diff --git a/datafusion/datasource/src/url.rs b/datafusion/datasource/src/url.rs
index bddfdbcc06d1..189d0c19f086 100644
--- a/datafusion/datasource/src/url.rs
+++ b/datafusion/datasource/src/url.rs
@@ -242,25 +242,51 @@ impl ListingTableUrl {
     ) -> Result<BoxStream<'a, Result<ObjectMeta>>> {
         let exec_options = &ctx.config_options().execution;
         let ignore_subdirectory = exec_options.listing_table_ignore_subdirectory;
-        // If the prefix is a file, use a head request, otherwise list
-        let list = match self.is_collection() {
-            true => match ctx.runtime_env().cache_manager.get_list_files_cache() {
-                None => store.list(Some(&self.prefix)),
+
+        async fn list_with_cache<'b>(
+            ctx: &'b dyn Session,
+            store: &'b dyn ObjectStore,
+            prefix: &'b Path,
+        ) -> Result<BoxStream<'b, Result<ObjectMeta>>> {
+            match ctx.runtime_env().cache_manager.get_list_files_cache() {
+                None => Ok(store
+                    .list(Some(prefix))
+                    .map(|res| res.map_err(DataFusionError::ObjectStore))
+                    .boxed()),
                 Some(cache) => {
-                    if let Some(res) = cache.get(&self.prefix) {
+                    if let Some(res) = cache.get(prefix) {
                         debug!("Hit list all files cache");
-                        futures::stream::iter(res.as_ref().clone().into_iter().map(Ok))
-                            .boxed()
+                        Ok(futures::stream::iter(
+                            res.as_ref().clone().into_iter().map(Ok),
+                        )
+                        .map(|res| res.map_err(DataFusionError::ObjectStore))
+                        .boxed())
                     } else {
-                        let list_res = store.list(Some(&self.prefix));
-                        let vec = list_res.try_collect::<Vec<ObjectMeta>>().await?;
-                        cache.put(&self.prefix, Arc::new(vec.clone()));
-                        futures::stream::iter(vec.into_iter().map(Ok)).boxed()
+                        let vec = store
+                            .list(Some(prefix))
+                            .map(|res| res.map_err(DataFusionError::ObjectStore))
+                            .try_collect::<Vec<ObjectMeta>>()
+                            .await?;
+                        cache.put(prefix, Arc::new(vec.clone()));
+                        Ok(futures::stream::iter(vec.into_iter().map(Ok))
+                            .map(|res| res.map_err(DataFusionError::ObjectStore))
+                            .boxed())
                     }
                 }
-            },
-            false => futures::stream::once(store.head(&self.prefix)).boxed(),
+            }
+        }
+
+        let list: BoxStream<'a, Result<ObjectMeta>> = if self.is_collection() {
+            list_with_cache(ctx, store, &self.prefix).await?
+        } else {
+            match store.head(&self.prefix).await {
+                Ok(meta) => futures::stream::once(async { Ok(meta) })
+                    .map(|res| res.map_err(DataFusionError::ObjectStore))
+                    .boxed(),
+                Err(_) => list_with_cache(ctx, store, &self.prefix).await?,
+            }
         };
+
         Ok(list
             .try_filter(move |meta| {
                 let path = &meta.location;
@@ -268,7 +294,6 @@ impl ListingTableUrl {
                 let glob_match = self.contains(path, ignore_subdirectory);
                 futures::future::ready(extension_match && glob_match)
             })
-            .map_err(DataFusionError::ObjectStore)
             .boxed())
     }