diff --git a/lib/livebook/fly_api.ex b/lib/livebook/fly_api.ex
index e2b29175b..f34902e6e 100644
--- a/lib/livebook/fly_api.ex
+++ b/lib/livebook/fly_api.ex
@@ -188,6 +188,21 @@ defmodule Livebook.FlyAPI do
     %{id: machine["id"], private_ip: machine["private_ip"]}
   end
 
+  @doc """
+  Waits for the machine to start.
+  """
+  @spec await_machine_started(String.t(), String.t(), String.t()) :: :ok | {:error, error}
+  def await_machine_started(token, app_name, machine_id) do
+    with {:ok, _data} <-
+           flaps_request(token, "/v1/apps/#{app_name}/machines/#{machine_id}/wait",
+             params: %{state: "started", timeout: 60},
+             receive_timeout: 90_000,
+             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 fefd2066e..9d908320f 100644
--- a/lib/livebook/runtime/fly.ex
+++ b/lib/livebook/runtime/fly.ex
@@ -123,6 +123,10 @@ defmodule Livebook.Runtime.Fly do
            with_log(caller, "start proxy", fn ->
              start_fly_proxy(config.app_name, machine_ip, local_port, remote_port, config.token)
            end),
+         :ok <-
+           with_log(caller, "machine starting", fn ->
+             await_machine_started(config, machine_id)
+           end),
          :ok <-
            with_log(caller, "connect to node", fn ->
              connect_loop(child_node, 40, 250)
@@ -203,6 +207,21 @@ defmodule Livebook.Runtime.Fly do
     end
   end
 
+  defp await_machine_started(config, machine_id) do
+    case Livebook.FlyAPI.await_machine_started(config.token, config.app_name, machine_id) do
+      :ok ->
+        :ok
+
+      {:error, %{status: 408}} ->
+        {:error,
+         "timed out while waiting for the machine to start. See the app" <>
+           " logs in the Fly.io dashboard to determine the reason"}
+
+      {:error, %{message: message}} ->
+        {:error, "failed while waiting for the machine to started, reason: #{message}"}
+    end
+  end
+
   defp connect_loop(_node, 0, _interval) do
     {:error, "could not establish connection with the node"}
   end
diff --git a/test/livebook/runtime/fly_test.exs b/test/livebook/runtime/fly_test.exs
index d4c9e750c..207e3a6ca 100644
--- a/test/livebook/runtime/fly_test.exs
+++ b/test/livebook/runtime/fly_test.exs
@@ -26,6 +26,7 @@ defmodule Livebook.Runtime.FlyTest do
 
     assert_receive {:runtime_connect_info, ^pid, "create machine"}, @assert_receive_timeout
     assert_receive {:runtime_connect_info, ^pid, "start proxy"}, @assert_receive_timeout
+    assert_receive {:runtime_connect_info, ^pid, "machine starting"}, @assert_receive_timeout
     assert_receive {:runtime_connect_info, ^pid, "connect to node"}, @assert_receive_timeout
     assert_receive {:runtime_connect_info, ^pid, "initialize node"}, @assert_receive_timeout
     assert_receive {:runtime_connect_done, ^pid, {:ok, runtime}}, @assert_receive_timeout