diff --git a/ExtractorUtils/Unstable/Tasks/CheckInWorker.cs b/ExtractorUtils/Unstable/Tasks/CheckInWorker.cs
index ca5fb0ba..c4c575ef 100644
--- a/ExtractorUtils/Unstable/Tasks/CheckInWorker.cs
+++ b/ExtractorUtils/Unstable/Tasks/CheckInWorker.cs
@@ -254,14 +254,37 @@ private async Task ReportCheckIn(CancellationToken token)
                 }
                 else
                 {
-                    newErrors = _errors.Values.ToList();
+                    newErrors = new List<ErrorWithTask>(_errors.Values);
+                    foreach (var err in _errors.Values)
+                    {
+                        // Modifying err since it's an object reference in the dictionary, so changes will be reflected when we write the check-in,
+                        // but we want to log the full error before truncating.
+                        _logger.LogInformation("Error: {ExternalId}, Level: {Level}, Description: {Description}, Details: {Details}, Task: {Task}, StartTime: {StartTime}, EndTime: {EndTime}",
+                            err.ExternalId, err.Level, err.Description, err.Details, err.Task, err.StartTime, err.EndTime);
+                        if (err.Description != null && err.Description.Length > 5000)
+                        {
+                            _logger.LogWarning("Truncating description for error {ExternalId} to 5,000 characters. Original length was {OriginalLength}", err.ExternalId, err.Description.Length);
+                            err.Description = err.Description.Substring(0, 5000);
+                        }
+                        else if (err.Details != null && err.Details.Length > 5000)
+                        {
+                            _logger.LogWarning("Error {ExternalId} has details exceeding 5,000 characters, truncating. Original length was {OriginalLength}", err.ExternalId, err.Details.Length);
+                            err.Details = err.Details.Substring(0, 5000);
+                        }
+                    }
                     _errors.Clear();
                     taskUpdates = _taskUpdates;
                     _taskUpdates = new List<TaskUpdate>();
                 }
             }
 
-            newErrors.Sort((a, b) => (a.EndTime ?? a.StartTime).CompareTo(b.EndTime ?? b.StartTime));
+            newErrors.Sort((a, b) =>
+            {
+                long? aTime = a.EndTime ?? a.StartTime;
+                long? bTime = b.EndTime ?? b.StartTime;
+                // Handle null timestamps by treating them as 0 (earliest possible time)
+                return (aTime ?? 0).CompareTo(bTime ?? 0);
+            });
             taskUpdates.Sort((a, b) => a.Timestamp.CompareTo(b.Timestamp));
 
             while (!token.IsCancellationRequested)