diff --git a/src/daft-io/src/lib.rs b/src/daft-io/src/lib.rs
index d83a486e65..e83a9768a9 100644
--- a/src/daft-io/src/lib.rs
+++ b/src/daft-io/src/lib.rs
@@ -84,6 +84,12 @@ pub enum Error {
     #[snafu(display("Unhandled Error for path: {}\nDetails:\n{}", path, msg))]
     Unhandled { path: String, msg: String },
 
+    #[snafu(
+        display("Error sending data over a tokio channel: {}", source),
+        context(false)
+    )]
+    UnableToSendDataOverChannel { source: DynError },
+
     #[snafu(display("Error joining spawned task: {}", source), context(false))]
     JoinError { source: tokio::task::JoinError },
 }
diff --git a/src/daft-io/src/object_io.rs b/src/daft-io/src/object_io.rs
index d793c129c8..3e624cb27f 100644
--- a/src/daft-io/src/object_io.rs
+++ b/src/daft-io/src/object_io.rs
@@ -127,18 +127,22 @@ pub(crate) async fn recursive_iter(
             let mut s = match s {
                 Ok(s) => s,
                 Err(e) => {
-                    tx.send(Err(e)).await.unwrap();
-                    return;
+                    tx.send(Err(e)).await.map_err(|se| {
+                        super::Error::UnableToSendDataOverChannel { source: se.into() }
+                    })?;
+                    return super::Result::<_, super::Error>::Ok(());
                 }
             };
             let tx = &tx;
             while let Some(tr) = s.next().await {
-                let tr = tr;
                 if let Ok(ref tr) = tr && matches!(tr.filetype, FileType::Directory) {
                     add_to_channel(source.clone(), tx.clone(), tr.filepath.clone())
                 }
-                tx.send(tr).await.unwrap();
+                tx.send(tr)
+                    .await
+                    .map_err(|e| super::Error::UnableToSendDataOverChannel { source: e.into() })?;
             }
+            super::Result::Ok(())
         });
     }
 
diff --git a/src/daft-io/src/s3_like.rs b/src/daft-io/src/s3_like.rs
index cc1c9c8c71..f9bf4ec16b 100644
--- a/src/daft-io/src/s3_like.rs
+++ b/src/daft-io/src/s3_like.rs
@@ -699,14 +699,15 @@ impl ObjectSource for S3LikeSource {
             }),
         }?;
         let key = parsed.path();
-
-        let key = key.strip_prefix('/').unwrap_or("");
+        let key = key
+            .trim_start_matches(delimiter)
+            .trim_end_matches(delimiter);
         let key = if key.is_empty() {
             "".to_string()
         } else {
-            let key = key.strip_suffix('/').unwrap_or(key);
-            format!("{key}/")
+            format!("{key}{delimiter}")
         };
+
         // assume its a directory first
         let lsr = {
             let permit = self
@@ -725,26 +726,25 @@ impl ObjectSource for S3LikeSource {
             )
             .await?
         };
-        if lsr.files.is_empty() && key.contains('/') {
+        if lsr.files.is_empty() && key.contains(delimiter) {
             let permit = self
                 .connection_pool_sema
                 .acquire()
                 .await
                 .context(UnableToGrabSemaphoreSnafu)?;
             // Might be a File
-            let split = key.rsplit_once('/');
-            let (new_key, _) = split.unwrap();
+            let key = key.trim_end_matches(delimiter);
             let mut lsr = self
                 ._list_impl(
                     permit,
                     bucket,
-                    new_key,
+                    key,
                     delimiter.into(),
                     continuation_token.map(String::from),
                     &self.default_region,
                 )
                 .await?;
-            let target_path = format!("s3://{bucket}/{new_key}");
+            let target_path = format!("s3://{bucket}/{key}");
             lsr.files.retain(|f| f.filepath == target_path);
 
             if lsr.files.is_empty() {
diff --git a/tests/integration/io/test_list_files_s3_minio.py b/tests/integration/io/test_list_files_s3_minio.py
index 7a1744c307..66aae58418 100644
--- a/tests/integration/io/test_list_files_s3_minio.py
+++ b/tests/integration/io/test_list_files_s3_minio.py
@@ -70,6 +70,24 @@ def test_single_file_directory_listing(minio_io_config, recursive):
         compare_s3_result(daft_ls_result, s3fs_result)
 
 
+@pytest.mark.integration()
+@pytest.mark.parametrize(
+    "recursive",
+    [False, True],
+)
+def test_single_file_directory_listing_trailing(minio_io_config, recursive):
+    bucket_name = "bucket"
+    with minio_create_bucket(minio_io_config, bucket_name=bucket_name) as fs:
+        files = ["a", "b/bb", "c/cc/ccc"]
+        for name in files:
+            fs.write_bytes(f"s3://{bucket_name}/{name}", b"")
+        daft_ls_result = io_list(f"s3://{bucket_name}/c/cc///", io_config=minio_io_config, recursive=recursive)
+        fs.invalidate_cache()
+        s3fs_result = s3fs_recursive_list(fs, path=f"s3://{bucket_name}/c/cc///")
+        assert len(daft_ls_result) == 1
+        compare_s3_result(daft_ls_result, s3fs_result)
+
+
 @pytest.mark.integration()
 @pytest.mark.parametrize(
     "recursive",