refactor: reorganize file operations and extract test modules

- Extract mover and undo functionality into dedicated modules (mover/ and undo/ subdirectories)
- Move cross-platform file operations to separate file_ops.rs module for reusability
- Extract batch and categorizer tests into separate test files (batch_test.rs, categorizer_test.rs)
- Refactor orchestrator.rs with extracted helper functions for improved readability
  - Separate cache and undo log initialization
  - Extract path resolution and offline mode determination logic
  - Simplify main organization flow by delegating to helper functions
- Update module exports to expose new types and functions (MoveError, MoveSummary, UndoError, UndoSummary)
- Reduce code duplication of move_file_cross_platform implementation

src/cli/orchestrator.rs

@@ -7,39 +7,68 @@ use crate::settings::{Config, Prompter};
 use crate::storage::{Cache, UndoLog};
 use colored::*;
 
-/// Main entry point for file organization.
+fn initialize_cache() -> Result<(Cache, std::path::PathBuf), Box<dyn std::error::Error>> {
-/// Coordinates cache, undo log, and delegates to online/offline handlers.
+    const CACHE_RETENTION_SECONDS: u64 = 7 * 24 * 60 * 60;
-pub async fn handle_organization(
-    args: Args,
-    config: Config,
-) -> Result<(), Box<dyn std::error::Error>> {
     let data_dir = Config::get_data_dir()?;
     let cache_path = data_dir.join(".noentropy_cache.json");
     let mut cache = Cache::load_or_create(&cache_path);
-
-    const CACHE_RETENTION_SECONDS: u64 = 7 * 24 * 60 * 60; // 7 days
-    const UNDO_LOG_RETENTION_SECONDS: u64 = 30 * 24 * 60 * 60; // 30 days
-
     cache.cleanup_old_entries(CACHE_RETENTION_SECONDS);
+    Ok((cache, cache_path))
+}
 
+fn initialize_undo_log() -> Result<(UndoLog, std::path::PathBuf), Box<dyn std::error::Error>> {
+    const UNDO_LOG_RETENTION_SECONDS: u64 = 30 * 24 * 60 * 60;
     let undo_log_path = Config::get_undo_log_path()?;
     let mut undo_log = UndoLog::load_or_create(&undo_log_path);
     undo_log.cleanup_old_entries(UNDO_LOG_RETENTION_SECONDS);
+    Ok((undo_log, undo_log_path))
+}
 
-    // Use custom path if provided, otherwise fall back to configured download folder
+async fn resolve_target_path(args: &Args, config: &Config) -> Option<std::path::PathBuf> {
     let target_path = args
         .path
         .as_ref()
         .cloned()
         .unwrap_or_else(|| config.download_folder.clone());
 
-    // Validate and normalize the target path early
+    match validate_and_normalize_path(&target_path).await {
-    let target_path = match validate_and_normalize_path(&target_path).await {
+        Ok(normalized) => Some(normalized),
-        Ok(normalized) => normalized,
         Err(e) => {
             println!("{}", format!("ERROR: {}", e).red());
-            return Ok(());
+            None
         }
+    }
+}
+
+async fn determine_offline_mode(args: &Args, config: &Config) -> Option<bool> {
+    if args.offline {
+        println!("{}", "Using offline mode (--offline flag).".cyan());
+        return Some(true);
+    }
+
+    let client = GeminiClient::new(&config.api_key, &config.categories);
+    match client.check_connectivity().await {
+        Ok(()) => Some(false),
+        Err(e) => {
+            if Prompter::prompt_offline_mode(&e.to_string()) {
+                Some(true)
+            } else {
+                println!("{}", "Exiting.".yellow());
+                None
+            }
+        }
+    }
+}
+
+pub async fn handle_organization(
+    args: Args,
+    config: Config,
+) -> Result<(), Box<dyn std::error::Error>> {
+    let (mut cache, cache_path) = initialize_cache()?;
+    let (mut undo_log, undo_log_path) = initialize_undo_log()?;
+
+    let Some(target_path) = resolve_target_path(&args, &config).await else {
+        return Ok(());
     };
 
     let batch = FileBatch::from_path(&target_path, args.recursive);
@@ -51,23 +80,8 @@ pub async fn handle_organization(
 
     println!("Found {} files to organize.", batch.count());
 
-    // Determine if we should use offline mode
+    let Some(use_offline) = determine_offline_mode(&args, &config).await else {
-    let use_offline = if args.offline {
-        println!("{}", "Using offline mode (--offline flag).".cyan());
-        true
-    } else {
-        let client = GeminiClient::new(&config.api_key, &config.categories);
-        match client.check_connectivity().await {
-            Ok(()) => false,
-            Err(e) => {
-                if Prompter::prompt_offline_mode(&e.to_string()) {
-                    true
-                } else {
-                    println!("{}", "Exiting.".yellow());
         return Ok(());
-                }
-            }
-        }
     };
 
     let plan = if use_offline {
@@ -84,9 +98,8 @@ pub async fn handle_organization(
         .await?
     };
 
-    // Only save if we have a plan (online mode returns None after moving)
     if plan.is_none()
-        && let Err(e) = cache.save(cache_path.as_path())
+        && let Err(e) = cache.save(&cache_path)
     {
         eprintln!("Warning: Failed to save cache: {}", e);
     }

src/files/batch.rs

@@ -42,67 +42,5 @@ impl FileBatch {
 }
 
 #[cfg(test)]
-mod tests {
+#[path = "batch_test.rs"]
-    use super::*;
+mod tests;
-    use std::fs::{self, File};
-    use std::path::Path;
-
-    #[test]
-    fn test_file_batch_from_path() {
-        let temp_dir = tempfile::tempdir().unwrap();
-        let dir_path = temp_dir.path();
-
-        File::create(dir_path.join("file1.txt")).unwrap();
-        File::create(dir_path.join("file2.rs")).unwrap();
-        fs::create_dir(dir_path.join("subdir")).unwrap();
-
-        let batch = FileBatch::from_path(dir_path, false);
-        assert_eq!(batch.count(), 2);
-        assert!(batch.filenames.contains(&"file1.txt".to_string()));
-        assert!(batch.filenames.contains(&"file2.rs".to_string()));
-    }
-
-    #[test]
-    fn test_file_batch_from_path_nonexistent() {
-        let batch = FileBatch::from_path(Path::new("/nonexistent/path"), false);
-        assert_eq!(batch.count(), 0);
-    }
-
-    #[test]
-    fn test_file_batch_from_path_non_recursive() {
-        let temp_dir = tempfile::tempdir().unwrap();
-        let dir_path = temp_dir.path();
-        File::create(dir_path.join("file1.txt")).unwrap();
-        File::create(dir_path.join("file2.rs")).unwrap();
-        fs::create_dir(dir_path.join("subdir")).unwrap();
-        File::create(dir_path.join("subdir").join("file3.txt")).unwrap();
-        let batch = FileBatch::from_path(dir_path, false);
-        assert_eq!(batch.count(), 2);
-        assert!(batch.filenames.contains(&"file1.txt".to_string()));
-        assert!(batch.filenames.contains(&"file2.rs".to_string()));
-        assert!(!batch.filenames.contains(&"subdir/file3.txt".to_string()));
-    }
-
-    #[test]
-    fn test_file_batch_from_path_recursive() {
-        let temp_dir = tempfile::tempdir().unwrap();
-        let dir_path = temp_dir.path();
-        File::create(dir_path.join("file1.txt")).unwrap();
-        fs::create_dir(dir_path.join("subdir1")).unwrap();
-        File::create(dir_path.join("subdir1").join("file2.rs")).unwrap();
-        fs::create_dir(dir_path.join("subdir1").join("nested")).unwrap();
-        File::create(dir_path.join("subdir1").join("nested").join("file3.md")).unwrap();
-        fs::create_dir(dir_path.join("subdir2")).unwrap();
-        File::create(dir_path.join("subdir2").join("file4.py")).unwrap();
-        let batch = FileBatch::from_path(dir_path, true);
-        assert_eq!(batch.count(), 4);
-        assert!(batch.filenames.contains(&"file1.txt".to_string()));
-        assert!(batch.filenames.contains(&"subdir1/file2.rs".to_string()));
-        assert!(
-            batch
-                .filenames
-                .contains(&"subdir1/nested/file3.md".to_string())
-        );
-        assert!(batch.filenames.contains(&"subdir2/file4.py".to_string()));
-    }
-}

src/files/batch_test.rs

@@ -0,0 +1,62 @@
+use super::*;
+use std::fs::{self, File};
+use std::path::Path;
+
+#[test]
+fn test_file_batch_from_path() {
+    let temp_dir = tempfile::tempdir().unwrap();
+    let dir_path = temp_dir.path();
+
+    File::create(dir_path.join("file1.txt")).unwrap();
+    File::create(dir_path.join("file2.rs")).unwrap();
+    fs::create_dir(dir_path.join("subdir")).unwrap();
+
+    let batch = FileBatch::from_path(dir_path, false);
+    assert_eq!(batch.count(), 2);
+    assert!(batch.filenames.contains(&"file1.txt".to_string()));
+    assert!(batch.filenames.contains(&"file2.rs".to_string()));
+}
+
+#[test]
+fn test_file_batch_from_path_nonexistent() {
+    let batch = FileBatch::from_path(Path::new("/nonexistent/path"), false);
+    assert_eq!(batch.count(), 0);
+}
+
+#[test]
+fn test_file_batch_from_path_non_recursive() {
+    let temp_dir = tempfile::tempdir().unwrap();
+    let dir_path = temp_dir.path();
+    File::create(dir_path.join("file1.txt")).unwrap();
+    File::create(dir_path.join("file2.rs")).unwrap();
+    fs::create_dir(dir_path.join("subdir")).unwrap();
+    File::create(dir_path.join("subdir").join("file3.txt")).unwrap();
+    let batch = FileBatch::from_path(dir_path, false);
+    assert_eq!(batch.count(), 2);
+    assert!(batch.filenames.contains(&"file1.txt".to_string()));
+    assert!(batch.filenames.contains(&"file2.rs".to_string()));
+    assert!(!batch.filenames.contains(&"subdir/file3.txt".to_string()));
+}
+
+#[test]
+fn test_file_batch_from_path_recursive() {
+    let temp_dir = tempfile::tempdir().unwrap();
+    let dir_path = temp_dir.path();
+    File::create(dir_path.join("file1.txt")).unwrap();
+    fs::create_dir(dir_path.join("subdir1")).unwrap();
+    File::create(dir_path.join("subdir1").join("file2.rs")).unwrap();
+    fs::create_dir(dir_path.join("subdir1").join("nested")).unwrap();
+    File::create(dir_path.join("subdir1").join("nested").join("file3.md")).unwrap();
+    fs::create_dir(dir_path.join("subdir2")).unwrap();
+    File::create(dir_path.join("subdir2").join("file4.py")).unwrap();
+    let batch = FileBatch::from_path(dir_path, true);
+    assert_eq!(batch.count(), 4);
+    assert!(batch.filenames.contains(&"file1.txt".to_string()));
+    assert!(batch.filenames.contains(&"subdir1/file2.rs".to_string()));
+    assert!(
+        batch
+            .filenames
+            .contains(&"subdir1/nested/file3.md".to_string())
+    );
+    assert!(batch.filenames.contains(&"subdir2/file4.py".to_string()));
+}

src/files/categorizer.rs

@@ -146,52 +146,5 @@ pub fn categorize_files_offline(filenames: Vec<String>) -> OfflineCategorization
 }
 
 #[cfg(test)]
-mod tests {
+#[path = "categorizer_test.rs"]
-    use super::*;
+mod tests;
-
-    #[test]
-    fn test_categorize_known_extensions() {
-        assert_eq!(categorize_by_extension("photo.jpg"), Some("Images"));
-        assert_eq!(categorize_by_extension("document.pdf"), Some("Documents"));
-        assert_eq!(categorize_by_extension("setup.exe"), Some("Installers"));
-        assert_eq!(categorize_by_extension("song.mp3"), Some("Music"));
-        assert_eq!(categorize_by_extension("movie.mp4"), Some("Video"));
-        assert_eq!(categorize_by_extension("archive.zip"), Some("Archives"));
-        assert_eq!(categorize_by_extension("main.rs"), Some("Code"));
-    }
-
-    #[test]
-    fn test_categorize_case_insensitive() {
-        assert_eq!(categorize_by_extension("PHOTO.JPG"), Some("Images"));
-        assert_eq!(categorize_by_extension("Photo.Png"), Some("Images"));
-    }
-
-    #[test]
-    fn test_categorize_unknown_extension() {
-        assert_eq!(categorize_by_extension("file.xyz"), None);
-        assert_eq!(categorize_by_extension("file.unknown"), None);
-    }
-
-    #[test]
-    fn test_categorize_no_extension() {
-        assert_eq!(categorize_by_extension("README"), None);
-        assert_eq!(categorize_by_extension("Makefile"), None);
-    }
-
-    #[test]
-    fn test_categorize_files_offline() {
-        let filenames = vec![
-            "photo.jpg".to_string(),
-            "doc.pdf".to_string(),
-            "unknown".to_string(),
-            "file.xyz".to_string(),
-        ];
-
-        let result = categorize_files_offline(filenames);
-
-        assert_eq!(result.plan.files.len(), 2);
-        assert_eq!(result.skipped.len(), 2);
-        assert!(result.skipped.contains(&"unknown".to_string()));
-        assert!(result.skipped.contains(&"file.xyz".to_string()));
-    }
-}

src/files/categorizer_test.rs

@@ -0,0 +1,47 @@
+use super::*;
+
+#[test]
+fn test_categorize_known_extensions() {
+    assert_eq!(categorize_by_extension("photo.jpg"), Some("Images"));
+    assert_eq!(categorize_by_extension("document.pdf"), Some("Documents"));
+    assert_eq!(categorize_by_extension("setup.exe"), Some("Installers"));
+    assert_eq!(categorize_by_extension("song.mp3"), Some("Music"));
+    assert_eq!(categorize_by_extension("movie.mp4"), Some("Video"));
+    assert_eq!(categorize_by_extension("archive.zip"), Some("Archives"));
+    assert_eq!(categorize_by_extension("main.rs"), Some("Code"));
+}
+
+#[test]
+fn test_categorize_case_insensitive() {
+    assert_eq!(categorize_by_extension("PHOTO.JPG"), Some("Images"));
+    assert_eq!(categorize_by_extension("Photo.Png"), Some("Images"));
+}
+
+#[test]
+fn test_categorize_unknown_extension() {
+    assert_eq!(categorize_by_extension("file.xyz"), None);
+    assert_eq!(categorize_by_extension("file.unknown"), None);
+}
+
+#[test]
+fn test_categorize_no_extension() {
+    assert_eq!(categorize_by_extension("README"), None);
+    assert_eq!(categorize_by_extension("Makefile"), None);
+}
+
+#[test]
+fn test_categorize_files_offline() {
+    let filenames = vec![
+        "photo.jpg".to_string(),
+        "doc.pdf".to_string(),
+        "unknown".to_string(),
+        "file.xyz".to_string(),
+    ];
+
+    let result = categorize_files_offline(filenames);
+
+    assert_eq!(result.plan.files.len(), 2);
+    assert_eq!(result.skipped.len(), 2);
+    assert!(result.skipped.contains(&"unknown".to_string()));
+    assert!(result.skipped.contains(&"file.xyz".to_string()));
+}

src/files/file_ops.rs

@@ -0,0 +1,16 @@
+use std::{fs, io, path::Path};
+
+pub fn move_file_cross_platform(source: &Path, target: &Path) -> io::Result<()> {
+    match fs::rename(source, target) {
+        Ok(()) => Ok(()),
+        Err(e) => {
+            if cfg!(windows) || e.kind() == io::ErrorKind::CrossesDevices {
+                fs::copy(source, target)?;
+                fs::remove_file(source)?;
+                Ok(())
+            } else {
+                Err(e)
+            }
+        }
+    }
+}

src/files/mod.rs

@@ -1,14 +1,16 @@
 pub mod batch;
 pub mod categorizer;
 pub mod detector;
+mod file_ops;
 pub mod mover;
 pub mod undo;
 
 pub use batch::FileBatch;
 pub use categorizer::{OfflineCategorizationResult, categorize_files_offline};
 pub use detector::{is_text_file, read_file_sample};
-pub use mover::execute_move;
+pub use file_ops::move_file_cross_platform;
-pub use undo::undo_moves;
+pub use mover::{MoveError, MoveSummary, execute_move, execute_move_auto};
+pub use undo::{UndoError, UndoSummary, undo_moves, undo_moves_auto};
 
 #[cfg(test)]
 mod tests {

src/files/mover.rs

@@ -1,154 +0,0 @@
-use crate::models::OrganizationPlan;
-use crate::storage::UndoLog;
-use colored::*;
-use std::io;
-use std::path::MAIN_SEPARATOR;
-use std::{ffi::OsStr, fs, path::Path};
-
-pub fn execute_move(base_path: &Path, plan: OrganizationPlan, mut undo_log: Option<&mut UndoLog>) {
-    println!("\n{}", "--- EXECUTION PLAN ---".bold().underline());
-
-    if plan.files.is_empty() {
-        println!("{}", "No files to organize.".yellow());
-        return;
-    }
-
-    for item in &plan.files {
-        let mut target_display = format!("{}", item.category.green());
-        if !item.sub_category.is_empty() {
-            target_display = format!(
-                "{}{}{}",
-                target_display,
-                MAIN_SEPARATOR,
-                item.sub_category.blue()
-            );
-        }
-
-        println!(
-            "Plan: {} -> {}{}",
-            item.filename, target_display, MAIN_SEPARATOR
-        );
-    }
-
-    eprint!("\nDo you want to apply these changes? [y/N]: ");
-
-    let mut input = String::new();
-    if io::stdin().read_line(&mut input).is_err() {
-        eprintln!("\n{}", "Failed to read input. Operation cancelled.".red());
-        return;
-    }
-
-    let input = input.trim().to_lowercase();
-
-    if input != "y" && input != "yes" {
-        println!("\n{}", "Operation cancelled.".red());
-        return;
-    }
-
-    println!("\n{}", "--- MOVING FILES ---".bold().underline());
-
-    let mut moved_count = 0;
-    let mut error_count = 0;
-
-    for item in plan.files {
-        let source = base_path.join(&item.filename);
-
-        let mut final_path = base_path.join(&item.category);
-
-        if !item.sub_category.is_empty() {
-            final_path = final_path.join(&item.sub_category);
-        }
-
-        let file_name = Path::new(&item.filename)
-            .file_name()
-            .unwrap_or_else(|| OsStr::new(&item.filename))
-            .to_string_lossy()
-            .into_owned();
-
-        let target = final_path.join(&file_name);
-
-        if let Err(e) = fs::create_dir_all(&final_path) {
-            eprintln!(
-                "{} Failed to create dir {:?}: {}",
-                "ERROR:".red(),
-                final_path,
-                e
-            );
-            error_count += 1;
-            continue;
-        }
-
-        if let Ok(metadata) = fs::metadata(&source) {
-            if metadata.is_file() {
-                match move_file_cross_platform(&source, &target) {
-                    Ok(_) => {
-                        if item.sub_category.is_empty() {
-                            println!(
-                                "Moved: {} -> {}{}",
-                                item.filename,
-                                item.category.green(),
-                                MAIN_SEPARATOR
-                            );
-                        } else {
-                            println!(
-                                "Moved: {} -> {}{}{}",
-                                item.filename,
-                                item.category.green(),
-                                MAIN_SEPARATOR,
-                                item.sub_category.blue()
-                            );
-                        }
-                        moved_count += 1;
-
-                        if let Some(ref mut log) = undo_log {
-                            log.record_move(source, target);
-                        }
-                    }
-                    Err(e) => {
-                        eprintln!("{} Failed to move {}: {}", "ERROR:".red(), item.filename, e);
-                        error_count += 1;
-
-                        if let Some(ref mut log) = undo_log {
-                            log.record_failed_move(source, target);
-                        }
-                    }
-                }
-            } else {
-                eprintln!(
-                    "{} Skipping {}: Not a file",
-                    "WARN:".yellow(),
-                    item.filename
-                );
-            }
-        } else {
-            eprintln!(
-                "{} Skipping {}: File not found",
-                "WARN:".yellow(),
-                item.filename
-            );
-            error_count += 1;
-        }
-    }
-
-    println!("\n{}", "Organization Complete!".bold().green());
-    println!(
-        "Files moved: {}, Errors: {}",
-        moved_count.to_string().green(),
-        error_count.to_string().red()
-    );
-}
-
-fn move_file_cross_platform(source: &Path, target: &Path) -> io::Result<()> {
-    match fs::rename(source, target) {
-        Ok(()) => Ok(()),
-        Err(e) => {
-            if cfg!(windows) || e.kind() == io::ErrorKind::CrossesDevices {
-                fs::copy(source, target)?;
-                fs::remove_file(source)?;
-                Ok(())
-            } else {
-                Err(e)
-            }
-        }
-    }
-}

src/files/mover/confirmation.rs

@@ -0,0 +1,36 @@
+use super::types::MoveError;
+use std::io;
+
+pub trait ConfirmationStrategy {
+    fn confirm(&self) -> Result<bool, MoveError>;
+}
+
+pub struct StdinConfirmation;
+
+impl ConfirmationStrategy for StdinConfirmation {
+    fn confirm(&self) -> Result<bool, MoveError> {
+        eprint!("\nDo you want to apply these changes? [y/N]: ");
+
+        let mut input = String::new();
+        if io::stdin().read_line(&mut input).is_err() {
+            return Err(MoveError::InputReadFailed(
+                "Failed to read input. Operation cancelled.".to_string(),
+            ));
+        }
+
+        let input = input.trim().to_lowercase();
+        if input != "y" && input != "yes" {
+            return Err(MoveError::UserCancelled);
+        }
+
+        Ok(true)
+    }
+}
+
+pub struct AutoConfirm;
+
+impl ConfirmationStrategy for AutoConfirm {
+    fn confirm(&self) -> Result<bool, MoveError> {
+        Ok(true)
+    }
+}

src/files/mover/display.rs

@@ -0,0 +1,43 @@
+use crate::models::FileCategory;
+use colored::*;
+use std::path::MAIN_SEPARATOR;
+
+pub(super) fn display_plan(files: &[FileCategory]) {
+    println!("\n{}", "--- EXECUTION PLAN ---".bold().underline());
+
+    if files.is_empty() {
+        println!("{}", "No files to organize.".yellow());
+        return;
+    }
+
+    for item in files {
+        let target_display = format_target_path(&item.category, &item.sub_category);
+        println!(
+            "Plan: {} -> {}{}",
+            item.filename, target_display, MAIN_SEPARATOR
+        );
+    }
+}
+
+pub(super) fn print_summary(summary: &super::types::MoveSummary) {
+    println!("\n{}", "Organization Complete!".bold().green());
+    println!(
+        "Files moved: {}, Errors: {}",
+        summary.moved_count().to_string().green(),
+        summary.error_count().to_string().red()
+    );
+}
+
+pub(super) fn format_target_path(category: &str, sub_category: &str) -> String {
+    let target_display = format!("{}", category.green());
+    if sub_category.is_empty() {
+        target_display
+    } else {
+        format!(
+            "{}{}{}",
+            target_display,
+            MAIN_SEPARATOR,
+            sub_category.blue()
+        )
+    }
+}

src/files/mover/execution.rs

@@ -0,0 +1,91 @@
+use super::confirmation::ConfirmationStrategy;
+use super::display::{display_plan, format_target_path};
+use super::paths::{build_target_path, ensure_directory_exists};
+use super::types::{MoveError, MoveSummary};
+use crate::files::move_file_cross_platform;
+use crate::models::OrganizationPlan;
+use crate::storage::UndoLog;
+use colored::*;
+use std::fs;
+use std::path::{MAIN_SEPARATOR, Path};
+
+pub fn execute_move_with_strategy<C: ConfirmationStrategy>(
+    base_path: &Path,
+    plan: OrganizationPlan,
+    mut undo_log: Option<&mut UndoLog>,
+    confirmation: &C,
+) -> Result<MoveSummary, MoveError> {
+    if plan.files.is_empty() {
+        println!("{}", "No files to organize.".yellow());
+        return Ok(MoveSummary::new());
+    }
+
+    display_plan(&plan.files);
+
+    confirmation.confirm()?;
+
+    println!("\n{}", "--- MOVING FILES ---".bold().underline());
+
+    let mut summary = MoveSummary::new();
+
+    for item in plan.files {
+        let source = base_path.join(&item.filename);
+        let final_path = base_path.join(&item.category);
+        let target = build_target_path(
+            base_path,
+            &item.category,
+            &item.sub_category,
+            &item.filename,
+        );
+
+        if let Err(e) = ensure_directory_exists(&final_path) {
+            eprintln!("{} {}", "ERROR:".red(), e);
+            summary.errored();
+            continue;
+        }
+
+        match fs::metadata(&source) {
+            Ok(metadata) if metadata.is_file() => {
+                match move_file_cross_platform(&source, &target) {
+                    Ok(_) => {
+                        let target_display = format_target_path(&item.category, &item.sub_category);
+                        println!(
+                            "Moved: {} -> {}{}",
+                            item.filename, target_display, MAIN_SEPARATOR
+                        );
+                        summary.moved();
+
+                        if let Some(ref mut log) = undo_log {
+                            log.record_move(source, target);
+                        }
+                    }
+                    Err(e) => {
+                        eprintln!("{} Failed to move {}: {}", "ERROR:".red(), item.filename, e);
+                        summary.errored();
+
+                        if let Some(ref mut log) = undo_log {
+                            log.record_failed_move(source, target);
+                        }
+                    }
+                }
+            }
+            Ok(_) => {
+                eprintln!(
+                    "{} Skipping {}: Not a file",
+                    "WARN:".yellow(),
+                    item.filename
+                );
+            }
+            Err(_) => {
+                eprintln!(
+                    "{} Skipping {}: File not found",
+                    "WARN:".yellow(),
+                    item.filename
+                );
+                summary.errored();
+            }
+        }
+    }
+
+    Ok(summary)
+}

src/files/mover/mod.rs

@@ -0,0 +1,38 @@
+use crate::models::OrganizationPlan;
+use crate::storage::UndoLog;
+use colored::*;
+use std::path::Path;
+
+mod confirmation;
+mod display;
+mod execution;
+mod paths;
+mod types;
+
+use confirmation::{AutoConfirm, StdinConfirmation};
+use display::print_summary;
+
+pub use types::{MoveError, MoveSummary};
+
+pub fn execute_move(base_path: &Path, plan: OrganizationPlan, undo_log: Option<&mut UndoLog>) {
+    let confirmation = StdinConfirmation;
+    match execution::execute_move_with_strategy(base_path, plan, undo_log, &confirmation) {
+        Ok(summary) => print_summary(&summary),
+        Err(e) => {
+            if matches!(e, MoveError::UserCancelled) {
+                println!("\n{}", "Operation cancelled.".red());
+            } else {
+                eprintln!("\n{}", format!("{}", e).red());
+            }
+        }
+    }
+}
+
+pub fn execute_move_auto(
+    base_path: &Path,
+    plan: OrganizationPlan,
+    undo_log: Option<&mut UndoLog>,
+) -> Result<MoveSummary, MoveError> {
+    let confirmation = AutoConfirm;
+    execution::execute_move_with_strategy(base_path, plan, undo_log, &confirmation)
+}

src/files/mover/paths.rs

@@ -0,0 +1,30 @@
+use super::types::MoveError;
+use std::{
+    ffi::OsStr,
+    fs,
+    path::{Path, PathBuf},
+};
+
+pub fn build_target_path(
+    base_path: &Path,
+    category: &str,
+    sub_category: &str,
+    filename: &str,
+) -> PathBuf {
+    let mut final_path = base_path.join(category);
+    if !sub_category.is_empty() {
+        final_path = final_path.join(sub_category);
+    }
+
+    let file_name = Path::new(filename)
+        .file_name()
+        .unwrap_or_else(|| OsStr::new(filename))
+        .to_string_lossy()
+        .into_owned();
+
+    final_path.join(&file_name)
+}
+
+pub fn ensure_directory_exists(path: &Path) -> Result<(), MoveError> {
+    fs::create_dir_all(path).map_err(|e| MoveError::DirectoryCreationFailed(path.to_path_buf(), e))
+}

src/files/mover/types.rs

@@ -0,0 +1,62 @@
+use std::path::PathBuf;
+
+#[derive(Debug, Clone, Default)]
+pub struct MoveSummary {
+    moved_count: usize,
+    error_count: usize,
+}
+
+impl MoveSummary {
+    pub fn new() -> Self {
+        Self::default()
+    }
+
+    pub fn moved(&mut self) {
+        self.moved_count += 1;
+    }
+
+    pub fn errored(&mut self) {
+        self.error_count += 1;
+    }
+
+    pub fn moved_count(&self) -> usize {
+        self.moved_count
+    }
+
+    pub fn error_count(&self) -> usize {
+        self.error_count
+    }
+
+    pub fn has_errors(&self) -> bool {
+        self.error_count > 0
+    }
+
+    pub fn total_processed(&self) -> usize {
+        self.moved_count + self.error_count
+    }
+}
+
+#[derive(Debug)]
+pub enum MoveError {
+    InputReadFailed(String),
+    UserCancelled,
+    DirectoryCreationFailed(PathBuf, std::io::Error),
+    FileMoveFailed(PathBuf, PathBuf, std::io::Error),
+}
+
+impl std::fmt::Display for MoveError {
+    fn fmt(&self, f: &mut std::fmt::Formatter<'_>) -> std::fmt::Result {
+        match self {
+            MoveError::InputReadFailed(msg) => write!(f, "Failed to read input: {}", msg),
+            MoveError::UserCancelled => write!(f, "Operation cancelled by user"),
+            MoveError::DirectoryCreationFailed(path, err) => {
+                write!(f, "Failed to create directory {:?}: {}", path, err)
+            }
+            MoveError::FileMoveFailed(source, target, err) => {
+                write!(f, "Failed to move {:?} to {:?}: {}", source, target, err)
+            }
+        }
+    }
+}
+
+impl std::error::Error for MoveError {}

src/files/undo.rs

@@ -1,166 +0,0 @@
-use crate::storage::UndoLog;
-use colored::*;
-use std::fs;
-use std::io;
-use std::path::Path;
-
-pub fn undo_moves(
-    base_path: &Path,
-    undo_log: &mut UndoLog,
-    dry_run: bool,
-) -> Result<(usize, usize, usize), Box<dyn std::error::Error>> {
-    let completed_moves: Vec<_> = undo_log
-        .get_completed_moves()
-        .into_iter()
-        .cloned()
-        .collect();
-
-    if completed_moves.is_empty() {
-        println!("{}", "No completed moves to undo.".yellow());
-        return Ok((0, 0, 0));
-    }
-
-    println!("\n{}", "--- UNDO PREVIEW ---".bold().underline());
-    println!(
-        "{} will restore {} files:",
-        "INFO:".cyan(),
-        completed_moves.len()
-    );
-
-    for record in &completed_moves {
-        if let Ok(rel_dest) = record.destination_path.strip_prefix(base_path) {
-            if let Ok(rel_source) = record.source_path.strip_prefix(base_path) {
-                println!(
-                    "  {} -> {}",
-                    rel_dest.display().to_string().red(),
-                    rel_source.display().to_string().green()
-                );
-            } else {
-                println!(
-                    "  {} -> {}",
-                    record.destination_path.display(),
-                    record.source_path.display()
-                );
-            }
-        }
-    }
-
-    if dry_run {
-        println!("\n{}", "Dry run mode - skipping undo operation.".cyan());
-        return Ok((completed_moves.len(), 0, 0));
-    }
-
-    eprint!("\nDo you want to undo these changes? [y/N]: ");
-
-    let mut input = String::new();
-    if io::stdin().read_line(&mut input).is_err() {
-        eprintln!("\n{}", "Failed to read input. Undo cancelled.".red());
-        return Ok((0, 0, 0));
-    }
-
-    let input = input.trim().to_lowercase();
-
-    if input != "y" && input != "yes" {
-        println!("\n{}", "Undo cancelled.".red());
-        return Ok((0, 0, 0));
-    }
-
-    println!("\n{}", "--- UNDOING MOVES ---".bold().underline());
-
-    let mut restored_count = 0;
-    let mut skipped_count = 0;
-    let mut failed_count = 0;
-
-    for record in completed_moves {
-        let source = &record.source_path;
-        let destination = &record.destination_path;
-
-        if !destination.exists() {
-            eprintln!(
-                "{} File not found at destination: {}",
-                "WARN:".yellow(),
-                destination.display()
-            );
-            failed_count += 1;
-            continue;
-        }
-
-        if source.exists() {
-            eprintln!(
-                "{} Skipping {} - source already exists",
-                "WARN:".yellow(),
-                source.display()
-            );
-            skipped_count += 1;
-            continue;
-        }
-
-        match move_file_cross_platform(destination, source) {
-            Ok(_) => {
-                println!(
-                    "Restored: {} -> {}",
-                    destination.display().to_string().red(),
-                    source.display().to_string().green()
-                );
-                restored_count += 1;
-                undo_log.mark_as_undone(destination);
-            }
-            Err(e) => {
-                eprintln!(
-                    "{} Failed to restore {}: {}",
-                    "ERROR:".red(),
-                    source.display(),
-                    e
-                );
-                failed_count += 1;
-            }
-        }
-    }
-
-    cleanup_empty_directories(base_path, undo_log)?;
-
-    println!("\n{}", "UNDO COMPLETE!".bold().green());
-    println!(
-        "Files restored: {}, Skipped: {}, Failed: {}",
-        restored_count.to_string().green(),
-        skipped_count.to_string().yellow(),
-        failed_count.to_string().red()
-    );
-
-    Ok((restored_count, skipped_count, failed_count))
-}
-
-fn cleanup_empty_directories(
-    base_path: &Path,
-    undo_log: &mut UndoLog,
-) -> Result<(), Box<dyn std::error::Error>> {
-    let directory_usage = undo_log.get_directory_usage(base_path);
-
-    for dir_path in directory_usage.keys() {
-        let full_path = base_path.join(dir_path);
-        if full_path.is_dir()
-            && let Ok(mut entries) = fs::read_dir(&full_path)
-            && entries.next().is_none()
-            && fs::remove_dir(&full_path).is_ok()
-        {
-            println!("{} Removed empty directory: {}", "INFO:".cyan(), dir_path);
-        }
-    }
-
-    Ok(())
-}
-
-fn move_file_cross_platform(source: &Path, target: &Path) -> io::Result<()> {
-    match fs::rename(source, target) {
-        Ok(()) => Ok(()),
-        Err(e) => {
-            if cfg!(windows) || e.kind() == io::ErrorKind::CrossesDevices {
-                fs::copy(source, target)?;
-                fs::remove_file(source)?;
-                Ok(())
-            } else {
-                Err(e)
-            }
-        }
-    }
-}

src/files/undo/cleanup.rs

@@ -0,0 +1,24 @@
+use crate::storage::UndoLog;
+use colored::*;
+use std::fs;
+use std::path::Path;
+
+pub(super) fn cleanup_empty_directories(
+    base_path: &Path,
+    undo_log: &mut UndoLog,
+) -> Result<(), Box<dyn std::error::Error>> {
+    let directory_usage = undo_log.get_directory_usage(base_path);
+
+    for dir_path in directory_usage.keys() {
+        let full_path = base_path.join(dir_path);
+        if full_path.is_dir()
+            && let Ok(mut entries) = fs::read_dir(&full_path)
+            && entries.next().is_none()
+            && fs::remove_dir(&full_path).is_ok()
+        {
+            println!("{} Removed empty directory: {}", "INFO:".cyan(), dir_path);
+        }
+    }
+
+    Ok(())
+}

src/files/undo/confirmation.rs

@@ -0,0 +1,36 @@
+use super::types::UndoError;
+use std::io;
+
+pub trait ConfirmationStrategy {
+    fn confirm(&self) -> Result<bool, UndoError>;
+}
+
+pub struct StdinConfirmation;
+
+impl ConfirmationStrategy for StdinConfirmation {
+    fn confirm(&self) -> Result<bool, UndoError> {
+        eprint!("\nDo you want to undo these changes? [y/N]: ");
+
+        let mut input = String::new();
+        if io::stdin().read_line(&mut input).is_err() {
+            return Err(UndoError::InputReadFailed(
+                "Failed to read input. Undo cancelled.".to_string(),
+            ));
+        }
+
+        let input = input.trim().to_lowercase();
+        if input != "y" && input != "yes" {
+            return Err(UndoError::UserCancelled);
+        }
+
+        Ok(true)
+    }
+}
+
+pub struct AutoConfirm;
+
+impl ConfirmationStrategy for AutoConfirm {
+    fn confirm(&self) -> Result<bool, UndoError> {
+        Ok(true)
+    }
+}

src/files/undo/display.rs

@@ -0,0 +1,36 @@
+use crate::models::FileMoveRecord;
+use colored::*;
+use std::path::Path;
+
+pub(super) fn display_undo_preview(records: &[FileMoveRecord], base_path: &Path) {
+    println!("\n{}", "--- UNDO PREVIEW ---".bold().underline());
+    println!("{} will restore {} files:", "INFO:".cyan(), records.len());
+
+    for record in records {
+        if let Ok(rel_dest) = record.destination_path.strip_prefix(base_path) {
+            if let Ok(rel_source) = record.source_path.strip_prefix(base_path) {
+                println!(
+                    "  {} -> {}",
+                    rel_dest.display().to_string().red(),
+                    rel_source.display().to_string().green()
+                );
+            } else {
+                println!(
+                    "  {} -> {}",
+                    record.destination_path.display(),
+                    record.source_path.display()
+                );
+            }
+        }
+    }
+}
+
+pub(super) fn print_undo_summary(summary: &super::types::UndoSummary) {
+    println!("\n{}", "UNDO COMPLETE!".bold().green());
+    println!(
+        "Files restored: {}, Skipped: {}, Failed: {}",
+        summary.restored_count().to_string().green(),
+        summary.skipped_count().to_string().yellow(),
+        summary.failed_count().to_string().red()
+    );
+}

src/files/undo/execution.rs

@@ -0,0 +1,91 @@
+use super::cleanup::cleanup_empty_directories;
+use super::confirmation::ConfirmationStrategy;
+use super::display::display_undo_preview;
+use super::types::{UndoError, UndoSummary};
+use crate::files::move_file_cross_platform;
+use crate::storage::UndoLog;
+use colored::*;
+use std::path::Path;
+
+pub fn undo_with_strategy<C: ConfirmationStrategy>(
+    base_path: &Path,
+    undo_log: &mut UndoLog,
+    confirmation: &C,
+    dry_run: bool,
+) -> Result<UndoSummary, UndoError> {
+    let completed_moves: Vec<_> = undo_log
+        .get_completed_moves()
+        .into_iter()
+        .cloned()
+        .collect();
+
+    if completed_moves.is_empty() {
+        println!("{}", "No completed moves to undo.".yellow());
+        return Ok(UndoSummary::new());
+    }
+
+    display_undo_preview(&completed_moves, base_path);
+
+    if dry_run {
+        println!("\n{}", "Dry run mode - skipping undo operation.".cyan());
+        return Ok(UndoSummary::new());
+    }
+
+    confirmation.confirm()?;
+
+    println!("\n{}", "--- UNDOING MOVES ---".bold().underline());
+
+    let mut summary = UndoSummary::new();
+
+    for record in completed_moves {
+        let source = &record.source_path;
+        let destination = &record.destination_path;
+
+        if !destination.exists() {
+            eprintln!(
+                "{} File not found at destination: {}",
+                "WARN:".yellow(),
+                destination.display()
+            );
+            summary.failed();
+            continue;
+        }
+
+        if source.exists() {
+            eprintln!(
+                "{} Skipping {} - source already exists",
+                "WARN:".yellow(),
+                source.display()
+            );
+            summary.skipped();
+            continue;
+        }
+
+        match move_file_cross_platform(destination, source) {
+            Ok(_) => {
+                println!(
+                    "Restored: {} -> {}",
+                    destination.display().to_string().red(),
+                    source.display().to_string().green()
+                );
+                summary.restored();
+                undo_log.mark_as_undone(destination);
+            }
+            Err(e) => {
+                eprintln!(
+                    "{} Failed to restore {}: {}",
+                    "ERROR:".red(),
+                    source.display(),
+                    e
+                );
+                summary.failed();
+            }
+        }
+    }
+
+    if let Err(e) = cleanup_empty_directories(base_path, undo_log) {
+        eprintln!("{} Failed to cleanup directories: {}", "WARN:".yellow(), e);
+    }
+
+    Ok(summary)
+}

src/files/undo/mod.rs

@@ -0,0 +1,51 @@
+use crate::storage::UndoLog;
+use colored::*;
+use std::path::Path;
+
+mod cleanup;
+mod confirmation;
+mod display;
+mod execution;
+mod types;
+
+use confirmation::{AutoConfirm, StdinConfirmation};
+use display::print_undo_summary;
+
+pub use types::{UndoError, UndoSummary};
+
+pub fn undo_moves(
+    base_path: &Path,
+    undo_log: &mut UndoLog,
+    dry_run: bool,
+) -> Result<(usize, usize, usize), Box<dyn std::error::Error>> {
+    let confirmation = StdinConfirmation;
+    match execution::undo_with_strategy(base_path, undo_log, &confirmation, dry_run) {
+        Ok(summary) => {
+            if !dry_run {
+                print_undo_summary(&summary);
+            }
+            Ok((
+                summary.restored_count(),
+                summary.skipped_count(),
+                summary.failed_count(),
+            ))
+        }
+        Err(e) => {
+            if matches!(e, UndoError::UserCancelled) {
+                println!("\n{}", "Undo cancelled.".red());
+            } else {
+                eprintln!("\n{}", format!("{}", e).red());
+            }
+            Ok((0, 0, 0))
+        }
+    }
+}
+
+pub fn undo_moves_auto(
+    base_path: &Path,
+    undo_log: &mut UndoLog,
+    dry_run: bool,
+) -> Result<UndoSummary, UndoError> {
+    let confirmation = AutoConfirm;
+    execution::undo_with_strategy(base_path, undo_log, &confirmation, dry_run)
+}

src/files/undo/types.rs

@@ -0,0 +1,67 @@
+use std::fmt;
+
+#[derive(Debug, Clone, Default)]
+pub struct UndoSummary {
+    restored_count: usize,
+    skipped_count: usize,
+    failed_count: usize,
+}
+
+impl UndoSummary {
+    pub fn new() -> Self {
+        Self::default()
+    }
+
+    pub fn restored(&mut self) {
+        self.restored_count += 1;
+    }
+
+    pub fn skipped(&mut self) {
+        self.skipped_count += 1;
+    }
+
+    pub fn failed(&mut self) {
+        self.failed_count += 1;
+    }
+
+    pub fn restored_count(&self) -> usize {
+        self.restored_count
+    }
+
+    pub fn skipped_count(&self) -> usize {
+        self.skipped_count
+    }
+
+    pub fn failed_count(&self) -> usize {
+        self.failed_count
+    }
+
+    pub fn total_processed(&self) -> usize {
+        self.restored_count + self.skipped_count + self.failed_count
+    }
+
+    pub fn has_failures(&self) -> bool {
+        self.failed_count > 0
+    }
+}
+
+#[derive(Debug)]
+pub enum UndoError {
+    InputReadFailed(String),
+    UserCancelled,
+    FileRestoreFailed(String, String, std::io::Error),
+}
+
+impl fmt::Display for UndoError {
+    fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
+        match self {
+            UndoError::InputReadFailed(msg) => write!(f, "Failed to read input: {}", msg),
+            UndoError::UserCancelled => write!(f, "Undo cancelled by user"),
+            UndoError::FileRestoreFailed(dest, src, err) => {
+                write!(f, "Failed to restore from {} to {}: {}", dest, src, err)
+            }
+        }
+    }
+}
+
+impl std::error::Error for UndoError {}

src/lib.rs

@@ -6,7 +6,10 @@ pub mod settings;
 pub mod storage;
 
 pub use cli::Args;
-pub use files::{FileBatch, execute_move, is_text_file, read_file_sample, undo_moves};
+pub use files::{
+    FileBatch, MoveError, MoveSummary, execute_move, execute_move_auto, is_text_file,
+    read_file_sample, undo_moves,
+};
 pub use gemini::GeminiClient;
 pub use gemini::GeminiError;
 pub use models::{FileCategory, FileMoveRecord, MoveStatus, OrganizationPlan};