diff --git a/lib/pangea/widgets/chat/message_toolbar.dart b/lib/pangea/widgets/chat/message_toolbar.dart
index 0b27f41e2..a17e5b1e4 100644
--- a/lib/pangea/widgets/chat/message_toolbar.dart
+++ b/lib/pangea/widgets/chat/message_toolbar.dart
@@ -186,6 +186,8 @@ class MessageToolbarState extends State<MessageToolbar> {
     if (!subscribed) {
       child = MessageUnsubscribedCard(
         languageTool: getModeTitle(newMode),
+        mode: newMode,
+        toolbarModeStream: widget.toolbarModeStream,
       );
     } else {
       switch (currentMode) {
diff --git a/lib/pangea/widgets/chat/message_unsubscribed_card.dart b/lib/pangea/widgets/chat/message_unsubscribed_card.dart
index 542fb85e6..8219e2355 100644
--- a/lib/pangea/widgets/chat/message_unsubscribed_card.dart
+++ b/lib/pangea/widgets/chat/message_unsubscribed_card.dart
@@ -1,19 +1,40 @@
+import 'dart:async';
+
 import 'package:fluffychat/config/app_config.dart';
 import 'package:fluffychat/pangea/utils/bot_style.dart';
+import 'package:fluffychat/pangea/widgets/chat/message_toolbar.dart';
 import 'package:fluffychat/widgets/matrix.dart';
 import 'package:flutter/material.dart';
 import 'package:flutter_gen/gen_l10n/l10n.dart';
 
 class MessageUnsubscribedCard extends StatelessWidget {
   final String languageTool;
+  final MessageMode mode;
+  final StreamController<MessageMode> toolbarModeStream;
 
   const MessageUnsubscribedCard({
     super.key,
     required this.languageTool,
+    required this.mode,
+    required this.toolbarModeStream,
   });
 
   @override
   Widget build(BuildContext context) {
+    final bool inTrialWindow =
+        MatrixState.pangeaController.userController.inTrialWindow;
+
+    void onButtonPress() {
+      if (inTrialWindow) {
+        MatrixState.pangeaController.subscriptionController
+            .activateNewUserTrial();
+        toolbarModeStream.add(mode);
+      } else {
+        MatrixState.pangeaController.subscriptionController
+            .showPaywall(context);
+      }
+    }
+
     return Padding(
       padding: const EdgeInsets.fromLTRB(10, 10, 10, 0),
       child: Column(
@@ -27,17 +48,17 @@ class MessageUnsubscribedCard extends StatelessWidget {
           SizedBox(
             width: double.infinity,
             child: TextButton(
-              onPressed: () {
-                MatrixState.pangeaController.subscriptionController
-                    .showPaywall(context);
-                MatrixState.pAnyState.closeOverlay();
-              },
+              onPressed: onButtonPress,
               style: ButtonStyle(
                 backgroundColor: MaterialStateProperty.all<Color>(
                   (AppConfig.primaryColor).withOpacity(0.1),
                 ),
               ),
-              child: Text(L10n.of(context)!.getAccess),
+              child: Text(
+                inTrialWindow
+                    ? L10n.of(context)!.activateTrial
+                    : L10n.of(context)!.getAccess,
+              ),
             ),
           ),
         ],
diff --git a/lib/pangea/widgets/igc/paywall_card.dart b/lib/pangea/widgets/igc/paywall_card.dart
index 9b6cfd1b0..a9dc1a86d 100644
--- a/lib/pangea/widgets/igc/paywall_card.dart
+++ b/lib/pangea/widgets/igc/paywall_card.dart
@@ -14,6 +14,9 @@ class PaywallCard extends StatelessWidget {
 
   @override
   Widget build(BuildContext context) {
+    final bool inTrialWindow =
+        MatrixState.pangeaController.userController.inTrialWindow;
+
     return Column(
       mainAxisSize: MainAxisSize.max,
       crossAxisAlignment: CrossAxisAlignment.center,
@@ -40,8 +43,11 @@ class PaywallCard extends StatelessWidget {
                 width: double.infinity,
                 child: TextButton(
                   onPressed: () {
-                    MatrixState.pangeaController.subscriptionController
-                        .showPaywall(context);
+                    inTrialWindow
+                        ? MatrixState.pangeaController.subscriptionController
+                            .activateNewUserTrial()
+                        : MatrixState.pangeaController.subscriptionController
+                            .showPaywall(context);
                     MatrixState.pAnyState.closeOverlay();
                   },
                   style: ButtonStyle(
@@ -49,7 +55,11 @@ class PaywallCard extends StatelessWidget {
                       (AppConfig.primaryColor).withOpacity(0.1),
                     ),
                   ),
-                  child: Text(L10n.of(context)!.seeOptions),
+                  child: Text(
+                    inTrialWindow
+                        ? L10n.of(context)!.activateTrial
+                        : L10n.of(context)!.seeOptions,
+                  ),
                 ),
               ),
               const SizedBox(height: 5.0),