diff --git a/app/models/remind_assigns_frequency_site_settings.rb b/app/models/remind_assigns_frequency_site_settings.rb
new file mode 100644
index 0000000..38a40bd
--- /dev/null
+++ b/app/models/remind_assigns_frequency_site_settings.rb
@@ -0,0 +1,30 @@
+require_dependency 'enum_site_setting'
+
+class RemindAssignsFrequencySiteSettings < EnumSiteSetting
+
+  def self.valid_value?(val)
+    val.to_i.to_s == val.to_s &&
+    values.any? { |v| v[:value] == val.to_i }
+  end
+
+  def self.values
+    @values ||= [
+      { name: 'discourse_assign.reminders_frequency.never', value: 0 },
+      { name: 'discourse_assign.reminders_frequency.daily', value: 1440 },
+      { name: 'discourse_assign.reminders_frequency.monthly', value: 43200 },
+      { name: 'discourse_assign.reminders_frequency.quarterly', value: 131400 }
+    ]
+  end
+
+  def self.translate_names?
+    true
+  end
+
+  def self.frequency_for(minutes)
+    value = values.detect { |v| v[:value] == minutes }
+
+    raise Discourse::InvalidParameters(:task_reminders_frequency) if value.nil?
+
+    I18n.t(value[:name])
+  end
+end
diff --git a/config/locales/client.en.yml b/config/locales/client.en.yml
index eba1a21..633c349 100644
--- a/config/locales/client.en.yml
+++ b/config/locales/client.en.yml
@@ -12,7 +12,6 @@ en:
       unassign_all:
         title: "Unassign All"
         confirm: "Are you sure you want to unassign all topics from {{username}}?"
-
       unassign:
         title: "Unassign"
         help: "Unassign Topic"
@@ -26,6 +25,11 @@ en:
       claim:
         title: "claim"
         help: "Assign topic to yourself"
+      reminders_frequency:
+        never: 'Never'
+        daily: 'Daily'
+        monthly: 'Monthly'
+        quarterly: 'Quarterly'
     user:
       messages:
         assigned_title: "Assigned (%{count})"
diff --git a/config/locales/server.en.yml b/config/locales/server.en.yml
index d9a0f48..6e41032 100644
--- a/config/locales/server.en.yml
+++ b/config/locales/server.en.yml
@@ -12,6 +12,8 @@ en:
     assign_locks_flags: "When a topic is assigned to a staff member, its flags can only be handled by that person"
     assign_mailer_enabled: "When enabled, the assigned user will receive a notification email on each assignment"
     flags_require_assign: "When enabled, flags cannot be handled unless assigned to a user."
+    remind_assigns: "Remind users about pending assigns."
+    remind_assigns_frequency: "Frequency for reminding users about assigned topics."
   discourse_assign:
     assigned_to: "Topic assigned to @%{username}"
     unassigned: "Topic was unassigned"
@@ -20,6 +22,11 @@ en:
     flag_assigned: "Sorry, that flag's topic is assigned to another user"
     flag_unclaimed: "You must claim that topic before acting on the flag"
     topic_assigned_excerpt: "assigned you the topic '%{title}'"
+    reminders_frequency:
+        never: 'never'
+        daily: 'daily'
+        monthly: 'monthly'
+        quarterly: 'quarterly'
   assign_mailer:
     title: "Assign Mailer"
     subject_template: "[%{email_prefix}] %{assignee_name} assigned you to '%{topic_title}'!"
@@ -31,3 +38,22 @@ en:
 
       If you're interested, click the link below:
       [%{topic_link}](%{topic_link})
+  pending_assigns_reminder:
+    title: "You have %{pending_assignments} pending assignments"
+    body: |
+      You currently have [%{pending_assignments} pending assignments](%{assignments_link}).
+
+      %{newest_assignments}
+      %{oldest_assignments}
+      
+      This reminder will be sent %{frequency} if you have more than one assigned topic.
+    newest: |
+      ### Newest
+      %{topic_0}
+      %{topic_1}
+      %{topic_2}
+    oldest: |
+      ### Oldest
+      %{topic_0}
+      %{topic_1}
+      %{topic_2}
diff --git a/config/settings.yml b/config/settings.yml
index 44c98f6..f722435 100644
--- a/config/settings.yml
+++ b/config/settings.yml
@@ -19,3 +19,7 @@ plugins:
     default: false
     client: true
   assign_mailer_enabled: false
+  remind_assigns_frequency:
+    client: true
+    enum: "RemindAssignsFrequencySiteSettings"
+    default: 43200
\ No newline at end of file
diff --git a/db/migrate/20190422200243_add_last_reminded_at_index.rb b/db/migrate/20190422200243_add_last_reminded_at_index.rb
new file mode 100644
index 0000000..9113382
--- /dev/null
+++ b/db/migrate/20190422200243_add_last_reminded_at_index.rb
@@ -0,0 +1,6 @@
+class AddLastRemindedAtIndex < ActiveRecord::Migration[5.2]
+  def change
+    add_index :user_custom_fields, %i[name user_id], name: :idx_user_custom_fields_last_reminded_at,
+                                                     unique: true, where: "name = 'last_reminded_at'"
+  end
+end
diff --git a/jobs/regular/remind_user.rb b/jobs/regular/remind_user.rb
new file mode 100644
index 0000000..9a8cd78
--- /dev/null
+++ b/jobs/regular/remind_user.rb
@@ -0,0 +1,12 @@
+module Jobs
+  class RemindUser < Jobs::Base
+    sidekiq_options queue: 'low'
+
+    def execute(args)
+      user = User.find_by(args[:user_id])
+      raise Discourse::InvalidParameters.new(:user_id) if user.nil?
+
+      PendingAssignsReminder.new.remind(user)
+    end
+  end
+end
diff --git a/jobs/scheduled/enqueue_reminders.rb b/jobs/scheduled/enqueue_reminders.rb
new file mode 100644
index 0000000..dada73a
--- /dev/null
+++ b/jobs/scheduled/enqueue_reminders.rb
@@ -0,0 +1,34 @@
+module Jobs
+  class EnqueueReminders < Jobs::Scheduled
+    every 2.hours
+
+    def execute(_args)
+      return if skip_enqueue?
+      user_ids.each { |id| Jobs.enqueue(:remind_user, user_id: id) }
+    end
+
+    private
+
+    def skip_enqueue?
+      SiteSetting.remind_assigns_frequency.nil? || SiteSetting.remind_assigns_frequency.zero?
+    end
+
+    def user_ids
+      interval = SiteSetting.remind_assigns_frequency
+
+      TopicCustomField
+        .joins(<<~SQL
+          LEFT OUTER JOIN user_custom_fields ON topic_custom_fields.value::INT = user_custom_fields.user_id
+          AND user_custom_fields.name = '#{PendingAssignsReminder::REMINDED_AT}'
+        SQL
+        ).where(<<~SQL
+          user_custom_fields.value IS NULL OR
+          user_custom_fields.value::TIMESTAMP <= CURRENT_TIMESTAMP - ('1 MINUTE'::INTERVAL * #{interval})
+        SQL
+        ).where("topic_custom_fields.updated_at::TIMESTAMP <= CURRENT_TIMESTAMP - ('1 MINUTE'::INTERVAL * ?)", interval)
+        .where(name: TopicAssigner::ASSIGNED_TO_ID)
+        .group('topic_custom_fields.value').having('COUNT(topic_custom_fields.value) > 1')
+        .pluck('topic_custom_fields.value')
+    end
+  end
+end
diff --git a/lib/pending_assigns_reminder.rb b/lib/pending_assigns_reminder.rb
new file mode 100644
index 0000000..9996db2
--- /dev/null
+++ b/lib/pending_assigns_reminder.rb
@@ -0,0 +1,85 @@
+# frozen_string_literal: true
+
+class PendingAssignsReminder
+  REMINDED_AT = 'last_reminded_at'
+  REMINDER_THRESHOLD = 2
+
+  def remind(user)
+    newest_topics = assigned_topics(user, order: :desc)
+    return if newest_topics.size < REMINDER_THRESHOLD
+    oldest_topics = assigned_topics(user, order: :asc).where.not(id: newest_topics.map(&:id))
+    assigned_topics_count = assigned_count_for(user)
+
+    title = I18n.t('pending_assigns_reminder.title', pending_assignments: assigned_topics_count)
+
+    PostCreator.create!(
+      Discourse.system_user,
+      title: title,
+      raw: reminder_body(user, assigned_topics_count, newest_topics, oldest_topics),
+      archetype: Archetype.private_message,
+      target_usernames: user.username,
+      validate: false
+    )
+
+    update_last_reminded(user)
+  end
+
+  private
+
+  def assigned_count_for(user)
+    TopicCustomField.where(name: TopicAssigner::ASSIGNED_TO_ID, value: user.id).count
+  end
+
+  def assigned_topics(user, order:)
+    Topic.joins(:_custom_fields).select(:slug, :id, :fancy_title, 'topic_custom_fields.created_at AS assigned_at')
+      .where('topic_custom_fields.name = ? AND topic_custom_fields.value = ?', TopicAssigner::ASSIGNED_TO_ID, user.id.to_s)
+      .order("topic_custom_fields.created_at #{order}")
+      .limit(3)
+  end
+
+  def reminder_body(user, assigned_topics_count, first_three_topics, last_three_topics)
+    newest_list = build_list_for(:newest, first_three_topics)
+    oldest_list = build_list_for(:oldest, last_three_topics)
+
+    I18n.t(
+      'pending_assigns_reminder.body',
+      pending_assignments: assigned_topics_count,
+      assignments_link: "#{Discourse.base_url}/u/#{user.username_lower}/assigned",
+      newest_assignments: newest_list,
+      oldest_assignments: oldest_list,
+      frequency: frequency_in_words
+    )
+  end
+
+  def build_list_for(key, topics)
+    return '' if topics.empty?
+    initial_list = { 'topic_0' => '', 'topic_1' => '', 'topic_2' => '' }
+    items = topics.each_with_index.reduce(initial_list) do |memo, (t, index)|
+      memo["topic_#{index}"] = "- [#{Emoji.gsub_emoji_to_unicode(t.fancy_title)}](#{t.relative_url}) - assigned #{time_in_words_for(t)}"
+      memo
+    end
+
+    I18n.t("pending_assigns_reminder.#{key}", items.symbolize_keys!)
+  end
+
+  def time_in_words_for(topic)
+    FreedomPatches::Rails4.distance_of_time_in_words(
+      Time.zone.now, topic.assigned_at.to_time, false, scope: 'datetime.distance_in_words_verbose'
+    )
+  end
+
+  def frequency_in_words
+    ::RemindAssignsFrequencySiteSettings.frequency_for(SiteSetting.remind_assigns_frequency)
+  end
+
+  def update_last_reminded(user)
+    update_last_reminded = { REMINDED_AT => DateTime.now }
+    # New API in Discouse that's better under concurrency
+    if user.respond_to?(:upsert_custom_fields)
+      user.upsert_custom_fields(update_last_reminded)
+    else
+      user.custom_fields.merge!(update_last_reminded)
+      user.save_custom_fields
+    end
+  end
+end
diff --git a/plugin.rb b/plugin.rb
index 935a306..fbcf71a 100644
--- a/plugin.rb
+++ b/plugin.rb
@@ -21,8 +21,11 @@ Discourse::Application.routes.append do
 end
 
 after_initialize do
-  require File.expand_path('../jobs/unassign_bulk', __FILE__)
+  require File.expand_path('../jobs/unassign_bulk.rb', __FILE__)
+  require File.expand_path('../jobs/scheduled/enqueue_reminders.rb', __FILE__)
+  require File.expand_path('../jobs/regular/remind_user.rb', __FILE__)
   require 'topic_assigner'
+  require 'pending_assigns_reminder'
 
   # Raise an invalid access error if a user tries to act on something
   # not assigned to them
diff --git a/spec/jobs/scheduled/enqueue_reminders_spec.rb b/spec/jobs/scheduled/enqueue_reminders_spec.rb
new file mode 100644
index 0000000..f5e50d0
--- /dev/null
+++ b/spec/jobs/scheduled/enqueue_reminders_spec.rb
@@ -0,0 +1,66 @@
+require 'rails_helper'
+
+RSpec.describe Jobs::EnqueueReminders do
+  let(:user) { Fabricate(:user) }
+
+  describe '#execute' do
+    it 'does not enqueue reminders when there are no assigned tasks' do
+      assert_reminders_enqueued(0)
+    end
+
+    it 'enqueues a reminder when the user has more than one task' do
+      assign_multiple_tasks_to(user)
+
+      assert_reminders_enqueued(1)
+    end
+
+    it 'does not enqueue a reminder when the user only has one task' do
+      assign_one_task_to(user)
+
+      assert_reminders_enqueued(0)
+    end
+
+    it "does not enqueue a reminder if it's too soon" do
+      user.upsert_custom_fields(PendingAssignsReminder::REMINDED_AT => 2.days.ago)
+      assign_multiple_tasks_to(user)
+
+      assert_reminders_enqueued(0)
+    end
+
+    it 'enqueues a reminder if the user was reminded more than a month ago' do
+      user.upsert_custom_fields(PendingAssignsReminder::REMINDED_AT => 31.days.ago)
+      assign_multiple_tasks_to(user)
+
+      assert_reminders_enqueued(1)
+    end
+
+    it 'does not enqueue reminders if the remind frequency is set to never' do
+      SiteSetting.remind_assigns_frequency = 0
+      assign_multiple_tasks_to(user)
+
+      assert_reminders_enqueued(0)
+    end
+
+    it 'does not enqueue reminders if the topic was just assigned to the user' do
+      just_assigned = DateTime.now
+      assign_multiple_tasks_to(user, just_assigned)
+
+      assert_reminders_enqueued(0)
+    end
+
+    def assert_reminders_enqueued(expected_amount)
+      expect { subject.execute({}) }.to change(Jobs::RemindUser.jobs, :size).by(expected_amount)
+    end
+
+    def assign_one_task_to(user, assigned_on = 3.months.ago)
+      freeze_time(assigned_on) do
+        post = Fabricate(:post)
+        TopicAssigner.new(post.topic, user).assign(user)
+      end
+    end
+
+    def assign_multiple_tasks_to(user, assigned_on = 3.months.ago)
+      PendingAssignsReminder::REMINDER_THRESHOLD.times { assign_one_task_to(user, assigned_on) }
+    end
+  end
+end
diff --git a/spec/lib/pending_assigns_reminder_spec.rb b/spec/lib/pending_assigns_reminder_spec.rb
new file mode 100644
index 0000000..534b63d
--- /dev/null
+++ b/spec/lib/pending_assigns_reminder_spec.rb
@@ -0,0 +1,56 @@
+require 'rails_helper'
+
+RSpec.describe PendingAssignsReminder do
+  let(:user) { Fabricate(:user) }
+
+  it 'does not create a reminder if the user has 0 assigned topics' do
+    assert_reminder_not_created
+  end
+
+  it 'does not create a reminder if the user only has one task' do
+    post = Fabricate(:post)
+    TopicAssigner.new(post.topic, user).assign(user)
+
+    assert_reminder_not_created
+  end
+
+  def assert_reminder_not_created
+    expect { subject.remind(user) }.to change { Post.count }.by(0)
+  end
+
+  describe 'when the user has multiple tasks' do
+    let(:system) { Discourse.system_user }
+
+    before do
+      @post = Fabricate(:post)
+      @another_post = Fabricate(:post)
+      TopicAssigner.new(@post.topic, user).assign(user)
+      TopicAssigner.new(@another_post.topic, user).assign(user)
+      @assigned_posts = 2
+    end
+
+    it 'creates a reminder for a particular user and sets the timestamp of the last reminder' do
+      expected_last_reminder = DateTime.now
+
+      freeze_time(expected_last_reminder) do
+        subject.remind(user)
+
+        created_post = Post.includes(topic: %i[topic_allowed_users]).last
+        reminded_at = user.reload.custom_fields[described_class::REMINDED_AT].to_datetime
+
+        assert_remind_was_created_correctly(created_post)
+        expect(reminded_at).to eq_time(expected_last_reminder)
+      end
+    end
+
+    def assert_remind_was_created_correctly(post)
+      topic = post.topic
+      expect(topic.user).to eq(system)
+      expect(topic.archetype).to eq(Archetype.private_message)
+      expect(topic.topic_allowed_users.pluck(:user_id)).to contain_exactly(system.id, user.id)
+      expect(topic.title).to eq(I18n.t('pending_assigns_reminder.title', pending_assignments: @assigned_posts))
+      expect(post.raw).to include(@post.topic.fancy_title)
+      expect(post.raw).to include(@another_post.topic.fancy_title)
+    end
+  end
+end