diff --git a/packages/databricks-vscode/src/extension.ts b/packages/databricks-vscode/src/extension.ts
index 06fe54a02..f53ae62f9 100644
--- a/packages/databricks-vscode/src/extension.ts
+++ b/packages/databricks-vscode/src/extension.ts
@@ -34,6 +34,7 @@ import {
 } from "./workspace-fs";
 import {generateBundleSchema} from "./bundle/GenerateBundle";
 import {CustomWhenContext} from "./vscode-objs/CustomWhenContext";
+import {WorkspaceStateManager} from "./vscode-objs/WorkspaceState";
 
 export async function activate(
     context: ExtensionContext
@@ -85,8 +86,11 @@ export async function activate(
         metadata: packageMetadata,
     });
 
+    const workspaceStateManager = new WorkspaceStateManager(context);
+
     const configureAutocomplete = new ConfigureAutocomplete(
         context,
+        workspaceStateManager,
         workspace.workspaceFolders[0].uri.fsPath
     );
     context.subscriptions.push(
@@ -115,6 +119,7 @@ export async function activate(
     );
     const workspaceFsCommands = new WorkspaceFsCommands(
         workspace.workspaceFolders[0].uri,
+        workspaceStateManager,
         connectionManager,
         workspaceFsDataProvider
     );
diff --git a/packages/databricks-vscode/src/language/ConfigureAutocomplete.ts b/packages/databricks-vscode/src/language/ConfigureAutocomplete.ts
index 997594371..39561b276 100644
--- a/packages/databricks-vscode/src/language/ConfigureAutocomplete.ts
+++ b/packages/databricks-vscode/src/language/ConfigureAutocomplete.ts
@@ -12,6 +12,7 @@ import {
     ConfigurationTarget,
 } from "vscode";
 import {Loggers} from "../logger";
+import {WorkspaceStateManager} from "../vscode-objs/WorkspaceState";
 
 type Resource = Uri | undefined;
 
@@ -65,6 +66,7 @@ export class ConfigureAutocomplete implements Disposable {
 
     constructor(
         private readonly context: ExtensionContext,
+        private readonly workspaceState: WorkspaceStateManager,
         private readonly workspaceFolder: string
     ) {
         this.configure();
@@ -113,12 +115,7 @@ export class ConfigureAutocomplete implements Disposable {
     }
 
     private async configure(force = false) {
-        if (
-            !force &&
-            this.context.workspaceState.get<boolean>(
-                "databricks.autocompletion.skipConfigure"
-            )
-        ) {
+        if (!force && this.workspaceState.skipAutocompleteConfigure) {
             return;
         }
 
@@ -181,10 +178,7 @@ export class ConfigureAutocomplete implements Disposable {
         }
 
         if (choice === "Never for this workspace") {
-            this.context.workspaceState.update(
-                "databricks.autocompletion.skipConfigure",
-                true
-            );
+            this.workspaceState.skipAutocompleteConfigure = true;
             return;
         }
 
diff --git a/packages/databricks-vscode/src/vscode-objs/WorkspaceState.ts b/packages/databricks-vscode/src/vscode-objs/WorkspaceState.ts
new file mode 100644
index 000000000..fd640ae3c
--- /dev/null
+++ b/packages/databricks-vscode/src/vscode-objs/WorkspaceState.ts
@@ -0,0 +1,31 @@
+import {randomUUID} from "crypto";
+import {ExtensionContext} from "vscode";
+
+export class WorkspaceStateManager {
+    constructor(private context: ExtensionContext) {}
+
+    get skipAutocompleteConfigure() {
+        return this.context.workspaceState.get(
+            "databricks.autocompletion.skipConfigure",
+            false
+        );
+    }
+
+    set skipAutocompleteConfigure(value: boolean) {
+        this.context.workspaceState.update(
+            "databricks.autocompletion.skipConfigure",
+            true
+        );
+    }
+
+    get fixedUUID() {
+        let uuid = this.context.workspaceState.get<string>(
+            "databricks.fixedUUID"
+        );
+        if (!uuid) {
+            uuid = randomUUID();
+            this.context.workspaceState.update("databricks.fixedUUID", uuid);
+        }
+        return uuid;
+    }
+}
diff --git a/packages/databricks-vscode/src/workspace-fs/WorkspaceFsCommands.ts b/packages/databricks-vscode/src/workspace-fs/WorkspaceFsCommands.ts
index 9c5cf8fe8..01590d456 100644
--- a/packages/databricks-vscode/src/workspace-fs/WorkspaceFsCommands.ts
+++ b/packages/databricks-vscode/src/workspace-fs/WorkspaceFsCommands.ts
@@ -12,15 +12,44 @@ import {Loggers} from "../logger";
 import {workspaceConfigs} from "../vscode-objs/WorkspaceConfigs";
 import {createDirWizard} from "./createDirectoryWizard";
 import {WorkspaceFsDataProvider} from "./WorkspaceFsDataProvider";
+import path from "node:path";
+import {WorkspaceStateManager} from "../vscode-objs/WorkspaceState";
 
 export class WorkspaceFsCommands implements Disposable {
     private disposables: Disposable[] = [];
 
     constructor(
         private _workspaceFolder: Uri,
+        private readonly _workspaceState: WorkspaceStateManager,
         private _connectionManager: ConnectionManager,
         private _workspaceFsDataProvider: WorkspaceFsDataProvider
-    ) {}
+    ) {
+        this.disposables.push(
+            this._connectionManager.onDidChangeState(async (state) => {
+                if (
+                    state !== "CONNECTED" ||
+                    !workspaceConfigs.enableFilesInWorkspace ||
+                    this._connectionManager.syncDestinationMapper !== undefined
+                ) {
+                    return;
+                }
+
+                const root = await this.getValidRoot(
+                    this._connectionManager.databricksWorkspace?.currentFsRoot
+                        .path
+                );
+
+                const element = await root?.mkdir(
+                    `${path.basename(
+                        this._workspaceFolder.fsPath
+                    )}-${this._workspaceState.fixedUUID.slice(0, 8)}`
+                );
+                if (element) {
+                    this.attachSyncDestination(element);
+                }
+            })
+        );
+    }
 
     async attachSyncDestination(element: WorkspaceFsEntity) {
         await this._connectionManager.attachSyncDestination(