diff --git a/.jules/bolt.md b/.jules/bolt.md
index 57daf471..bd3d478f 100644
--- a/.jules/bolt.md
+++ b/.jules/bolt.md
@@ -3,3 +3,7 @@
 **Learning:** `Date.parse(value)` returns the timestamp primitive directly, while `new Date(value).getTime()` also constructs a `Date` object. Both use the same ECMAScript string-parsing semantics for these call sites.
 
 **Action:** In frequently executed paths that only need a timestamp primitive, prefer `Date.parse(value)`. Treat the allocation reduction as a bounded micro-optimization unless a committed benchmark establishes a larger runtime effect.
+
+## 2026-09-04 - Avoid Expensive Operations in Sort Comparators
+**Learning:** Operations like `Date.parse()` execute `O(N log N)` times when placed directly inside `Array.prototype.sort()` comparators. This creates a severe performance bottleneck when sorting large datasets like timelines.
+**Action:** Use a Schwartzian transform (map-sort-map) to pre-compute the transformed values in O(N) time before sorting, passing a wrapper object `{ original, parsedValue }` to preserve memory efficiency.
diff --git a/packages/web/src/components/dashboard/session-timeline-chart.test.tsx b/packages/web/src/components/dashboard/session-timeline-chart.test.tsx
index 31d6758b..d7e7d81b 100644
--- a/packages/web/src/components/dashboard/session-timeline-chart.test.tsx
+++ b/packages/web/src/components/dashboard/session-timeline-chart.test.tsx
@@ -30,7 +30,7 @@ function readChartData(): Array<{
 describe('SessionTimelineChart', () => {
   afterEach(() => {
     cleanup()
-    vi.clearAllMocks()
+    vi.restoreAllMocks()
   })
 
   it('renders "No timeline data available" when usageTimeline is empty', () => {
@@ -275,4 +275,48 @@ describe('SessionTimelineChart', () => {
     expect(usageTimeline.map(({ timestamp }) => timestamp)).toEqual(originalUsageOrder)
     expect(messages.map(({ timestamp }) => timestamp)).toEqual(originalMessageOrder)
   })
+
+  it('parses each usage timestamp once while sorting and merging chart rows', () => {
+    const usageTimeline: SessionTimelineUsage[] = [
+      {
+        timestamp: '2023-01-01T00:03:00.000Z',
+        inputTokens: 300,
+        outputTokens: 30,
+        estimatedCostUsd: 0.003,
+        model: 'gpt-4',
+        isSubagent: false,
+      },
+      {
+        timestamp: '2023-01-01T00:01:00.000Z',
+        inputTokens: 100,
+        outputTokens: 10,
+        estimatedCostUsd: 0.001,
+        model: 'gpt-4',
+        isSubagent: false,
+      },
+      {
+        timestamp: '2023-01-01T00:02:00.000Z',
+        inputTokens: 200,
+        outputTokens: 20,
+        estimatedCostUsd: 0.002,
+        model: 'gpt-4',
+        isSubagent: false,
+      },
+    ]
+    const originalDateParse = Date.parse.bind(Date)
+    const parseSpy = vi
+      .spyOn(Date, 'parse')
+      .mockImplementation((timestamp) => originalDateParse(timestamp))
+
+    render(
+      <SessionTimelineChart
+        usageTimeline={usageTimeline}
+        messages={[]}
+        sessionStartedAt="2023-01-01T00:00:00.000Z"
+      />
+    )
+
+    expect(parseSpy).toHaveBeenCalledTimes(usageTimeline.length)
+    expect(readChartData().map(({ input }) => input)).toEqual([100, 200, 300])
+  })
 })
diff --git a/packages/web/src/components/dashboard/session-timeline-chart.tsx b/packages/web/src/components/dashboard/session-timeline-chart.tsx
index 222d0b22..9370fd36 100644
--- a/packages/web/src/components/dashboard/session-timeline-chart.tsx
+++ b/packages/web/src/components/dashboard/session-timeline-chart.tsx
@@ -67,9 +67,12 @@ function buildChartData(
   toolCalls: ToolCallPoint[],
   sessionStartedAt: string
 ): ChartDataItem[] {
-  const sortedUsage = [...usageTimeline].sort(
-    (a, b) => Date.parse(a.timestamp) - Date.parse(b.timestamp)
-  )
+  // [Bolt: Performance Optimization] Use Schwartzian transform (map-sort-map) to avoid
+  // O(N log N) Date.parse() calls during sort. This reduces parsing overhead to O(N).
+  const sortedUsage = usageTimeline
+    .map(usage => ({ original: usage, parsedTimestamp: Date.parse(usage.timestamp) }))
+    .sort((a, b) => a.parsedTimestamp - b.parsedTimestamp)
+
   const sortedTools = [...toolCalls].sort(
     (a, b) => a.parsedTimestamp - b.parsedTimestamp
   )
@@ -77,8 +80,7 @@ function buildChartData(
   let toolIndex = 0
   const cumulativeToolCounts = new Map<string, number>()
 
-  return sortedUsage.map((usage) => {
-    const currentTimestamp = Date.parse(usage.timestamp)
+  return sortedUsage.map(({ original: usage, parsedTimestamp: currentTimestamp }) => {
 
     while (
       toolIndex < sortedTools.length &&