diff --git a/app/controllers/uploads_controller.rb b/app/controllers/uploads_controller.rb
index b71240638ee..3eeb85e7149 100644
--- a/app/controllers/uploads_controller.rb
+++ b/app/controllers/uploads_controller.rb
@@ -221,7 +221,7 @@ class UploadsController < ApplicationController
   def validate_file_size(file_name:, file_size:)
     raise ExternalUploadValidationError.new(I18n.t("upload.size_zero_failure")) if file_size.zero?
 
-    if file_size_too_big?(file_name, file_size)
+    if attachment_too_big?(file_name, file_size)
       raise ExternalUploadValidationError.new(
               I18n.t(
                 "upload.attachments.too_large_humanized",
@@ -232,6 +232,18 @@ class UploadsController < ApplicationController
               ),
             )
     end
+
+    if image_too_big?(file_name, file_size)
+      raise ExternalUploadValidationError.new(
+              I18n.t(
+                "upload.images.too_large_humanized",
+                max_size:
+                  ActiveSupport::NumberHelper.number_to_human_size(
+                    SiteSetting.max_image_size_kb.kilobytes,
+                  ),
+              ),
+            )
+    end
   end
 
   def force_download?
@@ -306,14 +318,20 @@ class UploadsController < ApplicationController
 
   private
 
-  # We can preemptively check size for attachments, but not for images
+  # We can preemptively check size for attachments, but not for (most) images
   # as they may be further reduced in size by UploadCreator (at this point
   # they may have already been reduced in size by preprocessors)
-  def file_size_too_big?(file_name, file_size)
+  def attachment_too_big?(file_name, file_size)
     !FileHelper.is_supported_image?(file_name) &&
       file_size >= SiteSetting.max_attachment_size_kb.kilobytes
   end
 
+  # Gifs are not resized on the client and not reduced in size by UploadCreator
+  def image_too_big?(file_name, file_size)
+    FileHelper.is_supported_image?(file_name) && File.extname(file_name) == ".gif" &&
+      file_size >= SiteSetting.max_image_size_kb.kilobytes
+  end
+
   def send_file_local_upload(upload)
     opts = {
       filename: upload.original_filename,
diff --git a/spec/requests/uploads_controller_spec.rb b/spec/requests/uploads_controller_spec.rb
index 44eee47daec..e0101f269fd 100644
--- a/spec/requests/uploads_controller_spec.rb
+++ b/spec/requests/uploads_controller_spec.rb
@@ -853,6 +853,16 @@ RSpec.describe UploadsController do
         )
       end
 
+      it "returns 422 when the file is an gif and it's too big, since gifs cannot be resized on client" do
+        SiteSetting.max_image_size_kb = 1024
+        post "/uploads/create-multipart.json",
+             **{ params: { file_name: "test.gif", file_size: 9_999_999, upload_type: "composer" } }
+        expect(response.status).to eq(422)
+        expect(response.body).to include(
+          I18n.t("upload.images.too_large_humanized", max_size: "1 MB"),
+        )
+      end
+
       it "returns a sensible error if the file size is 0 bytes" do
         SiteSetting.authorized_extensions = "*"
         stub_create_multipart_request