diff --git a/packages/snjs/mocha/lib/AppContext.js b/packages/snjs/mocha/lib/AppContext.js
index 741e23ffd..cb290808b 100644
--- a/packages/snjs/mocha/lib/AppContext.js
+++ b/packages/snjs/mocha/lib/AppContext.js
@@ -679,6 +679,10 @@ export class AppContext {
 
     options.expiresAt = options.expiresAt || dateInAnHour
     options.subscriptionPlanName = options.subscriptionPlanName || 'PRO_PLAN'
+    options.cancelPreviousSubscription = options.cancelPreviousSubscription || false
+
+    const nextSubscriptionId = GlobalSubscriptionIdCounter++
+
     let uploadBytesLimit = -1
     switch (options.subscriptionPlanName) {
       case 'PLUS_PLAN':
@@ -690,9 +694,27 @@ export class AppContext {
     }
 
     try {
+      if (options.cancelPreviousSubscription) {
+        await Events.publishMockedEvent('SUBSCRIPTION_CANCELLED', {
+          userEmail: this.email,
+          subscriptionId: (nextSubscriptionId - 1),
+          subscriptionName: options.subscriptionPlanName,
+          subscriptionCreatedAt: 1,
+          subscriptionUpdatedAt: 1,
+          lastPayedAt: 1,
+          subscriptionEndsAt: (new Date()).getTime() * 1_000,
+          timestamp: (new Date()).getTime() * 1_000,
+          offline: false,
+          replaced: true,
+          userExistingSubscriptionsCount: 1,
+          billingFrequency: 12,
+          payAmount: 59.0,
+        })
+      }
+
       await Events.publishMockedEvent('SUBSCRIPTION_PURCHASED', {
         userEmail: this.email,
-        subscriptionId: GlobalSubscriptionIdCounter++,
+        subscriptionId: nextSubscriptionId,
         subscriptionName: options.subscriptionPlanName,
         subscriptionExpiresAt: options.expiresAt.getTime() * 1_000,
         timestamp: Date.now(),
@@ -713,7 +735,7 @@ export class AppContext {
       )
 
       try {
-        await HomeServer.activatePremiumFeatures(this.email, options.subscriptionPlanName, options.expiresAt, uploadBytesLimit)
+        await HomeServer.activatePremiumFeatures(this.email, nextSubscriptionId, options.subscriptionPlanName, options.expiresAt, uploadBytesLimit, options.cancelPreviousSubscription)
 
         await this.sleep(1, 'Waiting for premium features to be activated')
       } catch (error) {
diff --git a/packages/snjs/mocha/lib/HomeServer.js b/packages/snjs/mocha/lib/HomeServer.js
index bf8cdb2c4..ea95e1ed1 100644
--- a/packages/snjs/mocha/lib/HomeServer.js
+++ b/packages/snjs/mocha/lib/HomeServer.js
@@ -1,6 +1,13 @@
 import * as Defaults from './Defaults.js'
 
-export async function activatePremiumFeatures(username, subscriptionPlanName, endsAt, uploadBytesLimit) {
+export async function activatePremiumFeatures(
+  username,
+  subscriptionId,
+  subscriptionPlanName,
+  endsAt,
+  uploadBytesLimit,
+  cancelPreviousSubscription
+) {
   await fetch(`${Defaults.getDefaultHost()}/e2e/activate-premium`, {
     method: 'POST',
     headers: {
@@ -9,9 +16,11 @@ export async function activatePremiumFeatures(username, subscriptionPlanName, en
     },
     body: JSON.stringify({
       username,
+      subscriptionId,
       subscriptionPlanName,
       endsAt,
       uploadBytesLimit,
+      cancelPreviousSubscription,
     }),
   })
 }
diff --git a/packages/snjs/mocha/settings.test.js b/packages/snjs/mocha/settings.test.js
index 115541510..76db11e12 100644
--- a/packages/snjs/mocha/settings.test.js
+++ b/packages/snjs/mocha/settings.test.js
@@ -163,9 +163,13 @@ describe('settings service', function () {
     )
     expect(usedSettingBefore).to.equal('196')
 
-    await context.activatePaidSubscriptionForUser()
+    await context.activatePaidSubscriptionForUser({
+      cancelPreviousSubscription: true,
+    })
 
-    await context.activatePaidSubscriptionForUser()
+    await context.activatePaidSubscriptionForUser({
+      cancelPreviousSubscription: true,
+    })
 
     const limitSettingAfter = await application.settings.getSubscriptionSetting(
       SettingName.create(SettingName.NAMES.FileUploadBytesLimit).getValue(),
@@ -176,5 +180,22 @@ describe('settings service', function () {
       SettingName.create(SettingName.NAMES.FileUploadBytesUsed).getValue(),
     )
     expect(usedSettingAfter).to.equal(usedSettingBefore)
+
+    const afterResponse = await fetch('/packages/snjs/mocha/assets/small_file.md')
+    const afterBuffer = new Uint8Array(await afterResponse.arrayBuffer())
+
+    await Files.uploadFile(application.files, afterBuffer, 'my-file', 'md', 1000)
+
+    await Factory.sleep(1)
+
+    const limitSettingAfterSecondUpload = await application.settings.getSubscriptionSetting(
+      SettingName.create(SettingName.NAMES.FileUploadBytesLimit).getValue(),
+    )
+    expect(limitSettingAfterSecondUpload).to.equal(limitSettingBefore)
+
+    const usedSettingAfterSecondUpload = await application.settings.getSubscriptionSetting(
+      SettingName.create(SettingName.NAMES.FileUploadBytesUsed).getValue(),
+    )
+    expect(usedSettingAfterSecondUpload).to.equal('392')
   })
 })