diff --git a/ErsatzTV.Application/Channels/Commands/RefreshChannelDataHandler.cs b/ErsatzTV.Application/Channels/Commands/RefreshChannelDataHandler.cs
index 97dfd84c3..622c2dff6 100644
--- a/ErsatzTV.Application/Channels/Commands/RefreshChannelDataHandler.cs
+++ b/ErsatzTV.Application/Channels/Commands/RefreshChannelDataHandler.cs
@@ -1194,12 +1194,17 @@ public class RefreshChannelDataHandler : IRequestHandler<RefreshChannelData>
             // must deserialize channel from json
             foreach (ExternalJsonChannel channel in maybeChannel)
             {
-                // TODO: null start time should log and throw
+                if (!DateTimeOffset.TryParse(
+                        channel.StartTime,
+                        CultureInfo.InvariantCulture,
+                        DateTimeStyles.AssumeUniversal,
+                        out DateTimeOffset parsed))
+                {
+                    throw new InvalidOperationException(
+                        $"External json channel in file {path} has an invalid start time '{channel.StartTime}'");
+                }
 
-                DateTimeOffset startTime = DateTimeOffset.Parse(
-                    channel.StartTime ?? string.Empty,
-                    CultureInfo.InvariantCulture,
-                    DateTimeStyles.AssumeUniversal).ToLocalTime();
+                DateTimeOffset startTime = parsed.ToLocalTime();
 
                 for (var i = 0; i < channel.Programs.Length; i++)
                 {
diff --git a/ErsatzTV.Application/Playouts/Commands/ReplacePlayoutAlternateScheduleItemsHandler.cs b/ErsatzTV.Application/Playouts/Commands/ReplacePlayoutAlternateScheduleItemsHandler.cs
index 0cf6490a6..580558159 100644
--- a/ErsatzTV.Application/Playouts/Commands/ReplacePlayoutAlternateScheduleItemsHandler.cs
+++ b/ErsatzTV.Application/Playouts/Commands/ReplacePlayoutAlternateScheduleItemsHandler.cs
@@ -20,7 +20,10 @@ public class ReplacePlayoutAlternateScheduleItemsHandler(
         ReplacePlayoutAlternateScheduleItems request,
         CancellationToken cancellationToken)
     {
-        // TODO: validate that items is not empty
+        if (request.Items.Count == 0)
+        {
+            return BaseError.New("Playout alternate schedule items must not be empty");
+        }
 
         try
         {
diff --git a/ErsatzTV.Core/Scheduling/PlayoutBuilder.cs b/ErsatzTV.Core/Scheduling/PlayoutBuilder.cs
index 48e0b1202..a7ed7ef40 100644
--- a/ErsatzTV.Core/Scheduling/PlayoutBuilder.cs
+++ b/ErsatzTV.Core/Scheduling/PlayoutBuilder.cs
@@ -1448,10 +1448,10 @@ public class PlayoutBuilder : IPlayoutBuilder
                 }
 
                 // fall through to default case if we can't make the proper enumerator
+                _logger.LogWarning("Unable to build marathon enumerator; falling back to random");
                 goto default;
 
             default:
-                // TODO: handle this error case differently?
                 return new RandomizedMediaCollectionEnumerator(mediaItems, state);
         }
     }
diff --git a/ErsatzTV.Infrastructure/Streaming/ExternalJsonPlayoutItemProvider.cs b/ErsatzTV.Infrastructure/Streaming/ExternalJsonPlayoutItemProvider.cs
index 5e904d1cf..9ec345306 100644
--- a/ErsatzTV.Infrastructure/Streaming/ExternalJsonPlayoutItemProvider.cs
+++ b/ErsatzTV.Infrastructure/Streaming/ExternalJsonPlayoutItemProvider.cs
@@ -93,12 +93,21 @@ public class ExternalJsonPlayoutItemProvider : IExternalJsonPlayoutItemProvider
         // must deserialize channel from json
         foreach (ExternalJsonChannel channel in maybeChannel)
         {
-            // TODO: null start time should log and throw
+            if (!DateTimeOffset.TryParse(
+                    channel.StartTime,
+                    CultureInfo.InvariantCulture,
+                    DateTimeStyles.AssumeUniversal,
+                    out DateTimeOffset parsed))
+            {
+                _logger.LogError(
+                    "External json channel in file {ScheduleFile} has an invalid start time {StartTime}",
+                    playout.ScheduleFile,
+                    channel.StartTime);
+
+                return new UnableToLocatePlayoutItem();
+            }
 
-            DateTimeOffset startTime = DateTimeOffset.Parse(
-                channel.StartTime ?? string.Empty,
-                CultureInfo.InvariantCulture,
-                DateTimeStyles.AssumeUniversal).ToLocalTime();
+            DateTimeOffset startTime = parsed.ToLocalTime();
 
             //_logger.LogDebug("external json start time: {StartTime}", startTime);
 
@@ -208,14 +217,35 @@ public class ExternalJsonPlayoutItemProvider : IExternalJsonPlayoutItemProvider
             .Include(pms => pms.Connections)
             .SelectOneAsync(pms => pms.ServerName, pms => pms.ServerName == program.ServerKey, cancellationToken);
 
+        if (maybeServer.IsNone)
+        {
+            _logger.LogWarning(
+                "Unable to stream remotely; no Plex server found with server name {ServerName}",
+                program.ServerKey);
+        }
+
         foreach (PlexMediaSource server in maybeServer)
         {
             Option<PlexConnection> maybeConnection = server.Connections.SingleOrDefault(c => c.IsActive);
+            if (maybeConnection.IsNone)
+            {
+                _logger.LogWarning(
+                    "Unable to stream remotely; Plex server {ServerName} has no active connection",
+                    server.ServerName);
+            }
+
             foreach (PlexConnection connection in maybeConnection)
             {
                 Option<PlexServerAuthToken> maybeToken =
                     await _plexSecretStore.GetServerAuthToken(server.ClientIdentifier);
 
+                if (maybeToken.IsNone)
+                {
+                    _logger.LogWarning(
+                        "Unable to stream remotely; Plex server {ServerName} has no auth token",
+                        server.ServerName);
+                }
+
                 foreach (PlexServerAuthToken token in maybeToken)
                 {
                     MediaItem mediaItem = program.Type switch
@@ -241,7 +271,6 @@ public class ExternalJsonPlayoutItemProvider : IExternalJsonPlayoutItemProvider
             }
         }
 
-        // TODO: log errors?
         return new UnableToLocatePlayoutItem();
     }