143,993 - Pentesting IMAP - HackTricks

# 143,993 - Pentesting IMAP

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## Internet Message Access Protocol

The Internet Message Access Protocol (IMAP) is designed for the purpose of enabling users to access their email messages from any location, primarily through an Internet connection. In essence, emails are retained on a server rather than being downloaded and stored on an individual's personal device. This means that when an email is accessed or read, it is done directly from the server. This capability allows for the convenience of checking emails from multiple devices, ensuring that no messages are missed regardless of the device used.

By default, the IMAP protocol works on two ports:

- Port 143 - this is the default IMAP non-encrypted port
- Port 993 - this is the port you need to use if you want to connect using IMAP securely

    PORT    STATE SERVICE REASON
    143/tcp open  imap    syn-ack

## Banner grabbing

    nc -nv <IP> 143
    openssl s_client -connect <IP>:993 -quiet

### NTLM Auth - Information disclosure

If the server supports NTLM auth (Windows) you can obtain sensitive info (versions):

    root@kali: telnet example.com 143
    * OK The Microsoft Exchange IMAP4 service is ready.
    >> a1 AUTHENTICATE NTLM
    +
    >> TlRMTVNTUAABAAAAB4IIAAAAAAAAAAAAAAAAAAAAAAA=
    + TlRMTVNTUAACAAAACgAKADgAAAAFgooCBqqVKFrKPCMAAAAAAAAAAEgASABCAAAABgOAJQAAAA9JAEkAUwAwADEAAgAKAEkASQBTADAAMQABAAoASQBJAFMAMAAxAAQACgBJAEkAUwAwADEAAwAKAEkASQBTADAAMQAHAAgAHwMI0VPy1QEAAAAA

Or automate this with nmap plugin `imap-ntlm-info.nse`

### IMAP Bruteforce

## Syntax

IMAP Commands examples from here:

    Login
        A1 LOGIN username password
    Values can be quoted to enclose spaces and special characters. A " must then be escape with a \
        A1 LOGIN "username" "password"

    List Folders/Mailboxes
        A1 LIST "" *
        A1 LIST INBOX *
        A1 LIST "Archive" *

    Create new Folder/Mailbox
        A1 CREATE INBOX.Archive.2012
        A1 CREATE "To Read"

    Delete Folder/Mailbox
        A1 DELETE INBOX.Archive.2012
        A1 DELETE "To Read"

    Rename Folder/Mailbox
        A1 RENAME "INBOX.One" "INBOX.Two"

    List Subscribed Mailboxes
        A1 LSUB "" *

    Status of Mailbox (There are more flags than the ones listed)
        A1 STATUS INBOX (MESSAGES UNSEEN RECENT)

    Select a mailbox
        A1 SELECT INBOX

    List messages
        A1 FETCH 1:* (FLAGS)
        A1 UID FETCH 1:* (FLAGS)

    Retrieve Message Content
        A1 FETCH 2 body[text]
        A1 FETCH 2 all
        A1 UID FETCH 102 (UID RFC822.SIZE BODY.PEEK[])

    Close Mailbox
        A1 CLOSE

    Logout
        A1 LOGOUT

### Evolution

    apt install evolution

### CURL

Basic navigation is possible with CURL, but the documentation is light on details so checking the source is recommended for precise details.

1. Listing mailboxes (imap command `LIST "" "*"`)

    curl -k 'imaps://1.2.3.4/' --user user:pass

2. Listing messages in a mailbox (imap command `SELECT INBOX` and then `SEARCH ALL`)

    curl -k 'imaps://1.2.3.4/INBOX?ALL' --user user:pass

The result of this search is a list of message indicies.

Its also possible to provide more complex search terms. e.g. searching for drafts with password in mail body:

    curl -k 'imaps://1.2.3.4/Drafts?TEXT password' --user user:pass

A nice overview of the search terms possible is located here.

3. Downloading a message (imap command `SELECT Drafts` and then `FETCH 1 BODY[]`)

    curl -k 'imaps://1.2.3.4/Drafts;MAILINDEX=1' --user user:pass

The mail index will be the same index returned from the search operation.

It is also possible to use `UID` (unique id) to access messages, however it is less conveniant as the search command needs to be manually formatted. E.g.

    curl -k 'imaps://1.2.3.4/INBOX' -X 'UID SEARCH ALL' --user user:pass
    curl -k 'imaps://1.2.3.4/INBOX;UID=1' --user user:pass

Also, possible to download just parts of a message, e.g. subject and sender of first 5 messages (the `-v` is required to see the subject and sender):

    $ curl -k 'imaps://1.2.3.4/INBOX' -X 'FETCH 1:5 BODY[HEADER.FIELDS (SUBJECT FROM)]' --user user:pass -v 2>&1 | grep '^<'

Although, its probably cleaner to just write a little for loop:

    for m in {1..5}; do
      echo $m
      curl "imap://1.2.3.4/INBOX;MAILINDEX=$m;SECTION=HEADER.FIELDS%20(SUBJECT%20FROM)" --user user:pass
    done

## Shodan

- `port:143 CAPABILITY`
- `port:993 CAPABILITY`

## HackTricks Automatic Commands

    Protocol_Name: IMAP    #Protocol Abbreviation if there is one.
    Port_Number:  143,993     #Comma separated if there is more than one.
    Protocol_Description: Internet Message Access Protocol         #Protocol Abbreviation Spelled out

    Entry_1:
      Name: Notes
      Description: Notes for WHOIS
      Note: |
        The Internet Message Access Protocol (IMAP) is designed for the purpose of enabling users to access their email messages from any location, primarily through an Internet connection. In essence, emails are retained on a server rather than being downloaded and stored on an individual's personal device. This means that when an email is accessed or read, it is done directly from the server. This capability allows for the convenience of checking emails from multiple devices, ensuring that no messages are missed regardless of the device used.

        https://book.hacktricks.wiki/en/network-services-pentesting/pentesting-imap.html

    Entry_2:
      Name: Banner Grab
      Description: Banner Grab 143
      Command: nc -nv {IP} 143

    Entry_3:
      Name: Secure Banner Grab
      Description: Banner Grab 993
      Command: openssl s_client -connect {IP}:993 -quiet

    Entry_4:
      Name: consolesless mfs enumeration
      Description: IMAP enumeration without the need to run msfconsole
      Note: sourced from https://github.com/carlospolop/legion
      Command: msfconsole -q -x 'use auxiliary/scanner/imap/imap_version; set RHOSTS {IP}; set RPORT 143; run; exit'

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