diff --git a/internal/plugin/loopback/storage.go b/internal/plugin/loopback/storage.go
index 8ff18ef8e..984ef923c 100644
--- a/internal/plugin/loopback/storage.go
+++ b/internal/plugin/loopback/storage.go
@@ -7,7 +7,9 @@ import (
 	"bytes"
 	"context"
 	"crypto/sha256"
+	"fmt"
 	"io"
+	"strings"
 	"sync"
 	"time"
 
@@ -232,8 +234,12 @@ func (l *LoopbackStorage) headObject(ctx context.Context, req *plgpb.HeadObjectR
 			return nil, status.Errorf(err.errCode, "%s: %s", op, err.errMsg)
 		}
 	}
+	var contentLength int64
+	if object.contentLength != nil {
+		contentLength = *object.contentLength
+	}
 	return &plgpb.HeadObjectResponse{
-		ContentLength: *object.contentLength,
+		ContentLength: contentLength,
 		LastModified:  timestamppb.New(*object.lastModified),
 	}, nil
 }
@@ -359,6 +365,19 @@ func (l *LoopbackStorage) putObject(stream plgpb.StoragePluginService_PutObjectS
 		}
 		contentLength := int64(len(objectData))
 		lastModified := time.Now()
+
+		// Ensure all the directories within the object key exist
+		parts := strings.Split(request.Request.GetKey(), "/")
+		tempPath := request.Request.GetBucket().GetBucketPrefix()
+		for _, p := range parts[:len(parts)-1] {
+			// Directories should have trailing `/` in the key
+			tempPath = fmt.Sprintf("%v%v/", tempPath, p)
+			bucket[ObjectName(tempPath)] = &storagePluginStorageInfo{
+				lastModified: &lastModified,
+			}
+		}
+
+		// Now insert the object
 		objectPath := ObjectName(request.Request.GetBucket().GetBucketPrefix() + request.Request.GetKey())
 		bucket[objectPath] = &storagePluginStorageInfo{
 			DataChunks:    objectChunks,
diff --git a/internal/plugin/loopback/storage_test.go b/internal/plugin/loopback/storage_test.go
index da046c8a9..c7b66902a 100644
--- a/internal/plugin/loopback/storage_test.go
+++ b/internal/plugin/loopback/storage_test.go
@@ -813,6 +813,23 @@ func TestLoopbackPutObject(t *testing.T) {
 				},
 			},
 		},
+		{
+			name: "valid object with dir in key",
+			dataChunks: []Chunk{
+				[]byte("THIS IS A MOCKED OBJECT"),
+			},
+			request: &plgpb.PutObjectRequest{
+				Data: &plgpb.PutObjectRequest_Request{
+					Request: &plgpb.PutObjectMetadata{
+						Bucket: &storagebuckets.StorageBucket{
+							BucketName: "aws_s3_mock",
+							Secrets:    secrets,
+						},
+						Key: "foo/bar/zoo/mocked_object",
+					},
+				},
+			},
+		},
 		{
 			name: "valid object w/ prefix",
 			dataChunks: []Chunk{
@@ -948,7 +965,7 @@ func TestLoopbackStoragePlugin(t *testing.T) {
 		Data: &plgpb.PutObjectRequest_Request{
 			Request: &plgpb.PutObjectMetadata{
 				Bucket: bucket,
-				Key:    "mock_object",
+				Key:    "dir1/mock_object",
 			},
 		},
 	})
@@ -969,9 +986,19 @@ func TestLoopbackStoragePlugin(t *testing.T) {
 	require.NoError(err)
 	assert.EqualValues(hash.Sum(nil), putResponse.GetChecksumSha_256())
 
+	// Check directory was created
 	headResponse, err := plg.HeadObject(context.Background(), &plgpb.HeadObjectRequest{
 		Bucket: bucket,
-		Key:    "mock_object",
+		Key:    "dir1/",
+	})
+	require.NoError(err)
+	require.NotNil(headResponse)
+	require.NotNil(headResponse.LastModified)
+	require.Equal(int64(0), headResponse.ContentLength)
+
+	headResponse, err = plg.HeadObject(context.Background(), &plgpb.HeadObjectRequest{
+		Bucket: bucket,
+		Key:    "dir1/mock_object",
 	})
 	require.NoError(err)
 	require.NotNil(headResponse)
@@ -980,7 +1007,7 @@ func TestLoopbackStoragePlugin(t *testing.T) {
 
 	getObjectStream, err := client.GetObject(context.Background(), &plgpb.GetObjectRequest{
 		Bucket: bucket,
-		Key:    "mock_object",
+		Key:    "dir1/mock_object",
 	})
 	assert.NoError(err)