diff --git a/Services/TransportConnectionCalculator.cs b/Services/TransportConnectionCalculator.cs
index c8bebf2..98d3f16 100644
--- a/Services/TransportConnectionCalculator.cs
+++ b/Services/TransportConnectionCalculator.cs
@@ -47,36 +47,26 @@ public static class TransportConnectionCalculator
         // If we have valid connections (arriving before latest arrival time)
         if (validConnections.Count > 0)
         {
-            var sortedValid = validConnections
+            var bestValidConnection = validConnections
                 .OrderBy(c => c.ArrivalTime)
-                .ToList();
+                .Last();
 
-            var bestValidConnection = sortedValid.Last();
-
-            // Check if the best valid connection arrives too early (more than maxEarlyArrivalMinutes before shift)
-            if (bestValidConnection.ArrivalTime < earliestAcceptableTime && lateValidConnections.Count > 0)
+            if (bestValidConnection.ArrivalTime > earliestAcceptableTime)
             {
-                // Return the earliest connection that arrives after latest arrival time but within acceptable range
-                var sortedLateValid = lateValidConnections
-                    .OrderBy(c => c.ArrivalTime)
-                    .ToList();
-                
-                return sortedLateValid.First();
+                return bestValidConnection;
             }
-
-            return bestValidConnection;
         }
 
         // If no connections arrive before latest arrival time, check if any arrive within acceptable late range
         if (lateValidConnections.Count > 0)
         {
-            var sortedLateValid = lateValidConnections
+            var bestLateConnection = lateValidConnections
                 .OrderBy(c => c.ArrivalTime)
-                .ToList();
+                .First();
             
-            return sortedLateValid.First();
+            return bestLateConnection;
         }
 
-        return null;
+        return validConnections.FirstOrDefault();
     }
 }
\ No newline at end of file
diff --git a/ShiftScheduler.Services.Tests/TransportConnectionCalculatorTests.cs b/ShiftScheduler.Services.Tests/TransportConnectionCalculatorTests.cs
index 26724dd..c89b81b 100644
--- a/ShiftScheduler.Services.Tests/TransportConnectionCalculatorTests.cs
+++ b/ShiftScheduler.Services.Tests/TransportConnectionCalculatorTests.cs
@@ -162,6 +162,28 @@ public class TransportConnectionCalculatorTests
         result.ArrivalTime.ShouldBe(T("2023-12-15T08:05:00"));
     }
     
+    [Fact]
+    public void FindBestConnectionEnhanced_WithMyCase_ShouldChooseBasedOnTiming()
+    {
+        var connections = new List<TransportConnection>
+        {
+            new(arrivalTime: "2025-09-01T11:41:00"),
+            new(arrivalTime: "2025-09-01T12:41:00"),
+            new(arrivalTime: "2025-09-01T13:41:00"),
+            new(arrivalTime: "2025-09-01T14:41:00"),
+            new(arrivalTime: "2025-09-01T15:41:00")
+        };
+        var shiftStartTime = T("2025-09-01T15:30:00");
+
+        var result = TransportConnectionCalculator.FindBestConnection(
+            connections, 
+            new ConnectionPickArgument(shiftStartTime, 10, 60, 15),
+            loggerMock.Object);
+
+        result.ShouldNotBeNull();
+        result.ArrivalTime.ShouldBe(T("2025-09-01T14:41:00"));
+    }
+    
     private DateTimeOffset T(string dateTimeString)
     {
         return DateTimeOffset.Parse(dateTimeString);