diff --git a/vscode/microsoft-kiota/src/extension.ts b/vscode/microsoft-kiota/src/extension.ts
index cfc16c15b5..45576ea78b 100644
--- a/vscode/microsoft-kiota/src/extension.ts
+++ b/vscode/microsoft-kiota/src/extension.ts
@@ -201,7 +201,7 @@ export async function activate(
       `${treeViewId}.searchOrOpenApiDescription`,
       async () => {
         const yesAnswer = vscode.l10n.t("Yes, override it");
-        if (!openApiTreeProvider.isEmpty() && openApiTreeProvider.hasSelectionChanged()) {
+        if (!openApiTreeProvider.isEmpty() && openApiTreeProvider.hasChanges()) {
           const response = await vscode.window.showWarningMessage(
             vscode.l10n.t(
               "Before adding a new API description, consider that your changes and current selection will be lost."),
@@ -249,6 +249,7 @@ export async function activate(
      clientOrPluginObject = clientObject;
      workspaceGenerationType = generationType;
      await loadEditPaths(clientOrPluginKey, clientObject, openApiTreeProvider);
+     openApiTreeProvider.resetInitialState();
      await updateTreeViewIcons(treeViewId, false, true);
     }),
     registerCommandWithTelemetry(reporter,`${treeViewId}.regenerateButton`, async () => {
@@ -441,10 +442,10 @@ export async function activate(
   async function displayGenerationResults(context: vscode.ExtensionContext, openApiTreeProvider: OpenApiTreeProvider, config: any, outputPath: string) {
     const clientNameOrPluginName = config.clientClassName || config.pluginName;
     openApiTreeProvider.refreshView();
-    openApiTreeProvider.setSelectionChanged(false);
     const workspaceJsonPath = getWorkspaceJsonPath();
     await loadLockFile({fsPath: workspaceJsonPath}, openApiTreeProvider, clientNameOrPluginName );
     await vscode.commands.executeCommand('kiota.workspace.refresh');
+    openApiTreeProvider.resetInitialState();
     await updateTreeViewIcons(treeViewId, false, true);
   }
   async function regenerateClient(clientKey: string, clientObject:any, settings: ExtensionSettings,  selectedPaths?: string[]): Promise<void> {
@@ -480,7 +481,7 @@ export async function activate(
     return result;
     });
   void vscode.window.showInformationMessage(`Client ${clientKey} re-generated successfully.`);
-  openApiTreeProvider.setSelectionChanged(false);
+  openApiTreeProvider.resetInitialState();
   }
   async function regeneratePlugin(clientKey: string, clientObject:any, settings: ExtensionSettings,  selectedPaths?: string[]) {
     const pluginTypes =  Array.isArray(clientObject.types) ? parsePluginType(clientObject.types) : [KiotaPluginType.ApiPlugin];
@@ -514,7 +515,7 @@ export async function activate(
       return result;
     });
     void vscode.window.showInformationMessage(`Plugin ${clientKey} re-generated successfully.`);
-    openApiTreeProvider.setSelectionChanged(false);
+    openApiTreeProvider.resetInitialState();
   }
 
   // create a new status bar item that we can now manage
diff --git a/vscode/microsoft-kiota/src/openApiTreeProvider.ts b/vscode/microsoft-kiota/src/openApiTreeProvider.ts
index 9763cfa1e8..c84ae71c3a 100644
--- a/vscode/microsoft-kiota/src/openApiTreeProvider.ts
+++ b/vscode/microsoft-kiota/src/openApiTreeProvider.ts
@@ -3,6 +3,7 @@ import * as os from 'os';
 import * as path from 'path';
 import * as vscode from 'vscode';
 import * as rpc from 'vscode-jsonrpc/node';
+import * as crypto from 'crypto';
 import { 
     ClientObjectProperties, 
     ClientOrPluginProperties, 
@@ -23,7 +24,7 @@ export class OpenApiTreeProvider implements vscode.TreeDataProvider<OpenApiTreeN
     private _onDidChangeTreeData: vscode.EventEmitter<OpenApiTreeNode | undefined | null | void> = new vscode.EventEmitter<OpenApiTreeNode | undefined | null | void>();
     readonly onDidChangeTreeData: vscode.Event<OpenApiTreeNode | undefined | null | void> = this._onDidChangeTreeData.event;
     private apiTitle?: string;
-    private selectionChanged: boolean = false;
+    private initialStateHash: string = '';
     constructor(
         private readonly context: vscode.ExtensionContext,
         private readonly settingsGetter: () => ExtensionSettings,
@@ -168,17 +169,12 @@ export class OpenApiTreeProvider implements vscode.TreeDataProvider<OpenApiTreeN
     public isEmpty(): boolean {
         return this.rawRootNode === undefined;
     }
-    public hasSelectionChanged(): boolean {
-        return this.selectionChanged;
-    }
-    public setSelectionChanged(state: boolean) {
-        this.selectionChanged = state;
-    }
     public async setDescriptionUrl(descriptionUrl: string): Promise<void> {
         this.closeDescription(false);
         this._descriptionUrl = descriptionUrl;
         const settings = this.settingsGetter();
         await this.loadNodes(settings.clearCache);
+        this.initialStateHash = this.hashDescription(this.rawRootNode);
         this.refreshView();
     }
     public get descriptionUrl(): string {
@@ -196,7 +192,6 @@ export class OpenApiTreeProvider implements vscode.TreeDataProvider<OpenApiTreeN
     }
     private selectInternal(apiNode: KiotaOpenApiNode, selected: boolean, recursive: boolean) {
         apiNode.selected = selected;
-        this.setSelectionChanged(true);
         const isOperationNode = apiNode.isOperation ?? false;
         if (recursive) {
             apiNode.children.forEach(x => this.selectInternal(x, selected, recursive));
@@ -206,7 +201,6 @@ export class OpenApiTreeProvider implements vscode.TreeDataProvider<OpenApiTreeN
             const parent = this.findApiNode(getPathSegments(trimOperation(apiNode.path)), this.rawRootNode);
             if (parent) {
                 parent.selected = selected;
-                this.setSelectionChanged(true);
             }
         }
     }
@@ -238,6 +232,23 @@ export class OpenApiTreeProvider implements vscode.TreeDataProvider<OpenApiTreeN
         return undefined;
     }
 
+    private hashDescription(description: KiotaOpenApiNode | undefined): string {
+        const json = JSON.stringify(description);
+        return crypto.createHash('sha256').update(json).digest('hex');
+    }
+
+    public hasChanges(): boolean {
+        if (!this.rawRootNode) {
+            return false;
+        }
+        const currentStateHash = this.hashDescription(this.rawRootNode);
+        return currentStateHash !== this.initialStateHash;
+    }
+    
+    public resetInitialState(): void {
+        this.initialStateHash = this.hashDescription(this.rawRootNode);
+    }
+
     refreshView(): void {
         this._onDidChangeTreeData.fire();
     }