 
   
              width="214" valign="top">

MALWARE


   
              width="214" valign="top">

NANOCORE


   
     
       
   
              width="214" valign="top">

NANOCORE


   
     
       
   
              width="214" valign="top">

TURNEDUP


   
     
   
              width="214" valign="top">

TURNEDUP


   
     
       
   
     
       
   
              width="214" valign="top">

TURNEDUP

C2 Domain

managehelpdesk[.]com

microsoftupdated[.]com

NANOCORE

osupd[.]com

mywinnetwork.ddns[.]net

NETWIRE

www.chromup[.]com

www.securityupdated[.]com


     

TURNEDUP

googlmail[.]net

microsoftupdated[.]net

TURNEDUP

syn.broadcaster[.]rocks

TURNEDUP

www.googlmail[.]net


 

Publicly Available Tools used by APT33


 
   
     
   
     
       
   
     
       
   
     
       
   
     
       

MD5

        valign="top">

MALWARE

          valign="top">

Compile Time (UTC)

        valign="bottom">

3f5329cf2a829f8840ba6a903f17a1bf

NANOCORE

          valign="bottom">

2017/1/11 2:20

        valign="bottom">

10f58774cd52f71cd4438547c39b1aa7

NANOCORE

          valign="bottom">

2016/3/9 23:48

        valign="bottom">

663c18cfcedd90a3c91a09478f1e91bc

NETWIRE

          valign="bottom">

2016/6/29 13:44

        valign="bottom">

6f1d5c57b3b415edc3767b079999dd50

NETWIRE

          valign="bottom">

2016/5/29 14:11


 

Unattributed DROPSHOT / SHAPESHIFT MD5 Hashes


 
   
     
   
              width="115" valign="top">

DROPSHOT

(drops
        SHAPESHIFT


   
              width="115" valign="top">

DROPSHOT


   
              width="115" valign="top">

SHAPESHIFT


   
              width="115" valign="top">

SHAPESHIFT


          MD5


          MALWARE


          Compile Time (UTC)

        valign="top">

0ccc9ec82f1d44c243329014b82d3125

n/a -
        timestomped

        valign="top">

fb21f3cea1aa051ba2a45e75d46b98b8

          valign="top">

n/a - timestomped

        valign="top">

3e8a4d654d5baa99f8913d8e2bd8a184

          valign="top">

2016/11/14 21:16:40

        valign="top">

6b41980aa6966dda6c3f68aeeb9ae2e0

          valign="top">

2016/11/14 21:16:40


 

APT33 Malware MD5 Hashes


 
   
     
   
                width="143">

DROPSHOT (drops TURNEDUP)

          width="89">

2016/10/19 14:26


   
              width="143">

TURNEDUP


   
              width="143">

TURNEDUP


   
              width="143">

TURNEDUP


   
              width="143">

TURNEDUP


   
              width="143">

TURNEDUP


   
              width="143">

TURNEDUP


   
              width="143">

TURNEDUP


   
              width="143">

TURNEDUP


   
              width="143">

TURNEDUP


   
              width="143">

TURNEDUP


   
              width="143">

TURNEDUP


   
              width="143">

TURNEDUP


   
              width="143">

TURNEDUP


   
              width="143">

TURNEDUP


   
              width="143">

TURNEDUP


   
              width="143">

TURNEDUP


   
              width="143">

TURNEDUP


   
              width="143">

TURNEDUP


   
              width="143">

TURNEDUP


   
              width="143">

TURNEDUP


   
              width="143">

TURNEDUP


   
              width="143">

TURNEDUP


   
              width="143">

TURNEDUP


   
              width="143">

TURNEDUP


   
              width="143">

TURNEDUP


   
              width="143">

TURNEDUP


   
              width="143">

TURNEDUP


   
              width="143">

TURNEDUP


   
              width="143">

TURNEDUP


   
              width="143">

TURNEDUP


   
              width="143">

TURNEDUP


   
              width="143">

TURNEDUP

MD5

MALWARE


     

Compile Time (UTC)

8e67f4c98754a2373a49eaf53425d79a

c57c5529d91cffef3ec8dadf61c5ffb2

2014/6/1
        11:01

c02689449a4ce73ec79a52595ab590f6

2016/9/18
        10:50

59d0d27360c9534d55596891049eb3ef

2016/3/8
        12:34

59d0d27360c9534d55596891049eb3ef

2016/3/8
        12:34

797bc06d3e0f5891591b68885d99b4e1

2015/3/12
        5:59

8e6d5ef3f6912a7c49f8eb6a71e18ee2

2015/3/12
        5:59

32a9a9aa9a81be6186937b99e04ad4be

2015/3/12
        5:59

a272326cb5f0b73eb9a42c9e629a0fd8

2015/3/9
        16:56

a813dd6b81db331f10efaf1173f1da5d

2015/3/9
        16:56

de9e3b4124292b4fba0c5284155fa317

2015/3/9
        16:56

a272326cb5f0b73eb9a42c9e629a0fd8

2015/3/9
        16:56

b3d73364995815d78f6d66101e718837

2014/6/1
        11:01

de7a44518d67b13cda535474ffedf36b

2014/6/1
        11:01

b5f69841bf4e0e96a99aa811b52d0e90

2014/6/1
        11:01

a2af2e6bbb6551ddf09f0a7204b5952e

2014/6/1
        11:01

b189b21aafd206625e6c4e4a42c8ba76

2014/6/1
        11:01

aa63b16b6bf326dd3b4e82ffad4c1338

2014/6/1
        11:01

c55b002ae9db4dbb2992f7ef0fbc86cb

2014/6/1
        11:01

c2d472bdb8b98ed83cc8ded68a79c425

2014/6/1
        11:01

c6f2f502ad268248d6c0087a2538cad0

2014/6/1
        11:01

c66422d3a9ebe5f323d29a7be76bc57a

2014/6/1
        11:01

ae47d53fe8ced620e9969cea58e87d9a

2014/6/1
        11:01

b12faab84e2140dfa5852411c91a3474

2014/6/1
        11:01

c2fbb3ac76b0839e0a744ad8bdddba0e

2014/6/1
        11:01

a80c7ce33769ada7b4d56733d02afbe5

2014/6/1
        11:01

6a0f07e322d3b7bc88e2468f9e4b861b

2014/6/1
        11:01

b681aa600be5e3ca550d4ff4c884dc3d

2014/6/1
        11:01

ae870c46f3b8f44e576ffa1528c3ea37

2014/6/1
        11:01

bbdd6bb2e8827e64cd1a440e05c0d537

2014/6/1
        11:01

0753857710dcf96b950e07df9cdf7911

2013/4/10
        10:43

d01781f1246fd1b64e09170bd6600fe1

2013/4/10
        10:43

1381148d543c0de493b13ba8ca17c14f

2013/4/10
        10:43


Source: Insights into Iranian Cyber Espionage: APT33 Targets Aerospace and
Energy Sectors and has Ties to Destructive Malware

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