diff --git a/lua/codecompanion/interactions/chat/init.lua b/lua/codecompanion/interactions/chat/init.lua
index 3bf2e482e..eb7ce4d56 100644
--- a/lua/codecompanion/interactions/chat/init.lua
+++ b/lua/codecompanion/interactions/chat/init.lua
@@ -15,7 +15,6 @@
 ---@field context CodeCompanion.Chat.Context
 ---@field context_items? table<CodeCompanion.Chat.Context> Context which is sent to the LLM e.g. buffers, slash command output
 ---@field current_request table|nil The current request being executed
----@field current_tool table The current tool being executed
 ---@field cycle number Records the number of turn-based interactions (User -> LLM) that have taken place
 ---@field create_buf fun(): number The function that creates a new buffer for the chat
 ---@field edit_tracker? CodeCompanion.Chat.EditTracker Edit tracking information for the chat
@@ -31,6 +30,8 @@
 ---@field title? string The title of the chat buffer
 ---@field tokens? nil|number The number of tokens in the chat
 ---@field tools CodeCompanion.Tools The tools coordinator that executes available tools
+---@field tool_orchestrator CodeCompanion.Tools.Orchestrator The current tool orchestrator
+
 ---@field tool_registry CodeCompanion.Chat.ToolRegistry Methods for handling interactions between the chat buffer and tools
 ---@field ui CodeCompanion.Chat.UI The UI of the chat buffer
 ---@field variables? CodeCompanion.Variables The variables available to the user
@@ -1445,13 +1446,11 @@ function Chat:stop()
   self:dispatch("on_cancelled")
   utils.fire("ChatStopped", { bufnr = self.bufnr, id = self.id })
 
-  if self.current_tool then
-    local tool_job = self.current_tool
-    self.current_tool = nil
-
+  if self.tool_orchestrator then
     pcall(function()
-      tool_job.cancel()
+      self.tool_orchestrator:cancel()
     end)
+    self.tool_orchestrator = nil
   end
 
   if self.current_request then
diff --git a/lua/codecompanion/interactions/chat/keymaps/init.lua b/lua/codecompanion/interactions/chat/keymaps/init.lua
index 33a1ddc6b..709627b7f 100644
--- a/lua/codecompanion/interactions/chat/keymaps/init.lua
+++ b/lua/codecompanion/interactions/chat/keymaps/init.lua
@@ -304,7 +304,7 @@ M.close = {
 
 M.stop = {
   callback = function(chat)
-    if chat.current_request then
+    if chat.current_request or chat.tool_orchestrator then
       chat:stop()
     end
   end,
diff --git a/lua/codecompanion/interactions/chat/tools/init.lua b/lua/codecompanion/interactions/chat/tools/init.lua
index ad5fe4468..bd13b9468 100644
--- a/lua/codecompanion/interactions/chat/tools/init.lua
+++ b/lua/codecompanion/interactions/chat/tools/init.lua
@@ -289,7 +289,7 @@ function Tools:execute(chat, tools)
     -- NOTE: Set autocmds early so that errors can be handled properly
     self:set_autocmds()
 
-    local orchestrator = Orchestrator.new(self, id)
+    chat.tool_orchestrator = Orchestrator.new(self, id)
 
     for _, tool in ipairs(tools) do
       local resolved_tool, error_msg, is_json_error = self:_resolve_and_prepare_tool(tool, id)
@@ -304,11 +304,11 @@ function Tools:execute(chat, tools)
       end
 
       self.tool = resolved_tool --[[@as CodeCompanion.Tools.Tool]]
-      orchestrator.queue:push(resolved_tool)
+      chat.tool_orchestrator.queue:push(resolved_tool)
     end
 
     utils.fire("ToolsStarted", { id = id, bufnr = self.bufnr })
-    orchestrator:setup_next_tool()
+    chat.tool_orchestrator:setup_next_tool()
   end
 
   local ok, err = pcall(safe_execute)
diff --git a/lua/codecompanion/interactions/chat/tools/orchestrator.lua b/lua/codecompanion/interactions/chat/tools/orchestrator.lua
index f0e0a0baf..c96f01a40 100644
--- a/lua/codecompanion/interactions/chat/tools/orchestrator.lua
+++ b/lua/codecompanion/interactions/chat/tools/orchestrator.lua
@@ -1,3 +1,16 @@
+---@class CodeCompanion.Tools.Orchestrator
+---@field cancelled boolean? Whether the tool execution has been cancelled
+---@field handlers table<string, function>
+---@field id number The id of the tools coordinator
+---@field index number The index of the current command
+---@field output table<string, function>
+---@field queue CodeCompanion.Tools.Orchestrator.Queue
+---@field status string The status of the tool execution "success" | "error"
+---@field tool CodeCompanion.Tools.Tool The current tool being executed
+---@field tool_handle vim.SystemObj? SystemObj of the current tool execution
+---@field tool_output table? The output collected from the tool
+---@field tools CodeCompanion.Tools
+
 local Approvals = require("codecompanion.interactions.chat.tools.approvals")
 local Queue = require("codecompanion.interactions.chat.tools.runtime.queue")
 local Runner = require("codecompanion.interactions.chat.tools.runtime.runner")
@@ -7,6 +20,7 @@ local ui_utils = require("codecompanion.utils.ui")
 local utils = require("codecompanion.utils")
 
 local fmt = string.format
+local Orchestrator = {}
 
 ---Strip any ANSI color codes which don't render in the chat buffer
 ---@param tbl table
@@ -19,33 +33,32 @@ local function strip_ansi(tbl)
 end
 
 ---Add a response to the chat buffer regarding a tool's execution
----@param exec CodeCompanion.Tools.Orchestrator
 ---@param llm_message string
 ---@param user_message? string
-local send_response_to_chat = function(exec, llm_message, user_message)
-  exec.tools.chat:add_tool_output(exec.tool, llm_message, user_message)
+function Orchestrator:_send_response_to_chat(llm_message, user_message)
+  self.tools.chat:add_tool_output(self.tool, llm_message, user_message)
 end
 
 ---Execute a shell command with platform-specific handling
 ---@param cmd table
 ---@param callback function
-local function execute_shell_command(cmd, callback)
+function Orchestrator:_execute_shell_command(cmd, callback)
   if vim.fn.has("win32") == 1 then
     -- See PR #2186
     local shell_cmd = table.concat(cmd, " ") .. "\r\nEXIT %ERRORLEVEL%\r\n"
-    vim.system({ "cmd.exe", "/Q", "/K" }, {
+    self.tool_handle = vim.system({ "cmd.exe", "/Q", "/K" }, {
       stdin = shell_cmd,
       env = { PROMPT = "\r\n" },
     }, callback)
   else
-    vim.system(os_utils.build_shell_command(cmd), {}, callback)
+    self.tool_handle = vim.system(os_utils.build_shell_command(cmd), {}, callback)
   end
 end
 
 ---Converts a cmd-based tool to a function-based tool.
 ---@param tool CodeCompanion.Tools.Tool
 ---@return CodeCompanion.Tools.Tool
-local function cmd_to_func_tool(tool)
+function Orchestrator:_cmd_to_func_tool(tool)
   tool.cmds = vim
     .iter(tool.cmds)
     :map(function(cmd)
@@ -62,7 +75,7 @@ local function cmd_to_func_tool(tool)
       ---@param tools CodeCompanion.Tools
       return function(tools, _, _, cb)
         cb = vim.schedule_wrap(cb)
-        execute_shell_command(cmd, function(out)
+        self:_execute_shell_command(cmd, function(out)
           if flag then
             tools.chat.tool_registry.flags = tools.chat.tool_registry.flags or {}
             tools.chat.tool_registry.flags[flag] = (out.code == 0)
@@ -93,18 +106,6 @@ local function cmd_to_func_tool(tool)
   return tool
 end
 
----@class CodeCompanion.Tools.Orchestrator
----@field id number The id of the tools coordinator
----@field index number The index of the current command
----@field handlers table<string, function>
----@field output table<string, function>
----@field queue CodeCompanion.Tools.Orchestrator.Queue
----@field status string The status of the tool execution "success" | "error"
----@field tool CodeCompanion.Tools.Tool The current tool being executed
----@field tool_output table? The output collected from the tool
----@field tools CodeCompanion.Tools
-local Orchestrator = {}
-
 ---@param tools CodeCompanion.Tools
 ---@param id number
 function Orchestrator.new(tools, id)
@@ -184,7 +185,7 @@ function Orchestrator:_setup_handlers()
           rejection = rejection .. fmt(': "%s"', opts.reason)
         end
         -- If no handler is set then return a default message
-        send_response_to_chat(self, rejection)
+        self:_send_response_to_chat(rejection)
       end
     end,
     error = function(cmd)
@@ -195,7 +196,7 @@ function Orchestrator:_setup_handlers()
       if self.tool.output and self.tool.output.error then
         self.tool.output.error(self.tool, self.tools, cmd, self.tools.stderr)
       else
-        send_response_to_chat(self, fmt("Error calling `%s`", self.tool.name))
+        self:_send_response_to_chat(fmt("Error calling `%s`", self.tool.name))
       end
     end,
     cancelled = function(cmd)
@@ -206,8 +207,7 @@ function Orchestrator:_setup_handlers()
       if self.tool.output and self.tool.output.cancelled then
         self.tool.output.cancelled(self.tool, self.tools, cmd)
       else
-        send_response_to_chat(
-          self,
+        self:_send_response_to_chat(
           fmt("The user cancelled the execution of the %s tool", self.tool.name),
           fmt("Cancelled `%s`", self.tool.name)
         )
@@ -221,17 +221,18 @@ function Orchestrator:_setup_handlers()
       if self.tool.output and self.tool.output.success then
         self.tool.output.success(self.tool, self.tools, cmd, self.tool_output or {})
       else
-        send_response_to_chat(self, fmt("Executed `%s`", self.tool.name))
+        self:_send_response_to_chat(fmt("Executed `%s`", self.tool.name))
       end
     end,
   }
 end
 
 ---When the tools coordinator is finished, finalize it via an autocmd
----@param self CodeCompanion.Tools.Orchestrator
 ---@return nil
 function Orchestrator:_finalize_tools()
   self.tools.tool = nil
+  self.tools.chat.tool_orchestrator = nil
+
   return utils.fire("ToolsFinished", { id = self.id, bufnr = self.tools.bufnr })
 end
 
@@ -251,7 +252,7 @@ function Orchestrator:setup_next_tool(input)
   self.handlers.setup() -- Call this early as cmd_runner needs to setup its cmds dynamically
 
   -- Transform cmd-based tools to func-based
-  self.tool = cmd_to_func_tool(self.tool)
+  self.tool = self:_cmd_to_func_tool(self.tool)
 
   -- Get the first command to run
   local cmd = self.tool.cmds[1]
@@ -429,4 +430,43 @@ function Orchestrator:finalize_tool()
   end
 end
 
+---Cancel the currently running tool execution
+---@return nil
+function Orchestrator:cancel()
+  if self.cancelled then
+    return
+  end
+
+  log:debug("Orchestrator:cancel")
+  self.cancelled = true
+
+  -- Kill the running system command if one exists
+  if self.tool_handle then
+    if vim.fn.has("win32") == 1 then
+      -- /F flag forces process to end
+      -- /T ends child process (required since we are wrapping the child
+      --         process in a parent cmd.exe process)
+      vim.system({ "taskkill", "/F", "/T", "/PID", tostring(self.tool_handle.pid) })
+    else
+      self.tool_handle:kill("sigkill")
+    end
+
+    self.tool_handle = nil
+  end
+
+  -- Output the cancellation message to the chat buffer.
+  if self.tool and self.output then
+    self.output.cancelled(self.tool.cmds[1])
+  end
+
+  -- Clean up the cancelled tool.
+  self:finalize_tool()
+
+  -- Cancel any pending tools in the queue.
+  self:cancel_pending_tools()
+
+  -- Close the current tool.
+  self:_finalize_tools()
+end
+
 return Orchestrator
diff --git a/lua/codecompanion/interactions/chat/tools/runtime/runner.lua b/lua/codecompanion/interactions/chat/tools/runtime/runner.lua
index 0c4bfbce5..4301e74c8 100644
--- a/lua/codecompanion/interactions/chat/tools/runtime/runner.lua
+++ b/lua/codecompanion/interactions/chat/tools/runtime/runner.lua
@@ -82,7 +82,7 @@ function Runner:run_tool(cmd_func, action, args)
 
   ---@param msg {status:"success"|"error", data:any}
   local function output_handler(msg)
-    if tool_finished then
+    if tool_finished or self.orchestrator.cancelled then
       return
     end
     tool_finished = true
diff --git a/tests/interactions/chat/tools/runtime/test_queue_async.lua b/tests/interactions/chat/tools/runtime/test_queue_async.lua
index cc80d1584..1721f7d7b 100644
--- a/tests/interactions/chat/tools/runtime/test_queue_async.lua
+++ b/tests/interactions/chat/tools/runtime/test_queue_async.lua
@@ -56,7 +56,10 @@ T["Tools"]["queue"]["can queue multiple async functions"] = function()
       },
     }
     tools:execute(chat, tool_call)
-    vim.wait(2100)
+
+    while (chat.tool_orchestrator) do
+      vim.wait(100)
+    end
   ]])
 
   -- Test order
@@ -88,7 +91,9 @@ T["Tools"]["queue"]["can queue async function with sync function"] = function()
       },
     }
     tools:execute(chat, tool_call)
-    vim.wait(1100)
+    while (chat.tool_orchestrator) do
+      vim.wait(100)
+    end
   ]])
 
   -- Test order