diff --git a/lib/livebook/fly_api.ex b/lib/livebook/fly_api.ex
index 21ab280c9..8cb1fc216 100644
--- a/lib/livebook/fly_api.ex
+++ b/lib/livebook/fly_api.ex
@@ -188,6 +188,22 @@ defmodule Livebook.FlyAPI do
     %{id: machine["id"], private_ip: machine["private_ip"]}
   end
 
+  @doc """
+  Deletes the given machine.
+  """
+  @spec delete_machine(String.t(), String.t(), String.t()) :: :ok | {:error, error}
+  def delete_machine(token, app_name, machine_id) do
+    params = %{force: true}
+
+    with {:ok, _data} <-
+           flaps_request(token, "/v1/apps/#{app_name}/machines/#{machine_id}",
+             method: :delete,
+             params: params
+           ) do
+      :ok
+    end
+  end
+
   @doc """
   Waits for the machine to start.
   """
diff --git a/lib/livebook/runtime.ex b/lib/livebook/runtime.ex
index ef6824e50..85585b33a 100644
--- a/lib/livebook/runtime.ex
+++ b/lib/livebook/runtime.ex
@@ -806,13 +806,20 @@ defprotocol Livebook.Runtime do
   The `runtime` should be the struct updated with all information
   necessary for further communication.
 
-  In case the initialization is a particularly involved process, the
-  process may send updates to the caller:
+  In case the initialization is a particularly involved, the process
+  may send updates to the caller:
 
       * `{:runtime_connect_info, pid, info}`
 
   Where `info` is a few word text describing the current initialization
   step.
+
+  If the caller decides to abort the initialization, they can forecefully
+  kill the process. The runtime resources should already be tolerant
+  to abrupt Livebook termination and autodestroy through monitoring
+  and timeouts. However, when the initialization process gets killed,
+  it may be desirable to eagerly remove the resources it has already
+  allocated, which can be achieved with an additional watcher process.
   """
   @spec connect(t()) :: pid()
   def connect(runtime)
diff --git a/lib/livebook/runtime/fly.ex b/lib/livebook/runtime/fly.ex
index 8213060cb..9ea467806 100644
--- a/lib/livebook/runtime/fly.ex
+++ b/lib/livebook/runtime/fly.ex
@@ -116,6 +116,14 @@ defmodule Livebook.Runtime.Fly do
       |> :erlang.term_to_binary()
       |> Base.encode64()
 
+    parent = self()
+
+    {:ok, watcher_pid} =
+      DynamicSupervisor.start_child(
+        Livebook.RuntimeSupervisor,
+        {Task, fn -> watcher(parent, config) end}
+      )
+
     with :ok <-
            (if config.volume_id && runtime.previous_machine_id do
               with_log(caller, "await resources", fn ->
@@ -128,6 +136,7 @@ defmodule Livebook.Runtime.Fly do
            with_log(caller, "create machine", fn ->
              create_machine(config, runtime_data)
            end),
+         _ <- send(watcher_pid, {:machine_created, machine_id}),
          child_node <- :"#{node_base}@#{machine_id}.vm.#{config.app_name}.internal",
          {:ok, proxy_port} <-
            with_log(caller, "start proxy", fn ->
@@ -151,6 +160,8 @@ defmodule Livebook.Runtime.Fly do
 
       send(primary_pid, :node_initialized)
 
+      send(watcher_pid, :done)
+
       runtime = %{runtime | node: child_node, server_pid: server_pid, machine_id: machine_id}
       send(caller, {:runtime_connect_done, self(), {:ok, runtime}})
 
@@ -172,6 +183,29 @@ defmodule Livebook.Runtime.Fly do
     {:noreply, state}
   end
 
+  defp watcher(parent, config) do
+    ref = Process.monitor(parent)
+    watcher_loop(%{ref: ref, config: config, machine_id: nil})
+  end
+
+  defp watcher_loop(state) do
+    receive do
+      {:DOWN, ref, :process, _pid, _reason} when ref == state.ref ->
+        # If the parent process is killed, we try to eagerly free the
+        # created resources
+        if machine_id = state.machine_id do
+          config = state.config
+          _ = Livebook.FlyAPI.delete_machine(config.token, config.app_name, machine_id)
+        end
+
+      {:machine_created, machine_id} ->
+        watcher_loop(%{state | machine_id: machine_id})
+
+      :done ->
+        :ok
+    end
+  end
+
   defp create_machine(config, runtime_data) do
     base_image = Enum.find(Livebook.Config.docker_images(), &(&1.tag == config.docker_tag))
     image = "ghcr.io/livebook-dev/livebook:#{base_image.tag}"
diff --git a/lib/livebook/session.ex b/lib/livebook/session.ex
index 9a15e485c..1d09dcb05 100644
--- a/lib/livebook/session.ex
+++ b/lib/livebook/session.ex
@@ -2424,9 +2424,15 @@ defmodule Livebook.Session do
   end
 
   defp handle_action(state, {:disconnect_runtime, runtime}) do
-    Runtime.disconnect(runtime)
-    state = %{state | runtime_monitor_ref: nil}
-    after_runtime_disconnected(state)
+    if state.runtime_connect do
+      Process.demonitor(state.runtime_connect.ref, [:flush])
+      Process.exit(state.runtime_connect.pid, :kill)
+      %{state | runtime_connect: nil}
+    else
+      Runtime.disconnect(runtime)
+      state = %{state | runtime_monitor_ref: nil}
+      after_runtime_disconnected(state)
+    end
   end
 
   defp handle_action(state, {:start_evaluation, cell, section, evaluation_opts}) do
diff --git a/lib/livebook/session/data.ex b/lib/livebook/session/data.ex
index 83dd7caed..9af001556 100644
--- a/lib/livebook/session/data.ex
+++ b/lib/livebook/session/data.ex
@@ -921,7 +921,7 @@ defmodule Livebook.Session.Data do
   end
 
   def apply_operation(data, {:disconnect_runtime, _client_id}) do
-    with :connected <- data.runtime_status do
+    with true <- data.runtime_status in [:connecting, :connected] do
       data
       |> with_actions()
       |> disconnect_runtime()
diff --git a/lib/livebook_web/live/session_live/fly_runtime_component.ex b/lib/livebook_web/live/session_live/fly_runtime_component.ex
index e2fc4f4d9..5693fa987 100644
--- a/lib/livebook_web/live/session_live/fly_runtime_component.ex
+++ b/lib/livebook_web/live/session_live/fly_runtime_component.ex
@@ -122,16 +122,27 @@ defmodule LivebookWeb.SessionLive.FlyRuntimeComponent do
           />
 
           <div class="mt-8">
-            <.button
-              phx-click="init"
-              phx-target={@myself}
-              disabled={
-                @runtime_status == :connecting or not @specs_changeset.valid? or
-                  volume_errors(@volume_id, @volumes, @region) != []
-              }
-            >
-              <%= label(@app_name, @runtime, @runtime_status) %>
-            </.button>
+            <div class="flex gap-2">
+              <.button
+                phx-click="init"
+                phx-target={@myself}
+                disabled={
+                  @runtime_status == :connecting or not @specs_changeset.valid? or
+                    volume_errors(@volume_id, @volumes, @region) != []
+                }
+              >
+                <%= label(@app_name, @runtime, @runtime_status) %>
+              </.button>
+              <.button
+                :if={@runtime_status == :connecting}
+                color="red"
+                outlined
+                phx-click="disconnect"
+                phx-target={@myself}
+              >
+                Disconnect
+              </.button>
+            </div>
             <div
               :if={reconnecting?(@app_name, @runtime) && @runtime_connect_info}
               class="mt-4 scroll-mb-8"
@@ -582,6 +593,11 @@ defmodule LivebookWeb.SessionLive.FlyRuntimeComponent do
     {:noreply, socket}
   end
 
+  def handle_event("disconnect", %{}, socket) do
+    Session.disconnect_runtime(socket.assigns.session.pid)
+    {:noreply, socket}
+  end
+
   def handle_event("open_save_config", %{}, socket) do
     changeset = config_secret_changeset(socket, %{name: @config_secret_prefix})
     save_config = %{changeset: changeset, inflight: false, error: false}
diff --git a/lib/livebook_web/live/session_live/render.ex b/lib/livebook_web/live/session_live/render.ex
index b6b570f34..f579bb91a 100644
--- a/lib/livebook_web/live/session_live/render.ex
+++ b/lib/livebook_web/live/session_live/render.ex
@@ -676,7 +676,7 @@ defmodule LivebookWeb.SessionLive.Render do
           </.button>
 
           <.button
-            :if={@data_view.runtime_status == :connected}
+            :if={@data_view.runtime_status in [:connected, :connecting]}
             color="red"
             outlined
             type="button"
diff --git a/test/livebook/session/data_test.exs b/test/livebook/session/data_test.exs
index e2ce553f8..42a361562 100644
--- a/test/livebook/session/data_test.exs
+++ b/test/livebook/session/data_test.exs
@@ -3940,11 +3940,8 @@ defmodule Livebook.Session.DataTest do
   end
 
   describe "apply_operation/2 given :disconnect_runtime" do
-    test "returns an error if the runtime is not connected" do
-      data =
-        data_after_operations!([
-          {:connect_runtime, @cid}
-        ])
+    test "returns an error if the runtime is disconnected" do
+      data = Data.new()
 
       operation = {:disconnect_runtime, @cid}