diff --git a/Myriad/Extensions/GuildExtensions.cs b/Myriad/Extensions/GuildExtensions.cs
index 2f97aa56..3e9cc674 100644
--- a/Myriad/Extensions/GuildExtensions.cs
+++ b/Myriad/Extensions/GuildExtensions.cs
@@ -1,7 +1,22 @@
+using Myriad.Types;
+
 namespace Myriad.Extensions
 {
     public static class GuildExtensions
     {
-
+        public static int FileSizeLimit(this Guild guild)
+        {
+            switch (guild.PremiumTier)
+            {
+                default:
+                case PremiumTier.NONE:
+                case PremiumTier.TIER_1:
+                    return 8;
+                case PremiumTier.TIER_2:
+                    return 50;
+                case PremiumTier.TIER_3:
+                    return 100;
+            }
+        }
     }
 }
\ No newline at end of file
diff --git a/Myriad/Types/Guild.cs b/Myriad/Types/Guild.cs
index fe39d0ff..75764b8e 100644
--- a/Myriad/Types/Guild.cs
+++ b/Myriad/Types/Guild.cs
@@ -1,5 +1,13 @@
 namespace Myriad.Types
 {
+    public enum PremiumTier
+    {
+        NONE,
+        TIER_1,
+        TIER_2,
+        TIER_3,
+    }
+
     public record Guild
     {
         public ulong Id { get; init; }
@@ -15,6 +23,7 @@ namespace Myriad.Types
         public bool? WidgetEnabled { get; init; }
         public ulong? WidgetChannelId { get; init; }
         public int VerificationLevel { get; init; }
+        public PremiumTier PremiumTier { get; init; }
 
         public Role[] Roles { get; init; }
         public string[] Features { get; init; }
diff --git a/PluralKit.Bot/Proxy/ProxyService.cs b/PluralKit.Bot/Proxy/ProxyService.cs
index fa59578c..978a8455 100644
--- a/PluralKit.Bot/Proxy/ProxyService.cs
+++ b/PluralKit.Bot/Proxy/ProxyService.cs
@@ -146,6 +146,7 @@ namespace PluralKit.Bot
             var messageChannel = _cache.GetChannel(trigger.ChannelId);
             var rootChannel = _cache.GetRootChannel(trigger.ChannelId);
             var threadId = messageChannel.IsThread() ? messageChannel.Id : (ulong?)null;
+            var guild = _cache.GetGuild(trigger.GuildId.Value);
 
             var proxyMessage = await _webhookExecutor.ExecuteWebhook(new ProxyRequest
             {
@@ -156,6 +157,7 @@ namespace PluralKit.Bot
                 AvatarUrl = AvatarUtils.TryRewriteCdnUrl(match.Member.ProxyAvatar(ctx)),
                 Content = content,
                 Attachments = trigger.Attachments,
+                FileSizeLimit = guild.FileSizeLimit(),
                 Embeds = embeds.ToArray(),
                 AllowEveryone = allowEveryone,
             });
diff --git a/PluralKit.Bot/Services/WebhookExecutorService.cs b/PluralKit.Bot/Services/WebhookExecutorService.cs
index d66be6c4..da5ebe23 100644
--- a/PluralKit.Bot/Services/WebhookExecutorService.cs
+++ b/PluralKit.Bot/Services/WebhookExecutorService.cs
@@ -40,6 +40,7 @@ namespace PluralKit.Bot
         public string? AvatarUrl { get; init; }
         public string? Content { get; init; }
         public Message.Attachment[] Attachments { get; init; }
+        public int FileSizeLimit { get; init; }
         public Embed[] Embeds { get; init; }
         public bool AllowEveryone { get; init; }
     }
@@ -122,7 +123,7 @@ namespace PluralKit.Bot
             };
 
             MultipartFile[] files = null;
-            var attachmentChunks = ChunkAttachmentsOrThrow(req.Attachments, 8 * 1024 * 1024);
+            var attachmentChunks = ChunkAttachmentsOrThrow(req.Attachments, req.FileSizeLimit * 1024 * 1024);
             if (attachmentChunks.Count > 0)
             {
                 _logger.Information("Invoking webhook with {AttachmentCount} attachments totalling {AttachmentSize} MiB in {AttachmentChunks} chunks",