diff --git a/lib/stylesheet/manager.rb b/lib/stylesheet/manager.rb
index 2d5f3614d10..fb7d5e18ecd 100644
--- a/lib/stylesheet/manager.rb
+++ b/lib/stylesheet/manager.rb
@@ -256,7 +256,7 @@ class Stylesheet::Manager
       raise "attempting to look up theme digest for invalid field"
     end
 
-    Digest::SHA1.hexdigest(scss.to_s + color_scheme_digest.to_s + settings_digest + plugins_digest)
+    Digest::SHA1.hexdigest(scss.to_s + color_scheme_digest.to_s + settings_digest + plugins_digest + uploads_digest)
   end
 
   # this protects us from situations where new versions of a plugin removed a file
@@ -274,6 +274,10 @@ class Stylesheet::Manager
     Digest::SHA1.hexdigest((theme&.included_settings || {}).to_json)
   end
 
+  def uploads_digest
+    Digest::SHA1.hexdigest(ThemeField.joins(:upload).where(id: theme&.all_theme_variables).pluck(:sha1).join(","))
+  end
+
   def color_scheme_digest
 
     cs = theme&.color_scheme
diff --git a/spec/components/stylesheet/manager_spec.rb b/spec/components/stylesheet/manager_spec.rb
index 9e5b6ff3475..b534133b9e2 100644
--- a/spec/components/stylesheet/manager_spec.rb
+++ b/spec/components/stylesheet/manager_spec.rb
@@ -87,6 +87,45 @@ describe Stylesheet::Manager do
 
       expect(digest1).not_to eq(digest2)
     end
+
+    let(:image) { file_from_fixtures("logo.png") }
+    let(:image2) { file_from_fixtures("logo-dev.png") }
+
+    it 'can correctly account for theme uploads in digest' do
+      theme = Theme.create!(
+        name: 'parent',
+        user_id: -1
+      )
+
+      upload = UploadCreator.new(image, "logo.png").create_for(-1)
+      field = ThemeField.create!(
+        theme_id: theme.id,
+        target_id: Theme.targets[:common],
+        name: "logo",
+        value: "",
+        upload_id: upload.id,
+        type_id: ThemeField.types[:theme_upload_var]
+      )
+
+      manager = Stylesheet::Manager.new(:desktop_theme, theme.key)
+      digest1 = manager.digest
+      field.destroy!
+
+      upload = UploadCreator.new(image2, "logo.png").create_for(-1)
+      field = ThemeField.create!(
+        theme_id: theme.id,
+        target_id: Theme.targets[:common],
+        name: "logo",
+        value: "",
+        upload_id: upload.id,
+        type_id: ThemeField.types[:theme_upload_var]
+      )
+
+      manager = Stylesheet::Manager.new(:desktop_theme, theme.key)
+      digest2 = manager.digest
+
+      expect(digest1).not_to eq(digest2)
+    end
   end
 
   describe 'color_scheme_digest' do