diff --git a/rustscout/src/replace/mod.rs b/rustscout/src/replace/mod.rs
index 21b0523..c06ad0c 100644
--- a/rustscout/src/replace/mod.rs
+++ b/rustscout/src/replace/mod.rs
@@ -398,17 +398,24 @@ impl FileReplacementPlan {
     /// Create a backup of the file if backup is enabled
     fn create_backup(&self, config: &ReplacementConfig) -> SearchResult<Option<PathBuf>> {
         if !config.backup_enabled {
+            println!("Debug: Backup not enabled");
             return Ok(None);
         }
 
         // 1) Figure out the workspace root
         let workspace_root = detect_workspace_root(&self.file_path)?;
+        println!("Debug: Workspace root = {}", workspace_root.display());
+
         // 2) Determine the "backups" subdirectory
         let backup_dir = if let Some(ref dir) = config.backup_dir {
+            println!("Debug: Using user-specified backup dir: {}", dir.display());
             dir.clone()
         } else {
-            workspace_root.join(".rustscout").join("backups")
+            let default_dir = workspace_root.join(".rustscout").join("backups");
+            println!("Debug: Using default backup dir: {}", default_dir.display());
+            default_dir
         };
+        println!("Debug: Creating backup dir: {}", backup_dir.display());
         fs::create_dir_all(&backup_dir)?;
 
         // 3) Compute a unique backup filename from the *relative path*
@@ -416,10 +423,12 @@ impl FileReplacementPlan {
             .file_path
             .strip_prefix(&workspace_root)
             .unwrap_or(&self.file_path);
+        println!("Debug: Relative path for backup: {}", relative.display());
         let relative_str = relative
             .to_string_lossy()
             .replace("\\", "_")
             .replace("/", "_");
+        println!("Debug: Sanitized relative path: {}", relative_str);
 
         let timestamp = SystemTime::now()
             .duration_since(UNIX_EPOCH)
@@ -430,9 +439,18 @@ impl FileReplacementPlan {
         // e.g. "crate_a_lib.rs.1737267859"
         let backup_name = format!("{}.{}", relative_str, timestamp);
         let backup_path = backup_dir.join(&backup_name);
+        println!("Debug: Final backup path: {}", backup_path.display());
 
         // 5) Copy original file to the new backup path
-        fs::copy(&self.file_path, &backup_path).map_err(SearchError::IoError)?;
+        println!(
+            "Debug: Copying from {} to {}",
+            self.file_path.display(),
+            backup_path.display()
+        );
+        match fs::copy(&self.file_path, &backup_path) {
+            Ok(_) => println!("Debug: Successfully created backup"),
+            Err(e) => println!("Debug: Failed to create backup: {}", e),
+        }
 
         if config.preserve_metadata {
             if let Ok(metadata) = fs::metadata(&self.file_path) {
diff --git a/rustscout/tests/cli_test.rs b/rustscout/tests/cli_test.rs
index 394650e..24b8385 100644
--- a/rustscout/tests/cli_test.rs
+++ b/rustscout/tests/cli_test.rs
@@ -68,12 +68,23 @@ fn test_replace_basic() -> Result<()> {
 fn test_replace_with_backup() -> Result<()> {
     let dir = tempdir()?;
     let backup_dir = dir.path().join("backups");
+    println!("Debug: Test backup dir = {}", backup_dir.display());
     fs::create_dir_all(&backup_dir)?;
+    println!(
+        "Debug: Created backup dir, exists = {}",
+        backup_dir.exists()
+    );
 
     let undo_dir = dir.path().join(".rustscout").join("undo");
     fs::create_dir_all(&undo_dir)?;
 
     create_test_files(&dir, &[("test.txt", "Hello world")])?;
+    let test_file = dir.path().join("test.txt");
+    println!(
+        "Debug: Test file = {}, exists = {}",
+        test_file.display(),
+        test_file.exists()
+    );
 
     let config = ReplacementConfig {
         patterns: vec![ReplacementPattern {
@@ -109,8 +120,25 @@ fn test_replace_with_backup() -> Result<()> {
         fs::read_to_string(dir.path().join("test.txt"))?,
         "World world"
     );
-    // Check that the backup directory is not empty
-    assert!(fs::read_dir(&backup_dir)?.next().is_some());
+
+    // Enhanced backup directory check with diagnostics
+    println!("Debug: Checking backup dir after replacement");
+    match fs::read_dir(&backup_dir) {
+        Ok(entries) => {
+            let entries: Vec<_> = entries.collect();
+            println!("Debug: Found {} entries in backup dir", entries.len());
+            for entry in &entries {
+                if let Ok(entry) = entry {
+                    println!("Debug: Found backup file: {}", entry.path().display());
+                }
+            }
+            assert!(!entries.is_empty(), "Backup directory should not be empty");
+        }
+        Err(e) => {
+            println!("Debug: Failed to read backup dir: {}", e);
+            assert!(false, "Failed to read backup directory: {}", e);
+        }
+    }
     Ok(())
 }