diff --git a/src/shell/filesystem_shell.rs b/src/shell/filesystem_shell.rs
index bb96565418..e6782a9335 100644
--- a/src/shell/filesystem_shell.rs
+++ b/src/shell/filesystem_shell.rs
@@ -252,7 +252,7 @@ impl Shell for FilesystemShell {
 
                 if entry.is_file() {
                     let strategy = |(source_file, _depth_level)| {
-                        if destination.exists() {
+                        if destination.is_dir() {
                             let mut new_dst = dunce::canonicalize(destination.clone())?;
                             if let Some(name) = entry.file_name() {
                                 new_dst.push(name);
diff --git a/tests/commands/cp.rs b/tests/commands/cp.rs
index e249b6d56e..7f0f41d719 100644
--- a/tests/commands/cp.rs
+++ b/tests/commands/cp.rs
@@ -165,3 +165,22 @@ fn copies_using_a_glob() {
         ));
     });
 }
+
+#[test]
+fn copies_same_file_twice() {
+    Playground::setup("cp_test_8", |dirs, _| {
+        nu!(
+            cwd: dirs.root(),
+            "cp \"{}\" cp_test_8/sample.ini",
+            dirs.formats().join("sample.ini")
+        );
+
+        nu!(
+            cwd: dirs.root(),
+            "cp \"{}\" cp_test_8/sample.ini",
+            dirs.formats().join("sample.ini")
+        );
+
+        assert!(dirs.test().join("sample.ini").exists());
+    });
+}