diff --git a/Extensions/Ansible/Src/Tasks/Ansible/ansibleRemoteMachineInterface.ts b/Extensions/Ansible/Src/Tasks/Ansible/ansibleRemoteMachineInterface.ts
index b1a61e4f3..e91f0ae8f 100644
--- a/Extensions/Ansible/Src/Tasks/Ansible/ansibleRemoteMachineInterface.ts
+++ b/Extensions/Ansible/Src/Tasks/Ansible/ansibleRemoteMachineInterface.ts
@@ -40,16 +40,15 @@ export class ansibleRemoteMachineInterface extends ansibleCommandLineInterface {
         if (!ansibleUtils.testIfFileExist(path.join(playbookRoot,playbookFile))) {
             throw tl.loc('PlaybookNotPresent', playbookFile, playbookRoot);
         }
-        var playbookFullPath = playbookRoot + '/' + playbookFile;
-        var remotePlaybookRoot = '/tmp/' + path.basename(playbookFile);
+        var remotePlaybookRoot = '/tmp/' + path.basename(playbookRoot);
         tl.debug('ansiblePlaybookRootPath = ' + '"' + remotePlaybookRoot + '"');
 
         let scpConfig = this._sshConfig || {};
         scpConfig.path = remotePlaybookRoot;
         tl.debug('Copying playbook to ansible machine.');
-        this._playbookPath = remotePlaybookRoot;
+        this._playbookPath = remotePlaybookRoot + "/" + playbookFile;
         this._cleanupCmd.push('rm -rf ' + remotePlaybookRoot);
-        await ansibleUtils.copyFileToRemoteMachine(playbookFullPath,remotePlaybookRoot, scpConfig);
+        await ansibleUtils.copyFileToRemoteMachine(playbookRoot, remotePlaybookRoot, scpConfig);
     }
 
     private async copyInventoryAndSetPathForAgentAsSource() {
diff --git a/Extensions/Ansible/Src/Tasks/Ansible/ansibleUtils.ts b/Extensions/Ansible/Src/Tasks/Ansible/ansibleUtils.ts
index b503254c5..ffb612888 100644
--- a/Extensions/Ansible/Src/Tasks/Ansible/ansibleUtils.ts
+++ b/Extensions/Ansible/Src/Tasks/Ansible/ansibleUtils.ts
@@ -1,6 +1,7 @@
 import tl = require("azure-pipelines-task-lib/task");
 import Q = require("q");
 import util = require("util");
+const fs = require('fs');
 import querystring = require('querystring');
 import * as SftpClient from 'ssh2-sftp-client';
 
@@ -35,11 +36,38 @@ export async function copyFileToRemoteMachine(src: string, dest: string, sftpCon
 
     try {
         await sftpClient.connect(sftpConfig);
-        await sftpClient.put(src, dest);
-        tl.debug('Copied script file to remote machine at: ${dest}');
+
+        // Upload
+        const isDirectory = fs.lstatSync(src).isDirectory();
+    
+        if (isDirectory) {
+            // Make sure the remote directory exists
+            try {
+                await sftpClient.mkdir(dest, true); // recursive = true
+            } catch (err) {
+                if (err.code !== 4 && !err.message.includes('Failure')) {
+                  throw err;
+                }
+                // Check if directory really exists
+                await sftpClient.stat(dest);
+                console.log(`Remote directory exists: ${dest}`);
+            }
+          tl.debug(`Copying directory to remote machine at: ${dest}`);
+          await sftpClient.uploadDir(src, dest);
+          tl.debug(`Copied directory to remote machine at: ${dest}`);
+        } else {
+          tl.debug(`Copying file to remote machine at: ${dest}`); 
+          try {
+            await sftpClient.put(src, dest);
+          } catch (err) {
+            console.error('PUT failed:', err.message);
+          }
+          tl.debug(`Copied file to remote machine at: ${dest}`);
+        }
+        
         defer.resolve('0');
     } catch (err) {
-        defer.reject(tl.loc('RemoteCopyFailed', err));
+            defer.reject(tl.loc('RemoteCopyFailed', err));
     }
 
     try {
diff --git a/Extensions/Ansible/Src/Tasks/Ansible/task.json b/Extensions/Ansible/Src/Tasks/Ansible/task.json
index 7759897e2..bed8f8145 100644
--- a/Extensions/Ansible/Src/Tasks/Ansible/task.json
+++ b/Extensions/Ansible/Src/Tasks/Ansible/task.json
@@ -17,7 +17,7 @@
     "version": {
         "Major": 0,
         "Minor": 256,
-        "Patch": 0
+        "Patch": 5
     },
     "demands": [],
     "instanceNameFormat": "Run playbook",
diff --git a/Extensions/Ansible/Src/vss-extension.json b/Extensions/Ansible/Src/vss-extension.json
index a8f08c30a..e8e1b18c4 100644
--- a/Extensions/Ansible/Src/vss-extension.json
+++ b/Extensions/Ansible/Src/vss-extension.json
@@ -3,7 +3,7 @@
   "id": "vss-services-ansible",
   "name": "Ansible",
   "publisher": "ms-vscs-rm",
-  "version": "0.256.2",
+  "version": "0.256.5",
   "public": true,
   "description": "This extension executes an Ansible playbook using a specified inventory via command line interface",
   "_description.comment": "The below format to define extensions is currently in preview and may change in future.",