diff --git a/openedx/core/djangoapps/schedules/README.md b/openedx/core/djangoapps/schedules/README.md
index 953d6c33fc..97247021c6 100644
--- a/openedx/core/djangoapps/schedules/README.md
+++ b/openedx/core/djangoapps/schedules/README.md
@@ -102,42 +102,118 @@ ACE_ENABLED_POLICIES = ['bulk_email_optout']
 ACE_CHANNEL_SAILTHRU_TEMPLATE_NAME = '<insert_sailthru_template_name_here>'
 ```
 
-### Configuration Models
+### Configuring Schedule Creation
 
 Make sure a Site has been created at `<lms_url>/admin/sites/site`.
 
+#### ScheduleConfig
+
 In the Django admin panel at `<lms_url>/admin/schedules/scheduleconfig/` create
 a ScheduleConfig and link it to the Site. Make sure to enable all of the
 settings:
 
 * `create_schedules`: enables creating new Schedules when new Course Enrollments
   are created.
-* `enqueue_*`: allows sending email tasks of this message type to celery.
-* `deliver_*`: allows delivering emails through ACE for this message type.
 * `hold_back_ratio`: ratio of all new Course Enrollments that should NOT have a
   Schedule created.
 
-If you are testing with a particular course, make sure that it is self-paced by
-going to `<studio_url>/admin/self_paced/selfpacedconfiguration/` and add an
-enabled self paced config. Then, go to Studio settings for the course and change
-the Course Pacing value to "Self-Paced". Note that the Course Start Date has to
-be set to sometime in the future in order to change the Course Pacing.
+#### Roll-out Waffle Flag
 
-### Waffle Flags and Switches
+There is one roll-out related course waffle flag that we plan to delete called
+`schedules.create_schedules_for_course`, which, if the
+`ScheduleConfig.create_schedules` is disabled, will enable schedule creation on
+a per-course basis.
 
-#### Global
+#### Self-paced Configuration
 
-All waffle flags and switches can be created at `<lms_url/admin/waffle/`.
+Schedules will only be created for a course if it is self-paced. A course can be
+configured to be self-paced by going to
+`<studio_url>/admin/self_paced/selfpacedconfiguration/` and adding an enabled
+self paced config. Then, go to Studio settings for the course and change the
+Course Pacing value to "Self-Paced". Note that the Course Start Date has to be
+set to sometime in the future in order to change the Course Pacing.
 
-#### Org-level
+### Configuring Upgrade Deadline on Schedule
 
-#### Course-level
+The upgrade reminder message type depends on there being a date in the
+`upgrade_deadline` field of the Schedule model. Up-sell messaging will also be
+added to the recurring nudge and course updates message types when an upgrade
+deadline date is present.
 
-Schedule creation: `schedules.create_schedules_for_course`
+#### DynamicUpgradeDeadlineConfiguration models
 
+In order to enable filling in the `upgrade_deadline` field of new Schedule
+models created, you must create and enable one of the following:
 
+* A DynamicUpgradeDeadlineConfiguration toggles the feature for all courses
+  globally.
+* A OrgDynamicUpgradeDeadlineConfiguration toggles the feature for all courses
+  in a particular organization.
+* A CourseDynamicUpgradeDeadlineConfiguration toggles the feature for a
+  particular course.
 
-### Other Requirements
+The CourseDynamicUpgradeDeadlineConfiguration takes precedence over the
+OrgDynamicUpgradeDeadlineConfiguration which takes precedence over the global
+DynamicUpgradeDeadlineConfiguration.
+
+The "deadline days" field specifies how many days from the day of the learner's
+enrollment will be their soft upgrade deadline on the Schedule model.
+
+#### Verified Course Mode
+
+The `upgrade_deadline` will only be filled for a course if it has a verified
+course mode. To add a verified course mode to a course, go to
+`<lms_url>/admin/course_modes/coursemode/` and add a course mode linked with
+the course with the "Mode" equal to "verified".
+
+### Configuring Email Sending
+
+#### ScheduleConfig
+
+The ScheduleConfig model at `<lms_url>/admin/schedules/scheduleconfig/` also has
+fields which configure enqueueing and delivering emails per message type:
+
+* `enqueue_*`: allows sending email tasks of this message type to celery.
+* `deliver_*`: allows delivering emails through ACE for this message type.
+
+#### Roll-out Waffle Flag
+
+Another roll-out related course waffle flag that we plan to delete called
+`schedules.send_updates_for_course` will enable sending specifically the course
+updates email per-course.
+
+### Configuring Highlights UI in Studio
+
+The button and modal on the course outline page that allows course authors to
+enter section highlights can be toggled globally by going to
+`<lms_url>/admin/waffle/switch/` and adding an active switch called
+`dynamic_pacing.studio_course_update`.
+
+This is a roll-out related waffle switch that we will eventually delete.
+
+### Configuring a Learner's Schedule
+
+Emails will only be sent to learners who have Schedule `start_date`s or
+`upgrade_deadline`s and ScheduleExperience that match the criteria for the
+message type.
+
+#### Recurring Nudge
+
+* Learners must have the ScheduleExperience type of "Recurring Nudge and Upgrade
+Reminder".
+* Their Schedule `start_date` must be 3 or 10 days before the current date.
+
+#### Upgrade Reminder
+
+* Learners must have the ScheduleExperience type of "Recurring Nudge and Upgrade
+Reminder".
+* Their Schedule `upgrade_deadline` must be 2 days after the current date.
+
+#### Course Update
+
+* Learners must have the ScheduleExperience type of "Course Updates".
+* Their Schedule `start_date` must be 7, 14, or any increment of 7 days up to 77
+  days before the current date.
 
 ## Testing Changes