diff --git a/src-tauri/src/commands.rs b/src-tauri/src/commands.rs
index 2b3ce85..beeae08 100644
--- a/src-tauri/src/commands.rs
+++ b/src-tauri/src/commands.rs
@@ -1,3 +1,4 @@
+use std::path::PathBuf;
 use tauri::{AppHandle, State};
 use tauri_plugin_http::reqwest;
 use tauri_plugin_store::StoreExt;
@@ -6,6 +7,7 @@ use crate::achievements::{get_achievement_info, load_achievements, AchievementUn
 use crate::bridge_manager::SharedBridgeManager;
 use crate::config::{ClaudeStartOptions, HikariConfig};
 use crate::stats::UsageStats;
+use crate::temp_manager::SharedTempFileManager;
 
 const CONFIG_STORE_KEY: &str = "config";
 
@@ -298,3 +300,76 @@ pub async fn check_for_updates() -> Result<UpdateInfo, String> {
         release_notes: latest.body.clone(),
     })
 }
+
+#[derive(Debug, Clone, serde::Serialize)]
+pub struct SavedFileInfo {
+    pub path: String,
+    pub filename: String,
+}
+
+#[tauri::command]
+pub async fn save_temp_file(
+    temp_manager: State<'_, SharedTempFileManager>,
+    conversation_id: String,
+    data: Vec<u8>,
+    filename: Option<String>,
+) -> Result<SavedFileInfo, String> {
+    let mut manager = temp_manager.lock();
+    let path = manager.save_file(&conversation_id, &data, filename.as_deref())?;
+
+    let filename = path
+        .file_name()
+        .map(|n| n.to_string_lossy().to_string())
+        .unwrap_or_else(|| "unknown".to_string());
+
+    Ok(SavedFileInfo {
+        path: path.to_string_lossy().to_string(),
+        filename,
+    })
+}
+
+#[tauri::command]
+pub async fn register_temp_file(
+    temp_manager: State<'_, SharedTempFileManager>,
+    conversation_id: String,
+    file_path: String,
+) -> Result<(), String> {
+    let mut manager = temp_manager.lock();
+    manager.register_file(&conversation_id, PathBuf::from(file_path));
+    Ok(())
+}
+
+#[tauri::command]
+pub async fn get_temp_files(
+    temp_manager: State<'_, SharedTempFileManager>,
+    conversation_id: String,
+) -> Result<Vec<String>, String> {
+    let manager = temp_manager.lock();
+    let files = manager.get_files_for_conversation(&conversation_id);
+    Ok(files.iter().map(|p| p.to_string_lossy().to_string()).collect())
+}
+
+#[tauri::command]
+pub async fn cleanup_temp_files(
+    temp_manager: State<'_, SharedTempFileManager>,
+    conversation_id: String,
+) -> Result<(), String> {
+    let mut manager = temp_manager.lock();
+    manager.cleanup_conversation(&conversation_id)
+}
+
+#[tauri::command]
+pub async fn cleanup_all_temp_files(
+    temp_manager: State<'_, SharedTempFileManager>,
+) -> Result<(), String> {
+    let mut manager = temp_manager.lock();
+    manager.cleanup_all()
+}
+
+#[tauri::command]
+pub async fn cleanup_orphaned_temp_files(
+    temp_manager: State<'_, SharedTempFileManager>,
+) -> Result<usize, String> {
+    let mut manager = temp_manager.lock();
+    manager.cleanup_orphaned_files()
+}
diff --git a/src-tauri/src/lib.rs b/src-tauri/src/lib.rs
index 685d3da..c402e7f 100644
--- a/src-tauri/src/lib.rs
+++ b/src-tauri/src/lib.rs
@@ -4,6 +4,7 @@ mod commands;
 mod config;
 mod notifications;
 mod stats;
+mod temp_manager;
 mod types;
 mod vbs_notification;
 mod windows_toast;
@@ -14,6 +15,7 @@ use bridge_manager::create_shared_bridge_manager;
 use commands::load_saved_achievements;
 use commands::*;
 use notifications::*;
+use temp_manager::create_shared_temp_manager;
 use vbs_notification::*;
 use windows_toast::*;
 use wsl_notifications::*;
@@ -21,6 +23,7 @@ use wsl_notifications::*;
 #[cfg_attr(mobile, tauri::mobile_entry_point)]
 pub fn run() {
     let bridge_manager = create_shared_bridge_manager();
+    let temp_manager = create_shared_temp_manager().expect("Failed to create temp file manager");
 
     tauri::Builder::default()
         .plugin(tauri_plugin_dialog::init())
@@ -31,9 +34,18 @@ pub fn run() {
         .plugin(tauri_plugin_os::init())
         .plugin(tauri_plugin_http::init())
         .manage(bridge_manager.clone())
+        .manage(temp_manager.clone())
         .setup(move |app| {
             // Initialize the app handle in the bridge manager
             bridge_manager.lock().set_app_handle(app.handle().clone());
+
+            // Clean up any orphaned temp files from previous sessions
+            if let Ok(count) = temp_manager.lock().cleanup_orphaned_files() {
+                if count > 0 {
+                    println!("Cleaned up {} orphaned temp files", count);
+                }
+            }
+
             Ok(())
         })
         .invoke_handler(tauri::generate_handler![
@@ -58,6 +70,12 @@ pub fn run() {
             validate_directory,
             list_skills,
             check_for_updates,
+            save_temp_file,
+            register_temp_file,
+            get_temp_files,
+            cleanup_temp_files,
+            cleanup_all_temp_files,
+            cleanup_orphaned_temp_files,
         ])
         .run(tauri::generate_context!())
         .expect("error while running tauri application");
diff --git a/src-tauri/src/temp_manager.rs b/src-tauri/src/temp_manager.rs
new file mode 100644
index 0000000..cfc8cea
--- /dev/null
+++ b/src-tauri/src/temp_manager.rs
@@ -0,0 +1,139 @@
+use parking_lot::Mutex;
+use std::collections::HashMap;
+use std::fs;
+use std::path::{Path, PathBuf};
+use std::sync::Arc;
+use uuid::Uuid;
+
+const TEMP_DIR_NAME: &str = "hikari-uploads";
+
+pub struct TempFileManager {
+    base_dir: PathBuf,
+    files: HashMap<String, Vec<PathBuf>>,
+}
+
+impl TempFileManager {
+    pub fn new() -> Result<Self, String> {
+        let base_dir = std::env::temp_dir().join(TEMP_DIR_NAME);
+
+        if !base_dir.exists() {
+            fs::create_dir_all(&base_dir)
+                .map_err(|e| format!("Failed to create temp directory: {}", e))?;
+        }
+
+        Ok(TempFileManager {
+            base_dir,
+            files: HashMap::new(),
+        })
+    }
+
+    #[allow(dead_code)]
+    pub fn get_base_dir(&self) -> &Path {
+        &self.base_dir
+    }
+
+    pub fn save_file(
+        &mut self,
+        conversation_id: &str,
+        data: &[u8],
+        original_filename: Option<&str>,
+    ) -> Result<PathBuf, String> {
+        let unique_id = Uuid::new_v4();
+        let extension = original_filename
+            .and_then(|name| Path::new(name).extension())
+            .and_then(|ext| ext.to_str())
+            .unwrap_or("bin");
+
+        let filename = format!("{}_{}.{}", conversation_id, unique_id, extension);
+        let file_path = self.base_dir.join(&filename);
+
+        fs::write(&file_path, data)
+            .map_err(|e| format!("Failed to write temp file: {}", e))?;
+
+        self.files
+            .entry(conversation_id.to_string())
+            .or_default()
+            .push(file_path.clone());
+
+        Ok(file_path)
+    }
+
+    pub fn register_file(&mut self, conversation_id: &str, file_path: PathBuf) {
+        self.files
+            .entry(conversation_id.to_string())
+            .or_default()
+            .push(file_path);
+    }
+
+    pub fn get_files_for_conversation(&self, conversation_id: &str) -> Vec<PathBuf> {
+        self.files
+            .get(conversation_id)
+            .cloned()
+            .unwrap_or_default()
+    }
+
+    pub fn cleanup_conversation(&mut self, conversation_id: &str) -> Result<(), String> {
+        if let Some(files) = self.files.remove(conversation_id) {
+            for file_path in files {
+                if file_path.exists() {
+                    if let Err(e) = fs::remove_file(&file_path) {
+                        eprintln!(
+                            "Warning: Failed to remove temp file {:?}: {}",
+                            file_path, e
+                        );
+                    }
+                }
+            }
+        }
+        Ok(())
+    }
+
+    pub fn cleanup_all(&mut self) -> Result<(), String> {
+        let conversation_ids: Vec<String> = self.files.keys().cloned().collect();
+
+        for conversation_id in conversation_ids {
+            self.cleanup_conversation(&conversation_id)?;
+        }
+
+        Ok(())
+    }
+
+    pub fn cleanup_orphaned_files(&mut self) -> Result<usize, String> {
+        let mut cleaned_count = 0;
+
+        if !self.base_dir.exists() {
+            return Ok(0);
+        }
+
+        let tracked_files: std::collections::HashSet<PathBuf> =
+            self.files.values().flatten().cloned().collect();
+
+        let entries = fs::read_dir(&self.base_dir)
+            .map_err(|e| format!("Failed to read temp directory: {}", e))?;
+
+        for entry in entries.flatten() {
+            let path = entry.path();
+            if path.is_file() && !tracked_files.contains(&path) {
+                if let Err(e) = fs::remove_file(&path) {
+                    eprintln!("Warning: Failed to remove orphaned file {:?}: {}", path, e);
+                } else {
+                    cleaned_count += 1;
+                }
+            }
+        }
+
+        Ok(cleaned_count)
+    }
+}
+
+impl Default for TempFileManager {
+    fn default() -> Self {
+        Self::new().expect("Failed to create TempFileManager")
+    }
+}
+
+pub type SharedTempFileManager = Arc<Mutex<TempFileManager>>;
+
+pub fn create_shared_temp_manager() -> Result<SharedTempFileManager, String> {
+    Ok(Arc::new(Mutex::new(TempFileManager::new()?)))
+}
diff --git a/src/lib/stores/conversations.ts b/src/lib/stores/conversations.ts
index 6948aaf..243d22a 100644
--- a/src/lib/stores/conversations.ts
+++ b/src/lib/stores/conversations.ts
@@ -272,7 +272,7 @@ function createConversationsStore() {
       return newConv.id;
     },
 
-    deleteConversation: (id: string) => {
+    deleteConversation: async (id: string) => {
       ensureInitialized();
       const convs = get(conversations);
       const activeId = get(activeConversationId);
@@ -282,8 +282,8 @@ function createConversationsStore() {
         return false;
       }
 
-      // Clean up tracking for this conversation
-      cleanupConversationTracking(id);
+      // Clean up tracking for this conversation (including temp files)
+      await cleanupConversationTracking(id);
 
       conversations.update((c) => {
         c.delete(id);
diff --git a/src/lib/tauri.ts b/src/lib/tauri.ts
index a1f7ec5..d14ded8 100644
--- a/src/lib/tauri.ts
+++ b/src/lib/tauri.ts
@@ -107,8 +107,15 @@ interface WorkingDirectoryPayload {
   conversation_id?: string;
 }
 
-export function cleanupConversationTracking(conversationId: string) {
+export async function cleanupConversationTracking(conversationId: string) {
   connectedConversations.delete(conversationId);
+
+  // Clean up any temp files associated with this conversation
+  try {
+    await invoke("cleanup_temp_files", { conversationId });
+  } catch (error) {
+    console.error("Failed to cleanup temp files for conversation:", error);
+  }
 }
 
 export async function initializeTauriListeners() {