diff --git a/app/models/period_highlights.rb b/app/models/period_highlights.rb
index 357e5380d..a45e5213a 100644
--- a/app/models/period_highlights.rb
+++ b/app/models/period_highlights.rb
@@ -1,14 +1,23 @@
 class PeriodHighlights < ApplicationRecord
   class << self
+    def create_or_find_for(collections, starts_at:, duration: 1.week)
+      starts_at = normalize_anchor_date(starts_at)
+
+      self.for(collections, starts_at:, duration:) || create_for(collections, starts_at:, duration:)
+    end
+
     def create_for(collections, starts_at:, duration: 1.week)
       starts_at = normalize_anchor_date(starts_at)
       key = key_for(collections)
       events = Event.where(collection: collections).where(created_at: starts_at..starts_at + duration)
 
-      create_or_find_by!(key:, starts_at:, duration:) do |record|
+      if events.any?
         summarizer = Event::Summarizer.new(events)
-        record.content = summarizer.summarized_content
-        record.cost_in_microcents = summarizer.cost.in_microcents
+        summarized_content = summarizer.summarized_content # outside of transaction as this can be slow
+        create_or_find_by!(key:, starts_at:, duration:) do |record|
+          record.content = summarized_content
+          record.cost_in_microcents = summarizer.cost.in_microcents
+        end
       end
     end
 
@@ -28,6 +37,10 @@ class PeriodHighlights < ApplicationRecord
       end
   end
 
+  def ends_at
+    starts_at + duration
+  end
+
   def to_html
     renderer = Redcarpet::Render::HTML.new
     markdowner = Redcarpet::Markdown.new(renderer, autolink: true, tables: true, fenced_code_blocks: true, strikethrough: true, superscript: true,)
diff --git a/app/models/user/day_timeline.rb b/app/models/user/day_timeline.rb
index 71b520c6d..26a15a05b 100644
--- a/app/models/user/day_timeline.rb
+++ b/app/models/user/day_timeline.rb
@@ -29,7 +29,19 @@ class User::DayTimeline
     day.yesterday.beginning_of_day
   end
 
+  def has_weekly_highlights?
+    first_day_with_activity_this_week? && weekly_highlights.present?
+  end
+
+  def weekly_highlights
+    @weekly_highlights ||= user.weekly_highlights_for(day - 1.week)
+  end
+
   private
+    def first_day_with_activity_this_week?
+      day.monday? || (earliest_time.present? && earliest_time < day.beginning_of_week(:monday))
+    end
+
     def filtered_events
       @filtered_events ||= begin
         events = Event.where(collection: collections)
diff --git a/app/models/user/highlights.rb b/app/models/user/highlights.rb
index d40abafdd..d65e10bda 100644
--- a/app/models/user/highlights.rb
+++ b/app/models/user/highlights.rb
@@ -13,16 +13,16 @@ module User::Highlights
     end
   end
 
-  def generate_weekly_highlights
-    PeriodHighlights.create_for collections, starts_at: current_highlights_starts_at, duration: 1.week
+  def generate_weekly_highlights(date = Time.current)
+    PeriodHighlights.create_or_find_for collections, starts_at: highlights_starts_at(date), duration: 1.week
   end
 
-  def current_weekly_highlights
-    PeriodHighlights.for collections, starts_at: current_highlights_starts_at, duration: 1.week
+  def weekly_highlights_for(date)
+    PeriodHighlights.for collections, starts_at: highlights_starts_at(date), duration: 1.week
   end
 
   private
-    def current_highlights_starts_at
-      Time.current.utc.beginning_of_week(:sunday)
+    def highlights_starts_at(date = Time.current)
+      date.utc.beginning_of_week(:sunday)
     end
 end
diff --git a/app/views/events/_day.html.erb b/app/views/events/_day.html.erb
index 6fbcc8b50..bb84ff713 100644
--- a/app/views/events/_day.html.erb
+++ b/app/views/events/_day.html.erb
@@ -1,16 +1,18 @@
 <section class="events__day" data-controller="related-element"
   data-related-element-highlight-class="event--related">
   <% if day_timeline.has_activity? %>
-    <h2 class="events__day-header">
-      <span class="events__day-time min-width max-width">
-        <span class="overflow-ellipsis">
-          <span>Highlights for</span>
-          <%= local_datetime_tag day_timeline.day, style: :agoorweekday %>
-        </span>
-      </span>
-    </h2>
 
-    <%= render "events/weekly_summary" %>
+    <% if day_timeline.has_weekly_highlights? %>
+      <h2 class="events__day-header">
+        <span class="events__day-time min-width max-width">
+          <span class="overflow-ellipsis">
+            <span>Highlights for this week</span>
+          </span>
+        </span>
+      </h2>
+    <% end %>
+
+    <%= render "events/weekly_highlights", day_timeline: day_timeline if day_timeline.has_weekly_highlights? %>
 
     <div class="events__columns">
       <%= render "events/day_timeline_column", event_type: "added", day_timeline: day_timeline %>
diff --git a/app/views/events/_weekly_highlights.html.erb b/app/views/events/_weekly_highlights.html.erb
new file mode 100644
index 000000000..51666e4b7
--- /dev/null
+++ b/app/views/events/_weekly_highlights.html.erb
@@ -0,0 +1,3 @@
+<div class="events__activity-summary txt-small">
+  <%= day_timeline.weekly_highlights.to_html %>
+</div>
diff --git a/app/views/events/_weekly_summary.html.erb b/app/views/events/_weekly_summary.html.erb
deleted file mode 100644
index 646669e27..000000000
--- a/app/views/events/_weekly_summary.html.erb
+++ /dev/null
@@ -1,5 +0,0 @@
-<% if weekly_highlights = Current.user.current_weekly_highlights %>
-  <div class="events__activity-summary txt-small">
-    <%= weekly_highlights.to_html %>
-  </div>
-<% end %>
diff --git a/script/migrations/backfill_weekly_highlights.rb b/script/migrations/backfill_weekly_highlights.rb
new file mode 100644
index 000000000..40668f586
--- /dev/null
+++ b/script/migrations/backfill_weekly_highlights.rb
@@ -0,0 +1,13 @@
+#!/usr/bin/env ruby
+
+require_relative "../config/environment"
+
+WEEKS_TO_BACKFILL = 20
+
+ApplicationRecord.with_each_tenant do |tenant|
+  WEEKS_TO_BACKFILL.times do |index|
+    User.find_each do |user|
+      user.generate_weekly_highlights(Time.current - index.weeks)
+    end
+  end
+end
diff --git a/test/models/period_highlights_test.rb b/test/models/period_highlights_test.rb
index b1c942a91..5bcfca99a 100644
--- a/test/models/period_highlights_test.rb
+++ b/test/models/period_highlights_test.rb
@@ -9,17 +9,17 @@ class PeriodHighlightTest < ActiveSupport::TestCase
 
   test "generate period highlights" do
     period_highlights = assert_difference -> { PeriodHighlights.count }, 1 do
-      PeriodHighlights.create_for(@user.collections, starts_at: 1.month.ago, duration: 2.months)
+      PeriodHighlights.create_or_find_for(@user.collections, starts_at: 1.month.ago, duration: 2.months)
     end
 
     assert_match /logo/i, period_highlights.to_html
   end
 
   test "don't generate highlights for existing periods" do
-    new_period_highlights = PeriodHighlights.create_for(@user.collections, starts_at: 1.month.ago, duration: 2.months)
+    new_period_highlights = PeriodHighlights.create_or_find_for(@user.collections, starts_at: 1.month.ago, duration: 2.months)
 
     existing_period_highlights = assert_no_difference -> { PeriodHighlights.count } do
-      PeriodHighlights.create_for(@user.collections, starts_at: 1.month.ago, duration: 2.months)
+      PeriodHighlights.create_or_find_for(@user.collections, starts_at: 1.month.ago, duration: 2.months)
     end
 
     assert_equal new_period_highlights, existing_period_highlights