diff --git a/crates/openshell-cli/src/ssh.rs b/crates/openshell-cli/src/ssh.rs
index 50bc2bbee9..5ef683a2b5 100644
--- a/crates/openshell-cli/src/ssh.rs
+++ b/crates/openshell-cli/src/ssh.rs
@@ -970,6 +970,28 @@ pub async fn sandbox_sync_up_files(
     if files.is_empty() {
         return Ok(());
     }
+
+    if files.len() == 1
+        && local_upload_path_is_file_like(local_path)
+        && let Some(path) = dest
+        && !path.ends_with('/')
+    {
+        let (parent, target_name) = split_sandbox_path(path);
+        if parent != "/" {
+            return ssh_tar_upload(
+                server,
+                name,
+                Some(parent),
+                UploadSource::SinglePath {
+                    local_path: base_dir.join(&files[0]),
+                    tar_name: target_name.into(),
+                },
+                tls,
+            )
+            .await;
+        }
+    }
+
     ssh_tar_upload(
         server,
         name,
diff --git a/e2e/rust/tests/sync.rs b/e2e/rust/tests/sync.rs
index a57793a74f..b799a58c8f 100644
--- a/e2e/rust/tests/sync.rs
+++ b/e2e/rust/tests/sync.rs
@@ -300,7 +300,8 @@ async fn upload_respects_gitignore_by_default() {
 }
 
 /// Verify that uploading a single tracked file from inside a git repo does not
-/// expand to the entire repository.
+/// expand to the entire repository, and that the destination basename is
+/// respected (cp-style semantics).
 #[tokio::test]
 async fn upload_single_file_from_git_repo_only_uploads_that_file() {
     let mut guard =
@@ -330,7 +331,7 @@ async fn upload_single_file_from_git_repo_only_uploads_that_file() {
     let local_path = repo.join("nested/config.txt");
     let local_str = local_path.to_str().expect("local path is UTF-8");
     guard
-        .upload_with_gitignore(local_str, "/sandbox/single-file", &repo)
+        .upload_with_gitignore(local_str, "/sandbox/renamed.txt", &repo)
         .await
         .expect("upload single tracked file with gitignore");
 
@@ -339,12 +340,16 @@ async fn upload_single_file_from_git_repo_only_uploads_that_file() {
     let download_str = download_dir.to_str().expect("download path is UTF-8");
 
     guard
-        .download("/sandbox/single-file", download_str)
+        .download("/sandbox/renamed.txt", download_str)
         .await
         .expect("download uploaded single file");
 
-    let uploaded = fs::read_to_string(download_dir.join("config.txt")).expect("read config.txt");
+    let uploaded = fs::read_to_string(download_dir.join("renamed.txt")).expect("read renamed.txt");
     assert_eq!(uploaded, "single-file-from-repo");
+    assert!(
+        !download_dir.join("config.txt").exists(),
+        "original basename config.txt should not appear — file must be renamed to dest basename"
+    );
     assert!(
         !download_dir.join("tracked.txt").exists(),
         "tracked.txt should not have been uploaded"