diff --git a/packages/backend/convex/apiKeys/helpers.ts b/packages/backend/convex/apiKeys/helpers.ts
index 4ba8406d..8114dfbb 100644
--- a/packages/backend/convex/apiKeys/helpers.ts
+++ b/packages/backend/convex/apiKeys/helpers.ts
@@ -1,6 +1,6 @@
 import { v } from "convex/values";
 import { internalQuery } from "../_generated/server";
-import { deriveEffectivePlan } from "../billing/plans";
+import { deriveEffectivePlan, getCanonicalSubscription } from "../billing/plans";
 
 /**
  * getActiveSubscriptionForUser — internalQuery
@@ -12,10 +12,12 @@ import { deriveEffectivePlan } from "../billing/plans";
 export const getActiveSubscriptionForUser = internalQuery({
   args: { userId: v.string() },
   handler: async (ctx, args) => {
-    const sub = await ctx.db
+    const subscriptions = await ctx.db
       .query("subscriptions")
       .withIndex("by_user", (q) => q.eq("userId", args.userId))
-      .first();
+      .order("desc")
+      .take(20);
+    const sub = getCanonicalSubscription(subscriptions);
     const plan = deriveEffectivePlan(sub);
     if (plan !== "pro") {
       return null;
diff --git a/packages/backend/convex/billing/limits.ts b/packages/backend/convex/billing/limits.ts
index e625878e..b5843003 100644
--- a/packages/backend/convex/billing/limits.ts
+++ b/packages/backend/convex/billing/limits.ts
@@ -12,7 +12,12 @@ import { components } from "../_generated/api";
 import type { MutationCtx } from "../_generated/server";
 import { internalMutation } from "../functions";
 import { throwLimitReached } from "../utils/errors";
-import { deriveEffectivePlan, getLimits, PLANS } from "./plans";
+import {
+  deriveEffectivePlan,
+  getCanonicalSubscription,
+  getLimits,
+  PLANS,
+} from "./plans";
 
 /**
  * startOfMonth — UTC start-of-month in milliseconds.
@@ -39,14 +44,15 @@ export async function assertCanCreateBookmark(
   });
   const metadata = (user as { metadata?: unknown } | null)?.metadata;
 
-  // 2. Get active subscription for this user.
-  const subscription = await ctx.db
+  // 2. Get canonical subscription for this user.
+  const subscriptions = await ctx.db
     .query("subscriptions")
     .withIndex("by_user", (q) => q.eq("userId", userId))
-    .first();
+    .order("desc")
+    .take(20);
 
   // 3. Derive plan.
-  const plan = deriveEffectivePlan(subscription);
+  const plan = deriveEffectivePlan(getCanonicalSubscription(subscriptions));
 
   // 4. Compute effective limits (custom overrides plan defaults).
   const limits = getLimits(plan as "free" | "pro", metadata);
@@ -95,12 +101,13 @@ export async function assertCanRunProcessing(
   });
   const metadata = (user as { metadata?: unknown } | null)?.metadata;
 
-  const subscription = await ctx.db
+  const subscriptions = await ctx.db
     .query("subscriptions")
     .withIndex("by_user", (q) => q.eq("userId", userId))
-    .first();
+    .order("desc")
+    .take(20);
 
-  const plan = deriveEffectivePlan(subscription);
+  const plan = deriveEffectivePlan(getCanonicalSubscription(subscriptions));
 
   const limits = getLimits(plan as "free" | "pro", metadata);
 
@@ -160,13 +167,14 @@ export async function shouldSendLimitEmail(
     | undefined;
 
   // 2. Check subscription status.
-  const subscription = await ctx.db
+  const subscriptions = await ctx.db
     .query("subscriptions")
     .withIndex("by_user", (q) => q.eq("userId", userId))
-    .first();
+    .order("desc")
+    .take(20);
 
   // Only applies to free plan users.
-  if (deriveEffectivePlan(subscription) === "pro") {
+  if (deriveEffectivePlan(getCanonicalSubscription(subscriptions)) === "pro") {
     return false;
   }
 
diff --git a/packages/backend/convex/billing/plans.test.ts b/packages/backend/convex/billing/plans.test.ts
index 9c126a1d..60076356 100644
--- a/packages/backend/convex/billing/plans.test.ts
+++ b/packages/backend/convex/billing/plans.test.ts
@@ -1,5 +1,8 @@
+import { readFileSync } from "node:fs";
+import path from "node:path";
+import { fileURLToPath } from "node:url";
 import { describe, expect, it } from "vitest";
-import { deriveEffectivePlan, getLimits } from "./plans";
+import { deriveEffectivePlan, getCanonicalSubscription, getLimits } from "./plans";
 
 describe("deriveEffectivePlan", () => {
   it("defaults missing subscriptions to free", () => {
@@ -52,6 +55,69 @@ describe("deriveEffectivePlan", () => {
   });
 });
 
+describe("getCanonicalSubscription", () => {
+  it("does not let an older active row grant Pro after a newer cancellation", () => {
+    const subscription = getCanonicalSubscription([
+      {
+        plan: "pro",
+        provider: "stripe",
+        status: "active",
+        createdAt: 100,
+      },
+      {
+        plan: "free",
+        provider: "stripe",
+        status: "canceled",
+        createdAt: 200,
+      },
+    ]);
+
+    expect(subscription?.status).toBe("canceled");
+    expect(deriveEffectivePlan(subscription)).toBe("free");
+  });
+
+  it("keeps a manual lifetime grant canonical regardless of later billing rows", () => {
+    const subscription = getCanonicalSubscription([
+      {
+        plan: "pro",
+        provider: "manual",
+        status: "lifetime",
+        createdAt: 100,
+      },
+      {
+        plan: "free",
+        provider: "stripe",
+        status: "canceled",
+        createdAt: 200,
+      },
+    ]);
+
+    expect(subscription?.provider).toBe("manual");
+    expect(deriveEffectivePlan(subscription)).toBe("pro");
+  });
+});
+
+describe("subscription entitlement call sites", () => {
+  it("uses canonical subscription selection for chat limit paths", () => {
+    for (const relativePath of [
+      "../chat/mutations.ts",
+      "../chat/queries.ts",
+      "../users/queries.ts",
+    ]) {
+      const source = readFileSync(
+        path.resolve(
+          path.dirname(fileURLToPath(import.meta.url)),
+          relativePath,
+        ),
+        "utf8",
+      );
+
+      expect(source).toContain("getCanonicalSubscription(");
+      expect(source).not.toMatch(/allSubs\.some\([\s\S]*deriveEffectivePlan/);
+    }
+  });
+});
+
 describe("getLimits", () => {
   it("honors Better Auth component custom metadata", () => {
     expect(
diff --git a/packages/backend/convex/billing/plans.ts b/packages/backend/convex/billing/plans.ts
index 0ccc0aec..e60b02e4 100644
--- a/packages/backend/convex/billing/plans.ts
+++ b/packages/backend/convex/billing/plans.ts
@@ -39,6 +39,8 @@ export type SubscriptionPlanState = {
   plan?: string | null;
   provider?: "stripe" | "appstore" | "manual" | null;
   status?: string | null;
+  createdAt?: number | null;
+  updatedAt?: number | null;
 };
 // Plain numeric shape (NOT the `as const` literal union) so merged/custom
 // limits and runtime-computed values assign cleanly.
@@ -73,6 +75,39 @@ export function isLifetimeSubscription(
   );
 }
 
+function subscriptionTimestamp(subscription: SubscriptionPlanState): number {
+  return subscription.updatedAt ?? subscription.createdAt ?? 0;
+}
+
+/**
+ * Pick the one subscription row that should drive entitlement/limits.
+ * Manual lifetime grants are durable and win over billing-provider rows;
+ * otherwise the newest row wins so an old active row cannot keep granting Pro
+ * after a later cancellation/downgrade row exists.
+ */
+export function getCanonicalSubscription<T extends SubscriptionPlanState>(
+  subscriptions: readonly T[],
+): T | null {
+  let best: T | null = null;
+
+  for (const subscription of subscriptions) {
+    if (isLifetimeSubscription(subscription)) {
+      if (!best || !isLifetimeSubscription(best)) {
+        best = subscription;
+        continue;
+      }
+    } else if (best && isLifetimeSubscription(best)) {
+      continue;
+    }
+
+    if (!best || subscriptionTimestamp(subscription) > subscriptionTimestamp(best)) {
+      best = subscription;
+    }
+  }
+
+  return best;
+}
+
 /**
  * Derive the effective entitlement from the canonical subscription row.
  * A stored plan name or an active-looking status alone must never grant Pro.
diff --git a/packages/backend/convex/bookmarks/mutations.ts b/packages/backend/convex/bookmarks/mutations.ts
index a5533bad..599e556c 100644
--- a/packages/backend/convex/bookmarks/mutations.ts
+++ b/packages/backend/convex/bookmarks/mutations.ts
@@ -19,7 +19,11 @@ import {
   assertCanRunProcessing,
   shouldSendLimitEmail,
 } from "../billing/limits";
-import { deriveEffectivePlan, getLimits } from "../billing/plans";
+import {
+  deriveEffectivePlan,
+  getCanonicalSubscription,
+  getLimits,
+} from "../billing/plans";
 import {
   buildBookmarkDetailDTO,
   type BookmarkDetailDTO,
@@ -574,12 +578,13 @@ export const exportCsv = authMutation({
     const userId = ctx.user.id;
 
     // Check export permission.
-    const subscription = await ctx.db
+    const subscriptions = await ctx.db
       .query("subscriptions")
       .withIndex("by_user", (q: any) => q.eq("userId", userId))
-      .first();
+      .order("desc")
+      .take(20);
 
-    const plan = deriveEffectivePlan(subscription);
+    const plan = deriveEffectivePlan(getCanonicalSubscription(subscriptions));
     const dbUser = await ctx.runQuery(components.betterAuth.data.getUserById, {
       userId,
     });
diff --git a/packages/backend/convex/chat/mutations.ts b/packages/backend/convex/chat/mutations.ts
index a7b88bf6..ffe4beb5 100644
--- a/packages/backend/convex/chat/mutations.ts
+++ b/packages/backend/convex/chat/mutations.ts
@@ -3,7 +3,7 @@ import { v } from "convex/values";
 import { components, internal } from "../_generated/api";
 import { internalMutation } from "../_generated/server";
 import { authMutation } from "../functions";
-import { deriveEffectivePlan } from "../billing/plans";
+import { deriveEffectivePlan, getCanonicalSubscription } from "../billing/plans";
 import { throwNotFound } from "../utils/errors";
 import { startOfMonth } from "./usage";
 import type { Id } from "../_generated/dataModel";
@@ -40,12 +40,9 @@ export const checkAndIncrementUsage = internalMutation({
     const allSubs = await ctx.db
       .query("subscriptions")
       .withIndex("by_user", (q) => q.eq("userId", userId))
-      .take(10);
-    const plan = allSubs.some(
-      (subscription) => deriveEffectivePlan(subscription) === "pro",
-    )
-      ? "pro"
-      : "free";
+      .order("desc")
+      .take(20);
+    const plan = deriveEffectivePlan(getCanonicalSubscription(allSubs));
 
     // 3. Fetch user metadata for custom limits.
     const user = await ctx.runQuery(components.betterAuth.data.getUserById, {
diff --git a/packages/backend/convex/chat/queries.ts b/packages/backend/convex/chat/queries.ts
index 5b21635c..303cb8ac 100644
--- a/packages/backend/convex/chat/queries.ts
+++ b/packages/backend/convex/chat/queries.ts
@@ -1,7 +1,10 @@
 import { v } from "convex/values";
 import { components } from "../_generated/api";
 import { internalQuery } from "../_generated/server";
-import { deriveEffectivePlan } from "../billing/plans";
+import {
+  deriveEffectivePlan,
+  getCanonicalSubscription,
+} from "../billing/plans";
 import { authQuery } from "../functions";
 import { startOfMonth } from "./usage";
 import type { Doc } from "../_generated/dataModel";
@@ -168,12 +171,9 @@ export const getChatUsage = authQuery({
     const allSubs = await ctx.db
       .query("subscriptions")
       .withIndex("by_user", (q) => q.eq("userId", userId))
-      .take(10);
-    const plan = allSubs.some(
-      (subscription) => deriveEffectivePlan(subscription) === "pro",
-    )
-      ? "pro"
-      : "free";
+      .order("desc")
+      .take(20);
+    const plan = deriveEffectivePlan(getCanonicalSubscription(allSubs));
 
     // Fetch user metadata for custom limits.
     const user = await ctx.runQuery(components.betterAuth.data.getUserById, {
diff --git a/packages/backend/convex/subscriptions/helpers.ts b/packages/backend/convex/subscriptions/helpers.ts
index 29a16191..374e6323 100644
--- a/packages/backend/convex/subscriptions/helpers.ts
+++ b/packages/backend/convex/subscriptions/helpers.ts
@@ -1,17 +1,18 @@
 import { v } from "convex/values";
 import { internalQuery } from "../_generated/server";
-import { deriveEffectivePlan } from "../billing/plans";
+import { deriveEffectivePlan, getCanonicalSubscription } from "../billing/plans";
 
 /** Server-only entitlement check for actions that cannot access ctx.db. */
 export const getEffectivePlanForUser = internalQuery({
   args: { userId: v.string() },
   returns: v.union(v.literal("free"), v.literal("pro")),
   handler: async (ctx, { userId }) => {
-    const subscription = await ctx.db
+    const subscriptions = await ctx.db
       .query("subscriptions")
       .withIndex("by_user", (q) => q.eq("userId", userId))
-      .first();
+      .order("desc")
+      .take(20);
 
-    return deriveEffectivePlan(subscription);
+    return deriveEffectivePlan(getCanonicalSubscription(subscriptions));
   },
 });
diff --git a/packages/backend/convex/subscriptions/queries.ts b/packages/backend/convex/subscriptions/queries.ts
index 5862940e..bd56a8d8 100644
--- a/packages/backend/convex/subscriptions/queries.ts
+++ b/packages/backend/convex/subscriptions/queries.ts
@@ -7,6 +7,7 @@ import { components } from "../_generated/api";
 import { authQuery } from "../functions";
 import {
   deriveEffectivePlan,
+  getCanonicalSubscription,
   getLimits,
   parseCustomLimits,
 } from "../billing/plans";
@@ -67,10 +68,12 @@ export const getMine = authQuery({
   handler: async (ctx): Promise<SubscriptionDTO | null> => {
     const { user } = ctx;
 
-    const sub = await ctx.db
+    const subscriptions = await ctx.db
       .query("subscriptions")
       .withIndex("by_user", (q) => q.eq("userId", user.id))
-      .first();
+      .order("desc")
+      .take(20);
+    const sub = getCanonicalSubscription(subscriptions);
 
     if (!sub) return null;
 
@@ -101,10 +104,12 @@ export const getUserPlan = authQuery({
     const { user } = ctx;
 
     // 1. Fetch subscription (may be null → free).
-    const sub = await ctx.db
+    const subscriptions = await ctx.db
       .query("subscriptions")
       .withIndex("by_user", (q) => q.eq("userId", user.id))
-      .first();
+      .order("desc")
+      .take(20);
+    const sub = getCanonicalSubscription(subscriptions);
 
     // 2. Derive plan from subscription status.
     const plan = deriveEffectivePlan(sub);
diff --git a/packages/backend/convex/users/queries.ts b/packages/backend/convex/users/queries.ts
index 5cc3276c..a7f6488d 100644
--- a/packages/backend/convex/users/queries.ts
+++ b/packages/backend/convex/users/queries.ts
@@ -1,5 +1,6 @@
 import {
   deriveEffectivePlan,
+  getCanonicalSubscription,
   getLimits as getPlansLimits,
   parseCustomLimits,
 } from "../billing/plans";
@@ -21,11 +22,13 @@ export const getLimits = authQuery({
   handler: async (ctx) => {
     const userId = ctx.user.id;
 
-    // Fetch active subscription
-    const sub = await ctx.db
+    // Fetch canonical subscription
+    const subscriptions = await ctx.db
       .query("subscriptions")
       .withIndex("by_user", (q) => q.eq("userId", userId))
-      .first();
+      .order("desc")
+      .take(20);
+    const sub = getCanonicalSubscription(subscriptions);
 
     const plan = deriveEffectivePlan(sub);
 
@@ -38,9 +41,9 @@ export const getLimits = authQuery({
 
     const subscription = sub
       ? {
-          id: sub._id as string,
+          id: (sub as { _id: string })._id,
           status: sub.status ?? "unknown",
-          periodEnd: sub.periodEnd ?? null,
+          periodEnd: (sub as { periodEnd?: number | null }).periodEnd ?? null,
         }
       : null;
 
@@ -69,10 +72,12 @@ export const getLimits = authQuery({
 export const getOnboardingFlowState = authQuery({
   args: {},
   handler: async (ctx) => {
-    const subscription = await ctx.db
+    const subscriptions = await ctx.db
       .query("subscriptions")
       .withIndex("by_user", (q) => q.eq("userId", ctx.user.id))
-      .first();
+      .order("desc")
+      .take(20);
+    const subscription = getCanonicalSubscription(subscriptions);
 
     return deriveOnboardingFlowState({
       onboarding: ctx.user.onboarding,