diff --git a/src/frontend/mod.rs b/src/frontend/mod.rs
index d0f225d..09febe6 100644
--- a/src/frontend/mod.rs
+++ b/src/frontend/mod.rs
@@ -1,8 +1,13 @@
-use std::{collections::BTreeMap, io, net::SocketAddr, sync::OnceLock, time::Duration};
+use std::{collections::BTreeMap, net::SocketAddr, sync::OnceLock, time::Duration};
 
 use crossterm::event::{Event, EventStream, KeyCode, KeyEvent, KeyEventKind};
 use futures::{FutureExt, StreamExt};
-use joecalsend::{Config, JoecalState, Listeners, models::Device};
+use joecalsend::{
+    Config, JoecalState, Listeners, TransferEvent, UploadDialog,
+    error::{LocalSendError, Result},
+    models::Device,
+};
+use native_dialog::MessageDialogBuilder;
 use ratatui::{
     DefaultTerminal,
     buffer::Buffer,
@@ -12,7 +17,10 @@ use ratatui::{
     text::{Line, Text},
     widgets::{Block, Paragraph, Widget},
 };
-use tokio::task::JoinSet;
+use tokio::{
+    sync::mpsc::{UnboundedReceiver, unbounded_channel},
+    task::JoinSet,
+};
 
 pub mod ui;
 
@@ -24,6 +32,9 @@ pub struct App {
     pub events: EventStream,
     // addr -> (alias, fingerprint)
     pub peers: Peers,
+    // for getting messages back from the web server or web client about things we've done; the
+    // other end is held by the state
+    transfer_event_rx: OnceLock<UnboundedReceiver<TransferEvent>>,
 }
 
 #[derive(Debug, Clone, Copy, PartialEq, Eq)]
@@ -34,6 +45,12 @@ pub enum CurrentScreen {
     Stopping,
 }
 
+impl Default for App {
+    fn default() -> Self {
+        Self::new()
+    }
+}
+
 impl App {
     pub fn new() -> Self {
         App {
@@ -41,6 +58,7 @@ impl App {
             screen: vec![CurrentScreen::Main],
             peers: Default::default(),
             events: Default::default(),
+            transfer_event_rx: Default::default(),
         }
     }
 
@@ -50,14 +68,18 @@ impl App {
         terminal: &mut DefaultTerminal,
         config: Config,
         device: Device,
-    ) -> io::Result<()> {
-        let state = JoecalState::new(device)
+    ) -> Result<()> {
+        let (transfer_event_tx, transfer_event_rx) = unbounded_channel();
+
+        let state = JoecalState::new(device, transfer_event_tx)
             .await
             .expect("Could not create JoecalState");
 
+        let _ = self.transfer_event_rx.set(transfer_event_rx);
+
         let mut handles = JoinSet::new();
         state.start(&config, &mut handles).await;
-        self.state.get_or_init(|| state);
+        let _ = self.state.set(state);
         loop {
             terminal.draw(|frame| self.draw(frame))?;
             self.handle_events().await?;
@@ -83,7 +105,7 @@ impl App {
         Ok(())
     }
 
-    async fn handle_events(&mut self) -> io::Result<()> {
+    async fn handle_events(&mut self) -> Result<()> {
         tokio::select! {
             event = self.events.next().fuse() => {
                 if let Some(Ok(evt)) = event {
@@ -97,6 +119,39 @@ impl App {
                     }
                 }
             }
+            transfer_event = self.transfer_event_rx.get_mut().unwrap().recv() => {
+                if let Some(event) = transfer_event {
+                    match event {
+                        TransferEvent::UploadRequest { alias, id } => {
+                            let sender =
+                                self
+                                .state
+                                .get()
+                                .unwrap()
+                                .upload_requests
+                                .lock()
+                                .await
+                                .get(&id).ok_or(LocalSendError::SessionInactive)?.clone();
+
+                            // TODO: replace this with ratatui widget dialog
+                            let upload_confirmed = MessageDialogBuilder::default()
+                                .set_title(&alias)
+                                .set_text("Do you want to receive files from this device?")
+                                .confirm()
+                                .show()
+                                .unwrap();
+
+                            if upload_confirmed {
+                                let _ = sender.send(UploadDialog::UploadConfirm);
+                            } else {
+                                let _ = sender.send(UploadDialog::UploadDeny);
+                            }
+                        }
+                        TransferEvent::Sent => {}
+                        _ => {}
+                    }
+                }
+            }
             _ = tokio::time::sleep(Duration::from_millis(200)) => {}
         }
 
diff --git a/src/lib.rs b/src/lib.rs
index b957cb2..b6ec164 100644
--- a/src/lib.rs
+++ b/src/lib.rs
@@ -10,11 +10,15 @@ use std::{
     sync::{Arc, OnceLock},
 };
 
+use julid::Julid;
 use models::Device;
 use serde::{Deserialize, Serialize};
 use tokio::{
     net::UdpSocket,
-    sync::{Mutex, mpsc},
+    sync::{
+        Mutex,
+        mpsc::{self, UnboundedSender},
+    },
     task::JoinSet,
 };
 use transfer::Session;
@@ -33,6 +37,19 @@ pub enum Listeners {
     Multicast,
 }
 
+#[derive(Debug, Clone, PartialEq, Eq)]
+pub enum UploadDialog {
+    UploadDeny,
+    UploadConfirm,
+}
+
+pub enum TransferEvent {
+    Sent,
+    Received,
+    Failed,
+    UploadRequest { alias: String, id: Julid },
+}
+
 /// Contains the main network and backend state for an application session.
 #[derive(Clone)]
 pub struct JoecalState {
@@ -42,11 +59,18 @@ pub struct JoecalState {
     pub running_state: Arc<Mutex<RunningState>>,
     pub socket: Arc<UdpSocket>,
     pub client: reqwest::Client,
-    stop_tx: OnceLock<ShutdownSender>,
+    pub upload_requests: Arc<Mutex<HashMap<Julid, UnboundedSender<UploadDialog>>>>,
+    shutdown_sender: OnceLock<ShutdownSender>,
+    // the receiving end will be held by the application so it can update the UI based on backend
+    // events
+    transfer_event_tx: UnboundedSender<TransferEvent>,
 }
 
 impl JoecalState {
-    pub async fn new(device: Device) -> crate::error::Result<Self> {
+    pub async fn new(
+        device: Device,
+        transfer_event_tx: UnboundedSender<TransferEvent>,
+    ) -> crate::error::Result<Self> {
         let socket = UdpSocket::bind(LISTENING_SOCKET_ADDR).await?;
         socket.set_multicast_loop_v4(true)?;
         socket.set_multicast_ttl_v4(2)?; // one hop out from localnet
@@ -59,7 +83,9 @@ impl JoecalState {
             peers: Default::default(),
             sessions: Default::default(),
             running_state: Default::default(),
-            stop_tx: Default::default(),
+            shutdown_sender: Default::default(),
+            upload_requests: Default::default(),
+            transfer_event_tx,
         })
     }
 
@@ -68,7 +94,7 @@ impl JoecalState {
         let konfig = config.clone();
         handles.spawn({
             let (tx, shutdown_rx) = mpsc::channel(1);
-            self.stop_tx.get_or_init(|| tx);
+            let _ = self.shutdown_sender.set(tx);
             async move {
                 if let Err(e) = state.start_http_server(shutdown_rx, &konfig).await {
                     eprintln!("HTTP server error: {e}");
@@ -110,7 +136,7 @@ impl JoecalState {
         let mut rstate = self.running_state.lock().await;
         *rstate = RunningState::Stopping;
         let _ = self
-            .stop_tx
+            .shutdown_sender
             .get()
             .expect("Could not get stop signal transmitter")
             .send(())
diff --git a/src/transfer.rs b/src/transfer.rs
index de88f30..c47b289 100644
--- a/src/transfer.rs
+++ b/src/transfer.rs
@@ -8,11 +8,11 @@ use axum::{
     response::IntoResponse,
 };
 use julid::Julid;
-use native_dialog::MessageDialogBuilder;
 use serde::{Deserialize, Serialize};
+use tokio::sync::mpsc::unbounded_channel;
 
 use crate::{
-    JoecalState,
+    JoecalState, TransferEvent, UploadDialog,
     error::{LocalSendError, Result},
     models::{Device, FileMetadata},
 };
@@ -62,7 +62,6 @@ impl JoecalState {
         }
 
         let peer = self.peers.lock().await.get(&peer).unwrap().clone();
-        println!("Peer: {peer:?}");
 
         let response = self
             .client
@@ -196,15 +195,34 @@ pub async fn register_prepare_upload(
 ) -> impl IntoResponse {
     println!("Received upload request from alias: {}", req.info.alias);
 
-    let result = MessageDialogBuilder::default()
-        .set_title(&req.info.alias)
-        .set_text("Do you want to receive files from this device?")
-        .confirm()
-        .show()
-        .unwrap();
+    let id = Julid::new();
+    let (tx, mut rx) = unbounded_channel();
+    state
+        .upload_requests
+        .lock()
+        .await
+        .entry(id)
+        .insert_entry(tx);
 
-    if result {
-        let session_id = Julid::new().to_string();
+    let dialog_send = state.transfer_event_tx.send(TransferEvent::UploadRequest {
+        alias: req.info.alias.clone(),
+        id,
+    });
+    match dialog_send {
+        Ok(_) => {}
+        Err(_e) => {
+            let _ = state.upload_requests.lock().await.remove(&id);
+            return StatusCode::INTERNAL_SERVER_ERROR.into_response();
+        }
+    }
+
+    // safe to unwrap because it's only `None` when there are no more transmitters,
+    // and we still have the `tx` we created earlier
+    let result = rx.recv().await.unwrap();
+    let _ = state.upload_requests.lock().await.remove(&id);
+
+    if result == UploadDialog::UploadConfirm {
+        let session_id = id.as_string();
 
         let file_tokens: HashMap<String, String> = req
             .files