diff --git a/common/djangoapps/util/tests/test_db.py b/common/djangoapps/util/tests/test_db.py
index 7567a83aba..108b66a827 100644
--- a/common/djangoapps/util/tests/test_db.py
+++ b/common/djangoapps/util/tests/test_db.py
@@ -197,7 +197,6 @@ class MigrationTests(TestCase):
     Tests for migrations.
     """
 
-    @unittest.skip('migration is purposely out of sync with models atm.')
     @override_settings(MIGRATION_MODULES={})
     def test_migrations_are_in_sync(self):
         """
diff --git a/docs/decisions/0005-studio-lms-subdomain-boundaries.rst b/docs/decisions/0005-studio-lms-subdomain-boundaries.rst
new file mode 100644
index 0000000000..1090e3f0bb
--- /dev/null
+++ b/docs/decisions/0005-studio-lms-subdomain-boundaries.rst
@@ -0,0 +1,178 @@
+Status
+======
+
+Proposed
+
+
+Context
+=======
+
+The ``edx-platform`` repo contains both Studio and the LMS for Open edX. These
+two systems roughly correspond to the Content Authoring and Learning subdomains,
+but the precise separation of responsibilities is currently unclear in many
+cases. This ADR is intended to clarify those boundaries and offer guidelines for
+how developers should compose new functionality across these systems, as well as
+providing a direction for migrating existing functionality over the long term.
+
+Note that it is likely that we'll further separate content authoring (e.g.
+content libraries) from course run administration (e.g. grading policy). It's
+possible that both of these will evolve under the umbrella of what users see as
+"Studio". Even if that happens, there will still be an architectural split
+between the Content Authoring and Learning subdomains within that new Studio.
+
+
+Decision
+========
+
+The high level guidelines for the interaction between the Content Authoring and
+Learning subdomains currently represented by Studio and LMS are:
+
+* Studio should not store Learner information.
+* Studio and LMS should use different representations of content.
+* Decouple content grouping concepts from user/learning grouping concepts.
+* Studio Content data acts as an input to LMS policy and Learner Experience data.
+* LMS data should not flow backward into Studio.
+* Content Authoring changes require explicit publishing of versioned data.
+
+
+Studio should not store Learner information.
+--------------------------------------------
+
+Studio's responsibility centers around the content itself. It should not store
+information about students, which brings with it many other concerns around
+data sensitivity and scale.
+
+
+Studio and LMS should use different representations of content.
+--------------------------------------------------------------------
+
+Content authoring will require versioned storage of data, ownership tracking,
+tagging, and other metadata. The LMS focuses on read-optimization at a much
+higher scale. We've long suffered from added code complexity and performance
+issues by trying to cover both usage patterns with ModuleStore.
+
+We have already taken steps to create a read-optimized store in the form of
+Block Transformers. We should continue this practice and encourage the LMS to
+transform content at publish-time into whatever representation its various
+systems (courseware, grading, scheduling, etc.) require to be performant.
+
+
+Decouple content grouping concepts from user/learning grouping concepts.
+------------------------------------------------------------------------
+
+A common use case for course content is to show different bits of content to
+different cohorts of users. For instance, a university might have a licensing
+agreement that allows it to show a set of vidoes only to its own staff and
+students, and not a wider MOOC audience. Studio needs to be able to annotate
+this data somehow, but the list of available cohorts for a given course is
+considered Learner information that may change from run to run.
+
+We solve this by using a level of indirection. Studio doesn't map content into
+Cohorts of students (an LMS concept). It maps content into Content Groups. The
+LMS is then responsible for both the creation of Cohorts as well as the mapping
+of Content Groups to Cohorts.
+
+While this might sound a little cumbersome, it actually allows for a cleaner
+separation of concerns. Content Groups describe what the content is: restricted
+copyright, advanced material, labratory exercises, etc. Cohorts describe who is
+consuming that material: on campus students, alumni, the general MOOC audience,
+etc. The Content Group is an Authoring decision based on the properties of the
+content itself. The Cohort mapping is a policy decision about the Learning
+experience of a particular set of students.
+
+Furthermore, the mapping of Content Groups to Cohorts is not 1:1. You could
+decide that both on-campus students and alumni get the same content group
+experience, while keeping those Cohorts separate for the purposes of other parts
+of the LMS like forums discussions.
+
+A more future looking example might be the interaction between Open edX
+courseware and third party forum services. The fact that certain units are
+marked as discussable topics might be a Content Authoring decision in Studio,
+while the choice of which forum service those discussions happen in might be a
+Learning decision in the LMS.
+
+
+Studio Content data acts as an input to LMS policy and Learner Experience data.
+-------------------------------------------------------------------------------
+
+As courseware becomes more dynamic, certain concepts in the LMS are becoming
+richer than their equivalent concepts in Studio. In these situations, we should
+think of the data relationship as a one way flow of data from Studio to the LMS.
+The LMS takes Studio data as an input that it can enrich, transform, or override
+as necessary to create the desired student learning experience.
+
+Content scheduling is a good example of this. In the early days of Open edX,
+course teams would set start and due dates for subsections in Studio, and that
+would be the end of it. Today, we have personalized schedules, individual due
+date extensions, and more. The pattern we use to accomplish this is:
+
+* Copy the schedule information from Studio to the LMS at the time a course is
+  published, transforming it into a more easily queryable form in the process.
+* Add additional data models in the LMS to support use cases like individual due
+  date extensions and personalized rescheduling. This is currently handled by
+  the edx_when app, developed in the edx-when repository.
+* Remap field data so that XBlocks in the LMS runtime query this richer data
+  model. Accessing an XBlock's ``start`` or ``due`` attribute in the Studio
+  runtime continues to work with simple key/values in ModuleStore, but the LMS
+  XBlock runtime will fetch those values from edx-when's in-process API.
+
+This approach allows us to add flexibility to the LMS, while preserving
+backwards compatibility with existing XBlock content.
+
+
+LMS data should not flow backward into Studio.
+----------------------------------------------
+
+Since LMS concepts extend Studio ones, we don't want changes to flow backwards
+from the LMS back into Studio. Some reasons:
+
+* There is no guarantee that Studio course runs will be 1:1 with LMS course
+  runs. In fact, one to many mappings of course runs already exist if CCX
+  courses are enabled.
+* A unidirectional data flow makes the system easier to debug and reason about.
+* The OLX import/export process stays much simpler if it doesn't have to
+  consider data that the LMS has added.
+
+
+Content Authoring changes require explicit publishing of versioned data.
+------------------------------------------------------------------------
+
+Changes to content data should be marked with an explicit, versioned publishing
+step. Many LMS systems update their representations of content data based on
+publish signals from Studio today. Studio also needs to differentiate draft
+changes authors want to make from changes that are ready for student use.
+
+The LMS is permitted to modify the learning experience without any such explicit
+publishing step. Deadlines may pass, blocking off student access to certain
+parts of a course. Individual students may be placed into different teams or
+cohorts, given extensions, re-graded, etc.
+
+
+Goals
+=====
+
+* Developers will have a clearer understanding of where to build authoring and
+  learning experience functionality.
+* Improved separation of these subdomains will allow for easier debugging and
+  better performance.
+* Decoupling these subdomains will allow for more rapid interation and
+  innovation.
+
+
+Alternatives Considered
+=======================
+
+An early alternative approach (that periodically resurfaces) is to make the
+content editing and publishing process happen in a much more integrated way. The
+learning and authoring experience blend together so closely that the author is
+essentially looking at the same interface as the student, supplemented with an
+edit button to modify thing in-line.
+
+This approach was rejected early on because:
+
+* Authoring needs differed in the workflow and information that they had to
+  surface to course authors.
+* Separating the authoring and student experience allows multiple authoring
+  systems (e.g. GitHub based OLX authoring).
+* At various points, the content authoring experience has been owned by a
+  different team than the learning experience.
diff --git a/lms/djangoapps/courseware/courses.py b/lms/djangoapps/courseware/courses.py
index 4beabc17b1..58db73568e 100644
--- a/lms/djangoapps/courseware/courses.py
+++ b/lms/djangoapps/courseware/courses.py
@@ -501,14 +501,14 @@ def get_course_assignment_date_blocks(course, user, request, num_return=None,
     if num_return is None in date increasing order.
     """
     date_blocks = []
-    for assignment in get_course_assignments(course.id, user, request, include_access=include_access):
+    for assignment in get_course_assignments(course.id, user, include_access=include_access):
         date_block = CourseAssignmentDate(course, user)
         date_block.date = assignment.date
         date_block.contains_gated_content = assignment.contains_gated_content
         date_block.complete = assignment.complete
         date_block.assignment_type = assignment.assignment_type
         date_block.past_due = assignment.past_due
-        date_block.link = assignment.url
+        date_block.link = request.build_absolute_uri(assignment.url) if assignment.url else ''
         date_block.set_title(assignment.title, link=assignment.url)
         date_blocks.append(date_block)
     date_blocks = sorted((b for b in date_blocks if b.is_enabled or include_past_dates), key=date_block_key_fn)
@@ -518,7 +518,7 @@ def get_course_assignment_date_blocks(course, user, request, num_return=None,
 
 
 @request_cached()
-def get_course_assignments(course_key, user, request, include_access=False):
+def get_course_assignments(course_key, user, include_access=False):
     """
     Returns a list of assignment (at the subsection/sequential level) due dates for the given course.
 
@@ -544,12 +544,11 @@ def get_course_assignments(course_key, user, request, include_access=False):
 
             assignment_type = block_data.get_xblock_field(subsection_key, 'format', None)
 
-            url = ''
+            url = None
             start = block_data.get_xblock_field(subsection_key, 'start')
             assignment_released = not start or start < now
             if assignment_released:
                 url = reverse('jump_to', args=[course_key, subsection_key])
-                url = request and request.build_absolute_uri(url)
 
             complete = block_data.get_xblock_field(subsection_key, 'complete', False)
             past_due = not complete and due < now
diff --git a/openedx/core/djangoapps/oauth_dispatch/docs/decisions/0006-enforce-scopes-in-LMS-APIs.rst b/openedx/core/djangoapps/oauth_dispatch/docs/decisions/0006-enforce-scopes-in-LMS-APIs.rst
index d9d1679889..547d8a7427 100644
--- a/openedx/core/djangoapps/oauth_dispatch/docs/decisions/0006-enforce-scopes-in-LMS-APIs.rst
+++ b/openedx/core/djangoapps/oauth_dispatch/docs/decisions/0006-enforce-scopes-in-LMS-APIs.rst
@@ -4,7 +4,7 @@
 Status
 ------
 
-Proposed
+Accepted
 
 Context
 -------
diff --git a/openedx/core/djangoapps/oauth_dispatch/docs/decisions/0007-include-organizations-in-tokens.rst b/openedx/core/djangoapps/oauth_dispatch/docs/decisions/0007-include-organizations-in-tokens.rst
index 134bdc4509..5f3e4d181c 100644
--- a/openedx/core/djangoapps/oauth_dispatch/docs/decisions/0007-include-organizations-in-tokens.rst
+++ b/openedx/core/djangoapps/oauth_dispatch/docs/decisions/0007-include-organizations-in-tokens.rst
@@ -4,7 +4,7 @@
 Status
 ------
 
-Proposed
+Accepted
 
 Context
 -------
@@ -42,9 +42,9 @@ Here are a few organizational relationships that exist in the edX system:
     do so either via
 
     a. bulk APIs using the *Client Credentials grant type* (e.g., to
-       synchronize their own data in a background process) or 
+       synchronize their own data in a background process) or
 
-    b. a user-specific API on behalf of a logged-in user via the 
+    b. a user-specific API on behalf of a logged-in user via the
        *Authorization grant type* and *edX as the identity provider*
        (e.g., to display user-specific data on their own portal).
 
@@ -100,7 +100,7 @@ organization information to the granting end-user.
 
     "content_org:Microsoft"
 
-* For a token created on behalf of a user (*not* created via a 
+* For a token created on behalf of a user (*not* created via a
   *Client Credentials grant type*), the token
   is further restricted specifically for the granting user.  And so, a
   "user" filter with the value "me" would be added for this grant type.
@@ -137,7 +137,7 @@ Token Examples
 Client Credentials (server-to-server) grant type
 ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
 
-When a trusted application makes server-to-server calls, the application's 
+When a trusted application makes server-to-server calls, the application's
 service user info is included in the JWT and the *filters* field
 includes the organization identifier and type associated with the application.
 
@@ -166,7 +166,7 @@ filter “me” in the *filters* field.
     "version": "1.0",
     "preferred_username": "ajay_mehta",
     ...
-  } 
+  }
 
 Consequences
 ------------
@@ -191,7 +191,7 @@ Consequences
   make sure there are no security issues introduced where old endpoints
   that are not aware of the new filter do not enforce it.  Possible
   ways of doing so are:
- 
+
   * Endpoints that are highly security sensitive should reject any
     token that includes an unrecognized filter.
 
@@ -206,7 +206,7 @@ Consequences
   they don't recognize. For example:
 
     "grades:read:content_org"
-  
+
   Additionally, this alternative would allow tokens to specify different filters
   for different scopes.
 
diff --git a/openedx/features/calendar_sync/__init__.py b/openedx/features/calendar_sync/__init__.py
index 77fd2dd0b2..47f76c832d 100644
--- a/openedx/features/calendar_sync/__init__.py
+++ b/openedx/features/calendar_sync/__init__.py
@@ -1,6 +1,7 @@
 """
 Calendar syncing Course dates with a User.
 """
+default_app_config = 'openedx.features.calendar_sync.apps.UserCalendarSyncConfig'
 
 
 def get_calendar_event_id(user, block_key, date_type, hostname):
diff --git a/openedx/features/calendar_sync/admin.py b/openedx/features/calendar_sync/admin.py
new file mode 100644
index 0000000000..02609df7da
--- /dev/null
+++ b/openedx/features/calendar_sync/admin.py
@@ -0,0 +1,4 @@
+from django.contrib import admin
+from .models import UserCalendarSyncConfig
+
+admin.site.register(UserCalendarSyncConfig)
diff --git a/openedx/features/calendar_sync/apps.py b/openedx/features/calendar_sync/apps.py
new file mode 100644
index 0000000000..ac835080de
--- /dev/null
+++ b/openedx/features/calendar_sync/apps.py
@@ -0,0 +1,18 @@
+"""
+Define the calendar_sync Django App.
+"""
+
+# -*- coding: utf-8 -*-
+
+
+from django.apps import AppConfig
+
+
+class UserCalendarSyncConfig(AppConfig):
+    name = 'openedx.features.calendar_sync'
+
+    def ready(self):
+        super(UserCalendarSyncConfig, self).ready()
+
+        # noinspection PyUnresolvedReferences
+        import openedx.features.calendar_sync.signals  # pylint: disable=import-outside-toplevel,unused-import
diff --git a/openedx/features/calendar_sync/ics.py b/openedx/features/calendar_sync/ics.py
index 706b092768..fc465443e7 100644
--- a/openedx/features/calendar_sync/ics.py
+++ b/openedx/features/calendar_sync/ics.py
@@ -9,12 +9,13 @@ from icalendar import Calendar, Event, vCalAddress, vText
 
 from lms.djangoapps.courseware.courses import get_course_assignments
 from openedx.core.djangoapps.site_configuration.helpers import get_value
+from openedx.core.djangoapps.site_configuration.models import SiteConfiguration
 from openedx.core.djangolib.markup import HTML
 
 from . import get_calendar_event_id
 
 
-def generate_ics_for_event(uid, title, course_name, now, start, organizer_name, organizer_email):
+def generate_ics_for_event(uid, title, course_name, now, start, organizer_name, organizer_email, config):
     """
     Generates an ics-formatted bytestring for the given assignment information.
 
@@ -36,6 +37,7 @@ def generate_ics_for_event(uid, title, course_name, now, start, organizer_name,
     event.add('dtstart', start)
     event.add('duration', timedelta(0))
     event.add('transp', 'TRANSPARENT')  # available, rather than busy
+    event.add('sequence', config.ics_sequence)
 
     cal = Calendar()
     cal.add('prodid', '-//Open edX//calendar_sync//EN')
@@ -46,28 +48,31 @@ def generate_ics_for_event(uid, title, course_name, now, start, organizer_name,
     return cal.to_ical()
 
 
-def generate_ics_for_user_course(course, user, request):
+def generate_ics_files_for_user_course(course, user, user_calendar_sync_config_instance):
     """
     Generates ics-formatted bytestrings of all assignments for a given course and user.
 
     To pretty-print each bytestring, do: `ics.decode('utf8').replace('\r\n', '\n')`
 
-    Returns an iterable of ics files, each one representing an assignment.
+    Returns a dictionary of ics files, each one representing an assignment.
     """
-    assignments = get_course_assignments(course.id, user, request)
+    assignments = get_course_assignments(course.id, user)
     platform_name = get_value('platform_name', settings.PLATFORM_NAME)
     platform_email = get_value('email_from_address', settings.DEFAULT_FROM_EMAIL)
     now = datetime.now(pytz.utc)
+    site_config = SiteConfiguration.get_configuration_for_org(course.org)
 
-    return (
-        generate_ics_for_event(
+    ics_files = {}
+    for assignment in assignments:
+        ics_files[assignment.title] = generate_ics_for_event(
             now=now,
             organizer_name=platform_name,
             organizer_email=platform_email,
             start=assignment.date,
             title=assignment.title,
             course_name=course.display_name_with_default,
-            uid=get_calendar_event_id(user, str(assignment.block_key), 'due', request.site.domain),
+            uid=get_calendar_event_id(user, str(assignment.block_key), 'due', site_config.site.domain),
+            config=user_calendar_sync_config_instance,
         )
-        for assignment in assignments
-    )
+
+    return ics_files
diff --git a/openedx/features/calendar_sync/migrations/0002_auto_20200709_1743.py b/openedx/features/calendar_sync/migrations/0002_auto_20200709_1743.py
new file mode 100644
index 0000000000..5b78da35c7
--- /dev/null
+++ b/openedx/features/calendar_sync/migrations/0002_auto_20200709_1743.py
@@ -0,0 +1,23 @@
+# Generated by Django 2.2.14 on 2020-07-09 17:43
+
+from django.db import migrations, models
+
+
+class Migration(migrations.Migration):
+
+    dependencies = [
+        ('calendar_sync', '0001_initial'),
+    ]
+
+    operations = [
+        migrations.AddField(
+            model_name='historicalusercalendarsyncconfig',
+            name='ics_sequence',
+            field=models.IntegerField(default=0),
+        ),
+        migrations.AddField(
+            model_name='usercalendarsyncconfig',
+            name='ics_sequence',
+            field=models.IntegerField(default=0),
+        ),
+    ]
diff --git a/openedx/features/calendar_sync/models.py b/openedx/features/calendar_sync/models.py
index 49608c6a42..b3c817575a 100644
--- a/openedx/features/calendar_sync/models.py
+++ b/openedx/features/calendar_sync/models.py
@@ -19,6 +19,7 @@ class UserCalendarSyncConfig(models.Model):
     user = models.ForeignKey(User, db_index=True, on_delete=models.CASCADE)
     course_key = CourseKeyField(max_length=255, db_index=True)
     enabled = models.BooleanField(default=False)
+    ics_sequence = models.IntegerField(default=0)
 
     history = HistoricalRecords()
 
diff --git a/openedx/features/calendar_sync/signals.py b/openedx/features/calendar_sync/signals.py
new file mode 100644
index 0000000000..86915623f0
--- /dev/null
+++ b/openedx/features/calendar_sync/signals.py
@@ -0,0 +1,35 @@
+"""
+Signal handler for calendar sync models
+"""
+from django.db.models.signals import post_save
+from django.dispatch.dispatcher import receiver
+
+from openedx.core.djangoapps.content.course_overviews.models import CourseOverview
+from openedx.features.course_experience import CALENDAR_SYNC_FLAG, RELATIVE_DATES_FLAG
+
+from .ics import generate_ics_files_for_user_course
+from .models import UserCalendarSyncConfig
+from .utils import send_email_with_attachment
+
+
+@receiver(post_save, sender=UserCalendarSyncConfig)
+def handle_calendar_sync_email(sender, instance, created, **kwargs):
+    if (
+        CALENDAR_SYNC_FLAG.is_enabled(instance.course_key) and
+        RELATIVE_DATES_FLAG.is_enabled(instance.course_key) and
+        created
+    ):
+        user = instance.user
+        email = user.email
+        course_overview = CourseOverview.objects.get(id=instance.course_key)
+        ics_files = generate_ics_files_for_user_course(course_overview, user, instance)
+        send_email_with_attachment(
+            [email],
+            ics_files,
+            course_overview.display_name,
+            created
+        )
+        post_save.disconnect(handle_calendar_sync_email, sender=UserCalendarSyncConfig)
+        instance.ics_sequence = instance.ics_sequence + 1
+        instance.save()
+        post_save.connect(handle_calendar_sync_email, sender=UserCalendarSyncConfig)
diff --git a/openedx/features/calendar_sync/tests/factories.py b/openedx/features/calendar_sync/tests/factories.py
new file mode 100644
index 0000000000..4240219620
--- /dev/null
+++ b/openedx/features/calendar_sync/tests/factories.py
@@ -0,0 +1,12 @@
+from factory.django import DjangoModelFactory
+from openedx.features.calendar_sync.models import UserCalendarSyncConfig
+
+
+class UserCalendarSyncConfigFactory(DjangoModelFactory):
+    """
+    Factory class for SiteConfiguration model
+    """
+    class Meta(object):
+        model = UserCalendarSyncConfig
+
+    enabled = True
diff --git a/openedx/features/calendar_sync/tests/test_ics.py b/openedx/features/calendar_sync/tests/test_ics.py
index bd0892ce36..8e053134d1 100644
--- a/openedx/features/calendar_sync/tests/test_ics.py
+++ b/openedx/features/calendar_sync/tests/test_ics.py
@@ -9,9 +9,10 @@ from mock import patch
 
 from lms.djangoapps.courseware.courses import _Assignment
 from openedx.core.djangoapps.content.course_overviews.tests.factories import CourseOverviewFactory
-from openedx.core.djangoapps.site_configuration.tests.factories import SiteFactory
+from openedx.core.djangoapps.site_configuration.tests.factories import SiteConfigurationFactory, SiteFactory
 from openedx.features.calendar_sync import get_calendar_event_id
-from openedx.features.calendar_sync.ics import generate_ics_for_user_course
+from openedx.features.calendar_sync.ics import generate_ics_files_for_user_course
+from openedx.features.calendar_sync.tests.factories import UserCalendarSyncConfigFactory
 from student.tests.factories import UserFactory
 
 
@@ -30,6 +31,13 @@ class TestIcsGeneration(TestCase):
         self.request = RequestFactory().request()
         self.request.site = SiteFactory()
         self.request.user = self.user
+        self.site_config = SiteConfigurationFactory.create(
+            site_values={'course_org_filter': self.course.org}
+        )
+        self.user_calendar_sync_config = UserCalendarSyncConfigFactory.create(
+            user=self.user,
+            course_key=self.course.id,
+        )
 
     def make_assigment(
         self, block_key=None, title=None, url=None, date=None, contains_gated_content=False, complete=False,
@@ -50,6 +58,7 @@ DTSTART;VALUE=DATE-TIME:{timedue}
 DURATION:P0D
 DTSTAMP;VALUE=DATE-TIME:20131003T082455Z
 UID:{uid}
+SEQUENCE:{sequence}
 DESCRIPTION:{summary} is due for {course}.
 ORGANIZER;CN=édX:mailto:registration@example.com
 TRANSP:TRANSPARENT
@@ -61,7 +70,8 @@ END:VCALENDAR
                 summary=assignment.title,
                 course=self.course.display_name_with_default,
                 timedue=assignment.date.strftime('%Y%m%dT%H%M%SZ'),
-                uid=get_calendar_event_id(self.user, str(assignment.block_key), 'due', self.request.site.domain),
+                uid=get_calendar_event_id(self.user, str(assignment.block_key), 'due', self.site_config.site.domain),
+                sequence=self.user_calendar_sync_config.ics_sequence
             )
             for assignment in assignments
         )
@@ -70,11 +80,13 @@ END:VCALENDAR
         """ Uses generate_ics_for_user_course to create ics files for the given assignments """
         with patch('openedx.features.calendar_sync.ics.get_course_assignments') as mock_get_assignments:
             mock_get_assignments.return_value = assignments
-            return generate_ics_for_user_course(self.course, self.user, self.request)
+            return generate_ics_files_for_user_course(self.course, self.user, self.user_calendar_sync_config)
 
     def assert_ics(self, *assignments):
         """ Asserts that the generated and expected ics for the given assignments are equal """
-        generated = [ics.decode('utf8').replace('\r\n', '\n') for ics in self.generate_ics(*assignments)]
+        generated = [
+            file.decode('utf8').replace('\r\n', '\n') for file in sorted(self.generate_ics(*assignments).values())
+        ]
         self.assertEqual(len(generated), len(assignments))
         self.assertListEqual(generated, list(self.expected_ics(*assignments)))
 
diff --git a/openedx/features/calendar_sync/utils.py b/openedx/features/calendar_sync/utils.py
index 7bade9b7fd..4ecbbf6285 100644
--- a/openedx/features/calendar_sync/utils.py
+++ b/openedx/features/calendar_sync/utils.py
@@ -6,43 +6,50 @@ from django.conf import settings
 from django.utils.html import format_html
 from django.utils.translation import ugettext_lazy as _
 import os
-
 import boto3
 
 logger = logging.getLogger(__name__)
 
 
 def calendar_sync_initial_email_content(course_name):
-    subject = _('Stay on Track')
-    body_text = _('Sticking to a schedule is the best way to ensure that you successfully complete your self-paced '
-                  'course. This schedule of assignment due dates for {course} will help you stay on track!'
-                  ).format(course=course_name)
-    body = format_html('<div>{text}</div>', text=body_text)
+    subject = _('Sync {course} to your calendar').format(course=course_name)
+    body_paragraph_1 = _('Sticking to a schedule is the best way to ensure that you successfully complete your '
+                         'self-paced course. This schedule for {course} will help you stay on track!'
+                         ).format(course=course_name)
+    body_paragraph_2 = _('Once you sync your course schedule to your calendar, any updates to the course from your '
+                         'instructor will be automatically reflected. You can remove the course from your calendar '
+                         'at any time.')
+    body = format_html(
+        '<div style="margin-bottom:10px">{bp1}</div><div>{bp2}</div>',
+        bp1=body_paragraph_1,
+        bp2=body_paragraph_2
+    )
+
     return subject, body
 
 
 def calendar_sync_update_email_content(course_name):
-    subject = _('Updates for Your {course} Schedule').format(course=course_name)
-    body_text = _('Your assignment due dates for {course} were recently adjusted. Update your calendar with your new '
-                  'schedule to ensure that you stay on track!').format(course=course_name)
-    body = format_html('<div>{text}</div>', text=body_text)
+    subject = _('{course} dates have been updated on your calendar').format(course=course_name)
+    body_paragraph = _('You have successfully shifted your course schedule and your calendar is up to date.'
+                       ).format(course=course_name)
+    body = format_html('<div>{text}</div>', text=body_paragraph)
+
     return subject, body
 
 
-def prepare_attachments(attachment_data):
+def prepare_attachments(attachment_data, file_ext=''):
     """
     Helper function to create a list contain file attachment objects
     for use with MIMEMultipart
     Returns a list of MIMEApplication objects
     """
-
     attachments = []
     for filename, data in attachment_data.items():
         msg_attachment = MIMEApplication(data)
         msg_attachment.add_header(
             'Content-Disposition',
             'attachment',
-            filename=os.path.basename(filename)
+            filename=os.path.basename(filename) + file_ext
         )
         msg_attachment.set_type('text/calendar')
         attachments.append(msg_attachment)
@@ -50,17 +57,17 @@ def prepare_attachments(attachment_data):
     return attachments
 
 
-def send_email_with_attachment(to_emails, attachment_data, course_name, is_update=False):
+def send_email_with_attachment(to_emails, attachment_data, course_name, is_initial):
     # connect to SES
     client = boto3.client('ses', region_name=settings.AWS_SES_REGION_NAME)
 
-    subject, body = (calendar_sync_update_email_content(course_name) if is_update else
-                     calendar_sync_initial_email_content(course_name))
+    subject, body = (calendar_sync_initial_email_content(course_name) if is_initial else
+                     calendar_sync_update_email_content(course_name))
 
     # build email body as html
     msg_body = MIMEText(body, 'html')
 
-    attachments = prepare_attachments(attachment_data)
+    attachments = prepare_attachments(attachment_data, '.ics')
 
     # iterate over each email in the list to send emails independently
     for email in to_emails:
diff --git a/requirements/edx/base.txt b/requirements/edx/base.txt
index be86ce5c74..efad80c60c 100644
--- a/requirements/edx/base.txt
+++ b/requirements/edx/base.txt
@@ -6,7 +6,7 @@
 #
 -e git+https://github.com/edx/acid-block.git@98aecba94ecbfa934e2d00262741c0ea9f557fc9#egg=acid-xblock  # via -r requirements/edx/github.in
 -e common/lib/capa  # via -r requirements/edx/local.in
--e git+https://github.com/edx/codejail.git@4127fc4bd5775cc72aee8d7f0a70e31405e22439#egg=codejail  # via -r requirements/edx/github.in
+-e git+https://github.com/edx/codejail.git@56abd45fcf68c6ab7b523768aa5991d6e04d8241#egg=codejail==3.0.0  # via -r requirements/edx/github.in
 -e git+https://github.com/edx/django-wiki.git@0.0.27#egg=django-wiki  # via -r requirements/edx/github.in
 -e git+https://github.com/edx/DoneXBlock.git@2.0.2#egg=done-xblock  # via -r requirements/edx/github.in
 -e git+https://github.com/jazkarta/edx-jsme.git@690dbf75441fa91c7c4899df0b83d77f7deb5458#egg=edx-jsme  # via -r requirements/edx/github.in
@@ -111,7 +111,7 @@ edx-rest-api-client==5.2.1  # via -r requirements/edx/base.in, edx-enterprise, e
 edx-search==1.4.1         # via -r requirements/edx/base.in
 edx-sga==0.11.0           # via -r requirements/edx/base.in
 edx-submissions==3.1.11   # via -r requirements/edx/base.in, ora2
-edx-tincan-py35==0.0.5    # via edx-enterprise
+edx-tincan-py35==0.0.9    # via edx-enterprise
 edx-user-state-client==1.2.0  # via -r requirements/edx/base.in
 edx-when==1.2.9           # via -r requirements/edx/base.in, edx-proctoring
 edxval==1.3.8             # via -r requirements/edx/base.in
diff --git a/requirements/edx/development.txt b/requirements/edx/development.txt
index c5ed78ed57..8f7ff7565d 100644
--- a/requirements/edx/development.txt
+++ b/requirements/edx/development.txt
@@ -6,7 +6,7 @@
 #
 -e git+https://github.com/edx/acid-block.git@98aecba94ecbfa934e2d00262741c0ea9f557fc9#egg=acid-xblock  # via -r requirements/edx/testing.txt
 -e common/lib/capa  # via -r requirements/edx/testing.txt
--e git+https://github.com/edx/codejail.git@4127fc4bd5775cc72aee8d7f0a70e31405e22439#egg=codejail  # via -r requirements/edx/testing.txt
+-e git+https://github.com/edx/codejail.git@56abd45fcf68c6ab7b523768aa5991d6e04d8241#egg=codejail==3.0.0  # via -r requirements/edx/testing.txt
 -e git+https://github.com/edx/django-wiki.git@0.0.27#egg=django-wiki  # via -r requirements/edx/testing.txt
 -e git+https://github.com/edx/DoneXBlock.git@2.0.2#egg=done-xblock  # via -r requirements/edx/testing.txt
 -e git+https://github.com/jazkarta/edx-jsme.git@690dbf75441fa91c7c4899df0b83d77f7deb5458#egg=edx-jsme  # via -r requirements/edx/testing.txt
@@ -125,7 +125,7 @@ edx-search==1.4.1         # via -r requirements/edx/testing.txt
 edx-sga==0.11.0           # via -r requirements/edx/testing.txt
 edx-sphinx-theme==1.5.0   # via -r requirements/edx/development.in
 edx-submissions==3.1.11   # via -r requirements/edx/testing.txt, ora2
-edx-tincan-py35==0.0.5    # via -r requirements/edx/testing.txt, edx-enterprise
+edx-tincan-py35==0.0.9    # via -r requirements/edx/testing.txt, edx-enterprise
 edx-user-state-client==1.2.0  # via -r requirements/edx/testing.txt
 edx-when==1.2.9           # via -r requirements/edx/testing.txt, edx-proctoring
 edxval==1.3.8             # via -r requirements/edx/testing.txt
diff --git a/requirements/edx/github.in b/requirements/edx/github.in
index 767e19f786..fcbb4f4044 100644
--- a/requirements/edx/github.in
+++ b/requirements/edx/github.in
@@ -59,7 +59,7 @@ git+https://github.com/edx/MongoDBProxy.git@d92bafe9888d2940f647a7b2b2383b29c752
 -e git+https://github.com/jazkarta/edx-jsme.git@690dbf75441fa91c7c4899df0b83d77f7deb5458#egg=edx-jsme
 
 # Our libraries:
--e git+https://github.com/edx/codejail.git@4127fc4bd5775cc72aee8d7f0a70e31405e22439#egg=codejail
+-e git+https://github.com/edx/codejail.git@56abd45fcf68c6ab7b523768aa5991d6e04d8241#egg=codejail==3.0.0
 -e git+https://github.com/edx/acid-block.git@98aecba94ecbfa934e2d00262741c0ea9f557fc9#egg=acid-xblock
 -e git+https://github.com/edx/RateXBlock.git@2.0#egg=rate-xblock
 -e git+https://github.com/edx/DoneXBlock.git@2.0.2#egg=done-xblock
diff --git a/requirements/edx/testing.txt b/requirements/edx/testing.txt
index 4fd02cbf9e..a040b3b7fc 100644
--- a/requirements/edx/testing.txt
+++ b/requirements/edx/testing.txt
@@ -6,7 +6,7 @@
 #
 -e git+https://github.com/edx/acid-block.git@98aecba94ecbfa934e2d00262741c0ea9f557fc9#egg=acid-xblock  # via -r requirements/edx/base.txt
 -e common/lib/capa  # via -r requirements/edx/base.txt
--e git+https://github.com/edx/codejail.git@4127fc4bd5775cc72aee8d7f0a70e31405e22439#egg=codejail  # via -r requirements/edx/base.txt
+-e git+https://github.com/edx/codejail.git@56abd45fcf68c6ab7b523768aa5991d6e04d8241#egg=codejail==3.0.0  # via -r requirements/edx/base.txt
 -e git+https://github.com/edx/django-wiki.git@0.0.27#egg=django-wiki  # via -r requirements/edx/base.txt
 -e git+https://github.com/edx/DoneXBlock.git@2.0.2#egg=done-xblock  # via -r requirements/edx/base.txt
 -e git+https://github.com/jazkarta/edx-jsme.git@690dbf75441fa91c7c4899df0b83d77f7deb5458#egg=edx-jsme  # via -r requirements/edx/base.txt
@@ -121,7 +121,7 @@ edx-rest-api-client==5.2.1  # via -r requirements/edx/base.txt, edx-enterprise,
 edx-search==1.4.1         # via -r requirements/edx/base.txt
 edx-sga==0.11.0           # via -r requirements/edx/base.txt
 edx-submissions==3.1.11   # via -r requirements/edx/base.txt, ora2
-edx-tincan-py35==0.0.5    # via -r requirements/edx/base.txt, edx-enterprise
+edx-tincan-py35==0.0.9    # via -r requirements/edx/base.txt, edx-enterprise
 edx-user-state-client==1.2.0  # via -r requirements/edx/base.txt
 edx-when==1.2.9           # via -r requirements/edx/base.txt, edx-proctoring
 edxval==1.3.8             # via -r requirements/edx/base.txt