diff --git a/lib/skylight/probes/delayed_job.rb b/lib/skylight/probes/delayed_job.rb
index ae7a7886..7a846f74 100644
--- a/lib/skylight/probes/delayed_job.rb
+++ b/lib/skylight/probes/delayed_job.rb
@@ -8,21 +8,36 @@ module DelayedJob
       begin
         require "delayed/plugin"
 
+        UNKNOWN = "<Delayed::Job Unknown>"
+
         class Plugin < ::Delayed::Plugin
           callbacks do |lifecycle|
             lifecycle.around(:perform) { |worker, job, &block| sk_instrument(worker, job, &block) }
-
             lifecycle.after(:error) { |_worker, _job| Skylight.trace&.segment = "error" }
+            lifecycle.after(:failure) { |_worker, _job| Skylight.trace&.segment = "error" }
           end
 
           class << self
             include Skylight::Util::Logging
 
+            # This is called quite early in Delayed::Worker
+            #
+            # Typically, the `:perform` lifecycle hook is called before the
+            # `payload_object` has been deserialized, so we can't name the
+            # trace yet.
+            #
+            # If we call `payload_object` here, we would move the work of
+            # loading the object ahead of where it naturally happens, which
+            # means the database load time won't be instrumented. On the other
+            # hand, should the deserialization fail, we would have moved the
+            # timing of the error as well. Crucially – it would have moved it
+            # outside of the spot where these errors are normally caught and
+            # reported by the worker.
+            #
+            # See https://github.com/skylightio/skylight-ruby/issues/491
             def sk_instrument(_worker, job)
-              endpoint = Skylight::Probes::DelayedJob.handler_name(job)
-
               Skylight.trace(
-                endpoint,
+                UNKNOWN,
                 "app.delayed_job.worker",
                 "Delayed::Worker#run",
                 component: :worker,
@@ -41,15 +56,6 @@ def sk_instrument(_worker, job)
         $stderr.puts "[SKYLIGHT] The delayed_job probe was requested, but Delayed::Plugin was not defined."
       end
 
-      UNKNOWN = "<Delayed::Job Unknown>"
-
-      def self.handler_name(job)
-        payload_object =
-          job.respond_to?(:payload_object_without_sk) ? job.payload_object_without_sk : job.payload_object
-
-        payload_object_name(payload_object)
-      end
-
       def self.payload_object_name(payload_object)
         if payload_object.is_a?(::Delayed::PerformableMethod)
           payload_object.display_name
@@ -77,18 +83,27 @@ def self.payload_object_source_meta(payload_object)
 
       class InstrumentationProxy < SimpleDelegator
         def perform
-          source_meta = Skylight::Probes::DelayedJob.payload_object_source_meta(__getobj__)
-
-          opts = {
-            category: "app.delayed_job.job",
-            title: format_source(*source_meta),
-            meta: {
-              source_location_hint: source_meta
-            },
-            internal: true
-          }
-
-          Skylight.instrument(opts) { __getobj__.perform }
+          if (trace = Skylight.instrumenter&.current_trace)
+            if trace.endpoint == UNKNOWN
+              # At this point, deserialization was, by definition, successful.
+              # So it'd be safe to set the endpoint name based on the payload
+              # object here.
+              trace.endpoint = Skylight::Probes::DelayedJob.payload_object_name(__getobj__)
+            end
+
+            source_meta = Skylight::Probes::DelayedJob.payload_object_source_meta(__getobj__)
+
+            opts = {
+              category: "app.delayed_job.job",
+              title: format_source(*source_meta),
+              meta: {
+                source_location_hint: source_meta
+              },
+              internal: true
+            }
+
+            Skylight.instrument(opts) { __getobj__.perform }
+          end
         end
 
         # Used by Delayed::Backend::Base to determine Job#name
diff --git a/spec/integration/delayed_job_spec.rb b/spec/integration/delayed_job_spec.rb
index ada4917d..7455a1d4 100644
--- a/spec/integration/delayed_job_spec.rb
+++ b/spec/integration/delayed_job_spec.rb
@@ -276,6 +276,88 @@ def enqueue_job(*args)
           )
         end
       end
+
+      context "with ActiveRecord model" do
+        let(:users_migration) do
+          base = ActiveRecord::Migration
+          base = base::Current if defined?(base::Current)
+
+          Class.new(base) do
+            def self.up
+              create_table :users, force: true do |table|
+                table.string :name, null: false
+                table.timestamps null: true
+              end
+            end
+
+            def self.down
+              drop_table :users
+            end
+          end
+        end
+
+        around do |example|
+          with_sqlite(migration: users_migration) do
+            example.call
+          end
+        end
+
+        before do
+          stub_const("SkDelayedRecord", Class.new(ActiveRecord::Base) do
+            self.table_name = "users"
+            
+            def good_method
+              Skylight.instrument(category: "app.zomg") do
+                SpecHelper.clock.skip 1
+              end
+            end
+
+            def self.good_method
+              new.good_method
+            end
+          end)
+        end
+
+        # overrides enqueue_job on the outer context
+        def enqueue_job(_method_name, *, class_method: false)
+          if class_method
+            SkDelayedRecord.delay(queue: "queue-name").good_method
+          else
+            SkDelayedRecord.create!(name: "test-record").tap do |record|
+              record.delay(queue: "queue-name").good_method
+            end
+          end
+        end
+
+        specify "instance method" do
+          enqueue_and_process_job(:good_method)
+
+          server.wait resource: "/report"
+          report = server.reports[0].to_simple_report
+          expect(report.endpoint.name).to eq("SkDelayedRecord#good_method<sk-segment>queue-name</sk-segment>")
+        end
+
+        specify "class method" do
+          enqueue_and_process_job(:good_method, class_method: true)
+
+          server.wait resource: "/report"
+          report = server.reports[0].to_simple_report
+          expect(report.endpoint.name).to eq("SkDelayedRecord.good_method<sk-segment>queue-name</sk-segment>")
+        end
+
+        specify "instance method on a deleted record" do
+          SkDelayedRecord.create!(name: "test-record").tap do |record|
+            record.delay(queue: "queue-name").good_method
+            record.destroy!
+          end
+
+          expect { worker.work_off }.not_to raise_error
+          
+          server.wait resource: "/report"
+          report = server.reports[0].to_simple_report
+          expect(report.endpoint.name).to eq("<Delayed::Job Unknown><sk-segment>error</sk-segment>")
+        end
+      end
     end
 
     def enqueue_job(method_name, *, class_method: false)