diff --git a/db/migrate/20161202034856_add_uploads_to_categories.rb b/db/migrate/20161202034856_add_uploads_to_categories.rb
index 7aa3b646283..92522f76645 100644
--- a/db/migrate/20161202034856_add_uploads_to_categories.rb
+++ b/db/migrate/20161202034856_add_uploads_to_categories.rb
@@ -4,19 +4,19 @@ class AddUploadsToCategories < ActiveRecord::Migration[4.2]
     add_column :categories, :uploaded_background_id, :integer, index: true
 
     execute <<~SQL
-    UPDATE categories
+    UPDATE categories c1
     SET uploaded_logo_id = u.id
-    FROM categories c
-    LEFT JOIN uploads u ON u.url = c.logo_url
-    WHERE u.url IS NOT NULL
+    FROM categories c2
+    INNER JOIN uploads u ON u.url = c2.logo_url
+    WHERE c1.id = c2.id
     SQL
 
     execute <<~SQL
-    UPDATE categories
+    UPDATE categories c1
     SET uploaded_background_id = u.id
-    FROM categories c
-    LEFT JOIN uploads u ON u.url = c.background_url
-    WHERE u.url IS NOT NULL
+    FROM categories c2
+    INNER JOIN uploads u ON u.url = c2.background_url
+    WHERE c1.id = c2.id
     SQL
   end
 end
diff --git a/spec/db/migrate/add_uploads_to_categories_spec.rb b/spec/db/migrate/add_uploads_to_categories_spec.rb
new file mode 100644
index 00000000000..b349a3172fe
--- /dev/null
+++ b/spec/db/migrate/add_uploads_to_categories_spec.rb
@@ -0,0 +1,44 @@
+require 'rails_helper'
+require 'migration/column_dropper'
+require_relative '../../../db/migrate/20161202034856_add_uploads_to_categories'
+
+RSpec.describe AddUploadsToCategories do
+  before do
+    %i{logo_url background_url}.each do |column|
+      DB.exec("ALTER TABLE categories ADD COLUMN #{column} VARCHAR;")
+    end
+
+    %i{uploaded_logo_id uploaded_background_id}.each do |column|
+      DB.exec("ALTER TABLE categories DROP COLUMN IF EXISTS #{column}")
+    end
+  end
+
+  it "should migrate the data properly" do
+    upload1 = Fabricate(:upload)
+    upload2 = Fabricate(:upload)
+
+    category1 = Fabricate(:category,
+      logo_url: upload1.url,
+      background_url: upload2.url
+    )
+
+    category2 = Fabricate(:category,
+      logo_url: upload2.url,
+      background_url: upload1.url
+    )
+
+    silence_stdout { described_class.new.up }
+
+    Discourse.reset_active_record_cache
+
+    category1.reload
+
+    expect(category1.uploaded_logo_id).to eq(upload1.id)
+    expect(category1.uploaded_background_id).to eq(upload2.id)
+
+    category2.reload
+
+    expect(category2.uploaded_logo_id).to eq(upload2.id)
+    expect(category2.uploaded_background_id).to eq(upload1.id)
+  end
+end