diff --git a/core/src/main/java/org/opensearch/sql/utils/DateTimeUtils.java b/core/src/main/java/org/opensearch/sql/utils/DateTimeUtils.java
index 6b7e64a8865..671be3c647d 100644
--- a/core/src/main/java/org/opensearch/sql/utils/DateTimeUtils.java
+++ b/core/src/main/java/org/opensearch/sql/utils/DateTimeUtils.java
@@ -36,7 +36,8 @@ public class DateTimeUtils {
    * @return Rounded date/time value in utc millis
    */
   public static long roundFloor(long utcMillis, long unitMillis) {
-    return utcMillis - utcMillis % unitMillis;
+    long res = utcMillis - utcMillis % unitMillis;
+    return (utcMillis < 0 && res != utcMillis) ? res - unitMillis : res;
   }
 
   /**
@@ -65,7 +66,9 @@ public static long roundMonth(long utcMillis, int interval) {
         (zonedDateTime.getYear() - initDateTime.getYear()) * 12L
             + zonedDateTime.getMonthValue()
             - initDateTime.getMonthValue();
-    long monthToAdd = (monthDiff / interval - 1) * interval;
+    long multiplier = monthDiff / interval - 1;
+    if (monthDiff < 0 && monthDiff % interval != 0) --multiplier;
+    long monthToAdd = multiplier * interval;
     return initDateTime.plusMonths(monthToAdd).toInstant().toEpochMilli();
   }
 
@@ -84,7 +87,9 @@ public static long roundQuarter(long utcMillis, int interval) {
         ((zonedDateTime.getYear() - initDateTime.getYear()) * 12L
             + zonedDateTime.getMonthValue()
             - initDateTime.getMonthValue());
-    long monthToAdd = (monthDiff / (interval * 3L) - 1) * interval * 3;
+    long multiplier = monthDiff / (interval * 3L) - 1;
+    if (monthDiff < 0 && monthDiff % (interval * 3L) != 0) --multiplier;
+    long monthToAdd = multiplier * interval * 3;
     return initDateTime.plusMonths(monthToAdd).toInstant().toEpochMilli();
   }
 
@@ -99,7 +104,9 @@ public static long roundYear(long utcMillis, int interval) {
     ZonedDateTime initDateTime = ZonedDateTime.of(1970, 1, 1, 0, 0, 0, 0, UTC_ZONE_ID);
     ZonedDateTime zonedDateTime = Instant.ofEpochMilli(utcMillis).atZone(UTC_ZONE_ID);
     int yearDiff = zonedDateTime.getYear() - initDateTime.getYear();
-    int yearToAdd = (yearDiff / interval) * interval;
+    int multiplier = yearDiff / interval;
+    if (yearDiff < 0 && yearDiff % interval != 0) --multiplier;
+    int yearToAdd = multiplier * interval;
     return initDateTime.plusYears(yearToAdd).toInstant().toEpochMilli();
   }
 
diff --git a/core/src/test/java/org/opensearch/sql/utils/DateTimeUtilsTest.java b/core/src/test/java/org/opensearch/sql/utils/DateTimeUtilsTest.java
index 80e1f90eb9a..3130ac001f0 100644
--- a/core/src/test/java/org/opensearch/sql/utils/DateTimeUtilsTest.java
+++ b/core/src/test/java/org/opensearch/sql/utils/DateTimeUtilsTest.java
@@ -16,6 +16,7 @@
 import java.time.format.DateTimeFormatter;
 import java.util.concurrent.TimeUnit;
 import org.junit.jupiter.api.Test;
+import org.opensearch.sql.planner.physical.collector.Rounding.DateTimeUnit;
 
 public class DateTimeUtilsTest {
   @Test
@@ -105,4 +106,76 @@ void testRelativeZonedDateTimeWithWrongInput() {
             IllegalArgumentException.class, () -> getRelativeZonedDateTime("1d+1y", zonedDateTime));
     assertEquals(e.getMessage(), "Unexpected character '1' at position 0 in input: 1d+1y");
   }
+
+  @Test
+  void testRoundOnTimestampBeforeEpoch() {
+    long actual =
+        LocalDateTime.parse("1961-05-12T23:40:05")
+            .atZone(ZoneOffset.UTC)
+            .toInstant()
+            .toEpochMilli();
+    long rounded = DateTimeUnit.MINUTE.round(actual, 1);
+    assertEquals(
+        LocalDateTime.parse("1961-05-12T23:40:00")
+            .atZone(ZoneOffset.UTC)
+            .toInstant()
+            .toEpochMilli(),
+        Instant.ofEpochMilli(rounded).toEpochMilli());
+
+    rounded = DateTimeUnit.HOUR.round(actual, 1);
+    assertEquals(
+        LocalDateTime.parse("1961-05-12T23:00:00")
+            .atZone(ZoneOffset.UTC)
+            .toInstant()
+            .toEpochMilli(),
+        Instant.ofEpochMilli(rounded).toEpochMilli());
+
+    rounded = DateTimeUnit.DAY.round(actual, 1);
+    assertEquals(
+        LocalDateTime.parse("1961-05-12T00:00:00")
+            .atZone(ZoneOffset.UTC)
+            .toInstant()
+            .toEpochMilli(),
+        Instant.ofEpochMilli(rounded).toEpochMilli());
+
+    rounded = DateTimeUnit.DAY.round(actual, 3);
+    assertEquals(
+        LocalDateTime.parse("1961-05-12T00:00:00")
+            .atZone(ZoneOffset.UTC)
+            .toInstant()
+            .toEpochMilli(),
+        Instant.ofEpochMilli(rounded).toEpochMilli());
+
+    rounded = DateTimeUnit.WEEK.round(actual, 1);
+    assertEquals(
+        LocalDateTime.parse("1961-05-08T00:00:00")
+            .atZone(ZoneOffset.UTC)
+            .toInstant()
+            .toEpochMilli(),
+        Instant.ofEpochMilli(rounded).toEpochMilli());
+
+    rounded = DateTimeUnit.MONTH.round(actual, 1);
+    assertEquals(
+        LocalDateTime.parse("1961-05-01T00:00:00")
+            .atZone(ZoneOffset.UTC)
+            .toInstant()
+            .toEpochMilli(),
+        Instant.ofEpochMilli(rounded).toEpochMilli());
+
+    rounded = DateTimeUnit.QUARTER.round(actual, 1);
+    assertEquals(
+        LocalDateTime.parse("1961-04-01T00:00:00")
+            .atZone(ZoneOffset.UTC)
+            .toInstant()
+            .toEpochMilli(),
+        Instant.ofEpochMilli(rounded).toEpochMilli());
+
+    rounded = DateTimeUnit.YEAR.round(actual, 2);
+    assertEquals(
+        LocalDateTime.parse("1960-01-01T00:00:00")
+            .atZone(ZoneOffset.UTC)
+            .toInstant()
+            .toEpochMilli(),
+        Instant.ofEpochMilli(rounded).toEpochMilli());
+  }
 }
diff --git a/integ-test/src/test/java/org/opensearch/sql/calcite/remote/CalcitePPLAggregationIT.java b/integ-test/src/test/java/org/opensearch/sql/calcite/remote/CalcitePPLAggregationIT.java
index 77cb7372c04..0e64983861b 100644
--- a/integ-test/src/test/java/org/opensearch/sql/calcite/remote/CalcitePPLAggregationIT.java
+++ b/integ-test/src/test/java/org/opensearch/sql/calcite/remote/CalcitePPLAggregationIT.java
@@ -502,13 +502,7 @@ public void testCountBySpanForCustomFormats() throws IOException {
         actual,
         schema("timestamp_span", "timestamp"),
         schema("count(custom_no_delimiter_ts)", "bigint"));
-    // TODO: Span has different behavior between pushdown and non-pushdown for timestamp before
-    // 1971. V2 engine will have the same issue.
-    // https://github.com/opensearch-project/sql/issues/3827
-    verifyDataRows(
-        actual,
-        rows(1, isPushdownEnabled() ? "1961-04-12 09:00:00" : "1961-04-12 10:00:00"),
-        rows(1, "1984-10-20 15:00:00"));
+    verifyDataRows(actual, rows(1, "1961-04-12 09:00:00"), rows(1, "1984-10-20 15:00:00"));
 
     actual =
         executeQuery(