diff --git a/web/packages/teleport/src/lib/tdp/client.ts b/web/packages/teleport/src/lib/tdp/client.ts
index f570f559eaf18..1d1d93a212671 100644
--- a/web/packages/teleport/src/lib/tdp/client.ts
+++ b/web/packages/teleport/src/lib/tdp/client.ts
@@ -278,6 +278,7 @@ export default class Client extends EventEmitterWebAuthnSender {
             lastModified: BigInt(0),
             fileType: FileType.File,
             size: BigInt(0),
+            isEmpty: true,
             path: path,
           },
         });
@@ -306,6 +307,7 @@ export default class Client extends EventEmitterWebAuthnSender {
           lastModified: BigInt(0),
           fileType: FileType.File,
           size: BigInt(0),
+          isEmpty: true,
           path: req.path,
         },
       });
@@ -411,6 +413,7 @@ export default class Client extends EventEmitterWebAuthnSender {
       lastModified: BigInt(info.lastModified),
       fileType: info.kind === 'file' ? FileType.File : FileType.Directory,
       size: BigInt(info.size),
+      isEmpty: info.isEmpty,
       path: info.path,
     };
   }
diff --git a/web/packages/teleport/src/lib/tdp/codec.ts b/web/packages/teleport/src/lib/tdp/codec.ts
index 971073a8ee629..d90b3bd3877a7 100644
--- a/web/packages/teleport/src/lib/tdp/codec.ts
+++ b/web/packages/teleport/src/lib/tdp/codec.ts
@@ -221,11 +221,12 @@ export type SharedDirectoryListResponse = {
   fsoList: FileSystemObject[];
 };
 
-// | last_modified uint64 | size uint64 | file_type uint32 | path_length uint32 | path byte[] |
+// | last_modified uint64 | size uint64 | file_type uint32 | is_empty bool | path_length uint32 | path byte[] |
 export type FileSystemObject = {
   lastModified: bigint;
   size: bigint;
   fileType: FileType;
+  isEmpty: boolean;
   path: string;
 };
 
@@ -739,11 +740,12 @@ export default class Codec {
     return withFsoList.buffer;
   }
 
-  // | last_modified uint64 | size uint64 | file_type uint32 | path_length uint32 | path byte[] |
+  // | last_modified uint64 | size uint64 | file_type uint32 | is_empty bool | path_length uint32 | path byte[] |
   encodeFileSystemObject(fso: FileSystemObject): Message {
     const dataUtf8array = this.encoder.encode(fso.path);
 
-    const bufLen = 2 * uint64Length + 2 * uint32Length + dataUtf8array.length;
+    const bufLen =
+      byteLength + 2 * uint64Length + 2 * uint32Length + dataUtf8array.length;
     const buffer = new ArrayBuffer(bufLen);
     const view = new DataView(buffer);
     let offset = 0;
@@ -753,6 +755,8 @@ export default class Codec {
     offset += uint64Length;
     view.setUint32(offset, fso.fileType);
     offset += uint32Length;
+    view.setUint8(offset, fso.isEmpty ? 1 : 0);
+    offset += byteLength;
     view.setUint32(offset, dataUtf8array.length);
     offset += uint32Length;
     dataUtf8array.forEach(byte => {
diff --git a/web/packages/teleport/src/lib/tdp/sharedDirectoryManager.ts b/web/packages/teleport/src/lib/tdp/sharedDirectoryManager.ts
index 60b90e8a078da..16ceede2e7dc6 100644
--- a/web/packages/teleport/src/lib/tdp/sharedDirectoryManager.ts
+++ b/web/packages/teleport/src/lib/tdp/sharedDirectoryManager.ts
@@ -49,10 +49,27 @@ export class SharedDirectoryManager {
 
     const fileOrDir = await this.walkPath(path);
 
+    let isEmpty = true;
     if (fileOrDir.kind === 'directory') {
+      let dir = fileOrDir;
+      // If dir contains any files or directories, it will
+      // enter the loop below and we can register it as not
+      // empty. If it doesn't, it will skip over the loop.
+      // eslint-disable-next-line @typescript-eslint/no-unused-vars
+      for await (const _ of dir.keys()) {
+        isEmpty = false;
+        break;
+      }
+
       // Magic numbers are the values for directories where the true
       // value is unavailable, according to the TDP spec.
-      return { size: 4096, lastModified: 0, kind: fileOrDir.kind, path };
+      return {
+        size: 4096,
+        lastModified: 0,
+        kind: fileOrDir.kind,
+        isEmpty,
+        path,
+      };
     }
 
     let file = await fileOrDir.getFile();
@@ -60,6 +77,7 @@ export class SharedDirectoryManager {
       size: file.size,
       lastModified: file.lastModified,
       kind: fileOrDir.kind,
+      isEmpty,
       path,
     };
   }
@@ -260,5 +278,6 @@ export type FileOrDirInfo = {
   size: number; // bytes
   lastModified: number; // ms since unix epoch
   kind: 'file' | 'directory';
+  isEmpty: boolean;
   path: string;
 };