diff --git a/app/jobs/send_test_webhook_request_job.rb b/app/jobs/send_test_webhook_request_job.rb
index 158363ec..fe5cabce 100644
--- a/app/jobs/send_test_webhook_request_job.rb
+++ b/app/jobs/send_test_webhook_request_job.rb
@@ -26,7 +26,7 @@ class SendTestWebhookRequestJob
         Addressable::URI.parse(webhook_url.url).normalize
       end
 
-      raise HttpsError, 'Only HTTPS is allowed.' if uri.scheme != 'https'
+      raise HttpsError, 'Only HTTPS is allowed.' if uri.scheme != 'https' || uri.port != 443
       raise LocalhostError, "Can't send to localhost." if uri.host.in?(SendWebhookRequest::LOCALHOSTS)
     end
 
diff --git a/lib/download_utils.rb b/lib/download_utils.rb
index 668c6d96..3758239c 100644
--- a/lib/download_utils.rb
+++ b/lib/download_utils.rb
@@ -52,7 +52,7 @@ module DownloadUtils
   end
 
   def validate_uri!(uri)
-    raise UnableToDownload, "Error loading: #{uri}. Only HTTPS is allowed." if uri.scheme != 'https'
+    raise UnableToDownload, "Error loading: #{uri}. Only HTTPS is allowed." if uri.scheme != 'https' || uri.port != 443
     raise UnableToDownload, "Error loading: #{uri}. Can't download from localhost." if uri.host.in?(LOCALHOSTS)
   end
 
diff --git a/lib/send_webhook_request.rb b/lib/send_webhook_request.rb
index a3474eaf..d41c8cbc 100644
--- a/lib/send_webhook_request.rb
+++ b/lib/send_webhook_request.rb
@@ -22,7 +22,7 @@ module SendWebhookRequest
     end
 
     if Docuseal.multitenant?
-      raise HttpsError, 'Only HTTPS is allowed.' if uri.scheme != 'https' &&
+      raise HttpsError, 'Only HTTPS is allowed.' if (uri.scheme != 'https' || uri.port != 443) &&
                                                     !AccountConfig.exists?(key: :allow_http,
                                                                            account_id: webhook_url.account_id)
       raise LocalhostError, "Can't send to localhost." if uri.host.in?(LOCALHOSTS)