diff --git a/app/jobs/destroy_job.rb b/app/jobs/destroy_job.rb
index 74348555..692585de 100644
--- a/app/jobs/destroy_job.rb
+++ b/app/jobs/destroy_job.rb
@@ -3,5 +3,7 @@ class DestroyJob < ApplicationJob
 
   def perform(model)
     model.destroy
+  rescue => e
+    model.update!(scheduled_for_deletion: false) # Let's the user try again by resetting the state
   end
 end
diff --git a/app/models/plaid_item.rb b/app/models/plaid_item.rb
index 151b261e..25aa3e18 100644
--- a/app/models/plaid_item.rb
+++ b/app/models/plaid_item.rb
@@ -108,6 +108,15 @@ class PlaidItem < ApplicationRecord
   private
     def remove_plaid_item
       plaid_provider.remove_item(access_token)
+    rescue Plaid::ApiError => e
+      json_response = JSON.parse(e.response_body)
+
+      # If the item is not found, that means it was already deleted by the user on their
+      # Plaid portal OR by Plaid support.  Either way, we're not being billed, so continue
+      # with the deletion of our internal record.
+      unless json_response["error_code"] == "ITEM_NOT_FOUND"
+        raise e
+      end
     end
 
     # Plaid returns mutually exclusive arrays here.  If the item has made a request for a product,