diff --git a/src/timesheets/parser.py b/src/timesheets/parser.py
index 907dbd8..56d25f0 100644
--- a/src/timesheets/parser.py
+++ b/src/timesheets/parser.py
@@ -273,6 +273,11 @@ def _minutes_to_time(minutes: int) -> str:
     return f"{minutes // 60:02d}:{minutes % 60:02d}"
 
 
+def _round_to_5(minutes: int) -> int:
+    """Round minutes to the nearest 5-minute boundary."""
+    return round(minutes / 5) * 5
+
+
 def _make_closed_row(template: dict, start_m: int, end_m: int) -> dict | None:
     """
     Return a copy of *template* with updated start, end, and duration_hours.
@@ -330,7 +335,7 @@ def resolve_overlaps(rows: list[dict]) -> list[dict]:
                 if overlap_end_m <= b_start_m:
                     continue
 
-                midpoint_m = (b_start_m + overlap_end_m) // 2
+                midpoint_m = _round_to_5((b_start_m + overlap_end_m) // 2)
                 replacements: list[dict] = []
 
                 if b_end_m <= a_end_m:
diff --git a/tests/test_parser.py b/tests/test_parser.py
index a9a1d8e..96bcefd 100644
--- a/tests/test_parser.py
+++ b/tests/test_parser.py
@@ -678,3 +678,45 @@ class TestResolveOverlaps:
             assert result[i]["end"] <= result[i + 1]["start"], (
                 f"Overlap between entry {i} ({result[i]}) and {i + 1} ({result[i + 1]})"
             )
+
+    # --- midpoint rounding to 5 minutes ---
+
+    def test_partial_overlap_midpoint_rounds_down(self):
+        """Midpoint not on a 5-min boundary is rounded down to the nearest 5 min.
+
+        09:00-10:00 vs 09:33-10:33
+        overlap region: 09:33-10:00  raw midpoint: 09:46  rounded: 09:45
+        """
+        rows = [self._row("09:00", "10:00", "a"), self._row("09:33", "10:33", "b")]
+        result = self._sorted(resolve_overlaps(rows))
+        assert len(result) == 2
+        assert (result[0]["start"], result[0]["end"]) == ("09:00", "09:45")
+        assert (result[1]["start"], result[1]["end"]) == ("09:45", "10:33")
+
+    def test_partial_overlap_midpoint_rounds_up(self):
+        """Midpoint not on a 5-min boundary is rounded up to the nearest 5 min.
+
+        09:00-10:00 vs 09:37-10:37
+        overlap region: 09:37-10:00  raw midpoint: 09:48  rounded: 09:50
+        """
+        rows = [self._row("09:00", "10:00", "a"), self._row("09:37", "10:37", "b")]
+        result = self._sorted(resolve_overlaps(rows))
+        assert len(result) == 2
+        assert (result[0]["start"], result[0]["end"]) == ("09:00", "09:50")
+        assert (result[1]["start"], result[1]["end"]) == ("09:50", "10:37")
+
+    def test_containment_midpoint_rounded(self):
+        """Containment case: boundary is rounded to the nearest 5 min.
+
+        09:00-10:00 contains 09:14-09:44
+        overlap region: 09:14-09:44  raw midpoint: 09:29  rounded: 09:30
+        """
+        rows = [self._row("09:00", "10:00", "a"), self._row("09:14", "09:44", "b")]
+        result = self._sorted(resolve_overlaps(rows))
+        assert len(result) == 3
+        assert (result[0]["start"], result[0]["end"]) == ("09:00", "09:30")
+        assert result[0]["project"] == "a"
+        assert (result[1]["start"], result[1]["end"]) == ("09:30", "09:44")
+        assert result[1]["project"] == "b"
+        assert (result[2]["start"], result[2]["end"]) == ("09:44", "10:00")
+        assert result[2]["project"] == "a"