diff --git a/datafusion-examples/examples/large_string_sort.rs b/datafusion-examples/examples/large_string_sort.rs
new file mode 100644
index 000000000000..878f96904aec
--- /dev/null
+++ b/datafusion-examples/examples/large_string_sort.rs
@@ -0,0 +1,91 @@
+// Licensed to the Apache Software Foundation (ASF) under one
+// or more contributor license agreements.  See the NOTICE file
+// distributed with this work for additional information
+// regarding copyright ownership.  The ASF licenses this file
+// to you under the Apache License, Version 2.0 (the
+// "License"); you may not use this file except in compliance
+// with the License.  You may obtain a copy of the License at
+//
+//   http://www.apache.org/licenses/LICENSE-2.0
+//
+// Unless required by applicable law or agreed to in writing,
+// software distributed under the License is distributed on an
+// "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY
+// KIND, either express or implied.  See the License for the
+// specific language governing permissions and limitations
+// under the License.
+
+use arrow::array::{RecordBatch, StringBuilder};
+use arrow_schema::{DataType, Field, Schema};
+use datafusion::execution::disk_manager::DiskManagerConfig;
+use datafusion::execution::memory_pool::FairSpillPool;
+use datafusion::execution::runtime_env::RuntimeEnvBuilder;
+use datafusion::execution::SessionStateBuilder;
+use datafusion::parquet::arrow::ArrowWriter;
+use datafusion::prelude::{ParquetReadOptions, SessionContext};
+use futures::TryStreamExt;
+use std::sync::Arc;
+
+#[tokio::main(flavor = "multi_thread", worker_threads = 1)]
+pub async fn main() {
+    build_parquet();
+
+    let env = RuntimeEnvBuilder::new()
+        .with_disk_manager(DiskManagerConfig::default())
+        .with_memory_pool(Arc::new(FairSpillPool::new(100 * 1024 * 1024)))
+        .build_arc()
+        .unwrap();
+
+    let state = SessionStateBuilder::new().with_runtime_env(env).build();
+
+    let ctx = SessionContext::from(state);
+
+    ctx.register_parquet(
+        "big_strings",
+        "/tmp/big_strings.parquet",
+        ParquetReadOptions::default(),
+    )
+    .await
+    .unwrap();
+
+    let sql = "SELECT * FROM big_strings ORDER BY strings";
+    println!("Sorting strings");
+    ctx.sql(sql)
+        .await
+        .unwrap()
+        .execute_stream()
+        .await
+        .unwrap()
+        .try_for_each(|_| std::future::ready(Ok(())))
+        .await
+        .unwrap();
+}
+
+fn build_parquet() {
+    if std::fs::File::open("/tmp/big_strings.parquet").is_ok() {
+        println!("Using existing file at /tmp/big_strings.parquet");
+        return;
+    }
+    println!("Generating test file at /tmp/big_strings.parquet");
+    let file = std::fs::File::create("/tmp/big_strings.parquet").unwrap();
+    let schema = Arc::new(Schema::new(vec![Field::new(
+        "strings",
+        DataType::Utf8,
+        false,
+    )]));
+    let mut writer = ArrowWriter::try_new(file, schema.clone(), None).unwrap();
+
+    for batch_idx in 0..100 {
+        println!("Generating batch {} of 100", batch_idx);
+        let mut string_array_builder =
+            StringBuilder::with_capacity(1024 * 1024, 1024 * 1024 * 3 * 14);
+        for i in 0..(1024 * 1024) {
+            string_array_builder
+                .append_value(format!("string-{}string-{}string-{}", i, i, i));
+        }
+        let array = Arc::new(string_array_builder.finish());
+        let batch = RecordBatch::try_new(schema.clone(), vec![array]).unwrap();
+        writer.write(&batch).unwrap();
+    }
+    writer.close().unwrap();
+}
diff --git a/datafusion/physical-plan/src/sorts/sort.rs b/datafusion/physical-plan/src/sorts/sort.rs
index 33c8a2b2fee3..574737bbbaf8 100644
--- a/datafusion/physical-plan/src/sorts/sort.rs
+++ b/datafusion/physical-plan/src/sorts/sort.rs
@@ -402,6 +402,7 @@ impl ExternalSorter {
     ///
     /// Returns the amount of memory freed.
     async fn spill(&mut self) -> Result<usize> {
+        println!("Spilling");
         // we could always get a chance to free some memory as long as we are holding some
         if self.in_mem_batches.is_empty() {
             return Ok(0);
@@ -437,6 +438,13 @@ impl ExternalSorter {
         // allocation.
         self.merge_reservation.free();
 
+        let size: usize = self
+            .in_mem_batches
+            .iter()
+            .map(get_record_batch_memory_size)
+            .sum();
+        println!("Before sorting we have {} bytes of unsorted data", size);
+
         self.in_mem_batches = self
             .in_mem_sort_stream(self.metrics.baseline.intermediate())?
             .try_collect()
@@ -448,9 +456,12 @@ impl ExternalSorter {
             .map(get_record_batch_memory_size)
             .sum();
 
+        println!("After sorting we now have {} bytes of sorted data", size);
+
         // Reserve headroom for next sort/merge
         self.reserve_memory_for_merge()?;
 
+        // This is where the error occurs
         self.reservation.try_resize(size)?;
         self.in_mem_batches_sorted = true;
         Ok(())