diff --git a/lib/livebook/fly_api.ex b/lib/livebook/fly_api.ex
index ee83ee7fa..21ab280c9 100644
--- a/lib/livebook/fly_api.ex
+++ b/lib/livebook/fly_api.ex
@@ -210,6 +210,24 @@ defmodule Livebook.FlyAPI do
     end
   end
 
+  @doc """
+  Waits for the machine to be destroyed.
+  """
+  @spec await_machine_destroyed(String.t(), String.t(), String.t(), pos_integer()) ::
+          :ok | {:error, error}
+  def await_machine_destroyed(token, app_name, machine_id, timeout_s) when timeout_s <= 60 do
+    # Contrarily to the above, if we expect the machine to be destroying,
+    # it should take a short time, so we don't retry requests and expect
+    # a rather short timeout
+    with {:ok, _data} <-
+           flaps_request(token, "/v1/apps/#{app_name}/machines/#{machine_id}/wait",
+             params: %{state: "destroyed", timeout: timeout_s},
+             retry: false
+           ) do
+      :ok
+    end
+  end
+
   defp flaps_request(token, path, opts \\ []) do
     opts =
       [base_url: @flaps_url, url: path, auth: {:bearer, token}]
diff --git a/lib/livebook/runtime/fly.ex b/lib/livebook/runtime/fly.ex
index 5eb22f705..416305ba0 100644
--- a/lib/livebook/runtime/fly.ex
+++ b/lib/livebook/runtime/fly.ex
@@ -47,7 +47,7 @@ defmodule Livebook.Runtime.Fly do
   # configuration `inet_dist_listen_options` -> `ipv6_v6only`, which
   # has OS-specific value. However, we don't rely on this here.
 
-  defstruct [:config, :node, :server_pid]
+  defstruct [:config, :node, :server_pid, :machine_id, :previous_machine_id]
 
   use GenServer, restart: :temporary
 
@@ -56,7 +56,9 @@ defmodule Livebook.Runtime.Fly do
   @type t :: %__MODULE__{
           config: config(),
           node: node() | nil,
-          server_pid: pid() | nil
+          server_pid: pid() | nil,
+          machine_id: String.t() | nil,
+          previous_machine_id: String.t() | nil
         }
 
   @type config :: %{
@@ -114,7 +116,15 @@ defmodule Livebook.Runtime.Fly do
       |> :erlang.term_to_binary()
       |> Base.encode64()
 
-    with {:ok, machine_id, machine_ip} <-
+    with :ok <-
+           (if config.volume_id && runtime.previous_machine_id do
+              with_log(caller, "await resources", fn ->
+                await_previous_machine_destroyed(config, runtime.previous_machine_id)
+              end)
+            else
+              :ok
+            end),
+         {:ok, machine_id, machine_ip} <-
            with_log(caller, "create machine", fn ->
              create_machine(config, runtime_data)
            end),
@@ -141,7 +151,7 @@ defmodule Livebook.Runtime.Fly do
 
       send(primary_pid, :node_initialized)
 
-      runtime = %{runtime | node: child_node, server_pid: server_pid}
+      runtime = %{runtime | node: child_node, server_pid: server_pid, machine_id: machine_id}
       send(caller, {:runtime_connect_done, self(), {:ok, runtime}})
 
       {:noreply, %{state | primary_ref: primary_ref, proxy_port: proxy_port}}
@@ -209,6 +219,14 @@ defmodule Livebook.Runtime.Fly do
     end
   end
 
+  defp await_previous_machine_destroyed(config, machine_id) do
+    # We wait only to ensure the volume is detached. If waiting fails,
+    # we ignore the error and try to create the machine anyway, if the
+    # volume is attached, creation will fail
+    _ = Livebook.FlyAPI.await_machine_destroyed(config.token, config.app_name, machine_id, 5)
+    :ok
+  end
+
   defp await_machine_started(config, machine_id) do
     case Livebook.FlyAPI.await_machine_started(config.token, config.app_name, machine_id) do
       :ok ->
@@ -407,7 +425,10 @@ defimpl Livebook.Runtime, for: Livebook.Runtime.Fly do
   end
 
   def duplicate(runtime) do
-    Livebook.Runtime.Fly.new(runtime.config)
+    %Livebook.Runtime.Fly{
+      config: runtime.config,
+      previous_machine_id: runtime.machine_id
+    }
   end
 
   def evaluate_code(runtime, language, code, locator, parent_locators, opts \\ []) do