diff --git a/lib/livebook_cli/deploy.ex b/lib/livebook_cli/deploy.ex
index d99107f2c..78a2e4f5e 100644
--- a/lib/livebook_cli/deploy.ex
+++ b/lib/livebook_cli/deploy.ex
@@ -132,34 +132,45 @@ defmodule LivebookCLI.Deploy do
 
     log_info("Deploying notebooks:")
 
-    for path <- config.paths do
-      log_info(" * Preparing to deploy notebook #{Path.basename(path)}")
-      files_dir = Livebook.FileSystem.File.local(path)
+    deploy_results =
+      for path <- config.paths do
+        log_info(" * Preparing to deploy notebook #{Path.basename(path)}")
+        files_dir = Livebook.FileSystem.File.local(path)
 
-      with {:ok, content} <- File.read(path),
-           {:ok, app_deployment} <- prepare_app_deployment(path, content, files_dir) do
-        case Livebook.Teams.deploy_app_from_cli(team, app_deployment, config.deployment_group) do
-          {:ok, url} ->
-            log_info([:green, "  * #{app_deployment.title} deployed successfully. (#{url})"])
+        with {:ok, content} <- File.read(path),
+             {:ok, app_deployment} <- prepare_app_deployment(path, content, files_dir) do
+          case Livebook.Teams.deploy_app_from_cli(team, app_deployment, config.deployment_group) do
+            {:ok, url} ->
+              log_info([:green, "  * #{app_deployment.title} deployed successfully. (#{url})"])
+              :ok
 
-          {:error, errors} ->
-            log_error("  * #{app_deployment.title} failed to deploy.")
-            errors = normalize_errors(errors)
+            {:error, errors} ->
+              log_error("  * #{app_deployment.title} failed to deploy.")
 
-            raise LivebookCLI.Error, """
-            #{format_errors(errors, "  * ")}
+              error_message =
+                errors
+                |> normalize_errors
+                |> format_errors("    * ")
 
-            #{Teams.Requests.error_message()}\
-            """
+              log_error(error_message)
 
-          {:transport_error, reason} ->
-            log_error("  * #{app_deployment.title} failed to deploy.")
-            raise LivebookCLI.Error, reason
+              :error
+
+            {:transport_error, reason} ->
+              log_error(
+                "  * #{app_deployment.title} failed to deploy. Transport error: #{reason}"
+              )
+
+              :error
+          end
         end
       end
-    end
 
-    :ok
+    if Enum.any?(deploy_results, fn result -> result != :ok end) do
+      raise LivebookCLI.Error, "Some app deployments failed."
+    else
+      :ok
+    end
   end
 
   defp prepare_app_deployment(path, content, files_dir) do
@@ -168,13 +179,19 @@ defmodule LivebookCLI.Deploy do
         {:ok, app_deployment}
 
       {:warning, warnings} ->
-        raise LivebookCLI.Error, """
-        Deployment for notebook #{Path.basename(path)} failed because the notebook has some warnings:
-        #{format_list(warnings, " * ")}
+        error_message = """
+          * Deployment for notebook #{Path.basename(path)} failed because the notebook has some warnings:
+          #{format_list(warnings, " * ")}
         """
 
+        log_error(error_message)
+
+        :error
+
       {:error, reason} ->
-        raise LivebookCLI.Error, "Failed to handle I/O operations: #{reason}"
+        log_error("  * Failed to handle I/O operations: #{reason}")
+
+        :error
     end
   end
 
diff --git a/test/livebook_teams/cli/deploy_test.exs b/test/livebook_teams/cli/deploy_test.exs
index b61cb4d47..b9da2d6b2 100644
--- a/test/livebook_teams/cli/deploy_test.exs
+++ b/test/livebook_teams/cli/deploy_test.exs
@@ -199,16 +199,19 @@ defmodule LivebookCLI.Integration.DeployTest do
       ```
       """)
 
-      assert_raise LivebookCLI.Error, ~r/Deployment Group does not exist/s, fn ->
+      output =
         ExUnit.CaptureIO.capture_io(fn ->
-          deploy(
-            key,
-            team.teams_key,
-            Utils.random_short_id(),
-            app_path
-          )
+          assert_raise LivebookCLI.Error, "Some app deployments failed.", fn ->
+            deploy(
+              key,
+              team.teams_key,
+              Utils.random_short_id(),
+              app_path
+            )
+          end
         end)
-      end
+
+      assert output =~ ~r/Deployment Group does not exist/
 
       refute_receive {:app_deployment_started,
                       %{
@@ -247,14 +250,88 @@ defmodule LivebookCLI.Integration.DeployTest do
         )
       end
     end
+
+    test "handles partial failure when deploying multiple notebooks",
+         %{team: team, node: node, org: org, tmp_dir: tmp_dir} do
+      {deploy_key, _} = TeamsRPC.create_deploy_key(node, org: org)
+      deployment_group = TeamsRPC.create_deployment_group(node, org: org, url: @url)
+      hub_id = team.id
+
+      # Notebook without app settings (deploymeny should fail)
+      invalid_title = "Invalid App"
+      invalid_slug = "invalid-#{Utils.random_short_id()}"
+      invalid_app_path = Path.join(tmp_dir, "#{invalid_slug}.livemd")
+
+      File.write!(invalid_app_path, """
+      <!-- livebook:{"hub_id":"#{hub_id}"} -->
+
+      # #{invalid_title}
+
+      ```elixir
+      1 + 1
+      ```
+      """)
+
+      # Second notebook should succeed
+      valid_title = "Valid App"
+      valid_slug = "valid-#{Utils.random_short_id()}"
+      valid_app_path = Path.join(tmp_dir, "#{valid_slug}.livemd")
+
+      stamp_notebook(valid_app_path, """
+      <!-- livebook:{"app_settings":{"access_type":"public","slug":"#{valid_slug}"},"hub_id":"#{hub_id}"} -->
+
+      # #{valid_title}
+
+      ```elixir
+      1 + 1
+      ```
+      """)
+
+      output =
+        ExUnit.CaptureIO.capture_io(fn ->
+          assert_raise(LivebookCLI.Error, "Some app deployments failed.", fn ->
+            deploy(
+              deploy_key,
+              team.teams_key,
+              deployment_group.name,
+              [invalid_app_path, valid_app_path]
+            )
+          end)
+        end)
+
+      # The valid notebook should have been deployed successfully
+      assert output =~
+               "#{valid_title} deployed successfully. (#{@url}/apps/#{valid_slug})"
+
+      deployment_group_id = to_string(deployment_group.id)
+
+      assert_receive {:app_deployment_started,
+                      %{
+                        title: ^valid_title,
+                        slug: ^valid_slug,
+                        deployment_group_id: ^deployment_group_id,
+                        hub_id: ^hub_id,
+                        deployed_by: "CLI"
+                      }}
+
+      # And deployment of the invalide notebook shows an error message
+      invalid_app_filename = Path.basename(invalid_app_path)
+
+      assert output =~
+               "Deployment for notebook #{invalid_app_filename} failed"
+    end
   end
 
   defp deploy(deploy_key, teams_key, deployment_group_name, path) do
     paths =
-      case Path.wildcard(path) do
-        [] -> [path]
-        [path] -> [path]
-        paths -> paths
+      if is_list(path) do
+        path
+      else
+        case Path.wildcard(path) do
+          [] -> [path]
+          [path] -> [path]
+          paths -> paths
+        end
       end
 
     LivebookCLI.Deploy.call(