diff --git a/KfChatDotNetBot/Commands/ImageCommands.cs b/KfChatDotNetBot/Commands/ImageCommands.cs
index f5e7ed3..9bee3bb 100644
--- a/KfChatDotNetBot/Commands/ImageCommands.cs
+++ b/KfChatDotNetBot/Commands/ImageCommands.cs
@@ -1,4 +1,5 @@
-using System.Text.RegularExpressions;
+using System.Net.Http.Headers;
+using System.Text.RegularExpressions;
 using KfChatDotNetBot.Extensions;
 using KfChatDotNetBot.Models;
 using KfChatDotNetBot.Models.DbModels;
@@ -104,11 +105,13 @@ public class ListImageCommand : ICommand
     public UserRight RequiredRight => UserRight.TrueAndHonest;
     public TimeSpan Timeout => TimeSpan.FromSeconds(10);
     public RateLimitOptionsModel? RateLimitOptions => null;
+
     public async Task RunCommand(ChatBot botInstance, MessageModel message, UserDbModel user, GroupCollection arguments,
         CancellationToken ctx)
     {
         await using var db = new ApplicationDbContext();
-        var imageKeys = (await SettingsProvider.GetValueAsync(BuiltIn.Keys.BotImageAcceptableKeys)).JsonDeserialize<List<string>>();
+        var imageKeys = (await SettingsProvider.GetValueAsync(BuiltIn.Keys.BotImageAcceptableKeys))
+            .JsonDeserialize<List<string>>();
         if (imageKeys == null) throw new InvalidOperationException($"{BuiltIn.Keys.BotImageAcceptableKeys} was null");
         var key = arguments["key"].Value;
         if (!imageKeys.Contains(key))
@@ -119,6 +122,18 @@ public class ListImageCommand : ICommand
         }
 
         var images = db.Images.Where(i => i.Key == key);
+        if (await images.CountAsync(cancellationToken: ctx) > 20 && await Zipline.IsZiplineEnabled())
+        {
+            var content = string.Empty;
+            foreach (var image in images)
+            {
+                content += image.Url + Environment.NewLine;
+            }
+
+            var paste = await Zipline.Upload(content, new MediaTypeHeaderValue("text/plain"), "1d", ctx);
+            await botInstance.SendChatMessageAsync($"List of images for {key}: {paste}", true);
+        }
+
         var i = 0;
         var result = $"List of images for {key}:";
         foreach (var image in images)
diff --git a/KfChatDotNetBot/Services/Zipline.cs b/KfChatDotNetBot/Services/Zipline.cs
index 3e85875..a999f53 100644
--- a/KfChatDotNetBot/Services/Zipline.cs
+++ b/KfChatDotNetBot/Services/Zipline.cs
@@ -10,6 +10,26 @@ namespace KfChatDotNetBot.Services;
 public static class Zipline
 {
     public static async Task<string?> Upload(Stream content, MediaTypeHeaderValue mimeType, string? expiration = null, CancellationToken ct = default)
+    {
+        using var formContent = new MultipartFormDataContent();
+        var fileContent = new StreamContent(content);
+        fileContent.Headers.ContentType = mimeType;
+        formContent.Add(fileContent, "upload", Money.GenerateEventId());
+        var url = await DoUpload(formContent, expiration, ct);
+        return url;
+    }
+    
+    public static async Task<string?> Upload(string content, MediaTypeHeaderValue mimeType, string? expiration = null, CancellationToken ct = default)
+    {
+        using var formContent = new MultipartFormDataContent();
+        var fileContent = new StringContent(content);
+        fileContent.Headers.ContentType = mimeType;
+        formContent.Add(fileContent, "upload", Money.GenerateEventId());
+        var url = await DoUpload(formContent, expiration, ct);
+        return url;
+    }
+    
+    private static async Task<string?> DoUpload(MultipartFormDataContent content, string? expiration = null, CancellationToken ct = default)
     {
         var logger = LogManager.GetCurrentClassLogger();
         var settings =
@@ -30,17 +50,13 @@ public static class Zipline
         }
 
         using var client = new HttpClient(handler);
-        using var formContent = new MultipartFormDataContent();
-        var fileContent = new StreamContent(content);
-        fileContent.Headers.ContentType = mimeType;
-        formContent.Add(fileContent, "upload", Money.GenerateEventId());
         client.DefaultRequestHeaders.TryAddWithoutValidation("Authorization", settings[BuiltIn.Keys.ZiplineKey].Value);
         if (expiration != null)
         {
             client.DefaultRequestHeaders.Add("x-zipline-expiration", expiration);
         }
 
-        var response = await client.PostAsync($"{settings[BuiltIn.Keys.ZiplineUrl].Value}/api/upload", formContent, ct);
+        var response = await client.PostAsync($"{settings[BuiltIn.Keys.ZiplineUrl].Value}/api/upload", content, ct);
         var json = await response.Content.ReadFromJsonAsync<JsonElement>(cancellationToken: ct);
         string url;
         try
@@ -58,4 +74,10 @@ public static class Zipline
 
         return url;
     }
+
+    public static async Task<bool> IsZiplineEnabled()
+    {
+        var key = await SettingsProvider.GetValueAsync(BuiltIn.Keys.ZiplineKey);
+        return !string.IsNullOrEmpty(key.Value);
+    }
 }
\ No newline at end of file