diff --git a/CHANGELOG.md b/CHANGELOG.md
index 48a4daac0..fabc1048a 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -4,6 +4,7 @@
 
 - [#1301](https://github.com/rails-sqlserver/activerecord-sqlserver-adapter/pull/1301) Add support for INDEX INCLUDE.
 - [#1312](https://github.com/rails-sqlserver/activerecord-sqlserver-adapter/pull/1312) Add support for `insert_all` and `upsert_all`
+- [#1317](https://github.com/rails-sqlserver/activerecord-sqlserver-adapter/pull/1317) Reverse order of values when upserting
 
 #### Changed
 
diff --git a/lib/active_record/connection_adapters/sqlserver/database_statements.rb b/lib/active_record/connection_adapters/sqlserver/database_statements.rb
index 92e91665d..addc593d3 100644
--- a/lib/active_record/connection_adapters/sqlserver/database_statements.rb
+++ b/lib/active_record/connection_adapters/sqlserver/database_statements.rb
@@ -169,6 +169,8 @@ def build_insert_sql(insert) # :nodoc:
         end
 
         def build_sql_for_merge_insert(insert:, insert_all:, columns_with_uniqueness_constraints:) # :nodoc:
+          insert_all.inserts.reverse! if insert.update_duplicates?
+
           sql = <<~SQL
             MERGE INTO #{insert.model.quoted_table_name} WITH (UPDLOCK, HOLDLOCK) AS target
             USING (