diff --git a/monkey/infection_monkey/config.py b/monkey/infection_monkey/config.py
index 9c239fd93..8a920cc52 100644
--- a/monkey/infection_monkey/config.py
+++ b/monkey/infection_monkey/config.py
@@ -81,7 +81,7 @@ class Configuration(object):
     # monkey config
     ###########################
     # sets whether or not the monkey is alive. if false will stop scanning and exploiting
-    alive = True
+    should_stop = False
 
     # depth of propagation
     depth = 2
diff --git a/monkey/infection_monkey/example.conf b/monkey/infection_monkey/example.conf
index ebadf1429..f0cbb6e16 100644
--- a/monkey/infection_monkey/example.conf
+++ b/monkey/infection_monkey/example.conf
@@ -9,7 +9,7 @@
   "inaccessible_subnets": [],
   "blocked_ips": [],
   "current_server": "192.0.2.0:5000",
-  "alive": true,
+  "should_stop": false,
   "collect_system_info": true,
   "should_use_mimikatz": true,
   "depth": 2,
diff --git a/monkey/infection_monkey/exploit/HostExploiter.py b/monkey/infection_monkey/exploit/HostExploiter.py
index 3bda4b0d7..2e198ac4c 100644
--- a/monkey/infection_monkey/exploit/HostExploiter.py
+++ b/monkey/infection_monkey/exploit/HostExploiter.py
@@ -1,4 +1,5 @@
 import logging
+import threading
 from abc import abstractmethod
 from datetime import datetime
 from typing import Dict
@@ -66,12 +67,14 @@ class HostExploiter:
         telemetry_messenger: ITelemetryMessenger,
         agent_repository: IAgentRepository,
         options: Dict,
+        interrupt: threading.Event,
     ):
         self.host = host
         self.current_depth = current_depth
         self.telemetry_messenger = telemetry_messenger
         self.agent_repository = agent_repository
         self.options = options
+        self.interrupt = interrupt
 
         self.pre_exploit()
         try:
@@ -91,6 +94,15 @@ class HostExploiter:
         )
         self.set_start_time()
 
+    def is_interrupted(self):
+        # This method should be refactored to raise an exception to reduce duplication in the
+        # "if is_interrupted: return self.exploitation_results"
+        # Ideally the user should only do "check_for_interrupt()"
+        if self.interrupt.is_set():
+            logger.info("Exploiter has been interrupted")
+            self.exploit_result.error_message = "Exploiter has been interrupted"
+        return self.interrupt.is_set()
+
     def post_exploit(self):
         self.set_finish_time()
 
diff --git a/monkey/infection_monkey/exploit/exploiter_wrapper.py b/monkey/infection_monkey/exploit/exploiter_wrapper.py
index 5e855ff22..540e0b4a4 100644
--- a/monkey/infection_monkey/exploit/exploiter_wrapper.py
+++ b/monkey/infection_monkey/exploit/exploiter_wrapper.py
@@ -1,3 +1,4 @@
+import threading
 from typing import Dict, Type
 
 from infection_monkey.model import VictimHost
@@ -26,10 +27,17 @@ class ExploiterWrapper:
             self._telemetry_messenger = telemetry_messenger
             self._agent_repository = agent_repository
 
-        def exploit_host(self, host: VictimHost, current_depth: int, options: Dict):
+        def exploit_host(
+            self, host: VictimHost, current_depth: int, options: Dict, interrupt: threading.Event
+        ):
             exploiter = self._exploit_class()
             return exploiter.exploit_host(
-                host, current_depth, self._telemetry_messenger, self._agent_repository, options
+                host,
+                current_depth,
+                self._telemetry_messenger,
+                self._agent_repository,
+                options,
+                interrupt,
             )
 
     def __init__(
diff --git a/monkey/infection_monkey/exploit/tools/wmi_tools.py b/monkey/infection_monkey/exploit/tools/wmi_tools.py
index 5b21d2d9f..b6346ba14 100644
--- a/monkey/infection_monkey/exploit/tools/wmi_tools.py
+++ b/monkey/infection_monkey/exploit/tools/wmi_tools.py
@@ -49,6 +49,7 @@ class WmiTools(object):
             if not domain:
                 domain = host.ip_addr
 
+            # Impacket has a hard-coded timeout of 30 seconds
             dcom = DCOMConnection(
                 host.ip_addr,
                 username=username,
diff --git a/monkey/infection_monkey/exploit/wmiexec.py b/monkey/infection_monkey/exploit/wmiexec.py
index 7fc229ebe..7b7c9ad1e 100644
--- a/monkey/infection_monkey/exploit/wmiexec.py
+++ b/monkey/infection_monkey/exploit/wmiexec.py
@@ -15,6 +15,7 @@ from infection_monkey.utils.brute_force import (
     get_credential_string,
 )
 from infection_monkey.utils.commands import build_monkey_commandline
+from infection_monkey.utils.threading import interruptable_iter
 
 logger = logging.getLogger(__name__)
 
@@ -28,8 +29,15 @@ class WmiExploiter(HostExploiter):
     def _exploit_host(self) -> ExploiterResultData:
 
         creds = generate_brute_force_combinations(self.options["credentials"])
+        intp_creds = interruptable_iter(
+            creds,
+            self.interrupt,
+            "WMI exploiter has been interrupted",
+            logging.INFO,
+        )
+
+        for user, password, lm_hash, ntlm_hash in intp_creds:
 
-        for user, password, lm_hash, ntlm_hash in creds:
             creds_for_log = get_credential_string([user, password, lm_hash, ntlm_hash])
             logger.debug(f"Attempting to connect to {self.host} using WMI with {creds_for_log}")
 
@@ -60,21 +68,11 @@ class WmiExploiter(HostExploiter):
             self.report_login_attempt(True, user, password, lm_hash, ntlm_hash)
             self.exploit_result.exploitation_success = True
 
-            # query process list and check if monkey already running on victim
-            process_list = WmiTools.list_object(
-                wmi_connection,
-                "Win32_Process",
-                fields=("Caption",),
-                where=f"Name='{ntpath.split(self.options['dropper_target_path_win_64'])[-1]}'",
-            )
-            if process_list:
-                wmi_connection.close()
-
-                logger.debug("Skipping %r - already infected", self.host)
-                return self.exploit_result
-
             downloaded_agent = self.agent_repository.get_agent_binary(self.host.os["type"])
 
+            if self.is_interrupted():
+                return self.exploit_result
+
             remote_full_path = SmbTools.copy_file(
                 self.host,
                 downloaded_agent,
@@ -120,7 +118,7 @@ class WmiExploiter(HostExploiter):
                 self.add_vuln_port(port="unknown")
                 self.exploit_result.propagation_success = True
             else:
-                logger.debug(
+                error_message = (
                     "Error executing dropper '%s' on remote victim %r (pid=%d, exit_code=%d, "
                     "cmdline=%r)",
                     remote_full_path,
@@ -129,6 +127,8 @@ class WmiExploiter(HostExploiter):
                     result.ReturnValue,
                     cmdline,
                 )
+                logger.debug(error_message)
+                self.exploit_result.error_message = error_message
 
             result.RemRelease()
             wmi_connection.close()
diff --git a/monkey/infection_monkey/puppet/plugin_registry.py b/monkey/infection_monkey/puppet/plugin_registry.py
index 2ec1e3900..1fdca5bd5 100644
--- a/monkey/infection_monkey/puppet/plugin_registry.py
+++ b/monkey/infection_monkey/puppet/plugin_registry.py
@@ -1,4 +1,5 @@
 import logging
+from typing import Any
 
 from infection_monkey.i_puppet import PluginType, UnknownPluginError
 
@@ -27,7 +28,7 @@ class PluginRegistry:
 
         logger.debug(f"Plugin '{plugin_name}' loaded")
 
-    def get_plugin(self, plugin_name: str, plugin_type: PluginType) -> object:
+    def get_plugin(self, plugin_name: str, plugin_type: PluginType) -> Any:
         try:
             plugin = self._registry[plugin_type][plugin_name]
         except KeyError:
diff --git a/monkey/infection_monkey/puppet/puppet.py b/monkey/infection_monkey/puppet/puppet.py
index 95e72533f..d8bc8e0eb 100644
--- a/monkey/infection_monkey/puppet/puppet.py
+++ b/monkey/infection_monkey/puppet/puppet.py
@@ -66,7 +66,7 @@ class Puppet(IPuppet):
         interrupt: threading.Event,
     ) -> ExploiterResultData:
         exploiter = self._plugin_registry.get_plugin(name, PluginType.EXPLOITER)
-        return exploiter.exploit_host(host, current_depth, options)
+        return exploiter.exploit_host(host, current_depth, options, interrupt)
 
     def run_payload(self, name: str, options: Dict, interrupt: threading.Event):
         payload = self._plugin_registry.get_plugin(name, PluginType.PAYLOAD)
diff --git a/monkey/monkey_island/cc/models/config.py b/monkey/monkey_island/cc/models/config.py
index 437f73b44..db5fd9e94 100644
--- a/monkey/monkey_island/cc/models/config.py
+++ b/monkey/monkey_island/cc/models/config.py
@@ -8,6 +8,6 @@ class Config(EmbeddedDocument):
     See https://mongoengine-odm.readthedocs.io/apireference.html#mongoengine.FieldDoesNotExist
     """
 
-    alive = BooleanField()
+    should_stop = BooleanField()
     meta = {"strict": False}
     pass
diff --git a/monkey/monkey_island/cc/services/config_schema/internal.py b/monkey/monkey_island/cc/services/config_schema/internal.py
index 98ab8b95e..26326721c 100644
--- a/monkey/monkey_island/cc/services/config_schema/internal.py
+++ b/monkey/monkey_island/cc/services/config_schema/internal.py
@@ -19,11 +19,10 @@ INTERNAL = {
             "title": "Monkey",
             "type": "object",
             "properties": {
-                "alive": {
-                    "title": "Alive",
+                "should_stop": {
                     "type": "boolean",
-                    "default": True,
-                    "description": "Is the monkey alive",
+                    "default": False,
+                    "description": "Was stop command issued for this monkey",
                 },
                 "aws_keys": {
                     "type": "object",
diff --git a/monkey/monkey_island/cc/services/infection_lifecycle.py b/monkey/monkey_island/cc/services/infection_lifecycle.py
index 510e3deb6..865602168 100644
--- a/monkey/monkey_island/cc/services/infection_lifecycle.py
+++ b/monkey/monkey_island/cc/services/infection_lifecycle.py
@@ -16,7 +16,7 @@ logger = logging.getLogger(__name__)
 
 def set_stop_all(time: float):
     for monkey in Monkey.objects():
-        monkey.config.alive = False
+        monkey.config.should_stop = True
         monkey.save()
     agent_controls = AgentControls.objects.first()
     agent_controls.last_stop_all = time
@@ -25,11 +25,16 @@ def set_stop_all(time: float):
 
 def should_agent_die(guid: int) -> bool:
     monkey = Monkey.objects(guid=str(guid)).first()
-    return _is_monkey_marked_dead(monkey) or _is_monkey_killed_manually(monkey)
+    return _should_agent_stop(monkey) or _is_monkey_killed_manually(monkey)
 
 
-def _is_monkey_marked_dead(monkey: Monkey) -> bool:
-    return not monkey.config.alive
+def _should_agent_stop(monkey: Monkey) -> bool:
+    if monkey.config.should_stop:
+        # Only stop the agent once, to allow further runs on that machine
+        monkey.config.should_stop = False
+        monkey.save()
+        return True
+    return False
 
 
 def _is_monkey_killed_manually(monkey: Monkey) -> bool:
diff --git a/monkey/monkey_island/cc/services/node.py b/monkey/monkey_island/cc/services/node.py
index 688f67f92..6b672bc4d 100644
--- a/monkey/monkey_island/cc/services/node.py
+++ b/monkey/monkey_island/cc/services/node.py
@@ -249,7 +249,7 @@ class NodeService:
 
         # Cancel the force kill once monkey died
         if is_dead:
-            props_to_set["config.alive"] = True
+            props_to_set["config.should_stop"] = False
 
         mongo.db.monkey.update({"guid": monkey["guid"]}, {"$set": props_to_set}, upsert=False)
 
diff --git a/monkey/monkey_island/cc/ui/src/components/pages/MapPage.js b/monkey/monkey_island/cc/ui/src/components/pages/MapPage.js
index 3c1350f58..fa782eac7 100644
--- a/monkey/monkey_island/cc/ui/src/components/pages/MapPage.js
+++ b/monkey/monkey_island/cc/ui/src/components/pages/MapPage.js
@@ -88,10 +88,11 @@ class MapPageComponent extends AuthComponent {
       {
         method: 'POST',
         headers: {'Content-Type': 'application/json'},
-        body: JSON.stringify({kill_time: Date.now()})
+        // Python uses floating point seconds, Date.now uses milliseconds, so convert
+        body: JSON.stringify({kill_time: Date.now() / 1000.0})
       })
       .then(res => res.json())
-      .then(res => {this.setState({killPressed: true}); console.log(res)});
+      .then(res => {this.setState({killPressed: true})});
   };
 
   renderKillDialogModal = () => {
diff --git a/monkey/tests/unit_tests/infection_monkey/exploit/test_powershell.py b/monkey/tests/unit_tests/infection_monkey/exploit/test_powershell.py
index f75c57f17..21a0bdeb3 100644
--- a/monkey/tests/unit_tests/infection_monkey/exploit/test_powershell.py
+++ b/monkey/tests/unit_tests/infection_monkey/exploit/test_powershell.py
@@ -1,3 +1,4 @@
+import threading
 from io import BytesIO
 from unittest.mock import MagicMock
 
@@ -43,6 +44,7 @@ def powershell_arguments():
         "current_depth": 2,
         "telemetry_messenger": MagicMock(),
         "agent_repository": mock_agent_repository,
+        "interrupt": threading.Event(),
     }
     return arguments
 
diff --git a/monkey/tests/unit_tests/monkey_island/cc/services/test_infection_lifecycle.py b/monkey/tests/unit_tests/monkey_island/cc/services/test_infection_lifecycle.py
index 4d4c229c8..541124248 100644
--- a/monkey/tests/unit_tests/monkey_island/cc/services/test_infection_lifecycle.py
+++ b/monkey/tests/unit_tests/monkey_island/cc/services/test_infection_lifecycle.py
@@ -10,21 +10,21 @@ from monkey_island.cc.services.infection_lifecycle import should_agent_die
 @pytest.mark.usefixtures("uses_database")
 def test_should_agent_die_by_config(monkeypatch):
     monkey = Monkey(guid=str(uuid.uuid4()))
-    monkey.config = Config(alive=False)
+    monkey.config = Config(should_stop=True)
     monkey.save()
     assert should_agent_die(monkey.guid)
 
     monkeypatch.setattr(
         "monkey_island.cc.services.infection_lifecycle._is_monkey_killed_manually", lambda _: False
     )
-    monkey.config.alive = True
+    monkey.config.should_stop = True
     monkey.save()
     assert not should_agent_die(monkey.guid)
 
 
 def create_monkey(launch_time):
     monkey = Monkey(guid=str(uuid.uuid4()))
-    monkey.config = Config(alive=True)
+    monkey.config = Config(should_stop=False)
     monkey.launch_time = launch_time
     monkey.save()
     return monkey