diff --git a/app/helpers/insights_helper.rb b/app/helpers/insights_helper.rb
index 6ee5ca339..349d660f1 100644
--- a/app/helpers/insights_helper.rb
+++ b/app/helpers/insights_helper.rb
@@ -141,13 +141,15 @@ module InsightsHelper
         return facts["account"] || facts["name"]
       end
 
-      if start_date == start_date.beginning_of_month && end_date == start_date.end_of_month
-        format = start_date.year == Date.current.year ? "%B" : "%B %Y"
-        return I18n.l(start_date, format: format)
-      end
-
       days = (end_date - start_date).to_i
-      if start_date >= Date.current - 1
+      if rolling_period_insight?(insight) && start_date >= Date.current - 1
+        t("insights.meta.next_n_days", count: days)
+      elsif rolling_period_insight?(insight) && end_date >= Date.current - 1
+        t("insights.meta.last_n_days", count: days)
+      elsif start_date == start_date.beginning_of_month && end_date == start_date.end_of_month
+        format = start_date.year == Date.current.year ? "%B" : "%B %Y"
+        I18n.l(start_date, format: format)
+      elsif start_date >= Date.current - 1
         t("insights.meta.next_n_days", count: days)
       elsif end_date >= Date.current - 1
         t("insights.meta.last_n_days", count: days)
@@ -155,4 +157,8 @@ module InsightsHelper
         t("insights.meta.date_range", from: I18n.l(start_date, format: :short), to: I18n.l(end_date, format: :short))
       end
     end
+
+    def rolling_period_insight?(insight)
+      insight.insight_type.in?(%w[cash_flow_warning net_worth_milestone])
+    end
 end
diff --git a/test/helpers/insights_helper_test.rb b/test/helpers/insights_helper_test.rb
index 84af79661..038fcbcad 100644
--- a/test/helpers/insights_helper_test.rb
+++ b/test/helpers/insights_helper_test.rb
@@ -70,13 +70,39 @@ class InsightsHelperTest < ActionView::TestCase
   end
 
   test "meta line labels a forward-looking window as next N days" do
-    insight = build_insight(
-      "cash_flow_warning",
-      period_start: Date.current,
-      period_end: Date.current + 30
-    )
+    travel_to Date.new(2026, 8, 1) do
+      insight = build_insight(
+        "cash_flow_warning",
+        period_start: Date.current,
+        period_end: Date.current + 30
+      )
 
-    assert_equal "Cash flow · Next 30 days", insight_meta_line(insight)
+      assert_equal "Cash flow · Next 30 days", insight_meta_line(insight)
+    end
+  end
+
+  test "meta line labels a backward-looking rolling window as last N days" do
+    travel_to Date.new(2026, 8, 31) do
+      insight = build_insight(
+        "net_worth_milestone",
+        period_start: Date.current - 30,
+        period_end: Date.current
+      )
+
+      assert_equal "Net worth · Last 30 days", insight_meta_line(insight)
+    end
+  end
+
+  test "meta line keeps monthly insight periods labeled as the month on boundaries" do
+    travel_to Date.new(2026, 8, 1) do
+      insight = build_insight(
+        "budget_at_risk",
+        period_start: Date.current.beginning_of_month,
+        period_end: Date.current.end_of_month
+      )
+
+      assert_equal "Budget · August", insight_meta_line(insight)
+    end
   end
 
   test "meta line falls back to the subject when there is no period" do