diff --git a/ErsatzTV.Application/Channels/Commands/RefreshChannelDataHandler.cs b/ErsatzTV.Application/Channels/Commands/RefreshChannelDataHandler.cs
index fb43cb66f..771a05964 100644
--- a/ErsatzTV.Application/Channels/Commands/RefreshChannelDataHandler.cs
+++ b/ErsatzTV.Application/Channels/Commands/RefreshChannelDataHandler.cs
@@ -1189,10 +1189,18 @@ public class RefreshChannelDataHandler : IRequestHandler<RefreshChannelData>
             // must deserialize channel from json
             foreach (ExternalJsonChannel channel in maybeChannel)
             {
-                // TODO: null start time should log and throw
+                if (string.IsNullOrWhiteSpace(channel.StartTime))
+                {
+                    _logger.LogError(
+                        "External json channel in file {File} has no start time; unable to refresh channel data",
+                        path);
+
+                    throw new InvalidOperationException(
+                        $"External json channel in file {path} has no start time");
+                }
 
                 DateTimeOffset startTime = DateTimeOffset.Parse(
-                    channel.StartTime ?? string.Empty,
+                    channel.StartTime,
                     CultureInfo.InvariantCulture,
                     DateTimeStyles.AssumeUniversal).ToLocalTime();
 
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 d95f60a09..c5eea25ee 100644
--- a/ErsatzTV.Core/Scheduling/PlayoutBuilder.cs
+++ b/ErsatzTV.Core/Scheduling/PlayoutBuilder.cs
@@ -1488,7 +1488,10 @@ public class PlayoutBuilder : IPlayoutBuilder
                 goto default;
 
             default:
-                // TODO: handle this error case differently?
+                _logger.LogWarning(
+                    "Unsupported playback order {PlaybackOrder}; falling back to random",
+                    playbackOrder);
+
                 return new RandomizedMediaCollectionEnumerator(mediaItems, state);
         }
     }
diff --git a/ErsatzTV.Infrastructure/Streaming/ExternalJsonPlayoutItemProvider.cs b/ErsatzTV.Infrastructure/Streaming/ExternalJsonPlayoutItemProvider.cs
index 7e73234c4..28c7a216b 100644
--- a/ErsatzTV.Infrastructure/Streaming/ExternalJsonPlayoutItemProvider.cs
+++ b/ErsatzTV.Infrastructure/Streaming/ExternalJsonPlayoutItemProvider.cs
@@ -92,10 +92,18 @@ public class ExternalJsonPlayoutItemProvider : IExternalJsonPlayoutItemProvider
         // must deserialize channel from json
         foreach (ExternalJsonChannel channel in maybeChannel)
         {
-            // TODO: null start time should log and throw
+            if (string.IsNullOrWhiteSpace(channel.StartTime))
+            {
+                _logger.LogError(
+                    "External json channel in file {File} has no start time; unable to locate playout item",
+                    playout.ScheduleFile);
+
+                throw new InvalidOperationException(
+                    $"External json channel in file {playout.ScheduleFile} has no start time");
+            }
 
             DateTimeOffset startTime = DateTimeOffset.Parse(
-                channel.StartTime ?? string.Empty,
+                channel.StartTime,
                 CultureInfo.InvariantCulture,
                 DateTimeStyles.AssumeUniversal).ToLocalTime();
 
@@ -207,14 +215,35 @@ 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
@@ -230,7 +259,6 @@ public class ExternalJsonPlayoutItemProvider : IExternalJsonPlayoutItemProvider
             }
         }
 
-        // TODO: log errors?
         return new UnableToLocatePlayoutItem();
     }