diff --git a/app/controllers/qbo_controller.rb b/app/controllers/qbo_controller.rb
index 8cd4026..8216693 100644
--- a/app/controllers/qbo_controller.rb
+++ b/app/controllers/qbo_controller.rb
@@ -64,10 +64,15 @@ class QboController < ApplicationController
   def bill
     i = Issue.find_by_id params[:id]
     if i.customer
-      i.bill_time
-      redirect_to i, flash: { notice: I18n.t(:label_billed_success) + i.customer.name }
+      billed = i.bill_time
+
+      if i.bill_time
+        redirect_to i, flash: { notice: I18n.t( :label_billed_success ) + i.customer.name }
+      else
+        redirect_to i, flash: { error: I18n.t(:label_billing_error) }
+      end
     else
-      redirect_to i, flash: { error: I18n.t(:label_billing_error) }
+      redirect_to i, flash: { error: I18n.t(:label_billing_error_no_customer) }
     end
   end
   
diff --git a/config/locales/en.yml b/config/locales/en.yml
index e42e1d1..39931a2 100644
--- a/config/locales/en.yml
+++ b/config/locales/en.yml
@@ -74,7 +74,8 @@ en:
   label_connected: "Successfully connected to Quickbooks"
   label_error: "Error"
   label_billed_success: "Successfully Billed "
-  label_billing_error: "Cannot bill without a customer assigned"
+  label_billing_error: "Customer could not be billed, check for Customer or Assignee and try again"
+  label_billing_error_no_customer: "Cannot bill without a customer assigned"
   label_qbo_sync_success: "Successfully synced to Quickbooks"
   label_hours: "Hours"
   label_oauth2_refresh_token_expires_at: "Refresh Token Expires At"
diff --git a/lib/redmine_qbo/patches/issue_patch.rb b/lib/redmine_qbo/patches/issue_patch.rb
index 26e5949..1c08656 100644
--- a/lib/redmine_qbo/patches/issue_patch.rb
+++ b/lib/redmine_qbo/patches/issue_patch.rb
@@ -44,10 +44,9 @@ module RedmineQbo
         # Create billable time entries
         def bill_time
           logger.debug "QBO: Billing time for issue ##{id}"
-          return unless  status.is_closed?
-          return if assigned_to.nil?
-          return unless Qbo.first 
-          return unless customer 
+          return false if assigned_to.nil?
+          return false unless Qbo.first 
+          return false unless customer 
 
           Thread.new do
             spent_time = time_entries.where(billed: [false, nil])
@@ -102,6 +101,7 @@ module RedmineQbo
               end
             end
           end
+          return true
         end
       end