diff --git a/lib/octokit/default.rb b/lib/octokit/default.rb
index 35eba066a..ca2e2fb73 100644
--- a/lib/octokit/default.rb
+++ b/lib/octokit/default.rb
@@ -12,11 +12,6 @@
   rescue LoadError
     Octokit::Warnable.octokit_warn 'To use retry middleware with Faraday v2.0+, install `faraday-retry` gem'
   end
-  begin
-    require 'faraday/multipart'
-  rescue LoadError
-    Octokit::Warnable.octokit_warn 'To use multipart middleware with Faraday v2.0+, install `faraday-multipart` gem; note: this is used by the ManageGHES client for uploading licenses'
-  end
 end
 
 module Octokit
diff --git a/lib/octokit/enterprise_management_console_client/management_console.rb b/lib/octokit/enterprise_management_console_client/management_console.rb
index 4355ebfbb..587187063 100644
--- a/lib/octokit/enterprise_management_console_client/management_console.rb
+++ b/lib/octokit/enterprise_management_console_client/management_console.rb
@@ -171,7 +171,14 @@ def password_hash
     def faraday_configuration
       @faraday_configuration ||= Faraday.new(url: @management_console_endpoint) do |http|
         http.headers[:user_agent] = user_agent
-        http.request :multipart
+        begin
+          http.request :multipart
+        rescue Faraday::Error
+          raise Faraday::Error, <<~ERROR
+            The `faraday-multipart` gem is required to upload a license.
+            Please add `gem "faraday-multipart"` to your Gemfile.
+          ERROR
+        end
         http.request :url_encoded
 
         # Disabling SSL is essential for certain self-hosted Enterprise instances
diff --git a/lib/octokit/manage_ghes_client/manage_ghes.rb b/lib/octokit/manage_ghes_client/manage_ghes.rb
index 806614a8e..53ca79665 100644
--- a/lib/octokit/manage_ghes_client/manage_ghes.rb
+++ b/lib/octokit/manage_ghes_client/manage_ghes.rb
@@ -36,7 +36,14 @@ def set_maintenance_mode(enabled, options = {})
     # @return [nil]
     def upload_license(license)
       conn = authenticated_client
-      conn.request :multipart
+      begin
+        conn.request :multipart
+      rescue Faraday::Error
+        raise Faraday::Error, <<~ERROR
+          The `faraday-multipart` gem is required to upload a license.
+          Please add `gem "faraday-multipart"` to your Gemfile.
+        ERROR
+      end
       params = {}
       params[:license] = Faraday::FilePart.new(license, 'binary')
       params[:password] = @manage_ghes_password
diff --git a/spec/octokit/enterprise_management_console_client/management_console_spec.rb b/spec/octokit/enterprise_management_console_client/management_console_spec.rb
index 1cc802af7..a2049a1dc 100644
--- a/spec/octokit/enterprise_management_console_client/management_console_spec.rb
+++ b/spec/octokit/enterprise_management_console_client/management_console_spec.rb
@@ -14,6 +14,15 @@
       expect(@enterprise_management_console_client.last_response.status).to eq(202)
       assert_requested :post, github_management_console_url('setup/api/start')
     end
+
+    it 'raises an error if the faraday-multipart gem is not installed' do
+      middleware_key = :multipart
+      middleware = Faraday::Request.unregister_middleware(middleware_key)
+
+      expect { @enterprise_management_console_client.upload_license(@license) }.to raise_error Faraday::Error
+    ensure
+      Faraday::Request.register_middleware(middleware_key => middleware) if middleware
+    end
   end # .upload_license
 
   describe '.start_configuration', :vcr do
diff --git a/spec/octokit/ghes_manage_client/ghes_manage_spec.rb b/spec/octokit/ghes_manage_client/ghes_manage_spec.rb
index 4cbf3fac0..e63079904 100644
--- a/spec/octokit/ghes_manage_client/ghes_manage_spec.rb
+++ b/spec/octokit/ghes_manage_client/ghes_manage_spec.rb
@@ -38,6 +38,15 @@
       expect(@manage_ghes.last_response.status).to eq(202)
       assert_requested :post, github_manage_ghes_url('/manage/v1/config/init')
     end
+
+    it 'raises an error if the faraday-multipart gem is not installed' do
+      middleware_key = :multipart
+      middleware = Faraday::Request.unregister_middleware(middleware_key)
+
+      expect { @manage_ghes.upload_license(@license) }.to raise_error Faraday::Error
+    ensure
+      Faraday::Request.register_middleware(middleware_key => middleware) if middleware
+    end
   end # .upload_license
 
   describe '.start_configuration', :vcr do