diff --git a/crates/core/src/operations/optimize.rs b/crates/core/src/operations/optimize.rs
index f44f2cb5e6..8f2b5fa59b 100644
--- a/crates/core/src/operations/optimize.rs
+++ b/crates/core/src/operations/optimize.rs
@@ -331,6 +331,7 @@ impl<'a> std::future::IntoFuture for OptimizeBuilder<'a> {
                 this.filters,
                 this.target_size.to_owned(),
                 writer_properties,
+                this.preserve_insertion_order,
             )?;
             let metrics = plan
                 .execute(
@@ -877,12 +878,15 @@ pub fn create_merge_plan(
     filters: &[PartitionFilter],
     target_size: Option<i64>,
     writer_properties: WriterProperties,
+    preserve_insertion_order: bool,
 ) -> Result<MergePlan, DeltaTableError> {
     let target_size = target_size.unwrap_or_else(|| snapshot.table_config().target_file_size());
     let partitions_keys = &snapshot.metadata().partition_columns;
 
     let (operations, metrics) = match optimize_type {
-        OptimizeType::Compact => build_compaction_plan(snapshot, filters, target_size)?,
+        OptimizeType::Compact => {
+            build_compaction_plan(snapshot, filters, target_size, preserve_insertion_order)?
+        }
         OptimizeType::ZOrder(zorder_columns) => {
             build_zorder_plan(zorder_columns, snapshot, partitions_keys, filters)?
         }
@@ -958,6 +962,7 @@ fn build_compaction_plan(
     snapshot: &DeltaTableState,
     filters: &[PartitionFilter],
     target_size: i64,
+    perserve_insertion_order: bool,
 ) -> Result<(OptimizeOperations, Metrics), DeltaTableError> {
     let mut metrics = Metrics::default();
 
@@ -985,8 +990,13 @@ fn build_compaction_plan(
     }
 
     for (_, file) in partition_files.values_mut() {
-        // Sort files by size: largest to smallest
-        file.sort_by(|a, b| b.size.cmp(&a.size));
+        if perserve_insertion_order {
+            // sort files by modification date
+            file.sort_by(|a, b| b.last_modified.cmp(&a.last_modified));
+        } else {
+            // Sort files by size: largest to smallest
+            file.sort_by(|a, b| b.size.cmp(&a.size));
+        }
     }
 
     let mut operations: HashMap<String, (IndexMap<String, Scalar>, Vec<MergeBin>)> = HashMap::new();
diff --git a/crates/core/tests/command_optimize.rs b/crates/core/tests/command_optimize.rs
index 4826647750..64932f7072 100644
--- a/crates/core/tests/command_optimize.rs
+++ b/crates/core/tests/command_optimize.rs
@@ -289,6 +289,7 @@ async fn test_conflict_for_remove_actions() -> Result<(), Box<dyn Error>> {
         &filter,
         None,
         WriterProperties::builder().build(),
+        false,
     )?;
 
     let uri = context.tmp_dir.path().to_str().to_owned().unwrap();
@@ -351,6 +352,7 @@ async fn test_no_conflict_for_append_actions() -> Result<(), Box<dyn Error>> {
         &filter,
         None,
         WriterProperties::builder().build(),
+        false,
     )?;
 
     let uri = context.tmp_dir.path().to_str().to_owned().unwrap();
@@ -410,6 +412,7 @@ async fn test_commit_interval() -> Result<(), Box<dyn Error>> {
         &[],
         None,
         WriterProperties::builder().build(),
+        false,
     )?;
 
     let metrics = plan
@@ -867,6 +870,61 @@ async fn test_zorder_respects_target_size() -> Result<(), Box<dyn Error>> {
     Ok(())
 }
 
+#[tokio::test]
+async fn test_preserve_insertion_order() -> Result<(), Box<dyn Error>> {
+    let context = setup_test(true).await?;
+    let mut dt = context.table;
+    let mut writer = RecordBatchWriter::for_table(&dt)?;
+
+    // first file
+    write(
+        &mut writer,
+        &mut dt,
+        tuples_to_batch(vec![(1, 1), (1, 2), (1, 3), (1, 4)], "2022-05-22")?,
+    )
+    .await?;
+
+    // later file
+    write(
+        &mut writer,
+        &mut dt,
+        tuples_to_batch(vec![(2, 5), (2, 6), (2, 7), (2, 8)], "2022-05-22")?,
+    )
+    .await?;
+
+    let filter = vec![PartitionFilter::try_from(("date", "=", "2022-05-22"))?];
+
+    let optimize = DeltaOps(dt)
+        .optimize()
+        .with_target_size(2_000_000)
+        .with_filters(&filter)
+        .with_preserve_insertion_order(true);
+    let (dt, metrics) = optimize.await?;
+
+    assert_eq!(metrics.num_files_added, 1);
+    assert_eq!(metrics.num_files_removed, 2);
+    assert_eq!(metrics.total_files_skipped, 0);
+    assert_eq!(metrics.total_considered_files, 2);
+
+    // Check data
+    let files = dt.get_files_iter()?.collect::<Vec<_>>();
+    assert_eq!(files.len(), 1);
+
+    let actual = read_parquet_file(&files[0], dt.object_store()).await?;
+    let expected = RecordBatch::try_new(
+        actual.schema(),
+        // file created later is merged first
+        vec![
+            Arc::new(Int32Array::from(vec![2, 2, 2, 2, 1, 1, 1, 1])),
+            Arc::new(Int32Array::from(vec![5, 6, 7, 8, 1, 2, 3, 4])),
+        ],
+    )?;
+
+    assert_eq!(actual, expected);
+
+    Ok(())
+}
+
 async fn read_parquet_file(
     path: &Path,
     object_store: ObjectStoreRef,