diff --git a/lib/livebook/hubs/team.ex b/lib/livebook/hubs/team.ex
index d8a0c2127..e8639f414 100644
--- a/lib/livebook/hubs/team.ex
+++ b/lib/livebook/hubs/team.ex
@@ -94,23 +94,17 @@ defmodule Livebook.Hubs.Team do
       changeset
     end
   end
-
-  @doc """
-  Returns the public key prefix
-  """
-  @spec public_key_prefix() :: String.t()
-  def public_key_prefix(), do: "lb_opk_"
 end
 
 defimpl Livebook.Hubs.Provider, for: Livebook.Hubs.Team do
   alias Livebook.Hubs.{Team, TeamClient}
-  alias Livebook.Teams.Requests
+  alias Livebook.Teams
   alias Livebook.FileSystem
   alias Livebook.Secrets.Secret
 
-  @teams_key_prefix Livebook.Teams.Org.teams_key_prefix()
-  @public_key_prefix Team.public_key_prefix()
-  @deploy_key_prefix Requests.deploy_key_prefix()
+  @teams_key_prefix Teams.Constants.teams_key_prefix()
+  @public_key_prefix Teams.Constants.public_key_prefix()
+  @deploy_key_prefix Teams.Constants.deploy_key_prefix()
 
   def load(team, fields) do
     {offline?, fields} = Map.pop(fields, :offline?, false)
@@ -162,7 +156,7 @@ defimpl Livebook.Hubs.Provider, for: Livebook.Hubs.Team do
     @teams_key_prefix <> teams_key = team.teams_key
     token = Livebook.Stamping.chapoly_encrypt(metadata, notebook_source, teams_key)
 
-    case Requests.org_sign(team, token) do
+    case Teams.Requests.org_sign(team, token) do
       {:ok, %{"signature" => token_signature}} ->
         stamp = %{"version" => 1, "token" => token, "token_signature" => token_signature}
         {:ok, stamp}
@@ -203,7 +197,7 @@ defimpl Livebook.Hubs.Provider, for: Livebook.Hubs.Team do
   def get_secrets(team), do: TeamClient.get_secrets(team.id)
 
   def create_secret(%Team{} = team, %Secret{} = secret) do
-    case Requests.create_secret(team, secret) do
+    case Teams.Requests.create_secret(team, secret) do
       {:ok, %{"id" => _}} -> :ok
       {:error, %{"errors" => errors}} -> {:error, parse_secret_errors(errors)}
       any -> any
@@ -211,7 +205,7 @@ defimpl Livebook.Hubs.Provider, for: Livebook.Hubs.Team do
   end
 
   def update_secret(%Team{} = team, %Secret{} = secret) do
-    case Requests.update_secret(team, secret) do
+    case Teams.Requests.update_secret(team, secret) do
       {:ok, %{"id" => _}} -> :ok
       {:error, %{"errors" => errors}} -> {:error, parse_secret_errors(errors)}
       any -> any
@@ -219,7 +213,7 @@ defimpl Livebook.Hubs.Provider, for: Livebook.Hubs.Team do
   end
 
   def delete_secret(%Team{} = team, %Secret{} = secret) do
-    case Requests.delete_secret(team, secret) do
+    case Teams.Requests.delete_secret(team, secret) do
       {:ok, _} -> :ok
       {:error, %{"errors" => errors}} -> {:error, parse_secret_errors(errors)}
       any -> any
@@ -229,7 +223,7 @@ defimpl Livebook.Hubs.Provider, for: Livebook.Hubs.Team do
   def get_file_systems(team), do: TeamClient.get_file_systems(team.id)
 
   def create_file_system(%Team{} = team, file_system) do
-    case Requests.create_file_system(team, file_system) do
+    case Teams.Requests.create_file_system(team, file_system) do
       {:ok, %{"id" => _}} -> :ok
       {:error, %{"errors" => errors}} -> {:error, parse_file_system_errors(file_system, errors)}
       any -> any
@@ -237,7 +231,7 @@ defimpl Livebook.Hubs.Provider, for: Livebook.Hubs.Team do
   end
 
   def update_file_system(%Team{} = team, file_system) do
-    case Requests.update_file_system(team, file_system) do
+    case Teams.Requests.update_file_system(team, file_system) do
       {:ok, %{"id" => _}} -> :ok
       {:error, %{"errors" => errors}} -> {:error, parse_file_system_errors(file_system, errors)}
       any -> any
@@ -245,7 +239,7 @@ defimpl Livebook.Hubs.Provider, for: Livebook.Hubs.Team do
   end
 
   def delete_file_system(%Team{} = team, file_system) do
-    case Requests.delete_file_system(team, file_system) do
+    case Teams.Requests.delete_file_system(team, file_system) do
       {:ok, _} -> :ok
       {:error, %{"errors" => errors}} -> {:error, parse_file_system_errors(file_system, errors)}
       any -> any
@@ -266,12 +260,12 @@ defimpl Livebook.Hubs.Provider, for: Livebook.Hubs.Team do
   end
 
   defp parse_secret_errors(errors_map) do
-    Requests.to_error_list(Secret, errors_map)
+    Teams.Requests.to_error_list(Secret, errors_map)
   end
 
   defp parse_file_system_errors(%struct{} = file_system, errors_map) do
     %{error_field: field} = FileSystem.external_metadata(file_system)
     errors_map = Map.new(errors_map, fn {_key, values} -> {field, values} end)
-    Requests.to_error_list(struct, errors_map)
+    Teams.Requests.to_error_list(struct, errors_map)
   end
 end
diff --git a/lib/livebook/storage.ex b/lib/livebook/storage.ex
index 6554c12c6..80f7d133f 100644
--- a/lib/livebook/storage.ex
+++ b/lib/livebook/storage.ex
@@ -187,15 +187,9 @@ defmodule Livebook.Storage do
     Process.flag(:trap_exit, true)
 
     persist_storage? = Application.get_env(:livebook, :persist_storage, true)
-
-    table =
-      if persist_storage? do
-        load_or_create_table()
-      else
-        :ets.new(__MODULE__, [:protected, :duplicate_bag])
-      end
-
+    table = load_or_create_table(persist_storage?)
     :persistent_term.put(__MODULE__, table)
+
     {:ok, %{table: table, persist?: persist_storage?}}
   end
 
@@ -239,7 +233,11 @@ defmodule Livebook.Storage do
 
   defp table_name(), do: :persistent_term.get(__MODULE__)
 
-  defp load_or_create_table() do
+  defp load_or_create_table(false) do
+    :ets.new(__MODULE__, [:protected, :duplicate_bag])
+  end
+
+  defp load_or_create_table(true) do
     tab =
       if path = config_file_path_for_restore() do
         path
diff --git a/lib/livebook/teams.ex b/lib/livebook/teams.ex
index a889d8474..b7c54eecf 100644
--- a/lib/livebook/teams.ex
+++ b/lib/livebook/teams.ex
@@ -11,7 +11,7 @@ defmodule Livebook.Teams do
   import Ecto.Changeset,
     only: [add_error: 3, apply_action: 2, apply_action!: 2, get_field: 2]
 
-  @prefix Org.teams_key_prefix()
+  @teams_key_prefix Teams.Constants.teams_key_prefix()
 
   @doc """
   Creates an Org.
@@ -148,7 +148,7 @@ defmodule Livebook.Teams do
   Derives the secret and sign secret from given `teams_key`.
   """
   @spec derive_key(String.t()) :: bitstring()
-  def derive_key(@prefix <> teams_key) do
+  def derive_key(@teams_key_prefix <> teams_key) do
     binary_key = Base.url_decode64!(teams_key, padding: false)
     Plug.Crypto.KeyGenerator.generate(binary_key, "notebook secret", cache: Plug.Crypto.Keys)
   end
@@ -245,21 +245,17 @@ defmodule Livebook.Teams do
       id = "team-#{name}"
 
       hub =
-        if Hubs.hub_exists?(id) do
-          %{Hubs.fetch_hub!(id) | user_id: nil, session_token: config.session_token}
-        else
-          Hubs.save_hub(%Team{
-            id: id,
-            hub_name: name,
-            hub_emoji: "🚀",
-            user_id: nil,
-            org_id: attrs["org_id"],
-            org_key_id: attrs["org_key_id"],
-            session_token: config.session_token,
-            teams_key: config.teams_key,
-            org_public_key: attrs["public_key"]
-          })
-        end
+        Hubs.save_hub(%Team{
+          id: id,
+          hub_name: name,
+          hub_emoji: "🚀",
+          user_id: nil,
+          org_id: attrs["org_id"],
+          org_key_id: attrs["org_key_id"],
+          session_token: config.session_token,
+          teams_key: config.teams_key,
+          org_public_key: attrs["public_key"]
+        })
 
       {:ok, hub}
     end
diff --git a/lib/livebook/teams/constants.ex b/lib/livebook/teams/constants.ex
new file mode 100644
index 000000000..23fb6b7c6
--- /dev/null
+++ b/lib/livebook/teams/constants.ex
@@ -0,0 +1,25 @@
+defmodule Livebook.Teams.Constants do
+  @doc """
+  Returns the public key prefix
+  """
+  @spec public_key_prefix() :: String.t()
+  def public_key_prefix(), do: "lb_opk_"
+
+  @doc """
+  Returns the Agent Key prefix
+  """
+  @spec agent_key_prefix() :: String.t()
+  def agent_key_prefix, do: "lb_ak_"
+
+  @doc """
+  Returns the Deploy Key prefix
+  """
+  @spec deploy_key_prefix() :: String.t()
+  def deploy_key_prefix, do: "lb_dk_"
+
+  @doc """
+  Returns the Teams Key prefix
+  """
+  @spec teams_key_prefix() :: String.t()
+  def teams_key_prefix(), do: "lb_tk_"
+end
diff --git a/lib/livebook/teams/org.ex b/lib/livebook/teams/org.ex
index 568cda9ff..6a61ee784 100644
--- a/lib/livebook/teams/org.ex
+++ b/lib/livebook/teams/org.ex
@@ -2,8 +2,6 @@ defmodule Livebook.Teams.Org do
   use Ecto.Schema
   import Ecto.Changeset
 
-  @prefix "lb_tk_"
-
   @type t :: %__MODULE__{
           id: pos_integer() | nil,
           emoji: String.t() | nil,
@@ -31,7 +29,7 @@ defmodule Livebook.Teams.Org do
   @spec teams_key() :: String.t()
   def teams_key() do
     key = :crypto.strong_rand_bytes(@secret_key_size)
-    @prefix <> Base.url_encode64(key, padding: false)
+    Livebook.Teams.Constants.teams_key_prefix() <> Base.url_encode64(key, padding: false)
   end
 
   @doc """
@@ -50,10 +48,4 @@ defmodule Livebook.Teams.Org do
       message: "should only contain lowercase alphanumeric characters and dashes"
     )
   end
-
-  @doc """
-  Returns the teams key prefix
-  """
-  @spec teams_key_prefix() :: String.t()
-  def teams_key_prefix(), do: @prefix
 end
diff --git a/lib/livebook/teams/requests.ex b/lib/livebook/teams/requests.ex
index 1df8f33dc..4523cf0f0 100644
--- a/lib/livebook/teams/requests.ex
+++ b/lib/livebook/teams/requests.ex
@@ -5,7 +5,7 @@ defmodule Livebook.Teams.Requests do
   alias Livebook.Secrets.Secret
   alias Livebook.Teams
 
-  @deploy_key_prefix "lb_dk_"
+  @deploy_key_prefix Teams.Constants.deploy_key_prefix()
   @error_message "Something went wrong, try again later or please file a bug if it persists"
   @unauthorized_error_message "You are not authorized to perform this action, make sure you have the access and you are not in a Livebook App Server/Offline instance"
 
@@ -15,9 +15,6 @@ defmodule Livebook.Teams.Requests do
   @doc false
   def error_message(), do: @error_message
 
-  @doc false
-  def deploy_key_prefix(), do: @deploy_key_prefix
-
   @doc """
   Send a request to Livebook Team API to create a new org.
   """
@@ -303,8 +300,6 @@ defmodule Livebook.Teams.Requests do
   defp upload(path, content, params, team) do
     build_req(team)
     |> Req.Request.put_header("content-length", "#{byte_size(content)}")
-    |> Req.Request.put_private(:cli, path =~ "cli")
-    |> Req.Request.put_private(:deploy, true)
     |> Req.post(url: path, params: params, body: content)
     |> handle_response()
     |> dispatch_messages(team)
diff --git a/lib/livebook_cli.ex b/lib/livebook_cli.ex
index e07a0789b..9f7e2ecb5 100644
--- a/lib/livebook_cli.ex
+++ b/lib/livebook_cli.ex
@@ -21,7 +21,6 @@ defmodule LivebookCLI do
     extract_priv!()
 
     :ok = Application.load(:livebook)
-    Application.put_env(:livebook, :persist_storage, false)
 
     if unix?() do
       Application.put_env(:elixir, :ansi_enabled, true)
@@ -30,7 +29,7 @@ defmodule LivebookCLI do
     case args do
       [arg] when arg in @help_args -> display_help()
       [arg] when arg in @version_args -> display_version()
-      [name | [arg]] when arg in @help_args -> Task.usage(name)
+      [name, arg] when arg in @help_args -> Task.usage(name)
       [name | args] -> Task.call(name, List.delete(args, name))
       _args -> Utils.print_text(usage())
     end
diff --git a/lib/livebook_cli/deploy.ex b/lib/livebook_cli/deploy.ex
index 185c85228..e65b34ebd 100644
--- a/lib/livebook_cli/deploy.ex
+++ b/lib/livebook_cli/deploy.ex
@@ -4,8 +4,8 @@ defmodule LivebookCLI.Deploy do
 
   @behaviour LivebookCLI.Task
 
-  @deploy_key_prefix Teams.Requests.deploy_key_prefix()
-  @teams_key_prefix Teams.Org.teams_key_prefix()
+  @deploy_key_prefix Teams.Constants.deploy_key_prefix()
+  @teams_key_prefix Teams.Constants.teams_key_prefix()
 
   @impl true
   def usage() do
@@ -16,7 +16,7 @@ defmodule LivebookCLI.Deploy do
 
       --deploy-key        Sets the deploy key to authenticate with Livebook Teams
       --teams-key         Sets the Teams key to authenticate with Livebook Teams and encrypt the Livebook app
-      --deployment-group  The deployment group name which you want to deploy
+      --deployment-group  The deployment group name which you want to deploy to
 
     The --help option can be given to print this notice.
 
@@ -24,11 +24,11 @@ defmodule LivebookCLI.Deploy do
 
     Deploys a single notebook:
 
-        livebook deploy --deploy-key="lb_dk_..." --teams-key="lb_tk_..." -deployment-group "online" path/to/file.livemd
+        livebook deploy --deploy-key="lb_dk_..." --teams-key="lb_tk_..." --deployment-group "online" path/to/app1.livemd
 
-    Deploys a folder:
+    Deploys multiple notebooks:
 
-        livebook deploy --deploy-key="lb_dk_..." --teams-key="lb_tk_..." -deployment-group "online" path/to\
+        livebook deploy --deploy-key="lb_dk_..." --teams-key="lb_tk_..." --deployment-group "online" path/to/*.livemd\
     """
   end
 
@@ -40,6 +40,7 @@ defmodule LivebookCLI.Deploy do
 
   @impl true
   def call(args) do
+    Application.put_env(:livebook, :persist_storage, false)
     {:ok, _} = Application.ensure_all_started(:livebook)
     config = config_from_args(args)
     ensure_config!(config)
@@ -49,11 +50,10 @@ defmodule LivebookCLI.Deploy do
   end
 
   defp config_from_args(args) do
-    {opts, filename_or_directory} = OptionParser.parse!(args, strict: @switches)
-    filename_or_directory = Path.expand(filename_or_directory)
+    {opts, path} = OptionParser.parse!(args, strict: @switches)
 
     %{
-      path: filename_or_directory,
+      path: List.flatten(path),
       session_token: opts[:deploy_key],
       teams_key: opts[:teams_key],
       deployment_group: opts[:deployment_group]
@@ -83,11 +83,7 @@ defmodule LivebookCLI.Deploy do
           end
 
         {:path, value}, acc ->
-          if not File.exists?(value) do
-            add_error(acc, normalize_key(:path), "must be a valid path")
-          else
-            acc
-          end
+          Enum.reduce_while(value, acc, &validate_path/2)
 
         _otherwise, acc ->
           acc
@@ -96,7 +92,7 @@ defmodule LivebookCLI.Deploy do
     if Map.keys(errors) == [] do
       :ok
     else
-      raise """
+      raise LivebookCLI.Error, """
       You configuration is invalid, make sure you are using the correct options for this task.
 
       #{format_errors(errors, " * ")}\
@@ -104,21 +100,39 @@ defmodule LivebookCLI.Deploy do
     end
   end
 
+  defp validate_path(value, acc) do
+    cond do
+      not File.exists?(value) ->
+        {:halt, add_error(acc, normalize_key(:path), "must be a valid path")}
+
+      File.dir?(value) ->
+        {:halt, add_error(acc, normalize_key(:path), "must be a file path")}
+
+      true ->
+        {:cont, acc}
+    end
+  end
+
   defp authenticate_cli!(config) do
     log_debug("Authenticating CLI...")
 
     case Teams.fetch_cli_session(config) do
       {:ok, team} -> team
-      {:error, error} -> raise error
-      {:transport_error, error} -> raise error
+      {:error, error} -> raise LivebookCLI.Error, error
+      {:transport_error, error} -> raise LivebookCLI.Error, error
     end
   end
 
   defp deploy_to_teams(team, config) do
-    notebook_paths = list_notebooks!(config.path)
+    if length(config.path) == 1 do
+      log_debug("Found 1 notebook")
+    else
+      log_debug("Found #{length(config.path)} notebooks")
+    end
+
     log_info("Deploying notebooks:")
 
-    for path <- notebook_paths do
+    for path <- config.path do
       log_info(" * Preparing to deploy notebook #{Path.basename(path)}")
       files_dir = Livebook.FileSystem.File.local(path)
 
@@ -129,18 +143,18 @@ defmodule LivebookCLI.Deploy do
             print_text([:green, "  * #{app_deployment.title} deployed successfully. (#{url})"])
 
           {:error, errors} ->
-            print_text([:red, "  * #{app_deployment.title} failed to deployed."])
+            print_text([:red, "  * #{app_deployment.title} failed to deploy."])
             errors = normalize_errors(errors)
 
-            raise """
+            raise LivebookCLI.Error, """
             #{format_errors(errors, "  * ")}
 
             #{Teams.Requests.error_message()}\
             """
 
           {:transport_error, reason} ->
-            print_text([:red, "  * #{app_deployment.title} failed to deployed."])
-            raise reason
+            print_text([:red, "  * #{app_deployment.title} failed to deploy."])
+            raise LivebookCLI.Error, reason
         end
       end
     end
@@ -148,46 +162,19 @@ defmodule LivebookCLI.Deploy do
     :ok
   end
 
-  defp list_notebooks!(path) do
-    log_debug("Listing notebooks from: #{path}")
-
-    files =
-      if File.dir?(path) do
-        path
-        |> File.ls!()
-        |> Enum.map(&Path.join(path, &1))
-        |> Enum.reject(&File.dir?/1)
-        |> Enum.filter(&String.ends_with?(&1, ".livemd"))
-      else
-        [path]
-      end
-
-    if files == [] do
-      raise "There's no notebook available to deploy"
-    else
-      if length(files) == 1 do
-        log_debug("Found 1 notebook")
-      else
-        log_debug("Found #{length(files)} notebooks")
-      end
-
-      files
-    end
-  end
-
   defp prepare_app_deployment(path, content, files_dir) do
     case Livebook.Teams.AppDeployment.new(content, files_dir) do
       {:ok, app_deployment} ->
         {:ok, app_deployment}
 
       {:warning, warnings} ->
-        raise """
+        raise LivebookCLI.Error, """
         Deployment for notebook #{Path.basename(path)} failed because the notebook has some warnings:
         #{format_list(warnings, " * ")}
         """
 
       {:error, reason} ->
-        raise "Failed to handle I/O operations: #{reason}"
+        raise LivebookCLI.Error, "Failed to handle I/O operations: #{reason}"
     end
   end
 
diff --git a/lib/livebook_cli/error.ex b/lib/livebook_cli/error.ex
new file mode 100644
index 000000000..bf8843060
--- /dev/null
+++ b/lib/livebook_cli/error.ex
@@ -0,0 +1,3 @@
+defmodule LivebookCLI.Error do
+  defexception [:message]
+end
diff --git a/lib/livebook_cli/server.ex b/lib/livebook_cli/server.ex
index 09b95cdb9..bd1d2cfca 100644
--- a/lib/livebook_cli/server.ex
+++ b/lib/livebook_cli/server.ex
@@ -88,7 +88,8 @@ defmodule LivebookCLI.Server do
             open_from_args(base_url, extra_args)
 
           :taken ->
-            raise "Another application is already running on port #{port}." <>
+            raise LivebookCLI.Error,
+                  "Another application is already running on port #{port}." <>
                     " Either ensure this port is free or specify a different port using the --port option"
 
           :available ->
@@ -106,7 +107,7 @@ defmodule LivebookCLI.Server do
         Process.sleep(:infinity)
 
       {:error, error} ->
-        raise "Livebook failed to start with reason: #{inspect(error)}"
+        raise LivebookCLI.Error, "Livebook failed to start with reason: #{inspect(error)}"
     end
   end
 
@@ -174,7 +175,9 @@ defmodule LivebookCLI.Server do
   end
 
   defp open_from_args(_base_url, _extra_args) do
-    raise "Too many arguments entered. Ensure only one argument is used to specify the file path and all other arguments are preceded by the relevant switch"
+    raise OptionParser.ParseError,
+          "Too many arguments entered. Ensure only one argument is used to" <>
+            "specify the file path and all other arguments are preceded by the relevant switch"
   end
 
   @switches [
diff --git a/lib/livebook_cli/task.ex b/lib/livebook_cli/task.ex
index 1a0eb3823..22cd0d79a 100644
--- a/lib/livebook_cli/task.ex
+++ b/lib/livebook_cli/task.ex
@@ -68,8 +68,14 @@ defmodule LivebookCLI.Task do
     """
   end
 
-  defp format_exception(%RuntimeError{} = exception, _, _) do
-    Exception.message(exception)
+  defp format_exception(%LivebookCLI.Error{} = exception, command_name, _) do
+    """
+    #{Exception.message(exception)}
+
+    For more information try:
+
+       livebook #{command_name} --help
+    """
   end
 
   defp format_exception(exception, _, stacktrace) do
diff --git a/test/livebook_teams/cli/deploy_test.exs b/test/livebook_teams/cli/deploy_test.exs
index 89cdcd0e0..8c0ec3a70 100644
--- a/test/livebook_teams/cli/deploy_test.exs
+++ b/test/livebook_teams/cli/deploy_test.exs
@@ -4,7 +4,6 @@ defmodule LivebookCLI.Integration.DeployTest do
   import Livebook.AppHelpers
 
   alias Livebook.Utils
-  alias LivebookCLI.Deploy
 
   @url "http://localhost:4200"
 
@@ -15,7 +14,6 @@ defmodule LivebookCLI.Integration.DeployTest do
   @moduletag subscribe_to_teams_topics: [:clients, :deployment_groups, :app_deployments]
 
   @moduletag :tmp_dir
-  @moduletag :capture_io
 
   describe "CLI deploy integration" do
     test "successfully deploys a notebook via CLI",
@@ -42,15 +40,12 @@ defmodule LivebookCLI.Integration.DeployTest do
 
       output =
         ExUnit.CaptureIO.capture_io(fn ->
-          assert Deploy.call([
-                   "--deploy-key",
+          assert deploy(
                    key,
-                   "--teams-key",
                    team.teams_key,
-                   "--deployment-group",
                    deployment_group.name,
                    app_path
-                 ]) == :ok
+                 ) == :ok
         end)
 
       assert output =~ "* Preparing to deploy notebook #{slug}.livemd"
@@ -94,15 +89,12 @@ defmodule LivebookCLI.Integration.DeployTest do
 
       output =
         ExUnit.CaptureIO.capture_io(fn ->
-          assert Deploy.call([
-                   "--deploy-key",
+          assert deploy(
                    key,
-                   "--teams-key",
                    team.teams_key,
-                   "--deployment-group",
                    deployment_group.name,
-                   tmp_dir
-                 ]) == :ok
+                   Path.join(tmp_dir, "*.livemd")
+                 ) == :ok
         end)
 
       for {slug, title} <- apps do
@@ -131,16 +123,13 @@ defmodule LivebookCLI.Integration.DeployTest do
       # Test App
       """)
 
-      assert_raise RuntimeError, ~r/Deploy Key must be a Livebook Teams Deploy Key/s, fn ->
-        Deploy.call([
-          "--deploy-key",
+      assert_raise LivebookCLI.Error, ~r/Deploy Key must be a Livebook Teams Deploy Key/s, fn ->
+        deploy(
           "invalid_key",
-          "--teams-key",
           team.teams_key,
-          "--deployment-group",
           deployment_group.name,
           app_path
-        ])
+        )
       end
     end
 
@@ -156,16 +145,13 @@ defmodule LivebookCLI.Integration.DeployTest do
       # Test App
       """)
 
-      assert_raise RuntimeError, ~r/Teams Key must be a Livebook Teams Key/s, fn ->
-        Deploy.call([
-          "--deploy-key",
+      assert_raise LivebookCLI.Error, ~r/Teams Key must be a Livebook Teams Key/s, fn ->
+        deploy(
           key,
-          "--teams-key",
           "invalid-key",
-          "--deployment-group",
           deployment_group.name,
           app_path
-        ])
+        )
       end
     end
 
@@ -181,14 +167,13 @@ defmodule LivebookCLI.Integration.DeployTest do
       # Test App
       """)
 
-      assert_raise RuntimeError, ~r/Deployment Group can't be blank/s, fn ->
-        Deploy.call([
-          "--deploy-key",
+      assert_raise LivebookCLI.Error, ~r/Deployment Group can't be blank/s, fn ->
+        deploy(
           key,
-          "--teams-key",
           team.teams_key,
+          "",
           app_path
-        ])
+        )
       end
     end
 
@@ -214,17 +199,14 @@ defmodule LivebookCLI.Integration.DeployTest do
       ```
       """)
 
-      assert_raise RuntimeError, ~r/Deployment Group does not exist/s, fn ->
+      assert_raise LivebookCLI.Error, ~r/Deployment Group does not exist/s, fn ->
         ExUnit.CaptureIO.capture_io(fn ->
-          Deploy.call([
-            "--deploy-key",
+          deploy(
             key,
-            "--teams-key",
             team.teams_key,
-            "--deployment-group",
             Utils.random_short_id(),
             app_path
-          ])
+          )
         end)
       end
 
@@ -242,38 +224,42 @@ defmodule LivebookCLI.Integration.DeployTest do
       {key, _} = TeamsRPC.create_deploy_key(node, org: org)
       deployment_group = TeamsRPC.create_deployment_group(node, org: org, url: @url)
 
-      assert_raise RuntimeError, ~r/Path must be a valid path/s, fn ->
-        Deploy.call([
-          "--deploy-key",
+      assert_raise LivebookCLI.Error, ~r/Path must be a valid path/s, fn ->
+        deploy(
           key,
-          "--teams-key",
           team.teams_key,
-          "--deployment-group",
           deployment_group.name,
           Path.join(tmp_dir, "app.livemd")
-        ])
+        )
       end
     end
 
-    test "fails when directory contains no notebooks",
-         %{team: team, node: node, org: org, tmp_dir: tmp_dir} do
+    test "fails with directory argument", %{team: team, node: node, org: org, tmp_dir: tmp_dir} do
       {key, _} = TeamsRPC.create_deploy_key(node, org: org)
       deployment_group = TeamsRPC.create_deployment_group(node, org: org, url: @url)
 
-      File.write!(Path.join(tmp_dir, "readme.txt"), "No notebooks here")
-      File.write!(Path.join(tmp_dir, "config.json"), "{}")
-
-      assert_raise RuntimeError, ~r/There's no notebook available to deploy/, fn ->
-        Deploy.call([
-          "--deploy-key",
+      assert_raise LivebookCLI.Error, ~r/Path must be a file path/s, fn ->
+        deploy(
           key,
-          "--teams-key",
           team.teams_key,
-          "--deployment-group",
           deployment_group.name,
           tmp_dir
-        ])
+        )
       end
     end
   end
+
+  defp deploy(deploy_key, teams_key, deployment_group_name, path) do
+    path = if Path.wildcard(path) == [], do: path, else: Path.wildcard(path)
+
+    LivebookCLI.Deploy.call([
+      "--deploy-key",
+      deploy_key,
+      "--teams-key",
+      teams_key,
+      "--deployment-group",
+      deployment_group_name,
+      path
+    ])
+  end
 end
diff --git a/test/livebook_teams/teams_test.exs b/test/livebook_teams/teams_test.exs
index a6a491235..2ba6b1ffe 100644
--- a/test/livebook_teams/teams_test.exs
+++ b/test/livebook_teams/teams_test.exs
@@ -258,6 +258,7 @@ defmodule Livebook.TeamsTest do
     test "authenticates the deploy key", %{team: team} do
       config = %{teams_key: team.teams_key, session_token: team.session_token}
 
+      refute Livebook.Hubs.hub_exists?(team.id)
       assert Teams.fetch_cli_session(config) == {:ok, team}
       assert Livebook.Hubs.hub_exists?(team.id)
     end
@@ -272,7 +273,7 @@ defmodule Livebook.TeamsTest do
                {:ok,
                 %Livebook.Hubs.Team{
                   billing_status: team.billing_status,
-                  hub_emoji: team.hub_emoji,
+                  hub_emoji: "🚀",
                   hub_name: team.hub_name,
                   id: team.id,
                   offline: nil,
@@ -284,9 +285,8 @@ defmodule Livebook.TeamsTest do
                   user_id: nil
                 }}
 
-      # If the hub already exist, we don't update them from storage
       assert Livebook.Hubs.hub_exists?(team.id)
-      refute Livebook.Hubs.fetch_hub!(team.id).session_token == key
+      assert Livebook.Hubs.fetch_hub!(team.id).session_token == key
     end
 
     @tag teams_persisted: false
diff --git a/test/support/factory.ex b/test/support/factory.ex
index 2c673df24..4ce541ecc 100644
--- a/test/support/factory.ex
+++ b/test/support/factory.ex
@@ -21,7 +21,8 @@ defmodule Livebook.Factory do
       org_id: 1,
       user_id: 1,
       org_key_id: 1,
-      org_public_key: Livebook.Hubs.Team.public_key_prefix() <> Livebook.Utils.random_long_id(),
+      org_public_key:
+        Livebook.Teams.Constants.public_key_prefix() <> Livebook.Utils.random_long_id(),
       teams_key: org.teams_key,
       session_token: Livebook.Utils.random_short_id(),
       offline: nil