diff --git a/CHANGELOG.md b/CHANGELOG.md
index ef2afeba6f..bdfa0b3eea 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -35,6 +35,10 @@ and this project adheres to
   to send emails. This is now fixed for a limited number of use cases (see
   (DEPLOYMENT.md)[https://github.com/OpenFn/lightning/blob/main/DEPLOYMENT.md#mail]
   for details). [#4602](https://github.com/OpenFn/lightning/issues/4602)
+- Include `webhook_reply` and `cron_cursor_job_id` in the workflow version hash
+  so that changes to these trigger fields are properly detected by CLI deploy and
+  sandbox merge
+  [#4596](https://github.com/OpenFn/lightning/issues/4596)
 
 ## [2.16.1] - 2026-04-07
 
diff --git a/lib/lightning/workflow_versions.ex b/lib/lightning/workflow_versions.ex
index a4db0c45e8..011088f56c 100644
--- a/lib/lightning/workflow_versions.ex
+++ b/lib/lightning/workflow_versions.ex
@@ -246,7 +246,13 @@ defmodule Lightning.WorkflowVersions do
       :body
     ]
 
-    trigger_keys = [:type, :cron_expression, :enabled]
+    trigger_keys = [
+      :type,
+      :cron_expression,
+      :enabled,
+      :webhook_reply,
+      :cron_cursor_job_id
+    ]
 
     edge_keys = [
       :name,
diff --git a/test/lightning/workflow_versions_test.exs b/test/lightning/workflow_versions_test.exs
index e0bb6e4f77..fcdff6bbe0 100644
--- a/test/lightning/workflow_versions_test.exs
+++ b/test/lightning/workflow_versions_test.exs
@@ -493,6 +493,57 @@ defmodule Lightning.WorkflowVersionsTest do
       refute hash1 == hash2
     end
 
+    test "hash changes when webhook_reply changes" do
+      workflow = insert(:workflow, name: "Test")
+
+      trigger =
+        insert(:trigger,
+          workflow: workflow,
+          type: :webhook,
+          webhook_reply: :before_start
+        )
+
+      workflow = Repo.preload(workflow, [:triggers, :jobs, :edges])
+      hash1 = WorkflowVersions.generate_hash(workflow)
+
+      trigger
+      |> Ecto.Changeset.change(webhook_reply: :after_completion)
+      |> Repo.update!()
+
+      workflow = Repo.preload(workflow, [:triggers, :jobs, :edges], force: true)
+      hash2 = WorkflowVersions.generate_hash(workflow)
+
+      refute hash1 == hash2
+    end
+
+    test "hash changes when cron_cursor_job_id changes" do
+      workflow = insert(:workflow, name: "Test")
+      job1 = insert(:job, workflow: workflow, name: "Job A")
+      job2 = insert(:job, workflow: workflow, name: "Job B")
+
+      insert(:trigger,
+        workflow: workflow,
+        type: :cron,
+        cron_expression: "0 * * * *",
+        cron_cursor_job: job1
+      )
+
+      workflow = Repo.preload(workflow, [:triggers, :jobs, :edges])
+      hash1 = WorkflowVersions.generate_hash(workflow)
+
+      # Change the cron cursor job
+      [trigger] = workflow.triggers
+
+      trigger
+      |> Ecto.Changeset.change(cron_cursor_job_id: job2.id)
+      |> Repo.update!()
+
+      workflow = Repo.preload(workflow, [:triggers, :jobs, :edges], force: true)
+      hash2 = WorkflowVersions.generate_hash(workflow)
+
+      refute hash1 == hash2
+    end
+
     test "properly orders triggers by type" do
       workflow = insert(:workflow, name: "Test")