Proactively cancel inactive trials 3 days before end

front/lib/plans/subscription.ts

@@ -1,5 +1,6 @@
 import type { WorkspaceType } from "@dust-tt/types";
 import type { PlanType, SubscriptionType } from "@dust-tt/types";
+import type Stripe from "stripe";
 
 import type { Authenticator } from "@app/lib/auth";
 import { Plan, Subscription, Workspace } from "@app/lib/models";
@@ -20,6 +21,7 @@ import {
 import { redisClient } from "@app/lib/redis";
 import { frontSequelize } from "@app/lib/resources/storage";
 import { generateModelSId } from "@app/lib/utils";
+import { checkWorkspaceActivity } from "@app/lib/workspace_usage";
 import logger from "@app/logger/logger";
 
 // Helper function to render PlanType from PlanAttributes
@@ -463,3 +465,32 @@ export const updateWorkspacePerMonthlyActiveUsersSubscriptionUsage = async ({
     }
   }
 };
+
+/**
+ * Proactively cancel inactive trials.
+ */
+export async function maybeCancelInactiveTrials(
+  stripeSubscription: Stripe.Subscription
+) {
+  const { id: stripeSubscriptionId } = stripeSubscription;
+
+  const subscription = await Subscription.findOne({
+    where: { stripeSubscriptionId },
+    include: [Workspace],
+  });
+
+  if (!subscription || !subscription.trialing) {
+    return;
+  }
+
+  const { workspace } = subscription;
+  const isWorkspaceActive = await checkWorkspaceActivity(workspace);
+
+  if (!isWorkspaceActive) {
+    logger.info({ workspaceId: workspace.sId }, "Canceling inactive trial.");
+
+    await cancelSubscriptionImmediately({
+      stripeSubscriptionId,
+    });
+  }
+}

front/lib/workspace_usage.ts

@@ -1,5 +1,13 @@
 import { format } from "date-fns/format";
-import { QueryTypes } from "sequelize";
+import { Op, QueryTypes } from "sequelize";
+
+import type { Workspace } from "@app/lib/models";
+import {
+  AgentConfiguration,
+  AgentMessage,
+  Conversation,
+  DataSource,
+} from "@app/lib/models";
 
 import { frontSequelize } from "./resources/storage";
 
@@ -94,3 +102,28 @@ export async function unsafeGetUsageData(
 
   return csvHeader + csvContent;
 }
+
+/**
+ * Check if a workspace is active during a trial based on the following conditions:
+ *   - Existence of a connected data source
+ *   - Existence of a custom assistant
+ *   - A conversation occurred within the past 7 days
+ */
+export async function checkWorkspaceActivity(workspace: Workspace) {
+  const sevenDaysAgo = new Date();
+  sevenDaysAgo.setDate(sevenDaysAgo.getDate() - 7);
+
+  const hasConnectedDataSource = await DataSource.findOne({
+    where: { workspaceId: workspace.id },
+  });
+
+  const hasCreatedAssistant = await AgentConfiguration.findOne({
+    where: { workspaceId: workspace.id },
+  });
+
+  const hasRecentConversation = await Conversation.findOne({
+    where: { workspaceId: workspace.id, updatedAt: { [Op.gte]: sevenDaysAgo } },
+  });
+
+  return hasConnectedDataSource || hasCreatedAssistant || hasRecentConversation;
+}

front/pages/api/stripe/webhook.ts

@@ -15,6 +15,7 @@ import {
 } from "@app/lib/email";
 import { Plan, Subscription, Workspace } from "@app/lib/models";
 import { createCustomerPortalSession } from "@app/lib/plans/stripe";
+import { maybeCancelInactiveTrials } from "@app/lib/plans/subscription";
 import { countActiveSeatsInWorkspace } from "@app/lib/plans/workspace_usage";
 import { frontSequelize } from "@app/lib/resources/storage";
 import { generateModelSId } from "@app/lib/utils";
@@ -562,6 +563,14 @@ async function handler(
           }
 
           break;
+
+        case "customer.subscription.trial_will_end":
+          stripeSubscription = event.data.object as Stripe.Subscription;
+
+          await maybeCancelInactiveTrials(stripeSubscription);
+
+          break;
+
         default:
         // Unhandled event type
       }