diff --git a/server/src/services/tripService.ts b/server/src/services/tripService.ts
index 5d024b7e..63ae51b7 100644
--- a/server/src/services/tripService.ts
+++ b/server/src/services/tripService.ts
@@ -122,12 +122,26 @@ export function generateDays(tripId: number | bigint | string, startDate: string
     del.run(dated[i].id);
   }
 
-  // Any remaining unused dateless days: keep as dateless, just renumber.
+  // Any remaining unused dateless days: drop the empty placeholders so day_count
+  // reflects the dated range, but keep ones that still hold content (assignments,
+  // notes, accommodations) — mirrors the dateless-path trimming above (#1083).
   // Base must be max(targetDates.length, dated.length) to avoid colliding with
   // positives already assigned by the main loop or the overflow loop above.
+  const isEmptyDay = db.prepare(
+    `SELECT NOT EXISTS (SELECT 1 FROM day_assignments da WHERE da.day_id = @id)
+          AND NOT EXISTS (SELECT 1 FROM day_notes dn WHERE dn.day_id = @id)
+          AND NOT EXISTS (SELECT 1 FROM day_accommodations dac WHERE dac.start_day_id = @id OR dac.end_day_id = @id) AS empty`
+  );
   const maxAssigned = Math.max(targetDates.length, dated.length);
+  let keptDateless = 0;
   for (let i = datelessIdx; i < dateless.length; i++) {
-    setDayNumber.run(maxAssigned + (i - datelessIdx) + 1, dateless[i].id);
+    const empty = (isEmptyDay.get({ id: dateless[i].id }) as { empty: number }).empty;
+    if (empty) {
+      del.run(dateless[i].id);
+    } else {
+      setDayNumber.run(maxAssigned + keptDateless + 1, dateless[i].id);
+      keptDateless++;
+    }
   }
 
   // Final renumber to compact and eliminate any gaps/negatives
diff --git a/server/tests/unit/services/tripService.test.ts b/server/tests/unit/services/tripService.test.ts
index 795dbcb2..a4411b4d 100644
--- a/server/tests/unit/services/tripService.test.ts
+++ b/server/tests/unit/services/tripService.test.ts
@@ -242,6 +242,33 @@ describe('generateDays', () => {
     const nums = daysAfter.map(d => d.day_number).sort((a, b) => a - b);
     expect(nums).toEqual([1, 2, 3, 4, 5]);
   });
+
+  it('TRIP-SVC-017: switching a dateless trip to a shorter dated range drops empty leftover days but keeps ones with content (#1083)', () => {
+    const { user } = createUser(testDb);
+    // A 7-day trip, then cleared to dateless placeholders (day_count = 7).
+    const trip = createTrip(testDb, user.id, { start_date: '2025-12-01', end_date: '2025-12-07' });
+    generateDays(trip.id, null, null);
+    const dateless = getDays(trip.id);
+    expect(dateless).toHaveLength(7);
+    expect(dateless.every(d => d.date === null)).toBe(true);
+
+    // Give the LAST dateless day real content so it must be preserved.
+    const place = createPlace(testDb, trip.id);
+    const assignment = createDayAssignment(testDb, dateless[6].id, place.id);
+
+    // Now set an explicit 2-day range. The first two dateless days are reused for
+    // the dates; the four empty leftovers must be removed, the one with content kept.
+    generateDays(trip.id, '2026-01-10', '2026-01-11');
+
+    const daysAfter = getDays(trip.id);
+    const dated = daysAfter.filter(d => d.date !== null);
+    const stillDateless = daysAfter.filter(d => d.date === null);
+    expect(dated.map(d => d.date)).toEqual(['2026-01-10', '2026-01-11']);
+    // day_count is COUNT(*) FROM days: 2 dated + 1 content-bearing dateless = 3 (not the stale 7)
+    expect(daysAfter).toHaveLength(3);
+    expect(stillDateless).toHaveLength(1);
+    expect(getAssignments(stillDateless[0].id)[0].id).toBe(assignment.id);
+  });
 });
 
 describe('exportICS', () => {