diff --git a/extensions/sessions/sessions.ts b/extensions/sessions/sessions.ts
index 1517e19c..a6f29589 100644
--- a/extensions/sessions/sessions.ts
+++ b/extensions/sessions/sessions.ts
@@ -74,19 +74,37 @@ export function formatTimestamp(date: Date): string {
   return `${year}-${month}-${day} ${hours}:${minutes}`;
 }
 
-export function formatRelativeTime(date: Date): string {
-  const now = new Date();
+export function formatRelativeTime(date: Date, now: Date = new Date()): string {
   const diffMs = now.getTime() - date.getTime();
-  const diffSec = Math.floor(diffMs / 1000);
+  const diffSec = Math.max(0, Math.floor(diffMs / 1000));
   const diffMin = Math.floor(diffSec / 60);
   const diffHour = Math.floor(diffMin / 60);
   const diffDay = Math.floor(diffHour / 24);
 
-  if (diffSec < 60) return "Just now";
-  if (diffMin < 60) return `${diffMin}m ago`;
-  if (diffHour < 24) return `${diffHour}h ago`;
-  if (diffDay === 1) return "Yesterday";
-  return `${diffDay}d ago`;
+  // Within 24 hours: display clock time and relative duration (m/h ago)
+  // This avoids midnight flips showing "0d ago" or cross-year jumps in early January
+  if (diffHour < 24) {
+    const time = `${pad(date.getHours())}:${pad(date.getMinutes())}`;
+    if (diffSec < 60) return `${time} (just now)`;
+    if (diffMin < 60) return `${time} (${diffMin}m ago)`;
+    return `${time} (${diffHour}h ago)`;
+  }
+
+  // Older than 24 hours: display calendar date and day/month/year distance
+  // If under a year, show MM-DD so year transitions in January stay readable
+  if (diffDay < 365) {
+    const dateStr = `${pad(date.getMonth() + 1)}-${pad(date.getDate())}`;
+    if (diffDay < 60) {
+      return `${dateStr} (${diffDay}d ago)`;
+    }
+    const months = Math.max(1, Math.floor(diffDay / 30));
+    return `${dateStr} (${months}mo ago)`;
+  }
+
+  // Cross-year older than 365 days
+  const years = Math.max(1, Math.floor(diffDay / 365));
+  const dateStr = `${date.getFullYear()}-${pad(date.getMonth() + 1)}`;
+  return `${dateStr} (${years}y ago)`;
 }
 
 const cleanDisplayLine = (text: string) =>
@@ -127,6 +145,8 @@ export const buildSearchText = (session: SessionInfoLike): string =>
     session.id,
     session.cwd,
     session.firstMessage ?? "",
+    formatTimestamp(session.modified),
+    formatRelativeTime(session.modified),
   ]
     .join(" ")
     .toLowerCase();
diff --git a/tests/extensions/sessions/sessions.test.ts b/tests/extensions/sessions/sessions.test.ts
index 2f60f43a..04838c6b 100644
--- a/tests/extensions/sessions/sessions.test.ts
+++ b/tests/extensions/sessions/sessions.test.ts
@@ -4,10 +4,12 @@ import {
   buildSessionDescription,
   buildSessionLabel,
   buildSessionPreview,
+  buildSessionSearchEntries,
   filterSessionEntries,
+  formatRelativeTime,
   parseLimit,
-  selectSessionStatsWindow,
   type SessionInfoLike,
+  selectSessionStatsWindow,
 } from "../../../extensions/sessions/sessions.ts";
 
 const session: SessionInfoLike = {
@@ -144,3 +146,48 @@ test("bounded preview reports omitted messages and content bytes", () => {
   ]);
   assert.match(preview.subtitle, /100 messages/);
 });
+
+test("formatRelativeTime deterministically formats relative hours and calendar dates with frozen clocks", () => {
+  const baseNow = new Date("2026-09-21T12:00:00");
+  const tenMins = new Date("2026-09-21T11:50:00");
+  const twoHours = new Date("2026-09-21T10:00:00");
+  const threeDays = new Date("2026-09-18T12:00:00");
+  const twelveDays = new Date("2026-09-09T12:00:00");
+
+  assert.equal(formatRelativeTime(tenMins, baseNow), "11:50 (10m ago)");
+  assert.equal(formatRelativeTime(twoHours, baseNow), "10:00 (2h ago)");
+  assert.equal(formatRelativeTime(threeDays, baseNow), "09-18 (3d ago)");
+  assert.equal(formatRelativeTime(twelveDays, baseNow), "09-09 (12d ago)");
+
+  // Midnight boundary test case: 10 minutes ago across midnight (23:55 viewed at 00:05)
+  const midnightNow = new Date("2026-09-21T00:05:00");
+  const midnightTenMinsAgo = new Date("2026-09-20T23:55:00");
+  assert.equal(
+    formatRelativeTime(midnightTenMinsAgo, midnightNow),
+    "23:55 (10m ago)",
+  );
+
+  // Cross-year boundary test case: New Year 00:05 viewing New Year's Eve 23:55
+  const janNow = new Date("2027-01-01T00:05:00");
+  const decEve = new Date("2026-12-31T23:55:00");
+  assert.equal(formatRelativeTime(decEve, janNow), "23:55 (10m ago)");
+
+  // Cross-year within 60 days
+  const jan3rd = new Date("2027-01-03T12:00:00");
+  const dec30 = new Date("2026-12-30T12:00:00");
+  assert.equal(formatRelativeTime(dec30, jan3rd), "12-30 (4d ago)");
+
+  // Over 1 year ago
+  const twoYearsLater = new Date("2028-09-21T12:00:00");
+  assert.equal(formatRelativeTime(baseNow, twoYearsLater), "2026-09 (2y ago)");
+});
+
+test("session search matches formatted dates and years", () => {
+  const sample = {
+    ...session,
+    modified: new Date("2026-09-06T10:00:00Z"),
+  };
+  const entries = buildSessionSearchEntries([sample]);
+  assert.equal(filterSessionEntries(entries, "2026").length, 1);
+  assert.equal(filterSessionEntries(entries, "09-06").length, 1);
+});