diff --git a/lib/propshaft/output_path.rb b/lib/propshaft/output_path.rb
index f063134..6bb319b 100644
--- a/lib/propshaft/output_path.rb
+++ b/lib/propshaft/output_path.rb
@@ -25,11 +25,13 @@ def clean(count, age)
   def files
     Hash.new.tap do |files|
       all_files_from_tree(path).each do |file|
-        digested_path = file.relative_path_from(path)
-        logical_path, digest = Propshaft::Asset.extract_path_and_digest(digested_path.to_s)
+        digested_path = file.relative_path_from(path).to_s
 
-        files[digested_path.to_s] = {
-          logical_path: logical_path.to_s,
+        digest = digested_path[/-([0-9a-zA-Z]{7,128})\.(digested\.)?([^.]|.map)+\z/, 1]
+        logical_path = digest ? digested_path.sub("-#{digest}", "") : digested_path
+
+        files[digested_path] = {
+          logical_path: logical_path,
           digest: digest,
           mtime: File.mtime(file)
         }
diff --git a/test/fixtures/output/file-already-abcdefVWXYZ0123456789_-.digested.css b/test/fixtures/output/file-already-abcdefVWXYZ0123456789_-.digested.css
new file mode 100644
index 0000000..cb4cc48
--- /dev/null
+++ b/test/fixtures/output/file-already-abcdefVWXYZ0123456789_-.digested.css
@@ -0,0 +1,5 @@
+/* this is css */
+
+.btn {
+    background-image: asset-path("archive.svg");
+}
diff --git a/test/propshaft/output_path_test.rb b/test/propshaft/output_path_test.rb
index 49f1c83..40057b0 100644
--- a/test/propshaft/output_path_test.rb
+++ b/test/propshaft/output_path_test.rb
@@ -9,7 +9,8 @@ class Propshaft::OutputPathTest < ActiveSupport::TestCase
     @manifest    = {
       ".manifest.json": ".manifest.json",
       "one.txt": "one-f2e1ec14.txt",
-      "one.txt.map": "one-f2e1ec15.txt.map"
+      "one.txt.map": "one-f2e1ec15.txt.map",
+      "file-already-abcdefVWXYZ0123456789_-.digested.css": "file-already-abcdefVWXYZ0123456789_-.digested.css"
     }.stringify_keys
     @output_path = Propshaft::OutputPath.new(Pathname.new("#{__dir__}/../fixtures/output"), @manifest)
   end
@@ -21,6 +22,8 @@ class Propshaft::OutputPathTest < ActiveSupport::TestCase
     assert_equal "one.txt", file[:logical_path]
     assert_equal "f2e1ec14", file[:digest]
     assert file[:mtime].is_a?(Time)
+
+    assert files["file-already-abcdefVWXYZ0123456789_-.digested.css"]
   end
 
   test "clean always keeps most current versions" do
@@ -79,6 +82,19 @@ class Propshaft::OutputPathTest < ActiveSupport::TestCase
     FileUtils.rm(current) if File.exist?(current)
   end
 
+  test "clean keeps the correct number of predigested versions" do
+    old     = output_asset("Vue3Lottie-23af1d5aa7baee8b1ca8.digested.js", "old", created_at: Time.now - 300)
+    current = output_asset("Vue3Lottie-337a4df42c71a547bccd.digested.js", "current", created_at: Time.now - 180)
+
+    @output_path.clean(1, 0)
+
+    assert File.exist?(current), "#{current} should still exist"
+    assert_not File.exist?(old), "#{old} should be removed"
+  ensure
+    FileUtils.rm(old) if File.exist?(old)
+    FileUtils.rm(current) if File.exist?(current)
+  end
+
   private
     def output_asset(filename, content, created_at: Time.now)
       load_path = Propshaft::LoadPath.new([], compilers: Propshaft::Compilers.new(nil))