diff --git a/fixtures/test-multiple-files-upload-not-found/config.toml b/fixtures/test-multiple-files-upload-not-found/config.toml
new file mode 100644
index 0000000..a94fcc3
--- /dev/null
+++ b/fixtures/test-multiple-files-upload-not-found/config.toml
@@ -0,0 +1,9 @@
+[server]
+address = "127.0.0.1:8000"
+max_content_length = "10MB"
+upload_path = "./upload"
+
+[paste]
+default_extension = "txt"
+duplicate_files = true
+delete_expired_files = { enabled = true, interval = "1h" }
diff --git a/fixtures/test-multiple-files-upload-not-found/test.sh b/fixtures/test-multiple-files-upload-not-found/test.sh
new file mode 100755
index 0000000..3441e30
--- /dev/null
+++ b/fixtures/test-multiple-files-upload-not-found/test.sh
@@ -0,0 +1,20 @@
+#!/usr/bin/env bash
+
+content="test data"
+
+setup() {
+  echo "$content" > file
+}
+
+run_test() {
+  file_url=$(curl -s -F "file=@file" -H "expire:2s" localhost:8000)
+  file_url=$(curl -s -F "file=@file" -H "expire:1s" localhost:8000)
+  sleep 2
+  file_url=$(curl -s -F "file=@file" -H "expire:1m" localhost:8000)
+  test "$content" = "$(curl -s $file_url)"
+}
+
+teardown() {
+  rm file
+  rm -r upload
+}
diff --git a/src/util.rs b/src/util.rs
index d404cfc..ebc3c9d 100644
--- a/src/util.rs
+++ b/src/util.rs
@@ -37,7 +37,7 @@ pub fn glob_match_file(mut path: PathBuf) -> Result<PathBuf, ActixError> {
     );
     if let Some(glob_path) = glob(&format!("{}.[0-9]*", path.to_string_lossy()))
         .map_err(error::ErrorInternalServerError)?
-        .next()
+        .last()
     {
         let glob_path = glob_path.map_err(error::ErrorInternalServerError)?;
         if let Some(extension) = glob_path