diff --git a/crates/chat_ui/src/lib.rs b/crates/chat_ui/src/lib.rs
index afd44aec..ae37f311 100644
--- a/crates/chat_ui/src/lib.rs
+++ b/crates/chat_ui/src/lib.rs
@@ -33,6 +33,7 @@ use ui::input::{Input, InputEvent, InputState};
 use ui::menu::DropdownMenu;
 use ui::notification::Notification;
 use ui::scroll::Scrollbar;
+use ui::tooltip::Tooltip;
 use ui::{
     Disableable, Icon, IconName, InteractiveElementExt, Sizable, StyledExt, WindowExtension,
     h_flex, v_flex,
@@ -1651,7 +1652,7 @@ impl ChatPanel {
                     .size_16()
                     .when(cx.theme().shadow, |this| this.shadow_lg())
                     .rounded(cx.theme().radius)
-                    .object_fit(ObjectFit::ScaleDown),
+                    .object_fit(ObjectFit::Cover),
             )
             .child(
                 div()
@@ -1734,33 +1735,23 @@ impl ChatPanel {
         label: SharedString,
         cx: &Context<Self>,
     ) -> AnyElement {
-        div()
+        h_flex()
             .id(SharedString::from(format!("file-{id}")))
-            .flex()
-            .items_center()
+            .self_start()
+            .items_start()
+            .min_w_0()
             .gap_2()
-            .py_1()
-            .px_2()
+            .p_2()
             .border_1()
             .border_color(cx.theme().border_variant)
             .rounded(cx.theme().radius)
-            .hover(|this| this.bg(cx.theme().surface_background))
-            .child(
-                Icon::new(IconName::Lock)
-                    .small()
-                    .text_color(cx.theme().text_placeholder),
-            )
+            .child(Icon::new(IconName::Lock).text_color(cx.theme().icon_accent))
             .child(
                 v_flex()
-                    .flex_1()
+                    .min_w_0()
                     .overflow_hidden()
                     .text_sm()
-                    .child(
-                        div()
-                            .text_ellipsis()
-                            .line_clamp(1)
-                            .child(file.display_name()),
-                    )
+                    .child(div().line_height(relative(1.2)).child(file.display_name()))
                     .child(
                         div()
                             .text_xs()
@@ -1782,58 +1773,59 @@ impl ChatPanel {
     /// Render an uploaded, encrypted file which is not sent yet
     fn render_pending_file(&self, pending: &PendingFile, cx: &Context<Self>) -> impl IntoElement {
         let file = &pending.file;
+        let label = file.display_name();
 
         div()
             .id(SharedString::from(file.url.to_string()))
             .relative()
-            .flex()
-            .items_center()
-            .gap_2()
-            .p_1()
-            .pr_2()
-            .border_1()
-            .border_color(cx.theme().border_variant)
-            .rounded(cx.theme().radius)
-            .when(file.is_image(), |this| {
-                this.child(
-                    img(pending.path.clone())
-                        .size_8()
-                        .rounded(cx.theme().radius)
-                        .object_fit(ObjectFit::Cover),
-                )
+            .w_16()
+            .tooltip(move |window, cx| Tooltip::new(label.clone(), window, cx).into())
+            .map(|this| {
+                if file.is_image() {
+                    this.child(
+                        img(pending.path.clone())
+                            .size_16()
+                            .when(cx.theme().shadow, |this| this.shadow_sm())
+                            .rounded(cx.theme().radius)
+                            .object_fit(ObjectFit::Cover),
+                    )
+                } else {
+                    this.child(
+                        div()
+                            .size_16()
+                            .flex()
+                            .items_center()
+                            .justify_center()
+                            .rounded(cx.theme().radius)
+                            .border_1()
+                            .border_color(cx.theme().border_variant)
+                            .bg(cx.theme().surface_background)
+                            .text_xs()
+                            .text_center()
+                            .child("Preview not available"),
+                    )
+                }
             })
             .child(
                 v_flex()
-                    .text_sm()
-                    .child(
-                        div()
-                            .max_w(px(160.))
-                            .text_ellipsis()
-                            .line_clamp(1)
-                            .child(file.display_name()),
-                    )
-                    .child(
-                        h_flex()
-                            .gap_1()
-                            .items_center()
-                            .text_xs()
-                            .text_color(cx.theme().text_placeholder)
-                            .child(Icon::new(IconName::Lock).size_2())
-                            .child("End-to-end encrypted"),
-                    ),
-            )
-            .child(
-                Button::new(SharedString::from(format!("remove-{}", file.url)))
-                    .icon(IconName::Close)
-                    .xsmall()
-                    .ghost()
-                    .on_click({
-                        let url = file.url.clone();
-                        cx.listener(move |this, _, _, cx| {
-                            this.remove_pending_file(&url, cx);
-                        })
-                    }),
+                    .absolute()
+                    .top_neg_1()
+                    .right_neg_1()
+                    .size_4()
+                    .items_center()
+                    .justify_center()
+                    .rounded_full()
+                    .border_1()
+                    .border_color(cx.theme().border_variant)
+                    .bg(gpui::green())
+                    .child(Icon::new(IconName::Lock).size_2().text_color(gpui::white())),
             )
+            .on_click({
+                let url = file.url.clone();
+                cx.listener(move |this, _, _, cx| {
+                    this.remove_pending_file(&url, cx);
+                })
+            })
     }
 
     fn render_pending_file_list(
@@ -2026,6 +2018,10 @@ impl Focusable for ChatPanel {
 
 impl Render for ChatPanel {
     fn render(&mut self, window: &mut Window, cx: &mut Context<Self>) -> impl IntoElement {
+        const WARNING: &str = "Attachments added while typing are uploaded without encryption";
+
+        let is_typing = !self.input.read(cx).value().trim().is_empty();
+
         v_flex()
             .image_cache(coop_cache(self.id.clone(), 100))
             .on_action(cx.listener(Self::on_command))
@@ -2059,10 +2055,8 @@ impl Render for ChatPanel {
                     .map(|this| {
                         if self.messages.is_empty() {
                             this.child(
-                                div()
+                                h_flex()
                                     .size_full()
-                                    .flex()
-                                    .items_center()
                                     .justify_end()
                                     .child(self.render_announcement(cx)),
                             )
@@ -2089,20 +2083,15 @@ impl Render for ChatPanel {
                     .children(self.render_attachment_list(window, cx))
                     .children(self.render_pending_file_list(window, cx))
                     .children(self.render_reply_list(window, cx))
-                    .when(
-                        !self.input.read(cx).value().trim().is_empty(),
-                        |this| {
-                            this.child(
-                                div()
-                                    .px_1()
-                                    .text_xs()
-                                    .text_color(cx.theme().text_warning)
-                                    .child(
-                                        "Attachments added while typing are uploaded without encryption",
-                                    ),
-                            )
-                        },
-                    )
+                    .when(is_typing, |this| {
+                        this.child(
+                            div()
+                                .px_1()
+                                .text_xs()
+                                .text_color(cx.theme().text_warning)
+                                .child(WARNING),
+                        )
+                    })
                     .child(
                         h_flex()
                             .items_end()