diff --git a/crates/chat/src/room.rs b/crates/chat/src/room.rs
index f8829c1..ea69c2d 100644
--- a/crates/chat/src/room.rs
+++ b/crates/chat/src/room.rs
@@ -13,7 +13,6 @@ use state::{NostrRegistry, TIMEOUT};
 
 use crate::NewMessage;
 
-const NO_RELAY: &str = "User hasn't set up any messaging relays yet.";
 const NO_DEKEY: &str = "User hasn't set up a decoupled encryption key yet.";
 const USER_NO_DEKEY: &str = "You haven't set up a decoupled encryption key or it's not available.";
 
@@ -501,16 +500,9 @@ impl Room {
 
             // Process each member
             for member in members {
-                let relays = member.messaging_relays();
                 let announcement = member.announcement();
                 let public_key = member.public_key();
 
-                // Skip members with no relays
-                if relays.is_empty() {
-                    reports.push(SendReport::new(public_key).error(NO_RELAY));
-                    continue;
-                }
-
                 // Handle encryption signer requirements
                 if signer_kind.encryption() {
                     // Receiver didn't set up a decoupled encryption key
@@ -546,7 +538,7 @@ impl Room {
                 };
 
                 // Send the gift wrap event and collect the report
-                match send_gift_wrap(&client, &signer, &member, &rumor, signer_kind, relays).await {
+                match send_gift_wrap(&client, &signer, &member, &rumor, signer_kind).await {
                     Ok(report) => {
                         reports.push(report);
                         sents += 1;
@@ -561,7 +553,6 @@ impl Room {
             // Send backup to current user if needed
             if backup && sents >= 1 {
                 let public_key = sender.public_key();
-                let relays = sender.messaging_relays();
 
                 // Determine the signer to use
                 let signer = match signer_kind {
@@ -582,7 +573,7 @@ impl Room {
                     SignerKind::User => user_signer.clone(),
                 };
 
-                match send_gift_wrap(&client, &signer, &sender, &rumor, signer_kind, relays).await {
+                match send_gift_wrap(&client, &signer, &sender, &rumor, signer_kind).await {
                     Ok(report) => reports.push(report),
                     Err(error) => {
                         let report = SendReport::new(public_key).error(error.to_string());
@@ -603,7 +594,6 @@ async fn send_gift_wrap<T>(
     receiver: &Person,
     rumor: &UnsignedEvent,
     config: &SignerKind,
-    to: &[RelayUrl],
 ) -> Result<SendReport, Error>
 where
     T: NostrSigner + 'static,
@@ -634,15 +624,10 @@ where
     // Construct the gift wrap event
     let event = EventBuilder::gift_wrap(signer, &receiver, rumor.clone(), extra_tags).await?;
 
-    // Connect to each relay before sending
-    for url in to.iter() {
-        client.add_relay(url).and_connect().await.ok();
-    }
-
     // Send the gift wrap event and collect the report
     let report = client
         .send_event(&event)
-        .to(to)
+        .to_nip17()
         .ack_policy(AckPolicy::none())
         .await
         .map(|output| {
diff --git a/crates/chat_ui/src/lib.rs b/crates/chat_ui/src/lib.rs
index 177d672..7481d35 100644
--- a/crates/chat_ui/src/lib.rs
+++ b/crates/chat_ui/src/lib.rs
@@ -379,9 +379,13 @@ impl ChatPanel {
     /// Send message in the background and wait for the response
     fn send_and_wait(&mut self, rumor: UnsignedEvent, window: &mut Window, cx: &mut Context<Self>) {
         let sent_ids = self.sent_ids.clone();
+
         // This can't fail, because we already ensured that the ID is set
         let id = rumor.id.unwrap();
 
+        // Add empty reports
+        self.insert_reports(id, vec![], cx);
+
         // Upgrade room reference
         let Some(room) = self.room.upgrade() else {
             return;
@@ -430,7 +434,7 @@ impl ChatPanel {
     /// Insert reports
     fn insert_reports(&mut self, id: EventId, reports: Vec<SendReport>, cx: &mut Context<Self>) {
         self.reports_by_id.update(cx, |this, cx| {
-            this.insert(id, reports);
+            this.entry(id).or_default().extend(reports);
             cx.notify();
         });
     }
@@ -924,20 +928,26 @@ impl ChatPanel {
     fn render_sent_reports(&self, id: &EventId, cx: &App) -> impl IntoElement {
         let reports = self.sent_reports(id, cx);
 
+        let pending = reports
+            .as_ref()
+            .is_some_and(|reports| reports.is_empty() || reports.iter().any(|r| r.pending()));
+
         let success = reports
             .as_ref()
-            .is_some_and(|reports| reports.iter().any(|r| r.success()));
+            .is_some_and(|reports| !reports.is_empty() && reports.iter().any(|r| r.success()));
 
         let failed = reports
             .as_ref()
-            .is_some_and(|reports| reports.iter().all(|r| r.failed()));
+            .is_some_and(|reports| !reports.is_empty() && reports.iter().all(|r| r.failed()));
 
         let label = if success {
             SharedString::from("• Sent")
         } else if failed {
-            SharedString::from("• Failed")
-        } else {
+            SharedString::from("• Error")
+        } else if pending {
             SharedString::from("• Sending...")
+        } else {
+            SharedString::from("• Unknown")
         };
 
         div()
@@ -945,22 +955,24 @@ impl ChatPanel {
             .child(label)
             .when(failed, |this| this.text_color(cx.theme().text_danger))
             .when_some(reports, |this, reports| {
-                this.on_click(move |_e, window, cx| {
-                    let reports = reports.clone();
+                this.when(!pending, |this| {
+                    this.on_click(move |_e, window, cx| {
+                        let reports = reports.clone();
 
-                    window.open_modal(cx, move |this, _window, cx| {
-                        this.title(SharedString::from("Sent Reports"))
-                            .show_close(true)
-                            .child(v_flex().gap_4().children({
-                                let mut items = Vec::with_capacity(reports.len());
+                        window.open_modal(cx, move |this, _window, cx| {
+                            this.title(SharedString::from("Sent Reports"))
+                                .show_close(true)
+                                .child(v_flex().gap_4().children({
+                                    let mut items = Vec::with_capacity(reports.len());
 
-                                for report in reports.iter() {
-                                    items.push(Self::render_report(report, cx))
-                                }
+                                    for report in reports.iter() {
+                                        items.push(Self::render_report(report, cx))
+                                    }
 
-                                items
-                            }))
-                    });
+                                    items
+                                }))
+                        });
+                    })
                 })
             })
     }