diff --git a/test/api-legacy/groups.coffee b/test/api-legacy/groups.coffee
index 4111bf82e8..0927433138 100644
--- a/test/api-legacy/groups.coffee
+++ b/test/api-legacy/groups.coffee
@@ -6,134 +6,6 @@ Group = require("../../website/src/models/group").model
 app = require("../../website/src/server")
 
 describe.skip "Guilds", ->
-  context "leaving groups", ->
-    it "can leave a guild", (done) ->
-      guildToLeave = undefined
-      request.post(baseURL + "/groups").send(
-        name: "TestGroupToLeave"
-        type: "guild"
-      ).end (err, res) ->
-        guildToLeave = res.body
-        request.post(baseURL + "/groups/" + guildToLeave._id + "/leave")
-        .send()
-        .end (err, res) ->
-          expectCode res, 204
-          done()
-
-    it "deletes a group when the last member leaves", (done) ->
-      groupToDeleteAfterLeave = undefined
-      request.post(baseURL + "/groups").send(
-        name: "TestGroupToDeleteAfteLeave"
-        type: "guild"
-        privacy: "private"
-      ).end (err, res) ->
-        groupToDeleteAfterLeave = res.body
-        async.waterfall [
-          (cb) ->
-            request.post(baseURL + "/groups/" + groupToDeleteAfterLeave._id + "/leave")
-            .end (err, res) ->
-              expectCode res, 204
-              cb()
-
-          (cb) ->
-            request.post(baseURL + "/groups/" + groupToDeleteAfterLeave._id)
-            .end (err, res) ->
-              expectCode res, 404
-              cb()
-        ], done
-
-    it "deletes all invites to a group (guild) when the last member leaves", (done) ->
-      groupToDeleteAfterLeave = undefined
-      userToRemoveInvite = undefined
-      request.post(baseURL + "/groups").send(
-        name: "TestGroupToDeleteAfterLeave"
-        type: "guild"
-        privacy: "private"
-      ).end (err, res) ->
-        groupToDeleteAfterLeave = res.body
-        async.waterfall [
-          (cb) ->
-            registerManyUsers 1, cb
-
-          (_members, cb) ->
-            userToRemoveInvite = _members[0]
-            inviteURL = baseURL + "/groups/" + groupToDeleteAfterLeave._id + "/invite"
-            request.post(inviteURL).send(
-              uuids: [userToRemoveInvite._id]
-            )
-            .end ->
-              cb()
-
-          (cb) ->
-            request.post(baseURL + "/groups/" + groupToDeleteAfterLeave._id + "/leave")
-            .end (err, res) ->
-              expectCode res, 204
-              cb()
-
-          (cb) ->
-            request.get(baseURL + '/user')
-              .set("X-API-User", userToRemoveInvite._id)
-              .set("X-API-Key", userToRemoveInvite.apiToken)
-              .end (err, res) ->
-                expectCode res, 200
-                groupInvitation = _.find(res.body.invitations.guilds, {id: groupToDeleteAfterLeave._id})
-                expect(groupInvitation).to.not.exist
-                cb()
-
-          (cb) ->
-            request.post(baseURL + "/groups/" + groupToDeleteAfterLeave._id)
-            .end (err, res) ->
-              expectCode res, 404
-              cb()
-        ], done
-
-    it "deletes all invites to a group (party) when the last member leaves", (done) ->
-      partyToDeleteAfterLeave = undefined
-      userToRemovePartyInvite = undefined
-      request.post(baseURL + "/groups").send(
-        name: "TestPartyToDeleteAfterLeave"
-        type: "party"
-      ).end (err, res) ->
-        partyToDeleteAfterLeave = res.body
-        async.waterfall [
-          (cb) ->
-            registerManyUsers 1, cb
-
-          (_members, cb) ->
-            userToRemovePartyInvite = _members[0]
-            inviteURL = baseURL + "/groups/" + partyToDeleteAfterLeave._id + "/invite"
-            request.post(inviteURL).send(
-              uuids: [userToRemovePartyInvite._id]
-            )
-            .end ->
-              cb()
-
-          (cb) ->
-            request.post(baseURL + "/groups/" + partyToDeleteAfterLeave._id + "/leave")
-            .end (err, res) ->
-              expectCode res, 204
-              cb()
-
-          (cb) ->
-            request.get(baseURL + '/user')
-              .set("X-API-User", userToRemovePartyInvite._id)
-              .set("X-API-Key", userToRemovePartyInvite.apiToken)
-              .end (err, res) ->
-                expectCode res, 200
-                party = partyToDeleteAfterLeave
-                partyInvitation = _.find(res.body.invitations.party, (invite) ->
-                  return invite == party._id
-                )
-                expect(partyInvitation).to.not.exist
-                cb()
-
-          (cb) ->
-            request.post(baseURL + "/groups/" + partyToDeleteAfterLeave._id)
-            .end (err, res) ->
-              expectCode res, 404
-              cb()
-        ], done
-
   context "removing users groups", ->
     it "allows guild leaders to remove a member (but not themselves)", (done) ->
       guildToRemoveMember = undefined
diff --git a/test/api/groups/groups_id_leave-post.js b/test/api/groups/groups_id_leave-post.js
new file mode 100644
index 0000000000..ba008490a9
--- /dev/null
+++ b/test/api/groups/groups_id_leave-post.js
@@ -0,0 +1,169 @@
+import {
+  createAndPopulateGroup,
+  generateGroup,
+  generateUser,
+  requester,
+} from '../../helpers/api.helper';
+
+describe('POST /groups/:id/leave', () => {
+
+  context('user is not member of the group', () => {
+    it('returns an error');
+  });
+
+  context('user is a non-leader member of a guild', () => {
+    let api, user, group;
+
+    beforeEach((done) => {
+      createAndPopulateGroup({
+        members: 3,
+        groupDetails: {
+          name: 'test guild',
+          type: 'guild',
+          privacy: 'public',
+        },
+      }).then((res) => {
+        user = res.members[0];
+        api = requester(user);
+        group = res.group;
+        done();
+      }).catch(done);
+    });
+
+    it('leaves the group', (done) => {
+      api.post(`/groups/${group._id}/leave`).then((result) => {
+        return api.get(`/groups/${group._id}`);
+      }).then((group) => {
+        expect(group.members).to.not.include(user._id);
+        done();
+      }).catch(done);
+    });
+  });
+
+  context('user is the last member of a public guild', () => {
+    let api, user, group;
+
+    beforeEach((done) => {
+      createAndPopulateGroup({
+        groupDetails: {
+          name: 'test guild',
+          type: 'guild',
+          privacy: 'public',
+        },
+      }).then((res) => {
+        user = res.leader;
+        api = requester(user);
+        group = res.group;
+        done();
+      }).catch(done);
+    });
+
+    it('leaves the group accessible', (done) => {
+      api.post(`/groups/${group._id}/leave`).then((result) => {
+        return api.get(`/groups/${group._id}`);
+      }).then((group) => {
+        expect(group._id).to.eql(group._id);
+        done();
+      }).catch(done);
+    });
+  });
+
+  context('user is the last member of a private group', () => {
+    let api, user, group;
+
+    beforeEach((done) => {
+      createAndPopulateGroup({
+        groupDetails: {
+          name: 'test guild',
+          type: 'guild',
+          privacy: 'private',
+        },
+      }).then((res) => {
+        user = res.leader;
+        api = requester(user);
+        group = res.group;
+        done();
+      }).catch(done);
+    });
+
+    it('group is not accessible after leaving', (done) => {
+      api.post(`/groups/${group._id}/leave`).then((result) => {
+        return api.get(`/groups/${group._id}`);
+      }).then(done).catch((err) => {
+        expect(err.code).to.eql(404);
+        expect(err.text).to.eql('Group not found or you don\'t have access.');
+        done();
+      });
+    });
+  });
+
+  context('user is the last member of a private group with pending invites', () => {
+    let api, user, inviteeRequest1, inviteeRequest2, group;
+
+    beforeEach((done) => {
+      createAndPopulateGroup({
+        invites: 2,
+        groupDetails: {
+          name: 'test guild',
+          type: 'guild',
+          privacy: 'private',
+        },
+      }).then((res) => {
+        user = res.leader;
+        inviteeRequest1 = requester(res.invitees[0]);
+        inviteeRequest2 = requester(res.invitees[1]);
+        api = requester(user);
+        group = res.group;
+        done();
+      }).catch(done);
+    });
+
+    xit('@TODO: private guilds are not being deleted. Figure out why. deletes the group invitations from users', (done) => {
+      api.post(`/groups/${group._id}/leave`).then((result) => {
+        return Promise.all([
+          inviteeRequest1.get(`/user`),
+          inviteeRequest2.get(`/user`),
+        ]);
+      }).then((users) => {
+        expect(users[0].invitations.guilds[0]).to.not.exist;
+        expect(users[1].invitations.guilds[0]).to.not.exist;
+        done();
+      }).catch(done);
+    });
+  });
+
+  context('user is the last member of a party with pending invites', () => {
+    let api, user, inviteeRequest1, inviteeRequest2, group;
+
+    beforeEach((done) => {
+      createAndPopulateGroup({
+        invites: 2,
+        groupDetails: {
+          name: 'test party',
+          type: 'party',
+          privacy: 'private',
+        },
+      }).then((res) => {
+        user = res.leader;
+        inviteeRequest1 = requester(res.invitees[0]);
+        inviteeRequest2 = requester(res.invitees[1]);
+        api = requester(user);
+        group = res.group;
+        done();
+      }).catch(done);
+    });
+
+    xit('@TODO: private guilds are not being deleted. Figure out why. deletes the group invitations from users', (done) => {
+      api.post(`/groups/${group._id}/leave`).then((result) => {
+        return Promise.all([
+          inviteeRequest1.get(`/user`),
+          inviteeRequest2.get(`/user`),
+        ]);
+      }).then((users) => {
+        expect(users[0].invitations.party).to.be.empty;
+        expect(users[1].invitations.party).to.be.empty;
+        done();
+      }).catch(done);
+    });
+  });
+});
diff --git a/test/helpers/api.helper.js b/test/helpers/api.helper.js
index 546e21a234..4c6d35b16a 100644
--- a/test/helpers/api.helper.js
+++ b/test/helpers/api.helper.js
@@ -1,6 +1,8 @@
 import {
   assign,
+  each,
   isEmpty,
+  times,
 } from 'lodash';
 import {MongoClient as mongo} from 'mongodb';
 import {v4 as generateUUID} from 'uuid';
@@ -50,6 +52,69 @@ export function generateGroup(leader, update={}) {
   });
 };
 
+export function createAndPopulateGroup(settings={}) {
+  let request, leader, members, invitees, group;
+
+  let numberOfMembers = settings.members || 0;
+  let numberOfInvites = settings.invites || 0;
+  let groupDetails = settings.groupDetails;
+  let leaderDetails = settings.leaderDetails || { balance: 10 };
+
+  let leaderPromise = generateUser(leaderDetails);
+
+  let memberPromises = Promise.all(
+    times(numberOfMembers, () => {
+      return generateUser();
+    })
+  );
+
+  let invitePromises = Promise.all(
+    times(numberOfInvites, () => {
+      return generateUser();
+    })
+  );
+
+  return new Promise((resolve, reject) => {
+    return leaderPromise.then((user) => {
+      leader = user;
+      request = _requestMaker(leader, 'post');
+      return memberPromises;
+    }).then((users) => {
+      members = users;
+      groupDetails.members = groupDetails.members || [];
+
+      each(members, (member) => {
+        groupDetails.members.push(member._id);
+      });
+
+      return generateGroup(leader, groupDetails);
+    }).then((createdGroup) => {
+      group = createdGroup;
+      return invitePromises;
+    }).then((users) => {
+      invitees = users;
+
+      let invitePromises = [];
+
+      each(invitees, (invitee) => {
+        let invitePromise = request(`/groups/${group._id}/invite`, {
+          uuids: [invitee._id]
+        });
+       invitePromises.push(invitePromise);
+      });
+
+      return Promise.all(invitePromises);
+    }).then((inviteResults) => {
+      resolve({
+        leader: leader,
+        group: group,
+        members: members,
+        invitees: invitees,
+      });
+    }).catch(reject);
+  });
+};
+
 export function resetHabiticaDB() {
   return new Promise((resolve, reject) => {
     mongo.connect('mongodb://localhost/habitrpg_test', (err, db) => {