diff --git a/qdrant_client/local/order_by.py b/qdrant_client/local/order_by.py
index c695bae85..b98872931 100644
--- a/qdrant_client/local/order_by.py
+++ b/qdrant_client/local/order_by.py
@@ -1,13 +1,38 @@
-from datetime import datetime
+from datetime import datetime, timezone
 
 from qdrant_client.http.models import OrderValue
 from qdrant_client.local.datetime_utils import parse
 
 MICROS_PER_SECOND = 1_000_000
 
+_EPOCH = datetime(1970, 1, 1, tzinfo=timezone.utc)
+
 
 def datetime_to_microseconds(dt: datetime) -> int:
-    return int(dt.timestamp() * MICROS_PER_SECOND)
+    # Not `int(dt.timestamp() * MICROS_PER_SECOND)`: `timestamp()` returns a float, and
+    # both the float itself and multiplying it by 1e6 before truncating lose precision -
+    # off by one microsecond for a large fraction of timestamps in testing. The error grows
+    # with distance from 1970 (float64 has 52 mantissa bits, so the representable precision
+    # shrinks as the magnitude grows): dates near year 9999 can be off by up to ~32
+    # microseconds, though never anywhere near a full second.
+    #
+    # `datetime - datetime` (both aware) is exact integer arithmetic internally (no
+    # floats), so route through that instead. A naive `dt` is first attached to the
+    # system's local timezone via `astimezone()` - the same "assume local time" behavior
+    # `timestamp()` has for naive input - which itself returns a datetime, not a lossy
+    # float, so precision is preserved all the way through.
+    #
+    # `utcoffset() is None` (not `tzinfo is None`) is the correct naive-datetime check: a
+    # tzinfo subclass can be attached and still report no offset, and `dt - _EPOCH` raises
+    # TypeError if naive and aware datetimes are mixed.
+    if dt.utcoffset() is None:
+        dt = dt.astimezone()
+    delta = dt - _EPOCH
+    return (
+        delta.days * 86400 * MICROS_PER_SECOND
+        + delta.seconds * MICROS_PER_SECOND
+        + delta.microseconds
+    )
 
 
 def to_order_value(value: str | datetime | OrderValue | None) -> OrderValue | None:
diff --git a/tests/test_order_by.py b/tests/test_order_by.py
new file mode 100644
index 000000000..2f18e1abd
--- /dev/null
+++ b/tests/test_order_by.py
@@ -0,0 +1,69 @@
+from datetime import datetime, timezone, tzinfo
+
+from qdrant_client.local.order_by import datetime_to_microseconds
+
+
+class _OffsetlessTzInfo(tzinfo):
+    """A tzinfo subclass that's attached (`dt.tzinfo` is not None) but reports no
+    offset (`dt.utcoffset()` is None) - the correct definition of "naive" per the
+    datetime docs. Used to test that naive-detection doesn't rely on `tzinfo is None`."""
+
+    def utcoffset(self, dt):
+        return None
+
+    def dst(self, dt):
+        return None
+
+    def tzname(self, dt):
+        return None
+
+
+def _exact_microseconds_since_epoch(dt: datetime) -> int:
+    """Reference implementation using only exact integer arithmetic (no floats),
+    to cross-check `datetime_to_microseconds` against."""
+    epoch = datetime(1970, 1, 1, tzinfo=timezone.utc)
+    delta = dt - epoch
+    return delta.days * 86400 * 1_000_000 + delta.seconds * 1_000_000 + delta.microseconds
+
+
+def test_datetime_to_microseconds_matches_exact_arithmetic():
+    # Regression test: the previous implementation computed
+    # `int(dt.timestamp() * 1_000_000)`, which truncates a float64 that has
+    # already accumulated rounding error from the multiplication - off by one
+    # microsecond for a large fraction of timestamps (worse the further the
+    # date is from 1970, where the float has less precision to spare).
+    # These specific values are known to trigger that mismatch.
+    known_mismatching_datetimes = [
+        datetime(1970, 7, 21, 14, 9, 16, 146413, tzinfo=timezone.utc),
+        datetime(1970, 4, 9, 5, 50, 44, 113346, tzinfo=timezone.utc),
+        datetime(2024, 6, 15, 12, 30, 45, 123456, tzinfo=timezone.utc),
+        datetime(2100, 1, 1, 0, 0, 0, 1, tzinfo=timezone.utc),
+        datetime(9999, 12, 31, 23, 59, 59, 999999, tzinfo=timezone.utc),
+    ]
+    for dt in known_mismatching_datetimes:
+        assert datetime_to_microseconds(dt) == _exact_microseconds_since_epoch(dt)
+
+
+def test_datetime_to_microseconds_no_mismatch_across_range():
+    # Broader sweep: every microsecond value in one second, at a date far enough
+    # from 1970 that the float-multiplication bug reliably reproduces.
+    for micro in range(
+        0, 1_000_000, 997
+    ):  # every ~1000th microsecond, full coverage would be slow
+        dt = datetime(2100, 6, 15, 12, 30, 45, micro, tzinfo=timezone.utc)
+        assert datetime_to_microseconds(dt) == _exact_microseconds_since_epoch(dt)
+
+
+def test_datetime_to_microseconds_handles_tzinfo_with_no_offset():
+    # Regression test: naive-detection must check `dt.utcoffset() is None`, not
+    # `dt.tzinfo is None`. A tzinfo subclass can be attached (`tzinfo` is not None)
+    # while still reporting no offset - the datetime docs' actual definition of
+    # naive. Checking only `tzinfo is None` would skip the astimezone() fixup and
+    # crash with "can't subtract offset-naive and offset-aware datetimes".
+    dt = datetime(2024, 6, 15, 12, 30, 45, 123456, tzinfo=_OffsetlessTzInfo())
+    assert dt.tzinfo is not None
+    assert dt.utcoffset() is None
+
+    # Should behave the same as an actually-naive datetime with the same fields.
+    naive_equivalent = datetime(2024, 6, 15, 12, 30, 45, 123456)  # noqa: DTZ001 - naive on purpose
+    assert datetime_to_microseconds(dt) == datetime_to_microseconds(naive_equivalent)