diff --git a/src/main/java/io/leonard/OpeningHoursEvaluator.java b/src/main/java/io/leonard/OpeningHoursEvaluator.java
index bf9c3a62d93..046980fb816 100644
--- a/src/main/java/io/leonard/OpeningHoursEvaluator.java
+++ b/src/main/java/io/leonard/OpeningHoursEvaluator.java
@@ -202,21 +202,33 @@ private static boolean dateMatchesDateRanges(LocalDateTime time, List<DateRange>
   private static boolean dateMatchesDateRange(LocalDateTime time, DateRange range) {
     // if the end date is null it means that it's just a single date like in "2020 Aug 11"
     DateWithOffset startDate = range.getStartDate();
-    boolean afterStartDate =
-      time.getYear() >= startDate.getYear() &&
-      time.getMonth().ordinal() >= startDate.getMonth().ordinal() &&
-      time.getDayOfMonth() >= startDate.getDay();
+    boolean afterStartDate = isSameDateOrAfter(time, startDate);
+
     if (range.getEndDate() == null) {
       return afterStartDate;
     }
     DateWithOffset endDate = range.getEndDate();
-    boolean beforeEndDate =
-      time.getYear() <= endDate.getYear() &&
-      time.getMonth().ordinal() <= endDate.getMonth().ordinal() &&
-      time.getDayOfMonth() <= endDate.getDay();
+    boolean beforeEndDate = !isSameDateOrAfter(time.minusDays(1), endDate);
     return afterStartDate && beforeEndDate;
   }
 
+  private static boolean isSameDateOrAfter(LocalDateTime time, DateWithOffset startDate) {
+    return (
+      time.getYear() > startDate.getYear() ||
+      (
+        time.getYear() == startDate.getYear() &&
+        startDate.getMonth() != null &&
+        (
+          time.getMonth().ordinal() > startDate.getMonth().ordinal() ||
+          (
+            time.getMonth().ordinal() == startDate.getMonth().ordinal() &&
+            time.getDayOfMonth() >= startDate.getDay()
+          )
+        )
+      )
+    );
+  }
+
   private static boolean timeMatchesHours(LocalDateTime time, TimeSpan timeSpan) {
     var minutesAfterMidnight = minutesAfterMidnight(time.toLocalTime());
     return timeSpan.getStart() <= minutesAfterMidnight && timeSpan.getEnd() >= minutesAfterMidnight;
diff --git a/src/test/java/org/opentripplanner/street/model/OHRulesRestrictionTest.java b/src/test/java/org/opentripplanner/street/model/OHRulesRestrictionTest.java
index 294abcb2acb..b1a8216e5cb 100644
--- a/src/test/java/org/opentripplanner/street/model/OHRulesRestrictionTest.java
+++ b/src/test/java/org/opentripplanner/street/model/OHRulesRestrictionTest.java
@@ -35,7 +35,15 @@ public void testRepeatingTimePeriod() throws OpeningHoursParseException {
   @ParameterizedTest
   @ValueSource(
     strings = {
-      "mo-su 06:00-23:00", "fri", "none @ sat", "2024 Jul 26", "2024 Jul 25 - 2024 Jul 27",
+      "mo-su 06:00-23:00",
+      "fri",
+      "none @ sat",
+      "2024 Jul 26",
+      "2024 Jul 25 - 2024 Jul 27",
+      "2024 Jul 25 - 2024 Jul 26",
+      "2024 Jul 26 - 2024 Jul 26",
+      "2024 Jul 25 - 2025 May 27",
+      "2024 Jul 25 - 2024 Jul 27",
     }
   ) // six numbers
   // Note: hours only restrictions (e.g. "06:00-23:00") are not yet supported
@@ -50,4 +58,19 @@ public void testOHCalendarRestrictionOpen(String condition) throws OpeningHoursP
     long time = dateTime.getEpochSecond();
     assertTrue(tr.active(time));
   }
+
+  @ParameterizedTest
+  @ValueSource(strings = { "2024 Jul 1 - 2099 Dec 31" }) // six numbers
+  // Note: hours only restrictions (e.g. "06:00-23:00") are not yet supported
+  public void testOHCalendarRestrictionActive(String condition) throws OpeningHoursParseException {
+    TimeRestriction tr = OHRulesRestriction.parseFromCondition(
+      condition,
+      () -> {
+        return zoneId;
+      }
+    );
+    Instant dateTime = Instant.parse("2025-04-01T10:30:00Z");
+    long time = dateTime.getEpochSecond();
+    assertTrue(tr.active(time));
+  }
 }