Bypass Security Measures

SYN-Scan

eldeim@htb[/htb]$ sudo nmap 10.129.2.28 -p 21,22,25 -sS -Pn -n --disable-arp-ping --packet-trace

Starting Nmap 7.80 ( https://nmap.org ) at 2020-06-21 14:56 CEST
SENT (0.0278s) TCP 10.10.14.2:57347 > 10.129.2.28:22 S ttl=53 id=22412 iplen=44  seq=4092255222 win=1024 <mss 1460>
SENT (0.0278s) TCP 10.10.14.2:57347 > 10.129.2.28:25 S ttl=50 id=62291 iplen=44  seq=4092255222 win=1024 <mss 1460>
SENT (0.0278s) TCP 10.10.14.2:57347 > 10.129.2.28:21 S ttl=58 id=38696 iplen=44  seq=4092255222 win=1024 <mss 1460>
RCVD (0.0329s) ICMP [10.129.2.28 > 10.10.14.2 Port 21 unreachable (type=3/code=3) ] IP [ttl=64 id=40884 iplen=72 ]
RCVD (0.0341s) TCP 10.129.2.28:22 > 10.10.14.2:57347 SA ttl=64 id=0 iplen=44  seq=1153454414 win=64240 <mss 1460>
RCVD (1.0386s) TCP 10.129.2.28:22 > 10.10.14.2:57347 SA ttl=64 id=0 iplen=44  seq=1153454414 win=64240 <mss 1460>
SENT (1.1366s) TCP 10.10.14.2:57348 > 10.129.2.28:25 S ttl=44 id=6796 iplen=44  seq=4092320759 win=1024 <mss 1460>
Nmap scan report for 10.129.2.28
Host is up (0.0053s latency).

PORT   STATE    SERVICE
21/tcp filtered ftp
22/tcp open     ssh
25/tcp filtered smtp
MAC Address: DE:AD:00:00:BE:EF (Intel Corporate)

Nmap done: 1 IP address (1 host up) scanned in 0.07 seconds

ACK-Scan

eldeim@htb[/htb]$ sudo nmap 10.129.2.28 -p 21,22,25 -sA -Pn -n --disable-arp-ping --packet-trace

Starting Nmap 7.80 ( https://nmap.org ) at 2020-06-21 14:57 CEST
SENT (0.0422s) TCP 10.10.14.2:49343 > 10.129.2.28:21 A ttl=49 id=12381 iplen=40  seq=0 win=1024
SENT (0.0423s) TCP 10.10.14.2:49343 > 10.129.2.28:22 A ttl=41 id=5146 iplen=40  seq=0 win=1024
SENT (0.0423s) TCP 10.10.14.2:49343 > 10.129.2.28:25 A ttl=49 id=5800 iplen=40  seq=0 win=1024
RCVD (0.1252s) ICMP [10.129.2.28 > 10.10.14.2 Port 21 unreachable (type=3/code=3) ] IP [ttl=64 id=55628 iplen=68 ]
RCVD (0.1268s) TCP 10.129.2.28:22 > 10.10.14.2:49343 R ttl=64 id=0 iplen=40  seq=1660784500 win=0
SENT (1.3837s) TCP 10.10.14.2:49344 > 10.129.2.28:25 A ttl=59 id=21915 iplen=40  seq=0 win=1024
Nmap scan report for 10.129.2.28
Host is up (0.083s latency).

PORT   STATE      SERVICE
21/tcp filtered   ftp
22/tcp unfiltered ssh
25/tcp filtered   smtp
MAC Address: DE:AD:00:00:BE:EF (Intel Corporate)

Nmap done: 1 IP address (1 host up) scanned in 0.15 seconds

Scanning Options

Description

10.129.2.28

Scans the specified target.

-p 21,22,25

Scans only the specified ports.

-sS

Performs SYN scan on specified ports.

-sA

Performs ACK scan on specified ports.

-Pn

Disables ICMP Echo requests.

-n

Disables DNS resolution.

--disable-arp-ping

Disables ARP ping.

--packet-trace

Shows all packets sent and received.

Please pay attention to the RCVD packets and its set flag we receive from our target. With the SYN scan (-sS) our target tries to establish the TCP connection by sending a packet back with the SYN-ACK (SA) flags set and with the ACK scan (-sA) we get the RST flag because TCP port 22 is open. For the TCP port 25, we do not receive any packets back, which indicates that the packets will be dropped.

Scan by Using Decoys

eldeim@htb[/htb]$ sudo nmap 10.129.2.28 -p 80 -sS -Pn -n --disable-arp-ping --packet-trace -D RND:5

Starting Nmap 7.80 ( https://nmap.org ) at 2020-06-21 16:14 CEST
SENT (0.0378s) TCP 102.52.161.59:59289 > 10.129.2.28:80 S ttl=42 id=29822 iplen=44  seq=3687542010 win=1024 <mss 1460>
SENT (0.0378s) TCP 10.10.14.2:59289 > 10.129.2.28:80 S ttl=59 id=29822 iplen=44  seq=3687542010 win=1024 <mss 1460>
SENT (0.0379s) TCP 210.120.38.29:59289 > 10.129.2.28:80 S ttl=37 id=29822 iplen=44  seq=3687542010 win=1024 <mss 1460>
SENT (0.0379s) TCP 191.6.64.171:59289 > 10.129.2.28:80 S ttl=38 id=29822 iplen=44  seq=3687542010 win=1024 <mss 1460>
SENT (0.0379s) TCP 184.178.194.209:59289 > 10.129.2.28:80 S ttl=39 id=29822 iplen=44  seq=3687542010 win=1024 <mss 1460>
SENT (0.0379s) TCP 43.21.121.33:59289 > 10.129.2.28:80 S ttl=55 id=29822 iplen=44  seq=3687542010 win=1024 <mss 1460>
RCVD (0.1370s) TCP 10.129.2.28:80 > 10.10.14.2:59289 SA ttl=64 id=0 iplen=44  seq=4056111701 win=64240 <mss 1460>
Nmap scan report for 10.129.2.28
Host is up (0.099s latency).

PORT   STATE SERVICE
80/tcp open  http
MAC Address: DE:AD:00:00:BE:EF (Intel Corporate)

Nmap done: 1 IP address (1 host up) scanned in 0.15 seconds

Scanning Options

Description

10.129.2.28

Scans the specified target.

-p 80

Scans only the specified ports.

-sS

Performs SYN scan on specified ports.

-Pn

Disables ICMP Echo requests.

-n

Disables DNS resolution.

--disable-arp-ping

Disables ARP ping.

--packet-trace

Shows all packets sent and received.

-D RND:5

Generates five random IP addresses that indicates the source IP the connection comes from.

The spoofed packets are often filtered out by ISPs and routers, even though they come from the same network range. Therefore, we can also specify our VPS servers' IP addresses and use them in combination with "IP ID" manipulation in the IP headers to scan the target.

Another scenario would be that only individual subnets would not have access to the server's specific services. So we can also manually specify the source IP address (-S) to test if we get better results with this one. Decoys can be used for SYN, ACK, ICMP scans, and OS detection scans. So let us look at such an example and determine which operating system it is most likely to be.

Testing Firewall Rule

eldeim@htb[/htb]$ sudo nmap 10.129.2.28 -n -Pn -p445 -O

Starting Nmap 7.80 ( https://nmap.org ) at 2020-06-22 01:23 CEST
Nmap scan report for 10.129.2.28
Host is up (0.032s latency).

PORT    STATE    SERVICE
445/tcp filtered microsoft-ds
MAC Address: DE:AD:00:00:BE:EF (Intel Corporate)
Too many fingerprints match this host to give specific OS details
Network Distance: 1 hop

OS detection performed. Please report any incorrect results at https://nmap.org/submit/ .
Nmap done: 1 IP address (1 host up) scanned in 3.14 seconds

Scan by Using Different Source IP

eldeim@htb[/htb]$ sudo nmap 10.129.2.28 -n -Pn -p 445 -O -S 10.129.2.200 -e tun0

Starting Nmap 7.80 ( https://nmap.org ) at 2020-06-22 01:16 CEST
Nmap scan report for 10.129.2.28
Host is up (0.010s latency).

PORT    STATE SERVICE
445/tcp open  microsoft-ds
MAC Address: DE:AD:00:00:BE:EF (Intel Corporate)
Warning: OSScan results may be unreliable because we could not find at least 1 open and 1 closed port
Aggressive OS guesses: Linux 2.6.32 (96%), Linux 3.2 - 4.9 (96%), Linux 2.6.32 - 3.10 (96%), Linux 3.4 - 3.10 (95%), Linux 3.1 (95%), Linux 3.2 (95%), AXIS 210A or 211 Network Camera (Linux 2.6.17) (94%), Synology DiskStation Manager 5.2-5644 (94%), Linux 2.6.32 - 2.6.35 (94%), Linux 2.6.32 - 3.5 (94%)
No exact OS matches for host (test conditions non-ideal).
Network Distance: 1 hop

OS detection performed. Please report any incorrect results at https://nmap.org/submit/ .
Nmap done: 1 IP address (1 host up) scanned in 4.11 seconds

Scanning Options

Description

10.129.2.28

Scans the specified target.

-n

Disables DNS resolution.

-Pn

Disables ICMP Echo requests.

-p 445

Scans only the specified ports.

-O

Performs operation system detection scan.

-S

Scans the target by using different source IP address.

10.129.2.200

Specifies the source IP address.

-e tun0

Sends all requests through the specified interface.

DNS Proxying

By default, Nmap performs a reverse DNS resolution unless otherwise specified to find more important information about our target. These DNS queries are also passed in most cases because the given web server is supposed to be found and visited. The DNS queries are made over the UDP port 53. The TCP port 53 was previously only used for the so-called "Zone transfers" between the DNS servers or data transfer larger than 512 bytes. More and more, this is changing due to IPv6 and DNSSEC expansions. These changes cause many DNS requests to be made via TCP port 53.

However, Nmap still gives us a way to specify DNS servers ourselves (--dns-server <ns>,<ns>). This method could be fundamental to us if we are in a demilitarized zone (DMZ). The company's DNS servers are usually more trusted than those from the Internet. So, for example, we could use them to interact with the hosts of the internal network. As another example, we can use TCP port 53 as a source port (--source-port) for our scans. If the administrator uses the firewall to control this port and does not filter IDS/IPS properly, our TCP packets will be trusted and passed through.

SYN-Scan of a Filtered Port

eldeim@htb[/htb]$ sudo nmap 10.129.2.28 -p50000 -sS -Pn -n --disable-arp-ping --packet-trace

Starting Nmap 7.80 ( https://nmap.org ) at 2020-06-21 22:50 CEST
SENT (0.0417s) TCP 10.10.14.2:33436 > 10.129.2.28:50000 S ttl=41 id=21939 iplen=44  seq=736533153 win=1024 <mss 1460>
SENT (1.0481s) TCP 10.10.14.2:33437 > 10.129.2.28:50000 S ttl=46 id=6446 iplen=44  seq=736598688 win=1024 <mss 1460>
Nmap scan report for 10.129.2.28
Host is up.

PORT      STATE    SERVICE
50000/tcp filtered ibm-db2

Nmap done: 1 IP address (1 host up) scanned in 2.06 seconds

SYN-Scan From DNS Port

eldeim@htb[/htb]$ sudo nmap 10.129.2.28 -p50000 -sS -Pn -n --disable-arp-ping --packet-trace --source-port 53

SENT (0.0482s) TCP 10.10.14.2:53 > 10.129.2.28:50000 S ttl=58 id=27470 iplen=44  seq=4003923435 win=1024 <mss 1460>
RCVD (0.0608s) TCP 10.129.2.28:50000 > 10.10.14.2:53 SA ttl=64 id=0 iplen=44  seq=540635485 win=64240 <mss 1460>
Nmap scan report for 10.129.2.28
Host is up (0.013s latency).

PORT      STATE SERVICE
50000/tcp open  ibm-db2
MAC Address: DE:AD:00:00:BE:EF (Intel Corporate)

Nmap done: 1 IP address (1 host up) scanned in 0.08 seconds

Scanning Options

Description

10.129.2.28

Scans the specified target.

-p 50000

Scans only the specified ports.

-sS

Performs SYN scan on specified ports.

-Pn

Disables ICMP Echo requests.

-n

Disables DNS resolution.

--disable-arp-ping

Disables ARP ping.

--packet-trace

Shows all packets sent and received.

--source-port 53

Performs the scans from specified source port.

Now that we have found out that the firewall accepts TCP port 53, it is very likely that IDS/IPS filters might also be configured much weaker than others. We can test this by trying to connect to this port by using Netcat.

Connect To The Filtered Port

eldeim@htb[/htb]$ ncat -nv --source-port 53 10.129.2.28 50000

Ncat: Version 7.80 ( https://nmap.org/ncat )
Ncat: Connected to 10.129.2.28:50000.
220 ProFTPd

Firewall and IDS/IPS Evasion - Easy Lab

  • Our client wants to know if we can identify which operating system their provided machine is running on. Submit the OS name as the answer.

nmap -p- --open -sS -n -Pn -O --disable-arp-ping 10.129.2.80 --max-rate 1000
PORT      STATE SERVICE
22/tcp    open  ssh
80/tcp    open  http
10001/tcp open  scp-config

## NEXT
nmap -p 22,80,10001 -sCV -n -Pn -O --disable-arp-ping 10.129.2.80 --max-rate 1000
PORT      STATE SERVICE     VERSION
22/tcp    open  ssh         OpenSSH 7.6p1 Ubuntu 4ubuntu0.7 (Ubuntu Linux; protocol 2.0)
| ssh-hostkey: 
|   2048 71:c1:89:90:7f:fd:4f:60:e0:54:f3:85:e6:35:6c:2b (RSA)
|   256 e1:8e:53:18:42:af:2a:de:c0:12:1e:2e:54:06:4f:70 (ECDSA)
|_  256 1a:cc:ac:d4:94:5c:d6:1d:71:e7:39:de:14:27:3c:3c (ED25519)
80/tcp    open  http        Apache httpd 2.4.29 ((Ubuntu))
|_http-title: Apache2 Ubuntu Default Page: It works
|_http-server-header: Apache/2.4.29 (Ubuntu)
10001/tcp open  scp-config?
| fingerprint-strings: 
|   GetRequest: 
|_    220 HTB{pr0F7pDv3r510nb4nn3r}
1 service unrecognized despite returning data. If you know the service/version, please submit the following fingerprint at https://nmap.org/cgi-bin/submit.cgi?new-service :
SF-Port10001-TCP:V=7.94SVN%I=7%D=10/11%Time=68EA7138%P=x86_64-pc-linux-gnu
SF:%r(GetRequest,1F,"220\x20HTB{pr0F7pDv3r510nb4nn3r}\r\n");
Warning: OSScan results may be unreliable because we could not find at least 1 open and 1 closed port
Aggressive OS guesses: Linux 4.15 - 5.8 (95%), Linux 5.0 - 5.4 (95%), Linux 5.3 - 5.4 (95%), Linux 5.0 (95%), Linux 3.1 (94%), Linux 3.2 (94%), AXIS 210A or 211 Network Camera (Linux 2.6.17) (94%), Linux 2.6.32 (94%), Linux 5.0 - 5.5 (94%), HP P2000 G3 NAS device (93%)
No exact OS matches for host (test conditions non-ideal).
Network Distance: 2 hops
Service Info: OS: Linux; CPE: cpe:/o:linux:linux_kernel

Firewall and IDS/IPS Evasion - Medium Lab

Note: To successfully solve the exercise, we must use the UDP protocol on the VPN.

  • After the configurations are transferred to the system, our client wants to know if it is possible to find out our target's DNS server version. Submit the DNS server version of the target as the answer.

sudo nmap -sU -sCV --top-ports 100 -n -Pn --disable-arp-ping --max-rate 5000 10.129.2.48
PORT    STATE         SERVICE     VERSION
53/udp  open          domain      (unknown banner: HTB{GoTtgUnyze9Psw4vGjcuMpHRp})
| dns-nsid: 
|_  bind.version: HTB{GoTtgUnyze9Psw4vGjcuMpHRp}
| fingerprint-strings: 
|   DNSVersionBindReq: 
|     version
|     bind
|     HTB{GoTtgUnyze9Psw4vGjcuMpHRp}
|   NBTStat: 
|     CKAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA
|_    ROOT-SERVERS
68/udp  open|filtered dhcpc
137/udp open          netbios-ns  Samba nmbd netbios-ns (workgroup: WORKGROUP)
138/udp open|filtered netbios-dgm
1 service unrecognized despite returning data. If you know the service/version, please submit the following fingerprint at https://nmap.org/cgi-bin/submit.cgi?new-service :
SF-Port53-UDP:V=7.94SVN%I=7%D=10/11%Time=68EA77FF%P=x86_64-pc-linux-gnu%r(
SF:DNSVersionBindReq,57,"\0\x06\x85\0\0\x01\0\x01\0\x01\0\0\x07version\x04
SF:bind\0\0\x10\0\x03\xc0\x0c\0\x10\0\x03\0\0\0\0\0\x1f\x1eHTB{GoTtgUnyze9
SF:Psw4vGjcuMpHRp}\xc0\x0c\0\x02\0\x03\0\0\0\0\0\x02\xc0\x0c")%r(DNSStatus
SF:Request,C,"\0\0\x90\x04\0\0\0\0\0\0\0\0")%r(NBTStat,105,"\x80\xf0\x80\x
SF:90\0\x01\0\0\0\r\0\0\x20CKAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA\0\0!\0\x01\0\0
SF:\x02\0\x01\x006\xee\x80\0\x14\x01K\x0cROOT-SERVERS\x03NET\0\0\0\x02\0\x
SF:01\x006\xee\x80\0\x04\x01M\xc0\?\0\0\x02\0\x01\x006\xee\x80\0\x04\x01D\
SF:xc0\?\0\0\x02\0\x01\x006\xee\x80\0\x04\x01I\xc0\?\0\0\x02\0\x01\x006\xe
SF:e\x80\0\x04\x01A\xc0\?\0\0\x02\0\x01\x006\xee\x80\0\x04\x01E\xc0\?\0\0\
SF:x02\0\x01\x006\xee\x80\0\x04\x01C\xc0\?\0\0\x02\0\x01\x006\xee\x80\0\x0
SF:4\x01H\xc0\?\0\0\x02\0\x01\x006\xee\x80\0\x04\x01F\xc0\?\0\0\x02\0\x01\
SF:x006\xee\x80\0\x04\x01J\xc0\?\0\0\x02\0\x01\x006\xee\x80\0\x04\x01B\xc0
SF:\?\0\0\x02\0\x01\x006\xee\x80\0\x04\x01L\xc0\?\0\0\x02\0\x01\x006\xee\x
SF:80\0\x04\x01G\xc0\?");
Service Info: Host: HTB984NIFN97CBO

Firewall and IDS/IPS Evasion - Hard Lab

  • Now our client wants to know if it is possible to find out the version of the running services. Identify the version of service our client was talking about and submit the flag as the answer.

sudo nmap 10.129.2.47 -sS -Pn -n --disable-arp-ping --source-port 53 -p- -vvv
PORT      STATE SERVICE REASON
22/tcp    open  ssh     syn-ack ttl 63
80/tcp    open  http    syn-ack ttl 63
50000/tcp open  ibm-db2 syn-ack ttl 63

## NEXT
sudo nmap 10.129.2.47 -sCV -Pn -n --disable-arp-ping --source-port 53 -p50000 -vvv
PORT      STATE SERVICE    REASON         VERSION
50000/tcp open  tcpwrapped syn-ack ttl 63

## NEXT
netcat -nv -p 53 10.129.2.47 50000
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