diff --git a/app/controllers/api/v1/jobs_controller.rb b/app/controllers/api/v1/jobs_controller.rb
index 38f39d70c61..3a1a2130038 100644
--- a/app/controllers/api/v1/jobs_controller.rb
+++ b/app/controllers/api/v1/jobs_controller.rb
@@ -19,6 +19,7 @@ class Api::V1::JobsController < Api::ApplicationController
     "prepare_establish_claim" => PrepareEstablishClaimTasksJob,
     "push_priority_appeals_to_judges" => PushPriorityAppealsToJudgesJob,
     "reassign_old_tasks" => ReassignOldTasksJob,
+    "send_reminder_emails_job" => VirtualHearings::SendReminderEmailsJob,
     "retrieve_documents_for_reader" => RetrieveDocumentsForReaderJob,
     "set_appeal_age_aod" => SetAppealAgeAodJob,
     "stats_collector" => StatsCollectorJob,
diff --git a/app/jobs/virtual_hearings/send_email.rb b/app/jobs/virtual_hearings/send_email.rb
index f0c2f2f4bc0..c9b54cd5674 100644
--- a/app/jobs/virtual_hearings/send_email.rb
+++ b/app/jobs/virtual_hearings/send_email.rb
@@ -7,10 +7,16 @@ class RecipientIsDeceasedVeteran < StandardError; end
 
   def initialize(virtual_hearing:, type:)
     @virtual_hearing = virtual_hearing
-    @type = type
+    @type = type.to_s
   end
 
   def call
+    # Assumption: Reminders and confirmation/cancellation/change emails are sent
+    # separately, so this will return early if any reminder emails are sent. If
+    # reminder emails are being sent, we are assuming the other emails have all
+    # already been sent too.
+    return if send_reminder
+
     if !virtual_hearing.appellant_email_sent
       virtual_hearing.update!(appellant_email_sent: send_email(appellant_recipient))
     end
@@ -30,19 +36,39 @@ def call
   delegate :appeal, to: :hearing
   delegate :veteran, to: :appeal
 
+  def send_reminder
+    if type == "appellant_reminder" && send_email(appellant_recipient)
+      virtual_hearing.update!(appellant_reminder_sent_at: Time.zone.now)
+
+      return true
+    end
+
+    if type == "representative_reminder" &&
+       !virtual_hearing.representative_email.nil? &&
+       send_email(representative_recipient)
+      virtual_hearing.update!(representative_reminder_sent_at: Time.zone.now)
+
+      return true
+    end
+
+    false
+  end
+
   def email_for_recipient(recipient)
     args = {
       mail_recipient: recipient,
       virtual_hearing: virtual_hearing
     }
 
-    case type.to_s
+    case type
     when "confirmation"
       VirtualHearingMailer.confirmation(**args)
     when "cancellation"
       VirtualHearingMailer.cancellation(**args)
     when "updated_time_confirmation"
       VirtualHearingMailer.updated_time_confirmation(**args)
+    when "appellant_reminder", "representative_reminder"
+      VirtualHearingMailer.reminder(**args)
     else
       fail ArgumentError, "Invalid type of email to send: `#{type}`"
     end
@@ -57,7 +83,10 @@ def external_message_id(msg)
       DataDogService.increment_counter(
         app_name: Constants.DATADOG_METRICS.HEARINGS.APP_NAME,
         metric_group: Constants.DATADOG_METRICS.HEARINGS.VIRTUAL_HEARINGS_GROUP_NAME,
-        metric_name: "emails.submitted"
+        metric_name: "emails.submitted",
+        attrs: {
+          email_type: type
+        }
       )
 
       Rails.logger.info(
@@ -101,7 +130,7 @@ def send_email(recipient)
 
     msg = email.deliver_now!
   rescue StandardError, Savon::Error, BGS::ShareError => error
-    # Savon::Error and BGS::ShareError are sometimes thrown when making requests to BGS enpoints
+    # Savon::Error and BGS::ShareError are sometimes thrown when making requests to BGS endpoints
     Raven.capture_exception(error)
 
     Rails.logger.warn("Failed to send #{type} email to #{recipient.title}: #{error}")
@@ -126,11 +155,11 @@ def create_sent_hearing_email_event(recipient, external_id)
     )
     SentHearingEmailEvent.create!(
       hearing: hearing,
-      email_type: type,
+      email_type: type.ends_with?("reminder") ? "reminder" : type,
       email_address: recipient.email,
       external_message_id: external_id,
       recipient_role: recipient_is_veteran ? "veteran" : recipient.title.downcase,
-      sent_by: virtual_hearing.updated_by
+      sent_by: type.ends_with?("reminder") ? User.system_user : virtual_hearing.updated_by
     )
   rescue StandardError => error
     Raven.capture_exception(error)
@@ -185,6 +214,8 @@ def appellant_recipient
   end
 
   def should_judge_receive_email?
-    !virtual_hearing.judge_email.nil? && !virtual_hearing.judge_email_sent && type.to_s != "cancellation"
+    !virtual_hearing.judge_email.nil? &&
+      !virtual_hearing.judge_email_sent &&
+      %w[confirmation updated_time_confirmation].include?(type)
   end
 end
diff --git a/app/jobs/virtual_hearings/send_reminder_emails_job.rb b/app/jobs/virtual_hearings/send_reminder_emails_job.rb
new file mode 100644
index 00000000000..3ffac35467a
--- /dev/null
+++ b/app/jobs/virtual_hearings/send_reminder_emails_job.rb
@@ -0,0 +1,37 @@
+# frozen_string_literal: true
+
+class VirtualHearings::SendReminderEmailsJob < ApplicationJob
+  def perform
+    VirtualHearingRepository.maybe_ready_for_reminder_email.each do |virtual_hearing|
+      send_reminder_emails(virtual_hearing)
+    end
+  end
+
+  private
+
+  def send_reminder_emails(virtual_hearing)
+    if should_send_appellant_reminder?(virtual_hearing)
+      VirtualHearings::SendEmail
+        .new(virtual_hearing: virtual_hearing, type: :appellant_reminder)
+        .call
+    end
+
+    if virtual_hearing.representative_email.present? && should_sent_representative_reminder?(virtual_hearing)
+      VirtualHearings::SendEmail
+        .new(virtual_hearing: virtual_hearing, type: :representative_reminder)
+        .call
+    end
+  end
+
+  def should_send_appellant_reminder?(virtual_hearing)
+    VirtualHearings::ReminderService
+      .new(virtual_hearing, virtual_hearing.appellant_reminder_sent_at)
+      .should_send_reminder_email?
+  end
+
+  def should_sent_representative_reminder?(virtual_hearing)
+    VirtualHearings::ReminderService
+      .new(virtual_hearing, virtual_hearing.representative_reminder_sent_at)
+      .should_send_reminder_email?
+  end
+end
diff --git a/app/models/hearings/sent_hearing_email_event.rb b/app/models/hearings/sent_hearing_email_event.rb
index 4f4ac861f2d..d67fd0f4eb0 100644
--- a/app/models/hearings/sent_hearing_email_event.rb
+++ b/app/models/hearings/sent_hearing_email_event.rb
@@ -28,7 +28,8 @@ class << self; undef_method :sent_to_appellant; end
     {
       confirmation: "confirmation",
       cancellation: "cancellation",
-      updated_time_confirmation: "updated_time_confirmation"
+      updated_time_confirmation: "updated_time_confirmation",
+      reminder: "reminder"
     }
   ), _prefix: :is
 
diff --git a/app/models/hearings/virtual_hearing.rb b/app/models/hearings/virtual_hearing.rb
index 4be54591238..537757c3886 100644
--- a/app/models/hearings/virtual_hearing.rb
+++ b/app/models/hearings/virtual_hearing.rb
@@ -86,6 +86,7 @@ def base_url
     HearingDay::REQUEST_TYPES[:central]
   ].freeze
 
+  # Whether or not all non-reminder emails were sent.
   def all_emails_sent?
     appellant_email_sent &&
       (judge_email.nil? || judge_email_sent) &&
diff --git a/app/repositories/virtual_hearing_repository.rb b/app/repositories/virtual_hearing_repository.rb
index 5fe154536c8..bc4a1364079 100644
--- a/app/repositories/virtual_hearing_repository.rb
+++ b/app/repositories/virtual_hearing_repository.rb
@@ -3,20 +3,16 @@
 class VirtualHearingRepository
   class << self
     def ready_for_deletion
-      virtual_hearings_for_ama_hearings = VirtualHearing.eligible_for_deletion
-        .where(hearing_type: Hearing.name)
-        .joins("INNER JOIN hearings ON hearings.id = virtual_hearings.hearing_id")
-        .joins("INNER JOIN hearing_days ON hearing_days.id = hearings.hearing_day_id")
+      virtual_hearings_for_ama_hearings = virtual_hearings_joined_with_hearings_and_hearing_day(Hearing)
+        .eligible_for_deletion
         .where(
           "hearing_days.scheduled_for < :today OR
           hearings.disposition='postponed' OR hearings.disposition='cancelled' OR
           virtual_hearings.request_cancelled = true", today: Time.zone.today
         )
 
-      virtual_hearings_for_legacy_hearings = VirtualHearing.eligible_for_deletion
-        .where(hearing_type: LegacyHearing.name)
-        .joins("INNER JOIN legacy_hearings ON legacy_hearings.id = virtual_hearings.hearing_id")
-        .joins("INNER JOIN hearing_days ON hearing_days.id = legacy_hearings.hearing_day_id")
+      virtual_hearings_for_legacy_hearings = virtual_hearings_joined_with_hearings_and_hearing_day(LegacyHearing)
+        .eligible_for_deletion
         .where(
           "hearing_days.scheduled_for < :today OR
           legacy_hearings.vacols_id in (:postponed_or_cancelled_vacols_ids) OR
@@ -27,14 +23,36 @@ def ready_for_deletion
       virtual_hearings_for_ama_hearings + virtual_hearings_for_legacy_hearings
     end
 
-    def pending_appellant_or_rep_emails_sql
-      <<-SQL
-        NOT virtual_hearings.appellant_email_sent
-        OR (
-          virtual_hearings.representative_email IS NOT null
-          AND NOT virtual_hearings.representative_email_sent
+    # Get all virtual hearings that *might* need to have a reminder email sent.
+    #
+    # @note The logic to determine whether or not a reminder email needs to be sent is
+    #   complex enough that it's not worth putting in an SQL query for maintainability reasons.
+    #   This method will find all active virtual hearings that are occurring within the next 7
+    #   days.
+    def maybe_ready_for_reminder_email
+      ama_virtual_hearings_ready_for_email = virtual_hearings_joined_with_hearings_and_hearing_day(Hearing)
+        .not_cancelled
+        .where(
+          "hearings.disposition NOT IN (:non_active_hearing_dispositions) OR hearings.disposition IS NULL",
+          non_active_hearing_dispositions: [:postponed, :cancelled]
         )
-      SQL
+        .where(where_hearing_occurs_within_the_timeframe)
+
+      legacy_virtual_hearings_ready_for_email = virtual_hearings_joined_with_hearings_and_hearing_day(LegacyHearing)
+        .not_cancelled
+        .where(where_hearing_occurs_within_the_timeframe)
+
+      postponed_or_cancelled_legacy = postponed_or_cancelled_vacols_ids
+
+      unless postponed_or_cancelled_legacy.empty?
+        # Active Hearings
+        legacy_virtual_hearings_ready_for_email = legacy_virtual_hearings_ready_for_email.where(
+          "legacy_hearings.vacols_id NOT IN (:postponed_or_cancelled_vacols_ids)",
+          postponed_or_cancelled_vacols_ids: postponed_or_cancelled_vacols_ids
+        )
+      end
+
+      ama_virtual_hearings_ready_for_email + legacy_virtual_hearings_ready_for_email
     end
 
     def cancelled_hearings_with_pending_emails
@@ -61,13 +79,47 @@ def hearings_with_pending_conference_or_pending_emails
 
     private
 
+    # Returns virtual hearings joined with either the legacy hearing or hearings table,
+    # and joined with the hearing day table.
+    def virtual_hearings_joined_with_hearings_and_hearing_day(appeal_type)
+      table = appeal_type.table_name
+
+      VirtualHearing
+        .where(hearing_type: appeal_type.name)
+        .joins("INNER JOIN #{table} ON #{table}.id = virtual_hearings.hearing_id")
+        .joins("INNER JOIN hearing_days ON hearing_days.id = #{table}.hearing_day_id")
+    end
+
     def postponed_or_cancelled_vacols_ids
       VACOLS::CaseHearing.by_dispositions(
         [
           VACOLS::CaseHearing::HEARING_DISPOSITIONS.key("postponed"),
           VACOLS::CaseHearing::HEARING_DISPOSITIONS.key("cancelled")
         ]
-      ).pluck(:hearing_pkseq).map(&:to_s)
+      ).pluck(:hearing_pkseq).map(&:to_s) || []
+    end
+
+    def pending_appellant_or_rep_emails_sql
+      <<-SQL
+        NOT virtual_hearings.appellant_email_sent
+        OR (
+          virtual_hearings.representative_email IS NOT null
+          AND NOT virtual_hearings.representative_email_sent
+        )
+      SQL
+    end
+
+    # Returns a where clause that can be used to find all hearings that occur within
+    # a given timeframe (in days).
+    #
+    # @note Requires a join with the `hearing_days` table.
+    def where_hearing_occurs_within_the_timeframe
+      <<-SQL
+        DATE_PART(
+        'day',
+        hearing_days.scheduled_for::timestamp - '#{Time.zone.today}'::timestamp
+        ) BETWEEN 1 AND 7
+      SQL
     end
   end
 end
diff --git a/app/services/virtual_hearings/reminder_service.rb b/app/services/virtual_hearings/reminder_service.rb
new file mode 100644
index 00000000000..6e7913258d5
--- /dev/null
+++ b/app/services/virtual_hearings/reminder_service.rb
@@ -0,0 +1,60 @@
+# frozen_string_literal: true
+
+##
+# Service that determines whether or not a send a reminder to the appellant or representative
+# about their virtual hearing.
+
+class VirtualHearings::ReminderService
+  def initialize(virtual_hearing, last_sent_reminder)
+    @virtual_hearing = virtual_hearing
+    @last_sent_reminder = last_sent_reminder
+  end
+
+  def should_send_reminder_email?
+    return false if days_until_hearing <= 0
+
+    should_send_2_day_reminder? ||
+      should_send_3_day_friday_reminder? ||
+      should_send_7_day_reminder?
+  end
+
+  private
+
+  attr_reader :virtual_hearing
+  attr_reader :last_sent_reminder
+
+  def should_send_2_day_reminder?
+    days_between_hearing_and_created_at > 2 &&
+      days_until_hearing <= 2 && days_from_hearing_day_to_last_sent_reminder > 2
+  end
+
+  # The 3 day reminder is a special reminder that is sent on Friday, *only* if the hearing
+  # itself is on Monday.
+  def should_send_3_day_friday_reminder?
+    days_between_hearing_and_created_at > 3 &&
+      days_until_hearing <= 3 && virtual_hearing.hearing.scheduled_for.monday?
+  end
+
+  def should_send_7_day_reminder?
+    days_between_hearing_and_created_at > 7 &&
+      days_until_hearing <= 7 && days_from_hearing_day_to_last_sent_reminder > 7
+  end
+
+  # Determines the date between when the hearing is scheduled, and when the virtual hearing was scheduled.
+  # If the virtual hearing was scheduled within a reminder period, we skip sending the reminder for that period
+  # because the confirmation will have redundant information.
+  def days_between_hearing_and_created_at
+    (virtual_hearing.hearing.scheduled_for - virtual_hearing.created_at) / 1.day
+  end
+
+  def days_until_hearing
+    ((virtual_hearing.hearing.scheduled_for - Time.zone.now.utc) / 1.day).round
+  end
+
+  def days_from_hearing_day_to_last_sent_reminder
+    # Pick arbitrarily big value if the reminder has never been sent.
+    return Float::INFINITY if last_sent_reminder.nil?
+
+    (virtual_hearing.hearing.scheduled_for - last_sent_reminder) / 1.day
+  end
+end
diff --git a/db/migrate/20201104175215_add_reminder_email_flags_to_virtual_hearings.rb b/db/migrate/20201104175215_add_reminder_email_flags_to_virtual_hearings.rb
new file mode 100644
index 00000000000..d4225275622
--- /dev/null
+++ b/db/migrate/20201104175215_add_reminder_email_flags_to_virtual_hearings.rb
@@ -0,0 +1,12 @@
+class AddReminderEmailFlagsToVirtualHearings < Caseflow::Migration
+  def change
+    add_column :virtual_hearings,
+               :appellant_reminder_sent_at,
+               :datetime,
+               comment: "The datetime the last reminder email was sent to the appellant."
+    add_column :virtual_hearings,
+               :representative_reminder_sent_at,
+               :datetime,
+               comment: "The datetime the last reminder email was sent to the representative."
+  end
+end
diff --git a/db/schema.rb b/db/schema.rb
index 4a7de6f9bec..79810ac6c7a 100644
--- a/db/schema.rb
+++ b/db/schema.rb
@@ -10,7 +10,7 @@
 #
 # It's strongly recommended that you check this file into your version control system.
 
-ActiveRecord::Schema.define(version: 2020_10_20_135542) do
+ActiveRecord::Schema.define(version: 2020_11_04_175215) do
 
   # These are extensions that must be enabled in order to support this database
   enable_extension "plpgsql"
@@ -1491,6 +1491,7 @@
     t.string "alias_with_host", comment: "Alias for conference in pexip with client_host"
     t.string "appellant_email", comment: "Appellant's email address"
     t.boolean "appellant_email_sent", default: false, null: false, comment: "Determines whether or not a notification email was sent to the appellant"
+    t.datetime "appellant_reminder_sent_at", comment: "The datetime the last reminder email was sent to the appellant."
     t.string "appellant_tz", limit: 50, comment: "Stores appellant timezone"
     t.boolean "conference_deleted", default: false, null: false, comment: "Whether or not the conference was deleted from Pexip"
     t.integer "conference_id", comment: "ID of conference from Pexip"
@@ -1506,6 +1507,7 @@
     t.boolean "judge_email_sent", default: false, null: false, comment: "Whether or not a notification email was sent to the judge"
     t.string "representative_email", comment: "Veteran's representative's email address"
     t.boolean "representative_email_sent", default: false, null: false, comment: "Whether or not a notification email was sent to the veteran's representative"
+    t.datetime "representative_reminder_sent_at", comment: "The datetime the last reminder email was sent to the representative."
     t.string "representative_tz", limit: 50, comment: "Stores representative timezone"
     t.boolean "request_cancelled", default: false, comment: "Determines whether the user has cancelled the virtual hearing request"
     t.datetime "updated_at", null: false, comment: "Automatic timestamp of when virtual hearing was updated"
diff --git a/docs/schema/caseflow.csv b/docs/schema/caseflow.csv
index 8a16b68a493..c7d19c9f768 100644
--- a/docs/schema/caseflow.csv
+++ b/docs/schema/caseflow.csv
@@ -445,7 +445,7 @@ end_product_updates,original_decision_review_id,integer (8),,,,,x,The original d
 end_product_updates,original_decision_review_type,string,,,,,x,The original decision review type that this end product update belongs to
 end_product_updates,status,string,,,,,,"Status after an attempt to update the end product; expected values: 'success', 'error', ..."
 end_product_updates,updated_at,datetime ∗,x,,,,,
-end_product_updates,user_id,integer (8) ∗,x,,,,x,The ID of the user who makes an end product update.
+end_product_updates,user_id,integer (8) ∗ FK,x,,x,,x,The ID of the user who makes an end product update.
 form8s,,,,,,,,
 form8s,_initial_appellant_name,string,,,,,,
 form8s,_initial_appellant_relationship,string,,,,,,
@@ -1124,6 +1124,7 @@ virtual_hearings,alias,string,,,,,x,Alias for conference in Pexip
 virtual_hearings,alias_with_host,string,,,,,,Alias for conference in pexip with client_host
 virtual_hearings,appellant_email,string ∗,x,,,,,Appellant's email address
 virtual_hearings,appellant_email_sent,boolean ∗,x,,,,,Determines whether or not a notification email was sent to the appellant
+virtual_hearings,appellant_reminder_sent_at,datetime,,,,,,The datetime the last reminder email was sent to the appellant.
 virtual_hearings,appellant_tz,string (50),,,,,,Stores appellant timezone
 virtual_hearings,conference_deleted,boolean ∗,x,,,,,Whether or not the conference was deleted from Pexip
 virtual_hearings,conference_id,integer,,,,,x,ID of conference from Pexip
@@ -1140,6 +1141,7 @@ virtual_hearings,judge_email,string,,,,,,Judge's email address
 virtual_hearings,judge_email_sent,boolean ∗,x,,,,,Whether or not a notification email was sent to the judge
 virtual_hearings,representative_email,string,,,,,,Veteran's representative's email address
 virtual_hearings,representative_email_sent,boolean ∗,x,,,,,Whether or not a notification email was sent to the veteran's representative
+virtual_hearings,representative_reminder_sent_at,datetime,,,,,,The datetime the last reminder email was sent to the representative.
 virtual_hearings,representative_tz,string (50),,,,,,Stores representative timezone
 virtual_hearings,request_cancelled,boolean,,,,,,Determines whether the user has cancelled the virtual hearing request
 virtual_hearings,updated_at,datetime ∗,x,,,,x,Automatic timestamp of when virtual hearing was updated
diff --git a/spec/factories/virtual_hearing.rb b/spec/factories/virtual_hearing.rb
index 2ad33af5245..013d8c11b8b 100644
--- a/spec/factories/virtual_hearing.rb
+++ b/spec/factories/virtual_hearing.rb
@@ -20,6 +20,8 @@
     association :updated_by, factory: :user
     establishment { build(:virtual_hearing_establishment) }
     guest_pin_long { nil }
+    created_at { Time.zone.now }
+    updated_at { Time.zone.now }
 
     transient do
       status { nil }
diff --git a/spec/jobs/virtual_hearings/send_reminder_emails_job_spec.rb b/spec/jobs/virtual_hearings/send_reminder_emails_job_spec.rb
new file mode 100644
index 00000000000..eeae687ac26
--- /dev/null
+++ b/spec/jobs/virtual_hearings/send_reminder_emails_job_spec.rb
@@ -0,0 +1,154 @@
+# frozen_string_literal: true
+
+describe VirtualHearings::SendReminderEmailsJob do
+  let(:hearing_date) { Time.zone.now }
+  let(:ama_disposition) { nil }
+  let(:hearing_day) do
+    create(
+      :hearing_day,
+      regional_office: "RO42",
+      scheduled_for: hearing_date,
+      request_type: HearingDay::REQUEST_TYPES[:virtual]
+    )
+  end
+  let(:hearing) do
+    create(
+      :hearing,
+      hearing_day: hearing_day,
+      disposition: ama_disposition
+    )
+  end
+  let(:appellant_email) { "appellant@test.gov" }
+  let(:appellant_reminder_sent_at) { nil }
+  let(:representative_email) { "representative@test.gov" }
+  let(:representative_reminder_sent_at) { nil }
+  let!(:virtual_hearing) do
+    create(
+      :virtual_hearing,
+      :initialized,
+      status: :active,
+      appellant_email: appellant_email,
+      appellant_reminder_sent_at: appellant_reminder_sent_at,
+      representative_email: representative_email,
+      representative_reminder_sent_at: representative_reminder_sent_at,
+      hearing: hearing,
+      created_at: Time.zone.now - 14.days
+    )
+  end
+
+  describe "#perform" do
+    subject { VirtualHearings::SendReminderEmailsJob.new.perform }
+
+    context "hearing date is 7 days out" do
+      let(:hearing_date) { Time.zone.now + 7.days }
+
+      it "sends reminder emails", :aggregate_failures do
+        expect(VirtualHearingMailer).to receive(:reminder).twice.and_call_original
+
+        subject
+        virtual_hearing.reload
+        expect(virtual_hearing.appellant_reminder_sent_at).not_to be_nil
+        expect(virtual_hearing.representative_reminder_sent_at).not_to be_nil
+      end
+
+      it "creates sent email events" do
+        subject
+
+        expect(SentHearingEmailEvent.count).to eq(2)
+        expect(SentHearingEmailEvent.is_reminder.count).to eq(2)
+        expect(SentHearingEmailEvent.is_reminder.map(&:sent_by)).to all(eq(User.system_user))
+      end
+
+      context "representative email was already sent" do
+        let(:representative_reminder_sent_at) { hearing_date - 3.days }
+
+        it "sends reminder email for the appellant", :aggregate_failures do
+          expect(VirtualHearingMailer).to receive(:reminder).once.and_call_original
+
+          subject
+          virtual_hearing.reload
+          expect(virtual_hearing.appellant_reminder_sent_at).not_to be_nil
+          expect(virtual_hearing.representative_reminder_sent_at).to(
+            be_within(1.second).of(representative_reminder_sent_at)
+          )
+        end
+      end
+
+      context "appellant email was already sent" do
+        let(:appellant_reminder_sent_at) { hearing_date - 4.days }
+
+        it "sends reminder email for the representative", :aggregate_failures do
+          expect(VirtualHearingMailer).to receive(:reminder).once.and_call_original
+
+          subject
+          virtual_hearing.reload
+          expect(virtual_hearing.appellant_reminder_sent_at).to(
+            be_within(1.second).of(appellant_reminder_sent_at)
+          )
+          expect(virtual_hearing.representative_reminder_sent_at).not_to be_nil
+        end
+      end
+
+      context "representative email is nil" do
+        let(:representative_email) { nil }
+
+        it "sends reminder email to the appellant only", :aggregate_failures do
+          expect(VirtualHearingMailer).to receive(:reminder).once.and_call_original
+
+          subject
+          virtual_hearing.reload
+          expect(virtual_hearing.appellant_reminder_sent_at).not_to be_nil
+          expect(virtual_hearing.representative_reminder_sent_at).to be_nil
+        end
+      end
+    end
+
+    context "hearing date is 2 days out" do
+      let(:hearing_date) { Time.zone.now + 2.days }
+
+      context "sent reminder emails 5 days out" do
+        let(:appellant_reminder_sent_at) { hearing_date - 4.days }
+        let(:representative_reminder_sent_at) { hearing_date - 4.days }
+
+        it "sends reminder emails", :aggregate_failures do
+          expect(VirtualHearingMailer).to receive(:reminder).twice.and_call_original
+
+          subject
+          virtual_hearing.reload
+          # Expect appellant_reminder_sent_at and representative_reminder_sent_at to change
+          # from the value we setup because the emails were sent.
+          expect(virtual_hearing.appellant_reminder_sent_at).not_to(
+            be_within(1.second).of(representative_reminder_sent_at)
+          )
+          expect(virtual_hearing.representative_reminder_sent_at).not_to(
+            be_within(1.second).of(representative_reminder_sent_at)
+          )
+        end
+      end
+    end
+
+    context "hearing date is 1 day out" do
+      let(:hearing_date) { Time.zone.now + 1.day }
+
+      context "sent reminder emails 2 days out" do
+        let(:appellant_reminder_sent_at) { hearing_date - 2.days }
+        let(:representative_reminder_sent_at) { hearing_date - 2.days }
+
+        it "does not send reminder emails", :aggregate_failures do
+          expect(VirtualHearingMailer).not_to receive(:reminder)
+
+          subject
+          virtual_hearing.reload
+          # Expect appellant_reminder_sent_at and representative_reminder_sent_at to remain
+          # the same as the times we setup because the emails weren't sent.
+          expect(virtual_hearing.appellant_reminder_sent_at).to(
+            be_within(1.second).of(appellant_reminder_sent_at)
+          )
+          expect(virtual_hearing.representative_reminder_sent_at).to(
+            be_within(1.second).of(representative_reminder_sent_at)
+          )
+        end
+      end
+    end
+  end
+end
diff --git a/spec/repositories/virtual_hearing_repository_spec.rb b/spec/repositories/virtual_hearing_repository_spec.rb
index 1b9b576a078..4d26885e59d 100644
--- a/spec/repositories/virtual_hearing_repository_spec.rb
+++ b/spec/repositories/virtual_hearing_repository_spec.rb
@@ -172,4 +172,70 @@
       )
     end
   end
+
+  context ".maybe_ready_for_reminder_email" do
+    let!(:virtual_hearing) { create(:virtual_hearing, :initialized, status: :active, hearing: hearing) }
+
+    subject { described_class.maybe_ready_for_reminder_email }
+
+    shared_examples "include or exclude hearings depending on the number of days out from the hearing" do
+      context "within 7 days" do
+        let(:hearing_date) { Time.zone.now + 7.days }
+
+        it "returns the virtual hearing" do
+          expect(subject).to eq([virtual_hearing])
+        end
+      end
+
+      context "is in 10 days" do
+        let(:hearing_date) { Time.zone.now + 10.days }
+
+        it "returns nothing" do
+          expect(subject).to be_empty
+        end
+      end
+    end
+
+    context "for an AMA hearing" do
+      context "active virtual hearing" do
+        include_examples "include or exclude hearings depending on the number of days out from the hearing"
+      end
+
+      %w[postponed cancelled no_show held].each do |disposition|
+        context "#{disposition} virtual hearing" do
+          let(:ama_disposition) { disposition }
+
+          it "returns nothings" do
+            expect(subject).to be_empty
+          end
+        end
+      end
+    end
+
+    context "for a Legacy hearing" do
+      let(:legacy_dispositon) { nil }
+      let(:hearing) do
+        create(
+          :legacy_hearing,
+          regional_office: regional_office,
+          hearing_day_id: hearing_day.id,
+          case_hearing: create(:case_hearing, hearing_disp: legacy_dispositon)
+        )
+      end
+
+      context "active virtual hearing" do
+        include_examples "include or exclude hearings depending on the number of days out from the hearing"
+      end
+
+      %w[P C N H].each do |disposition_code|
+        context "#{VACOLS::CaseHearing::HEARING_DISPOSITIONS[disposition_code.to_sym]} virtual hearing" do
+          let(:ama_disposition) { disposition_code }
+
+          it "returns nothings" do
+            expect(subject).to be_empty
+          end
+        end
+      end
+    end
+  end
 end
diff --git a/spec/services/virtual_hearings/reminder_service_spec.rb b/spec/services/virtual_hearings/reminder_service_spec.rb
new file mode 100644
index 00000000000..9e19947a0bd
--- /dev/null
+++ b/spec/services/virtual_hearings/reminder_service_spec.rb
@@ -0,0 +1,157 @@
+# frozen_string_literal: true
+
+describe VirtualHearings::ReminderService do
+  let(:hearing_day) { build(:hearing_day, scheduled_for: hearing_date) }
+  let(:hearing) { build(:hearing, hearing_day: hearing_day) }
+  let(:virtual_hearing) do
+    build(
+      :virtual_hearing,
+      :initialized,
+      status: :active,
+      hearing: hearing,
+      created_at: created_at
+    )
+  end
+
+  before do
+    Timecop.freeze(Time.utc(2020, 11, 5, 12, 0, 0)) # Nov 5, 2020 (Thursday)
+  end
+
+  after { Timecop.return }
+
+  context ".should_send_reminder_email?" do
+    subject do
+      described_class.new(virtual_hearing, last_sent_reminder).should_send_reminder_email?
+    end
+
+    context "hearing date is 7 days out" do
+      let(:hearing_date) { Time.zone.now + 7.days }
+      let(:created_at) { hearing_date - 8.days }
+
+      context "last_sent_reminder is nil" do
+        let(:last_sent_reminder) { nil }
+
+        it "returns true" do
+          expect(subject).to eq(true)
+        end
+      end
+
+      context "last_sent_reminder is 5 days out" do
+        let(:last_sent_reminder) { hearing_date - 5.days }
+
+        it "returns false" do
+          expect(subject).to eq(false)
+        end
+      end
+    end
+
+    context "hearing date is 5 days out" do
+      let(:hearing_date) { Time.zone.now + 5.days }
+
+      context "created_at is 6 days from the hearing date" do
+        let(:created_at) { hearing_date - 6.days }
+
+        context "last_sent_reminder is nil" do
+          let(:last_sent_reminder) { nil }
+
+          it "returns false" do
+            expect(subject).to eq(false)
+          end
+        end
+      end
+    end
+
+    context "hearing date is 2 days out" do
+      let(:hearing_date) { Time.zone.now + 2.days }
+      let(:created_at) { hearing_date - 3.days }
+
+      context "last_sent_reminder is nil" do
+        let(:last_sent_reminder) { nil }
+
+        it "returns true" do
+          expect(subject).to eq(true)
+        end
+      end
+
+      context "last_sent_reminder is 4 days out" do
+        let(:last_sent_reminder) { hearing_date - 4.days }
+        let(:created_at) { hearing_date - 5.days }
+
+        it "returns true" do
+          expect(subject).to eq(true)
+        end
+      end
+
+      context "last_sent_reminder is 1 days out" do
+        let(:last_sent_reminder) { hearing_date - 1.day }
+        let(:created_at) { hearing_date - 2.days }
+
+        it "returns false" do
+          expect(subject).to eq(false)
+        end
+      end
+    end
+
+    context "hearing date is 1 day out" do
+      let(:hearing_date) { Time.zone.now + 1.day }
+
+      context "created_at is 1.5 days from the hearing date" do
+        let(:created_at) { hearing_date - 1.day - 12.hours }
+
+        context "last_sent_reminder is nil" do
+          let(:last_sent_reminder) { nil }
+
+          it "returns false" do
+            expect(subject).to eq(false)
+          end
+        end
+      end
+    end
+
+    context "hearing date is 3 days out" do
+      let(:created_at) { hearing_date - 4.days }
+
+      context "hearing date is on a monday" do
+        let(:hearing_date) { Time.utc(2020, 11, 9, 12, 0, 0) } # Nov 9, 2020 (Monday)
+
+        context "last_sent_reminder is 4 days out" do
+          let(:last_sent_reminder) { hearing_date - 4.days }
+
+          context "today is friday" do
+            before do
+              Timecop.freeze(Time.utc(2020, 11, 6, 12, 0, 0)) # Nov 6, 2020 (Friday)
+            end
+
+            it "returns true" do
+              expect(subject).to eq(true)
+            end
+          end
+
+          context "today is thursday" do
+            it "returns false" do
+              expect(subject).to eq(false)
+            end
+          end
+        end
+      end
+
+      context "hearing date is on a tuesday" do
+        let(:hearing_date) { Time.utc(2020, 11, 10, 12, 0, 0) } # Nov 10, 2020 (Tuesday)
+
+        context "last_sent_reminder is 4 days out" do
+          let(:last_sent_reminder) { hearing_date - 4.days }
+
+          context "today is saturday" do
+            before do
+              Timecop.freeze(Time.utc(2020, 11, 7, 12, 0, 0)) # Nov 7, 2020 (Saturday)
+            end
+
+            it "returns false" do
+              expect(subject).to eq(false)
+            end
+          end
+        end
+      end
+    end
+  end
+end