diff --git a/l10n/bundle.l10n.json b/l10n/bundle.l10n.json
index 9eb91fa082..82b9df2845 100644
--- a/l10n/bundle.l10n.json
+++ b/l10n/bundle.l10n.json
@@ -191,6 +191,9 @@
   "Fix All: ": "Fix All: ",
   "Pick a fix all scope": "Pick a fix all scope",
   "Fix All Code Action": "Fix All Code Action",
+  "No": "No",
+  ".NET: Generate Assets for Build and Debug": ".NET: Generate Assets for Build and Debug",
+  "The '{0}' command is not reccomended to be used when C# Dev Kit extension is installed. Would you like build and debug using a dynamic configuration instead?": "The '{0}' command is not reccomended to be used when C# Dev Kit extension is installed. Would you like build and debug using a dynamic configuration instead?",
   "Failed to set extension directory": "Failed to set extension directory",
   "Failed to set debugadpter directory": "Failed to set debugadpter directory",
   "Failed to set install complete file path": "Failed to set install complete file path",
diff --git a/package.json b/package.json
index d55402c5e8..877ab1de5f 100644
--- a/package.json
+++ b/package.json
@@ -1828,7 +1828,7 @@
         "command": "dotnet.generateAssets",
         "title": "%command.dotnet.generateAssets.currentProject%",
         "category": ".NET",
-        "enablement": "dotnet.server.activationContext == 'Roslyn' || dotnet.server.activationContext == 'OmniSharp'"
+        "enablement": "dotnet.server.activationContext == 'RoslynDevKit' || dotnet.server.activationContext == 'Roslyn' || dotnet.server.activationContext == 'OmniSharp'"
       },
       {
         "command": "dotnet.restore.project",
diff --git a/src/lsptoolshost/debugger/debugger.ts b/src/lsptoolshost/debugger/debugger.ts
index 01c5b6d2c3..79e706847c 100644
--- a/src/lsptoolshost/debugger/debugger.ts
+++ b/src/lsptoolshost/debugger/debugger.ts
@@ -51,9 +51,59 @@ export function registerDebugger(
     context.subscriptions.push(
         vscode.debug.registerDebugConfigurationProvider('coreclr', dotnetWorkspaceConfigurationProvider)
     );
+
     context.subscriptions.push(
-        vscode.commands.registerCommand('dotnet.generateAssets', async (selectedIndex) =>
-            generateAssets(workspaceInformationProvider, selectedIndex)
-        )
+        vscode.commands.registerCommand('dotnet.generateAssets', async (selectedIndex) => {
+            if (!(await promptForDevKitDebugConfigurations())) {
+                return;
+            }
+
+            await generateAssets(workspaceInformationProvider, selectedIndex);
+        })
     );
 }
+
+async function promptForDevKitDebugConfigurations(): Promise<boolean> {
+    if (getCSharpDevKit()) {
+        let result: boolean | undefined = undefined;
+
+        while (result === undefined) {
+            const labelYes = vscode.l10n.t('Yes');
+            const labelNo = vscode.l10n.t('No');
+            const labelMoreInfo = vscode.l10n.t('More Information');
+            const title: string = vscode.l10n.t('.NET: Generate Assets for Build and Debug');
+
+            const dialogResult = await vscode.window.showInformationMessage(
+                title,
+                {
+                    modal: true,
+                    detail: vscode.l10n.t(
+                        `The '{0}' command is not recommended to be used when C# Dev Kit extension is installed. Would you like build and debug using a dynamic configuration instead?`,
+                        title
+                    ),
+                },
+                labelYes,
+                labelNo,
+                labelMoreInfo
+            );
+
+            if (dialogResult === labelYes) {
+                await vscode.commands.executeCommand('workbench.action.debug.selectandstart', 'dotnet');
+                result = false;
+            } else if (dialogResult === labelNo) {
+                // User cancelled dialog and wishes to continue generating assets.
+                result = true;
+            } else if (dialogResult === labelMoreInfo) {
+                const launchjsonDescriptionURL = 'https://aka.ms/VSCode-CS-DynamicDebugConfig';
+                await vscode.env.openExternal(vscode.Uri.parse(launchjsonDescriptionURL));
+            } else if (dialogResult === undefined) {
+                // Do nothing, user closed the dialog.
+                result = false;
+            }
+        }
+
+        return result;
+    }
+
+    return false;
+}