IMAP POP3 (110, 143, 993, 995)

Nmap

sudo nmap 10.129.14.128 -sV -p110,143,993,995 -sC
nmap -Pn -sV -sC -p25,143,110,465,587,993,995 10.129.203.12

User enumeration

USER cmd

$ telnet 10.10.110.20 110

Trying 10.10.110.20...
Connected to 10.10.110.20.
Escape character is '^]'.
+OK POP3 Server ready

USER julio

-ERR


USER john

+OK

Evolution

Run nmap to know wich ports are open and use the good one on configuration

On ubuntu, not Exegol

osboxes@osboxes:~/Desktop$ sudo apt-get -y install evolution
osboxes@osboxes:~/Desktop$ evolution

Source: https://youtube.com/watch?v=no9UnySBQrU&t=770

Curl

curl -k 'imap://10.129.252.135' --user robin:robin -v
curl -k 'pop3://10.129.252.135' --user robin:robin -v
curl -k 'imaps://10.129.14.128' --user user:p4ssw0rd

* LIST (\HasNoChildren) "." Important
* LIST (\HasNoChildren) "." INBOX
$ curl -k 'imaps://10.129.14.128' --user cry0l1t3:1234 -v

*   Trying 10.129.14.128:993...
* TCP_NODELAY set
* Connected to 10.129.14.128 (10.129.14.128) port 993 (#0)
* successfully set certificate verify locations:
*   CAfile: /etc/ssl/certs/ca-certificates.crt
  CApath: /etc/ssl/certs
* TLSv1.3 (OUT), TLS handshake, Client hello (1):
* TLSv1.3 (IN), TLS handshake, Server hello (2):
* TLSv1.3 (IN), TLS handshake, Encrypted Extensions (8):
* TLSv1.3 (IN), TLS handshake, Certificate (11):
* TLSv1.3 (IN), TLS handshake, CERT verify (15):
* TLSv1.3 (IN), TLS handshake, Finished (20):
* TLSv1.3 (OUT), TLS change cipher, Change cipher spec (1):
* TLSv1.3 (OUT), TLS handshake, Finished (20):
* SSL connection using TLSv1.3 / TLS_AES_256_GCM_SHA384
* Server certificate:
*  subject: C=US; ST=California; L=Sacramento; O=Inlanefreight; OU=Customer Support; CN=mail1.inlanefreight.htb; emailAddress=cry0l1t3@inlanefreight.htb
*  start date: Sep 19 19:44:58 2021 GMT
*  expire date: Jul  4 19:44:58 2295 GMT
*  issuer: C=US; ST=California; L=Sacramento; O=Inlanefreight; OU=Customer Support; CN=mail1.inlanefreight.htb; emailAddress=cry0l1t3@inlanefreight.htb
*  SSL certificate verify result: self signed certificate (18), continuing anyway.
* TLSv1.3 (IN), TLS handshake, Newsession Ticket (4):
* TLSv1.3 (IN), TLS handshake, Newsession Ticket (4):
* old SSL session ID is stale, removing
< * OK [CAPABILITY IMAP4rev1 SASL-IR LOGIN-REFERRALS ID ENABLE IDLE LITERAL+ AUTH=PLAIN] HTB-Academy IMAP4 v.0.21.4
> A001 CAPABILITY
< * CAPABILITY IMAP4rev1 SASL-IR LOGIN-REFERRALS ID ENABLE IDLE LITERAL+ AUTH=PLAIN
< A001 OK Pre-login capabilities listed, post-login capabilities have more.
> A002 AUTHENTICATE PLAIN AGNyeTBsMXQzADEyMzQ=
< * CAPABILITY IMAP4rev1 SASL-IR LOGIN-REFERRALS ID ENABLE IDLE SORT SORT=DISPLAY THREAD=REFERENCES THREAD=REFS THREAD=ORDEREDSUBJECT MULTIAPPEND URL-PARTIAL CATENATE UNSELECT CHILDREN NAMESPACE UIDPLUS LIST-EXTENDED I18NLEVEL=1 CONDSTORE QRESYNC ESEARCH ESORT SEARCHRES WITHIN CONTEXT=SEARCH LIST-STATUS BINARY MOVE SNIPPET=FUZZY PREVIEW=FUZZY LITERAL+ NOTIFY SPECIAL-USE
< A002 OK Logged in
> A003 LIST "" *
< * LIST (\HasNoChildren) "." Important
* LIST (\HasNoChildren) "." Important
< * LIST (\HasNoChildren) "." INBOX
* LIST (\HasNoChildren) "." INBOX
< A003 OK List completed (0.001 + 0.000 secs).
* Connection #0 to host 10.129.14.128 left intact

OpenSSL - POP3S

openssl s_client -connect 10.129.14.128:pop3s

CONNECTED(00000003)
Can't use SSL_get_servername
depth=0 C = US, ST = California, L = Sacramento, O = Inlanefreight, OU = Customer Support, CN = mail1.inlanefreight.htb, emailAddress = cry0l1t3@inlanefreight.htb
verify error:num=18:self signed certificate
verify return:1
depth=0 C = US, ST = California, L = Sacramento, O = Inlanefreight, OU = Customer Support, CN = mail1.inlanefreight.htb, emailAddress = cry0l1t3@inlanefreight.htb
verify return:1
---
Certificate chain
 0 s:C = US, ST = California, L = Sacramento, O = Inlanefreight, OU = Customer Support, CN = mail1.inlanefreight.htb, emailAddress = cry0l1t3@inlanefreight.htb

...SNIP...

---
read R BLOCK
---
Post-Handshake New Session Ticket arrived:
SSL-Session:
    Protocol  : TLSv1.3
    Cipher    : TLS_AES_256_GCM_SHA384
    Session-ID: 3CC39A7F2928B252EF2FFA5462140B1A0A74B29D4708AA8DE1515BB4033D92C2
    Session-ID-ctx:
    Resumption PSK: 68419D933B5FEBD878FF1BA399A926813BEA3652555E05F0EC75D65819A263AA25FA672F8974C37F6446446BB7EA83F9
    PSK identity: None
    PSK identity hint: None
    SRP username: None
    TLS session ticket lifetime hint: 7200 (seconds)
    TLS session ticket:
    0000 - d7 86 ac 7e f3 f4 95 35-88 40 a5 b5 d6 a6 41 e4   ...~...5.@....A.
    0010 - 96 6c e6 12 4f 50 ce 72-36 25 df e1 72 d9 23 94   .l..OP.r6%..r.#.
    0020 - cc 29 90 08 58 1b 57 ab-db a8 6b f7 8f 31 5b ad   .)..X.W...k..1[.
    0030 - 47 94 f4 67 58 1f 96 d9-ca ca 56 f9 7a 12 f6 6d   G..gX.....V.z..m
    0040 - 43 b9 b6 68 de db b2 47-4f 9f 48 14 40 45 8f 89   C..h...GO.H.@E..
    0050 - fa 19 35 9c 6d 3c a1 46-5c a2 65 ab 87 a4 fd 5e   ..5.m<.F\.e....^
    0060 - a2 95 25 d4 43 b8 71 70-40 6c fe 6f 0e d1 a0 38   ..%.C.qp@l.o...8
    0070 - 6e bd 73 91 ed 05 89 83-f5 3e d9 2a e0 2e 96 f8   n.s......>.*....
    0080 - 99 f0 50 15 e0 1b 66 db-7c 9f 10 80 4a a1 8b 24   ..P...f.|...J..$
    0090 - bb 00 03 d4 93 2b d9 95-64 44 5b c2 6b 2e 01 b5   .....+..dD[.k...
    00a0 - e8 1b f4 a4 98 a7 7a 7d-0a 80 cc 0a ad fe 6e b3   ......z}......n.
    00b0 - 0a d6 50 5d fd 9a b4 5c-28 a4 c9 36 e4 7d 2a 1e   ..P]...\(..6.}*.

    Start Time: 1632081313
    Timeout   : 7200 (sec)
    Verify return code: 18 (self signed certificate)
    Extended master secret: no
    Max Early Data: 0
---
read R BLOCK
+OK HTB-Academy POP3 Server

OpenSSL - IMAPS

$ openssl s_client -connect 10.129.14.128:imaps

CONNECTED(00000003)
Can't use SSL_get_servername
depth=0 C = US, ST = California, L = Sacramento, O = Inlanefreight, OU = Customer Support, CN = mail1.inlanefreight.htb, emailAddress = cry0l1t3@inlanefreight.htb
verify error:num=18:self signed certificate
verify return:1
depth=0 C = US, ST = California, L = Sacramento, O = Inlanefreight, OU = Customer Support, CN = mail1.inlanefreight.htb, emailAddress = cry0l1t3@inlanefreight.htb
verify return:1
---
Certificate chain
 0 s:C = US, ST = California, L = Sacramento, O = Inlanefreight, OU = Customer Support, CN = mail1.inlanefreight.htb, emailAddress = cry0l1t3@inlanefreight.htb

...SNIP...

---
read R BLOCK
---
Post-Handshake New Session Ticket arrived:
SSL-Session:
    Protocol  : TLSv1.3
    Cipher    : TLS_AES_256_GCM_SHA384
    Session-ID: 2B7148CD1B7B92BA123E06E22831FCD3B365A5EA06B2CDEF1A5F397177130699
    Session-ID-ctx:
    Resumption PSK: 4D9F082C6660646C39135F9996DDA2C199C4F7E75D65FA5303F4A0B274D78CC5BD3416C8AF50B31A34EC022B619CC633
    PSK identity: None
    PSK identity hint: None
    SRP username: None
    TLS session ticket lifetime hint: 7200 (seconds)
    TLS session ticket:
    0000 - 68 3b b6 68 ff 85 95 7c-8a 8a 16 b2 97 1c 72 24   h;.h...|......r$
    0010 - 62 a7 84 ff c3 24 ab 99-de 45 60 26 e7 04 4a 7d   b....$...E`&..J}
    0020 - bc 6e 06 a0 ff f7 d7 41-b5 1b 49 9c 9f 36 40 8d   .n.....A..I..6@.
    0030 - 93 35 ed d9 eb 1f 14 d7-a5 f6 3f c8 52 fb 9f 29   .5........?.R..)
    0040 - 89 8d de e6 46 95 b3 32-48 80 19 bc 46 36 cb eb   ....F..2H...F6..
    0050 - 35 79 54 4c 57 f8 ee 55-06 e3 59 7f 5e 64 85 b0   5yTLW..U..Y.^d..
    0060 - f3 a4 8c a6 b6 47 e4 59-ee c9 ab 54 a4 ab 8c 01   .....G.Y...T....
    0070 - 56 bb b9 bb 3b f6 96 74-16 c9 66 e2 6c 28 c6 12   V...;..t..f.l(..
    0080 - 34 c7 63 6b ff 71 16 7f-91 69 dc 38 7a 47 46 ec   4.ck.q...i.8zGF.
    0090 - 67 b7 a2 90 8b 31 58 a0-4f 57 30 6a b6 2e 3a 21   g....1X.OW0j..:!
    00a0 - 54 c7 ba f0 a9 74 13 11-d5 d1 ec cc ea f9 54 7d   T....t........T}
    00b0 - 46 a6 33 ed 5d 24 ed b0-20 63 43 d8 8f 14 4d 62   F.3.]$.. cC...Mb

    Start Time: 1632081604
    Timeout   : 7200 (sec)
    Verify return code: 18 (self signed certificate)
    Extended master secret: no
    Max Early Data: 0
---
read R BLOCK
* OK [CAPABILITY IMAP4rev1 SASL-IR LOGIN-REFERRALS ID ENABLE IDLE LITERAL+ AUTH=PLAIN] HTB-Academy IMAP4 v.0.21.4

IMAP Commands

LogoIMAP Commands - Atmail email experts - IMAP tutorial - What is IMAP?Atmail
LogoIMAP Protocol Crib Sheet

Command

Description

1 LOGIN username password

User's login.

1 LIST "" *

Lists all directories.

1 CREATE "INBOX"

Creates a mailbox with a specified name.

1 DELETE "INBOX"

Deletes a mailbox.

1 RENAME "ToRead" "Important"

Renames a mailbox.

1 LSUB "" *

Returns a subset of names from the set of names that the User has declared as being active or subscribed.

1 SELECT INBOX

Selects a mailbox so that messages in the mailbox can be accessed.

1 UNSELECT INBOX

Exits the selected mailbox.

1 FETCH <ID> all

Retrieves data associated with a message in the mailbox.

1 CLOSE

Removes all messages with the Deleted flag set.

1 LOGOUT

Closes the connection with the IMAP server.

POP3 Commands

Command

Description

USER username

Identifies the user.

PASS password

Authentication of the user using its password.

STAT

Requests the number of saved emails from the server.

LIST

Requests from the server the number and size of all emails.

RETR id

Requests the server to deliver the requested email by ID.

DELE id

Requests the server to delete the requested email by ID.

CAPA

Requests the server to display the server capabilities.

RSET

Requests the server to reset the transmitted information.

QUIT

Closes the connection with the POP3 server.

Brute Force

POP3 Bruteforce
$ hydra -L users.txt -p 'Company01!' -f 10.10.110.20 pop3

Resources

Logo143,993 - Pentesting IMAPHackTricks

Interesting Books

Interesting Books

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  • Nmap Network Scanning The official guide to the Nmap Security Scanner, a free and open source utility used by millions of people for network discovery, administration, and security auditing. From explaining port scanning basics for novices to detailing low-level packet crafting methods used by advanced hackers, this book by Nmap's original author suits all levels of security and networking professionals.

  • The Art of Network Penetration Testing A guide to simulating an internal security breach. You’ll take on the role of the attacker and work through every stage of a professional pentest, from information gathering to seizing control of a system and owning the network.

  • Network Basics for Hackers The book offers one of the most complete and in-depth analyses of Wi-Fi and Bluetooth networks, then progresses through the various protocols such as DNS, ARP, SMTP, and others.

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