diff --git a/src/time/src/mcp_server_time/server.py b/src/time/src/mcp_server_time/server.py
index 2cb0926134..4ff0e7e9e7 100644
--- a/src/time/src/mcp_server_time/server.py
+++ b/src/time/src/mcp_server_time/server.py
@@ -24,6 +24,7 @@ class TimeResult(BaseModel):
     datetime: str
     day_of_week: str
     is_dst: bool
+    note: str | None = None
 
 
 class TimeConversionResult(BaseModel):
@@ -92,6 +93,22 @@ def convert_time(
             tzinfo=source_timezone,
         )
 
+        # A local wall-clock time can occur twice on the day a DST fall-back
+        # transition happens (e.g. 1:30 AM in America/New_York on the first
+        # Sunday of November occurs once before the clocks go back and once
+        # after). Attaching tzinfo directly, as above, always resolves to
+        # `fold=0` -- the earlier of the two real offsets -- with no
+        # indication to the caller that a second, equally valid answer
+        # exists. Detect that case by comparing both folds' offsets, and
+        # surface it instead of silently picking one.
+        source_note = None
+        other_fold_offset = source_time.replace(fold=1).utcoffset()
+        if other_fold_offset != source_time.utcoffset():
+            source_note = (
+                f"{parsed_time.strftime('%H:%M')} occurs twice in {source_tz} on this date due to a "
+                "DST transition; this result uses the earlier of the two occurrences."
+            )
+
         target_time = source_time.astimezone(target_timezone)
         source_offset = source_time.utcoffset() or timedelta()
         target_offset = target_time.utcoffset() or timedelta()
@@ -109,6 +126,7 @@ def convert_time(
                 datetime=source_time.isoformat(timespec="seconds"),
                 day_of_week=source_time.strftime("%A"),
                 is_dst=bool(source_time.dst()),
+                note=source_note,
             ),
             target=TimeResult(
                 timezone=target_tz,
diff --git a/src/time/test/time_server_test.py b/src/time/test/time_server_test.py
index 8d963508d7..ebc408a13b 100644
--- a/src/time/test/time_server_test.py
+++ b/src/time/test/time_server_test.py
@@ -462,6 +462,52 @@ def test_convert_time(test_time, source_tz, time_str, target_tz, expected):
         assert result.time_difference == expected["time_difference"]
 
 
+def test_convert_time_flags_ambiguous_fall_back_time():
+    # America/New_York's DST fall-back in 2024 happens at 2:00 AM on Nov 3,
+    # when clocks go back to 1:00 AM -- so 1:30 AM occurs twice that day.
+    # Freeze at noon UTC (already past the local transition) so `now` in NY
+    # time also lands on Nov 3, the actual transition date.
+    with freeze_time("2024-11-03 12:00:00+00:00"):
+        time_server = TimeServer()
+        result = time_server.convert_time("America/New_York", "01:30", "Europe/London")
+
+    assert result.source.note is not None
+    assert "occurs twice" in result.source.note
+    assert "America/New_York" in result.source.note
+    # The earlier (fold=0) occurrence is used: -04:00 (EDT), not -05:00 (EST).
+    assert result.source.datetime == "2024-11-03T01:30:00-04:00"
+
+
+def test_convert_time_no_note_for_an_unambiguous_time_on_the_same_day():
+    with freeze_time("2024-11-03 12:00:00+00:00"):
+        time_server = TimeServer()
+        result = time_server.convert_time("America/New_York", "10:00", "Europe/London")
+
+    assert result.source.note is None
+
+
+def test_convert_time_no_note_for_a_timezone_without_the_transition():
+    # Same real moment, but a source timezone with no DST fall-back at all --
+    # the note must not fire just because *some* zone somewhere is ambiguous.
+    with freeze_time("2024-11-03 12:00:00+00:00"):
+        time_server = TimeServer()
+        result = time_server.convert_time("UTC", "01:30", "Europe/London")
+
+    assert result.source.note is None
+
+
+def test_convert_time_flags_ambiguous_time_in_a_different_zone_and_month():
+    # Europe/Warsaw's DST fall-back in 2024 is Oct 27, a different date and
+    # a different offset pair (+02:00 -> +01:00) than the US case above --
+    # confirms the check isn't hardcoded to one zone's transition.
+    with freeze_time("2024-10-27 12:00:00+00:00"):
+        time_server = TimeServer()
+        result = time_server.convert_time("Europe/Warsaw", "02:30", "UTC")
+
+    assert result.source.note is not None
+    assert result.source.datetime == "2024-10-27T02:30:00+02:00"
+
+
 def test_get_local_tz_with_override():
     """Test that timezone override works correctly."""
     result = get_local_tz("America/New_York")