diff --git a/test/api/unit/libs/payments/stripe/calculate-termination-date.test.js b/test/api/unit/libs/payments/stripe/calculate-termination-date.test.js
new file mode 100644
index 0000000000..7badd7e62a
--- /dev/null
+++ b/test/api/unit/libs/payments/stripe/calculate-termination-date.test.js
@@ -0,0 +1,64 @@
+import moment from 'moment';
+import { calculateSubscriptionTerminationDate } from '../../../../../../website/server/libs/payments/util';
+import api from '../../../../../../website/server/libs/payments/payments';
+
+describe('#calculateSubscriptionTerminationDate', () => {
+  let plan;
+  let nextBill;
+
+  beforeEach(() => {
+    plan = {
+      customerId: 'customer-id',
+      extraMonths: 0,
+    };
+    nextBill = moment();
+  });
+  it('should extend date to the exact amount of days left before the next bill will occur', () => {
+    nextBill = moment()
+      .add(5, 'days');
+    const expectedTerminationDate = moment()
+      .add(5, 'days');
+
+    const terminationDate = calculateSubscriptionTerminationDate(nextBill, plan, api.constants);
+    expect(expectedTerminationDate.diff(terminationDate, 'days')).to.eql(0);
+  });
+  it('if nextBill is null, add 30 days to termination date', () => {
+    nextBill = null;
+    const expectedTerminationDate = moment()
+      .add(30, 'days');
+    const terminationDate = calculateSubscriptionTerminationDate(nextBill, plan, api.constants);
+
+    expect(expectedTerminationDate.diff(terminationDate, 'days')).to.eql(0);
+  });
+  it('if nextBill is null and it\'s a group plan, add 2 days instead of 30', () => {
+    nextBill = null;
+    plan.customerId = api.constants.GROUP_PLAN_CUSTOMER_ID;
+    const expectedTerminationDate = moment()
+      .add(2, 'days');
+
+    const terminationDate = calculateSubscriptionTerminationDate(nextBill, plan, api.constants);
+    expect(expectedTerminationDate.diff(terminationDate, 'days')).to.eql(0);
+  });
+  it('should add 30.5 days for each extraMonth', () => {
+    plan.extraMonths = 4;
+    const expectedTerminationDate = moment()
+      .add(30.5 * 4, 'days');
+
+    const terminationDate = calculateSubscriptionTerminationDate(nextBill, plan, api.constants);
+    expect(expectedTerminationDate.diff(terminationDate, 'days')).to.eql(0);
+  });
+  it('should round up if total days gained by extraMonth is a decimal number', () => {
+    plan.extraMonths = 5;
+    const expectedTerminationDate = moment()
+      .add(Math.ceil(30.5 * 5), 'days');
+
+    const terminationDate = calculateSubscriptionTerminationDate(nextBill, plan, api.constants);
+    expect(expectedTerminationDate.diff(terminationDate, 'days')).to.eql(0);
+  });
+  it('behaves like extraMonths is 0 if it\'s set to a negative number', () => {
+    plan.extraMonths = -5;
+    const expectedTerminationDate = moment();
+    const terminationDate = calculateSubscriptionTerminationDate(nextBill, plan, api.constants);
+    expect(expectedTerminationDate.diff(terminationDate, 'days')).to.eql(0);
+  });
+});
diff --git a/test/api/unit/models/group.test.js b/test/api/unit/models/group.test.js
index 5cb124d96f..c75d1dc7fc 100644
--- a/test/api/unit/models/group.test.js
+++ b/test/api/unit/models/group.test.js
@@ -2402,29 +2402,29 @@ describe('Group Model', () => {
       });
     });
 
-    context('isSubscribed', () => {
+    context('hasActiveGroupPlan', () => {
       it('returns false if group does not have customer id', () => {
-        expect(party.isSubscribed()).to.be.undefined;
+        expect(party.hasActiveGroupPlan()).to.be.undefined;
       });
 
       it('returns true if group does not have plan.dateTerminated', () => {
         party.purchased.plan.customerId = 'test-id';
 
-        expect(party.isSubscribed()).to.be.true;
+        expect(party.hasActiveGroupPlan()).to.be.true;
       });
 
       it('returns true if group if plan.dateTerminated is after today', () => {
         party.purchased.plan.customerId = 'test-id';
         party.purchased.plan.dateTerminated = moment().add(1, 'days').toDate();
 
-        expect(party.isSubscribed()).to.be.true;
+        expect(party.hasActiveGroupPlan()).to.be.true;
       });
 
       it('returns false if group if plan.dateTerminated is before today', () => {
         party.purchased.plan.customerId = 'test-id';
         party.purchased.plan.dateTerminated = moment().subtract(1, 'days').toDate();
 
-        expect(party.isSubscribed()).to.be.false;
+        expect(party.hasActiveGroupPlan()).to.be.false;
       });
     });
 
diff --git a/test/api/v3/integration/groups/POST-groups_groupId_leave.js b/test/api/v3/integration/groups/POST-groups_groupId_leave.test.js
similarity index 86%
rename from test/api/v3/integration/groups/POST-groups_groupId_leave.js
rename to test/api/v3/integration/groups/POST-groups_groupId_leave.test.js
index c4764e3428..fea70d3176 100644
--- a/test/api/v3/integration/groups/POST-groups_groupId_leave.js
+++ b/test/api/v3/integration/groups/POST-groups_groupId_leave.test.js
@@ -2,6 +2,7 @@ import { v4 as generateUUID } from 'uuid';
 import {
   each,
 } from 'lodash';
+import moment from 'moment';
 import {
   generateChallenge,
   checkExistence,
@@ -12,6 +13,7 @@ import {
 } from '../../../../helpers/api-integration/v3';
 import { model as User } from '../../../../../website/server/models/user';
 import payments from '../../../../../website/server/libs/payments/payments';
+import { calculateSubscriptionTerminationDate } from '../../../../../website/server/libs/payments/util';
 
 describe('POST /groups/:groupId/leave', () => {
   const typesOfGroups = {
@@ -338,4 +340,48 @@ describe('POST /groups/:groupId/leave', () => {
       });
     });
   });
+
+  each(typesOfGroups, (groupDetails, groupType) => {
+    context(`Leaving a group with extraMonths left plan when the group is a ${groupType}`, () => {
+      const extraMonths = 12;
+      let groupWithPlan;
+      let member;
+
+      beforeEach(async () => {
+        const { group, members } = await createAndPopulateGroup({
+          groupDetails,
+          members: 1,
+          upgradeToGroupPlan: true,
+        });
+        [member] = members;
+        groupWithPlan = group;
+        await member.update({
+          'purchased.plan.extraMonths': extraMonths,
+        });
+      });
+      it('calculates dateTerminated and sets extraMonths to zero after user leaves the group', async () => {
+        const userBeforeLeave = await User.findById(member._id).exec();
+
+        await member.post(`/groups/${groupWithPlan._id}/leave`);
+        const userAfterLeave = await User.findById(member._id).exec();
+
+        const dateTerminatedBefore = userBeforeLeave.purchased.plan.dateTerminated;
+        const extraMonthsBefore = userBeforeLeave.purchased.plan.extraMonths;
+        const dateTerminatedAfter = userAfterLeave.purchased.plan.dateTerminated;
+        const extraMonthsAfter = userAfterLeave.purchased.plan.extraMonths;
+
+        const expectedTerminationDate = calculateSubscriptionTerminationDate(null, {
+          customerId: payments.constants.GROUP_PLAN_CUSTOMER_ID,
+          extraMonths,
+        }, payments.constants);
+
+        expect(extraMonthsBefore).to.gte(12);
+        expect(extraMonthsAfter).to.equal(0);
+        expect(dateTerminatedBefore).to.be.null;
+        expect(dateTerminatedAfter).to.exist;
+
+        expect(moment(dateTerminatedAfter).diff(expectedTerminationDate, 'days')).to.equal(0);
+      });
+    });
+  });
 });
diff --git a/test/helpers/api-integration/v3/object-generators.js b/test/helpers/api-integration/v3/object-generators.js
index e713c1084c..b48dd862a9 100644
--- a/test/helpers/api-integration/v3/object-generators.js
+++ b/test/helpers/api-integration/v3/object-generators.js
@@ -5,6 +5,8 @@ import { v4 as generateUUID } from 'uuid';
 import { ApiUser, ApiGroup, ApiChallenge } from '../api-classes';
 import { requester } from '../requester';
 import * as Tasks from '../../../../website/server/models/task';
+import payments from '../../../../website/server/libs/payments/payments';
+import { model as User } from '../../../../website/server/models/user';
 
 // Creates a new user and returns it
 // If you need the user to have specific requirements,
@@ -83,14 +85,35 @@ export async function generateGroup (leader, details = {}, update = {}) {
   return apiGroup;
 }
 
+async function _upgradeToGroupPlan (groupLeader, group) {
+  const groupLeaderModel = await User.findById(groupLeader._id).exec();
+
+  // Create subscription
+  const paymentData = {
+    user: groupLeaderModel,
+    groupId: group._id,
+    sub: {
+      key: 'basic_3mo',
+    },
+    customerId: 'customer-id',
+    paymentMethod: 'Payment Method',
+    headers: {
+      'x-client': 'habitica-web',
+      'user-agent': '',
+    },
+  };
+  await payments.createSubscription(paymentData);
+}
+
 // This is generate group + the ability to create
 // real users to populate it. The settings object
 // takes in:
 // members: Number - the number of group members to create.
 // Defaults to 0. Does not include group leader.
-// inivtes: Number - the number of users to create and invite to the group. Defaults to 0.
+// invites: Number - the number of users to create and invite to the group. Defaults to 0.
 // groupDetails: Object - how to initialize the group
 // leaderDetails: Object - defaults for the leader, defaults with a gem balance so the user
+// addGroupPlan: boolean - will add group plan with basic subscription. Defaults to false
 // can create the group
 //
 // Returns an object with
@@ -101,6 +124,7 @@ export async function generateGroup (leader, details = {}, update = {}) {
 export async function createAndPopulateGroup (settings = {}) {
   const numberOfMembers = settings.members || 0;
   const numberOfInvites = settings.invites || 0;
+  const upgradeToGroupPlan = settings.upgradeToGroupPlan || false;
   const { groupDetails } = settings;
   const leaderDetails = settings.leaderDetails || { balance: 10 };
 
@@ -130,6 +154,10 @@ export async function createAndPopulateGroup (settings = {}) {
 
   await Promise.all(invitees.map(invitee => invitee.sync()));
 
+  if (upgradeToGroupPlan) {
+    await _upgradeToGroupPlan(groupLeader, group);
+  }
+
   return {
     groupLeader,
     group,
diff --git a/website/server/controllers/api-v3/groups.js b/website/server/controllers/api-v3/groups.js
index f411c9db1f..bf7119c02a 100644
--- a/website/server/controllers/api-v3/groups.js
+++ b/website/server/controllers/api-v3/groups.js
@@ -863,11 +863,6 @@ api.leaveGroup = {
       if (guildIndex >= 0) user.guilds.splice(guildIndex, 1);
     }
 
-    const isMemberOfGroupPlan = await user.isMemberOfGroupPlan();
-    if (!isMemberOfGroupPlan) {
-      await payments.cancelGroupSubscriptionForUser(user, group);
-    }
-
     if (group.hasNotCancelled()) await group.updateGroupPlan(true);
     res.respond(200, {});
   },
@@ -1317,7 +1312,7 @@ api.getGroupPlans = {
       .select('leaderOnly leader purchased name managers')
       .exec();
 
-    const groupPlans = groups.filter(group => group.isSubscribed());
+    const groupPlans = groups.filter(group => group.hasActiveGroupPlan());
 
     res.respond(200, groupPlans);
   },
diff --git a/website/server/libs/chat/group-chat.js b/website/server/libs/chat/group-chat.js
index 1a864b0f47..dc6b0d8278 100644
--- a/website/server/libs/chat/group-chat.js
+++ b/website/server/libs/chat/group-chat.js
@@ -10,7 +10,7 @@ const questScrolls = shared.content.quests;
 
 // @TODO: Don't use this method when the group can be saved.
 export async function getGroupChat (group) {
-  const maxChatCount = group.isSubscribed() ? MAX_SUBBED_GROUP_CHAT_COUNT : MAX_CHAT_COUNT;
+  const maxChatCount = group.hasActiveGroupPlan() ? MAX_SUBBED_GROUP_CHAT_COUNT : MAX_CHAT_COUNT;
 
   const groupChat = await Chat.find({ groupId: group._id })
     .limit(maxChatCount)
diff --git a/website/server/libs/invites/index.js b/website/server/libs/invites/index.js
index 58474510fb..1679b1bf73 100644
--- a/website/server/libs/invites/index.js
+++ b/website/server/libs/invites/index.js
@@ -73,7 +73,7 @@ function inviteUserToGuild (userToInvite, group, inviter, publicGuild, res) {
     publicGuild,
   };
 
-  if (group.isSubscribed() && !group.hasNotCancelled()) guildInvite.cancelledPlan = true;
+  if (group.hasActiveGroupPlan() && !group.hasNotCancelled()) guildInvite.cancelledPlan = true;
 
   userToInvite.invitations.guilds.push(guildInvite);
 }
@@ -94,7 +94,7 @@ async function inviteUserToParty (userToInvite, group, inviter, res) {
   }
 
   const partyInvite = { id: group._id, name: group.name, inviter: inviter._id };
-  if (group.isSubscribed() && !group.hasNotCancelled()) partyInvite.cancelledPlan = true;
+  if (group.hasActiveGroupPlan() && !group.hasNotCancelled()) partyInvite.cancelledPlan = true;
 
   userToInvite.invitations.parties.push(partyInvite);
   userToInvite.invitations.party = partyInvite;
@@ -167,7 +167,7 @@ async function inviteByEmail (invite, group, inviter, req, res) {
     userReturnInfo = invite.email;
 
     let cancelledPlan = false;
-    if (group.isSubscribed() && !group.hasNotCancelled()) cancelledPlan = true;
+    if (group.hasActiveGroupPlan() && !group.hasNotCancelled()) cancelledPlan = true;
 
     const groupQueryString = JSON.stringify({
       id: group._id,
diff --git a/website/server/libs/payments/subscriptions.js b/website/server/libs/payments/subscriptions.js
index fbf81b90fb..4718ab7f02 100644
--- a/website/server/libs/payments/subscriptions.js
+++ b/website/server/libs/payments/subscriptions.js
@@ -17,6 +17,7 @@ import {
 } from '../errors';
 import shared from '../../../common';
 import { sendNotification as sendPushNotification } from '../pushNotifications'; // eslint-disable-line import/no-cycle
+import { calculateSubscriptionTerminationDate } from './util';
 
 // @TODO: Abstract to shared/constant
 const JOINED_GROUP_PLAN = 'joined group plan';
@@ -73,6 +74,7 @@ async function createSubscription (data) {
   let itemPurchased = 'Subscription';
   let purchaseType = 'subscribe';
   let emailType = 'subscription-begins';
+  let recipientIsSubscribed = recipient.isSubscribed();
 
   //  If we are buying a group subscription
   if (data.groupId) {
@@ -93,6 +95,7 @@ async function createSubscription (data) {
     itemPurchased = 'Group-Subscription';
     purchaseType = 'group-subscribe';
     emailType = 'group-subscription-begins';
+    recipientIsSubscribed = group.hasActiveGroupPlan();
     groupId = group._id;
     recipient.purchased.plan.quantity = data.sub.quantity;
 
@@ -105,7 +108,7 @@ async function createSubscription (data) {
     if (plan.customerId && !plan.dateTerminated) { // User has active plan
       plan.extraMonths += months;
     } else {
-      if (!recipient.isSubscribed() || !plan.dateUpdated) plan.dateUpdated = today;
+      if (!recipientIsSubscribed || !plan.dateUpdated) plan.dateUpdated = today;
       if (moment(plan.dateTerminated).isAfter()) {
         plan.dateTerminated = moment(plan.dateTerminated).add({ months }).toDate();
       } else {
@@ -307,24 +310,11 @@ async function cancelSubscription (data) {
     if (data.cancellationReason && data.cancellationReason === JOINED_GROUP_PLAN) sendEmail = false;
   }
 
-  const now = moment();
-  let defaultRemainingDays = 30;
-
   if (plan.customerId === this.constants.GROUP_PLAN_CUSTOMER_ID) {
-    defaultRemainingDays = 2;
     sendEmail = false; // because group-member-cancel email has already been sent
   }
 
-  const remaining = data.nextBill ? moment(data.nextBill).diff(new Date(), 'days', true) : defaultRemainingDays;
-  if (plan.extraMonths < 0) plan.extraMonths = 0;
-  const extraDays = Math.ceil(30.5 * plan.extraMonths);
-  const nowStr = `${now.format('MM')}/${now.format('DD')}/${now.format('YYYY')}`;
-  const nowStrFormat = 'MM/DD/YYYY';
-
-  plan.dateTerminated = moment(nowStr, nowStrFormat)
-    .add({ days: remaining })
-    .add({ days: extraDays })
-    .toDate();
+  plan.dateTerminated = calculateSubscriptionTerminationDate(data.nextBill, plan, this.constants);
 
   // clear extra time. If they subscribe again, it'll be recalculated from p.dateTerminated
   plan.extraMonths = 0;
diff --git a/website/server/libs/payments/util.js b/website/server/libs/payments/util.js
new file mode 100644
index 0000000000..fb6b65daaa
--- /dev/null
+++ b/website/server/libs/payments/util.js
@@ -0,0 +1,32 @@
+import moment from 'moment';
+
+const DEFAULT_REMAINING_DAYS = 30;
+const DEFAULT_REMAINING_DAYS_FOR_GROUP_PLAN = 2;
+
+/**
+ * paymentsApiConstants is provided as parameter because of a dependency cycle
+ * with subscriptions api which will occur if api.constants would be used directly
+ */
+export function calculateSubscriptionTerminationDate (
+  nextBill, purchasedPlan, paymentsApiConstants,
+) {
+  const defaultRemainingDays = (
+    purchasedPlan.customerId === paymentsApiConstants.GROUP_PLAN_CUSTOMER_ID
+  ) ? DEFAULT_REMAINING_DAYS_FOR_GROUP_PLAN
+    : DEFAULT_REMAINING_DAYS;
+  const now = moment();
+
+  const remaining = nextBill
+    ? moment(nextBill).diff(new Date(), 'days', true)
+    : defaultRemainingDays;
+
+  const extraMonths = Math.max(purchasedPlan.extraMonths, 0);
+  const extraDays = Math.ceil(30.5 * extraMonths);
+  const nowStr = `${now.format('MM')}/${now.format('DD')}/${now.format('YYYY')}`;
+  const nowStrFormat = 'MM/DD/YYYY';
+
+  return moment(nowStr, nowStrFormat)
+    .add({ days: remaining })
+    .add({ days: extraDays })
+    .toDate();
+}
diff --git a/website/server/models/group.js b/website/server/models/group.js
index b1e4c439e3..f9548d994f 100644
--- a/website/server/models/group.js
+++ b/website/server/models/group.js
@@ -153,7 +153,7 @@ schema.plugin(baseModel, {
   noSet: ['_id', 'balance', 'quest', 'memberCount', 'chat', 'challengeCount', 'tasksOrder', 'purchased', 'managers'],
   private: ['purchased.plan'],
   toJSONTransform (plainObj, originalDoc) {
-    if (plainObj.purchased) plainObj.purchased.active = originalDoc.isSubscribed();
+    if (plainObj.purchased) plainObj.purchased.active = originalDoc.hasActiveGroupPlan();
   },
 });
 
@@ -1701,7 +1701,7 @@ schema.methods.checkChatSpam = function groupCheckChatSpam (user) {
   return false;
 };
 
-schema.methods.isSubscribed = function isSubscribed () {
+schema.methods.hasActiveGroupPlan = function hasActiveGroupPlan () {
   const now = new Date();
   const { plan } = this.purchased;
   return plan && plan.customerId
@@ -1710,12 +1710,12 @@ schema.methods.isSubscribed = function isSubscribed () {
 
 schema.methods.hasNotCancelled = function hasNotCancelled () {
   const { plan } = this.purchased;
-  return Boolean(this.isSubscribed() && !plan.dateTerminated);
+  return Boolean(this.hasActiveGroupPlan() && !plan.dateTerminated);
 };
 
-schema.methods.hasCancelled = function hasNotCancelled () {
+schema.methods.hasCancelled = function hasCancelled () {
   const { plan } = this.purchased;
-  return Boolean(this.isSubscribed() && plan.dateTerminated);
+  return Boolean(this.hasActiveGroupPlan() && plan.dateTerminated);
 };
 
 schema.methods.updateGroupPlan = async function updateGroupPlan (removingMember) {
diff --git a/website/server/models/user/methods.js b/website/server/models/user/methods.js
index 2bf8227e3a..70821e0b95 100644
--- a/website/server/models/user/methods.js
+++ b/website/server/models/user/methods.js
@@ -477,13 +477,13 @@ schema.methods.canGetGems = async function canObtainGems () {
   const groups = await getUserGroupData(user);
 
   return groups
-    .every(g => !g.isSubscribed() || g.leader === user._id || g.leaderOnly.getGems !== true);
+    .every(g => !g.hasActiveGroupPlan() || g.leader === user._id || g.leaderOnly.getGems !== true);
 };
 
 schema.methods.isMemberOfGroupPlan = async function isMemberOfGroupPlan () {
   const groups = await getUserGroupData(this);
 
-  return groups.some(g => g.isSubscribed());
+  return groups.some(g => g.hasActiveGroupPlan());
 };
 
 schema.methods.isAdmin = function isAdmin () {