diff --git a/db/db_iter.cc b/db/db_iter.cc
index 8626a4f81..dff251a40 100644
--- a/db/db_iter.cc
+++ b/db/db_iter.cc
@@ -1433,9 +1433,8 @@ void DBIter::SetSavedKeyToSeekForPrevTarget(const Slice& target) {
     if (timestamp_size_ > 0) {
       const std::string kTsMax(timestamp_size_, '\xff');
       Slice ts = kTsMax;
-      saved_key_.UpdateInternalKey(
-          kMaxSequenceNumber, kValueTypeForSeekForPrev,
-          timestamp_lb_ != nullptr ? timestamp_lb_ : &ts);
+      saved_key_.UpdateInternalKey(kMaxSequenceNumber, kValueTypeForSeekForPrev,
+                                   &ts);
     }
   }
 }
@@ -1637,24 +1636,15 @@ void DBIter::SeekToLast() {
   if (iterate_upper_bound_ != nullptr) {
     // Seek to last key strictly less than ReadOptions.iterate_upper_bound.
     SeekForPrev(*iterate_upper_bound_);
-    const bool is_ikey = (timestamp_size_ > 0 && timestamp_lb_ != nullptr);
+#ifndef NDEBUG
     Slice k = Valid() ? key() : Slice();
-    if (is_ikey && Valid()) {
+    if (Valid() && timestamp_size_ > 0 && timestamp_lb_) {
       k.remove_suffix(kNumInternalBytes + timestamp_size_);
     }
-    while (Valid() && 0 == user_comparator_.CompareWithoutTimestamp(
-                               *iterate_upper_bound_, /*a_has_ts=*/false, k,
-                               /*b_has_ts=*/false)) {
-      ReleaseTempPinnedData();
-      ResetBlobValue();
-      ResetValueAndColumns();
-      PrevInternal(nullptr);
-
-      k = key();
-      if (is_ikey) {
-        k.remove_suffix(kNumInternalBytes + timestamp_size_);
-      }
-    }
+    assert(!Valid() || user_comparator_.CompareWithoutTimestamp(
+                           k, /*a_has_ts=*/false, *iterate_upper_bound_,
+                           /*b_has_ts=*/false) < 0);
+#endif
     return;
   }
 
diff --git a/db/db_with_timestamp_basic_test.cc b/db/db_with_timestamp_basic_test.cc
index 31ebb25c2..4b8132df3 100644
--- a/db/db_with_timestamp_basic_test.cc
+++ b/db/db_with_timestamp_basic_test.cc
@@ -3892,6 +3892,32 @@ TEST_F(DBBasicTestWithTimestamp, RangeTombstoneApproximateSize) {
       std::numeric_limits<uint64_t>::max() /* max_file_num_to_ignore */,
       "" /*trim_ts*/));
 }
+
+TEST_F(DBBasicTestWithTimestamp, IterSeekToLastWithIterateUpperbound) {
+  // Test for a bug fix where DBIter::SeekToLast() could fail when
+  // iterate_upper_bound and iter_start_ts are both set.
+  Options options = CurrentOptions();
+  const size_t kTimestampSize = Timestamp(0, 0).size();
+  TestComparator test_cmp(kTimestampSize);
+  options.comparator = &test_cmp;
+  DestroyAndReopen(options);
+
+  ASSERT_OK(db_->Put(WriteOptions(), Key(1), Timestamp(2, 0), "val"));
+  ReadOptions ro;
+  std::string k = Key(1);
+  Slice k_slice = k;
+  ro.iterate_upper_bound = &k_slice;
+  std::string ts = Timestamp(3, 0);
+  Slice read_ts = ts;
+  ro.timestamp = &read_ts;
+  std::string start_ts = Timestamp(0, 0);
+  Slice start_ts_slice = start_ts;
+  ro.iter_start_ts = &start_ts_slice;
+  std::unique_ptr<Iterator> iter{db_->NewIterator(ro)};
+  iter->SeekToLast();
+  ASSERT_FALSE(iter->Valid());
+  ASSERT_OK(iter->status());
+}
 }  // namespace ROCKSDB_NAMESPACE
 
 int main(int argc, char** argv) {