diff --git a/Catalogger.Backend/Extensions/DiscordExtensions.cs b/Catalogger.Backend/Extensions/DiscordExtensions.cs
index 9487a88..b7be6f6 100644
--- a/Catalogger.Backend/Extensions/DiscordExtensions.cs
+++ b/Catalogger.Backend/Extensions/DiscordExtensions.cs
@@ -1,15 +1,11 @@
 using System.Drawing;
 using Catalogger.Backend.Cache.InMemoryCache;
 using Humanizer;
-using OneOf;
 using Remora.Discord.API.Abstractions.Gateway.Events;
 using Remora.Discord.API.Abstractions.Objects;
-using Remora.Discord.API.Abstractions.Rest;
-using Remora.Discord.API.Objects;
 using Remora.Discord.Commands.Contexts;
 using Remora.Discord.Commands.Extensions;
 using Remora.Discord.Commands.Services;
-using Remora.Discord.Extensions.Embeds;
 using Remora.Rest.Core;
 using Remora.Results;
 
@@ -165,5 +161,17 @@ public static class DiscordExtensions
             : $"*(unknown user {actionData.ModeratorId}) <@{actionData.ModeratorId}>*";
     }
 
+    public static int TextLength(this IEmbed embed)
+    {
+        var length = OptionalStringLength(embed.Description) + OptionalStringLength(embed.Title);
+        var fieldLength = (embed.Fields.OrDefault() ?? [])
+            .Select(f => f.Name.Length + f.Value.Length)
+            .Sum();
+
+        return length + fieldLength;
+    }
+
+    private static int OptionalStringLength(Optional<string> s) => s.OrDefault()?.Length ?? 0;
+
     public class DiscordRestException(string message) : Exception(message);
 }
diff --git a/Catalogger.Backend/Services/WebhookExecutorService.cs b/Catalogger.Backend/Services/WebhookExecutorService.cs
index 20d48a6..764c0bf 100644
--- a/Catalogger.Backend/Services/WebhookExecutorService.cs
+++ b/Catalogger.Backend/Services/WebhookExecutorService.cs
@@ -1,4 +1,5 @@
 using System.Collections.Concurrent;
+using System.Diagnostics.CodeAnalysis;
 using Catalogger.Backend.Cache;
 using Catalogger.Backend.Cache.InMemoryCache;
 using Catalogger.Backend.Extensions;
@@ -11,6 +12,11 @@ using Guild = Catalogger.Backend.Database.Models.Guild;
 
 namespace Catalogger.Backend.Services;
 
+[SuppressMessage(
+    "ReSharper",
+    "InconsistentlySynchronizedField",
+    Justification = "ILogger doesn't need to be synchronized"
+)]
 public class WebhookExecutorService(
     Config config,
     ILogger logger,
@@ -76,6 +82,14 @@ public class WebhookExecutorService(
             .Select<FileData, OneOf.OneOf<FileData, IPartialAttachment>>(f => f)
             .ToList();
 
+        if (embeds.Count == 0 && attachments.Count == 0)
+        {
+            _logger.Error(
+                "SendLogAsync was called with zero embeds and zero attachments, bailing to prevent a bad request error"
+            );
+            return;
+        }
+
         _logger.Debug(
             "Sending {EmbedCount} embeds/{FileCount} files to channel {ChannelId}",
             embeds.Count,
@@ -108,9 +122,7 @@ public class WebhookExecutorService(
         _timers[channelId] = new Timer(
             _ =>
             {
-                _logger.Debug("Sending 5 queued embeds");
-
-                var __ = SendLogAsync(channelId, TakeFromQueue(channelId).ToList(), []);
+                var __ = SendLogAsync(channelId, TakeFromQueue(channelId), []);
                 if (!queue.IsEmpty)
                 {
                     if (_timers.TryGetValue(channelId, out var timer))
@@ -124,8 +136,11 @@ public class WebhookExecutorService(
         );
     }
 
+    private const int MaxContentLength = 6000;
+
     /// <summary>
-    /// Takes 5 embeds from the queue for the given channel.
+    /// Takes as many embeds as possible from the queue for the given channel.
+    /// Up to ten embeds are returned, or less if their combined length is longer than 6000 characters.
     /// Note that this locks the queue to prevent duplicate embeds from being sent.
     /// </summary>
     private List<IEmbed> TakeFromQueue(ulong channelId)
@@ -134,14 +149,43 @@ public class WebhookExecutorService(
         var channelLock = _locks.GetOrAdd(channelId, channelId);
         lock (channelLock)
         {
+            var totalContentLength = 0;
             var embeds = new List<IEmbed>();
-            for (var i = 0; i < 5; i++)
+            while (embeds.Count < 10 && totalContentLength < MaxContentLength)
             {
-                if (!queue.TryDequeue(out var embed))
+                if (!queue.TryPeek(out var embed))
                     break;
+
+                var length = embed.TextLength();
+                if (length > MaxContentLength)
+                {
+                    _logger.Warning(
+                        "Queued embed for {ChannelId} exceeds maximum length, discarding it",
+                        channelId
+                    );
+                    queue.TryDequeue(out _);
+                    break;
+                }
+
+                if (totalContentLength + length > MaxContentLength)
+                    break;
+
+                totalContentLength += length;
+
+                queue.TryDequeue(out _);
                 embeds.Add(embed);
             }
 
+            if (embeds.Count == 0)
+                return embeds;
+
+            _logger.Debug(
+                "Took {EmbedCount} embeds from queue for {ChannelId}, total length is {TotalLength}",
+                embeds.Count,
+                channelId,
+                totalContentLength
+            );
+
             return embeds;
         }
     }