diff --git a/apps/maple-agent/app/src/ui/chat/mod.rs b/apps/maple-agent/app/src/ui/chat/mod.rs
index 1072395c8..da5e5eba7 100644
--- a/apps/maple-agent/app/src/ui/chat/mod.rs
+++ b/apps/maple-agent/app/src/ui/chat/mod.rs
@@ -132,9 +132,9 @@ impl SidebarTransition {
 /// Height of the task header and the clear strip above the collapsed rail.
 const CHAT_HEADER_HEIGHT: gpui::Pixels = px(40.);
 /// Left inset for the header beside the rail: the traffic lights reach
-/// 30 px past it when the bar is transparent.
+/// 30 px past it, followed by an 8 px gap when the bar is transparent.
 const SIDEBAR_COLLAPSED_INSET: gpui::Pixels = if titlebar::TRANSPARENT_TITLEBAR {
-    px(30.)
+    px(38.)
 } else {
     px(16.)
 };
@@ -7023,7 +7023,7 @@ impl ChatScreen {
                     this.execute_command(ChatCommand::ToggleSidebar, window, cx);
                 }))
                 .child(
-                    crate::ui::icons::wordmark(sidebar::WORDMARK_HEIGHT, theme::text_primary())
+                    crate::ui::icons::wordmark(sidebar::WORDMARK_HEIGHT, theme::text_sidebar())
                         .path("icons/maple-mark.svg")
                         .debug_selector(|| "sidebar-rail-mark".to_string()),
                 ),
@@ -7263,12 +7263,10 @@ fn head_change_event(event: &notify::Event) -> bool {
         .any(|path| path.file_name().is_some_and(|name| name == "HEAD"))
 }
 
-/// Last path component of a project root, for chips and the sidebar.
-/// Upper-case section heading in the sidebar.
+/// Section heading in the sidebar.
 fn section_label(text: &'static str) -> Div {
     div()
-        .text_xs()
-        .font_weight(gpui::FontWeight::SEMIBOLD)
+        .text_sm()
         .text_color(gpui::rgb(theme::text_muted()))
         .child(text)
 }
diff --git a/apps/maple-agent/app/src/ui/chat/sidebar.rs b/apps/maple-agent/app/src/ui/chat/sidebar.rs
index e753d5508..2e620052a 100644
--- a/apps/maple-agent/app/src/ui/chat/sidebar.rs
+++ b/apps/maple-agent/app/src/ui/chat/sidebar.rs
@@ -85,6 +85,9 @@ use crate::ui::widgets;
 
 const SEARCH_ROW_RADIUS: gpui::Pixels = px(6.);
 
+/// Corner radius of a sidebar row's hover and selected highlight.
+const ROW_RADIUS: gpui::Pixels = px(6.);
+
 /// Geometry shared by the expanded wordmark row and the collapsed mark.
 pub(super) const WORDMARK_LEFT: gpui::Pixels = px(16.);
 pub(super) const WORDMARK_HEIGHT: gpui::Pixels = px(16.);
@@ -357,9 +360,9 @@ pub(super) enum SidebarSection {
 impl SidebarSection {
     pub(super) fn label(self) -> &'static str {
         match self {
-            Self::Pinned => "PINNED",
-            Self::Active => "ACTIVE",
-            Self::Settled => "SETTLED",
+            Self::Pinned => "Pinned",
+            Self::Active => "Active",
+            Self::Settled => "Settled",
         }
     }
 
@@ -420,6 +423,7 @@ pub(super) struct Sidebar {
     // The list and its sections.
     list: gpui::ListState,
     entries: Vec<SidebarEntry>,
+    heading_gaps: Vec<bool>,
     rows: Vec<SidebarRow>,
     pinned_rows: Vec<usize>,
     active_rows: Vec<usize>,
@@ -684,6 +688,7 @@ impl Sidebar {
             vim_active: false,
             list: gpui::ListState::new(0, gpui::ListAlignment::Top, px(200.)),
             entries: Vec::new(),
+            heading_gaps: Vec::new(),
             rows: Vec::new(),
             pinned_rows: Vec::new(),
             active_rows: Vec::new(),
@@ -1450,6 +1455,20 @@ impl Sidebar {
         if self.computers.len() > 1 && self.project_filter.is_none() {
             entries = self.computer_entries();
         }
+        let heading_gaps = entries
+            .iter()
+            .enumerate()
+            .map(|(ix, entry)| {
+                matches!(
+                    entry,
+                    SidebarEntry::SectionLabel(_) | SidebarEntry::ArchivedHeader
+                ) && !matches!(
+                    ix.checked_sub(1).and_then(|ix| entries.get(ix)),
+                    Some(SidebarEntry::SectionLabel(_) | SidebarEntry::ArchivedHeader)
+                )
+            })
+            .collect();
+        let old_gaps = std::mem::replace(&mut self.heading_gaps, heading_gaps);
         let old = std::mem::replace(&mut self.entries, entries);
         if self.application_vim_enabled {
             self.rebuild_vim_targets();
@@ -1476,6 +1495,14 @@ impl Sidebar {
                 self.entries.len() - prefix - suffix,
             );
         }
+        // A retained heading can gain or lose its gap when its predecessor
+        // changes. Invalidate its cached height even when it is off screen.
+        if suffix > 0 {
+            let row = self.entries.len() - suffix;
+            if self.heading_gaps[row] != old_gaps[old.len() - suffix] {
+                self.list.remeasure_items(row..row + 1);
+            }
+        }
         if self.application_vim_enabled {
             self.vim_reconcile();
         }
@@ -2388,6 +2415,7 @@ impl Sidebar {
     ) -> AnyElement {
         let selected = self.selected.as_deref();
         let chat = self.chat.clone();
+        let heading_gap = self.heading_gaps.get(ix).copied().unwrap_or(false);
         let entry = match self.entries.get(ix).copied() {
             Some(
                 entry @ (SidebarEntry::ComputerProject(_)
@@ -2416,7 +2444,7 @@ impl Sidebar {
                             "New Task",
                             ChatCommand::NewTask,
                             &super::NewTask,
-                            theme::accent(),
+                            theme::text_sidebar(),
                         )
                     };
                 div()
@@ -2476,15 +2504,16 @@ impl Sidebar {
                 let expanded = self.section_expanded(section);
                 div()
                     .id(gpui::SharedString::from(section.element_id()))
-                    .mt_4()
-                    .w_full()
+                    .w_auto()
+                    .mx_2()
+                    .my(px(1.))
+                    .when(heading_gap, |row| row.mt_3())
                     .flex()
                     .items_center()
-                    .gap_1p5()
-                    .mb_1()
-                    .px_4()
+                    .gap_1()
+                    .px_2()
                     .py_1()
-                    .rounded(theme::RADIUS_SM)
+                    .rounded(ROW_RADIUS)
                     .hover(|style| {
                         style
                             .bg(gpui::rgb(theme::bg_sidebar_row_hover()))
@@ -2493,6 +2522,7 @@ impl Sidebar {
                     .on_click(cx.listener(move |this, _event, _window, cx| {
                         this.toggle_section_expanded(section, cx);
                     }))
+                    .child(section_label(section.label()))
                     .child(icon(
                         if expanded {
                             "chevron-down"
@@ -2502,7 +2532,6 @@ impl Sidebar {
                         px(14.),
                         theme::text_secondary(),
                     ))
-                    .child(section_label(section.label()))
                     .into_any_element()
             }
             Some(SidebarEntry::Empty(reason)) => {
@@ -2568,15 +2597,16 @@ impl Sidebar {
                     .role(gpui::Role::Button)
                     .aria_label(format!("Archived tasks {count_label}"))
                     .aria_expanded(expanded)
-                    .mt_5()
-                    .w_full()
+                    .w_auto()
+                    .mx_2()
+                    .my(px(1.))
+                    .when(heading_gap, |row| row.mt_3())
                     .flex()
                     .items_center()
-                    .gap_1p5()
-                    .mb_1()
-                    .px_4()
+                    .gap_1()
+                    .px_2()
                     .py_1()
-                    .rounded(theme::RADIUS_SM)
+                    .rounded(ROW_RADIUS)
                     .hover(|style| {
                         style
                             .bg(gpui::rgb(theme::bg_sidebar_row_hover()))
@@ -2585,6 +2615,13 @@ impl Sidebar {
                     .on_click(cx.listener(|this, _event, _window, cx| {
                         this.toggle_archived_visibility(cx);
                     }))
+                    .child(section_label("Archived"))
+                    .child(
+                        div()
+                            .text_xs()
+                            .text_color(gpui::rgb(theme::text_muted()))
+                            .child(count_label),
+                    )
                     .child(icon(
                         if expanded {
                             "chevron-down"
@@ -2594,13 +2631,6 @@ impl Sidebar {
                         px(14.),
                         theme::text_secondary(),
                     ))
-                    .child(section_label("ARCHIVED"))
-                    .child(
-                        div()
-                            .text_xs()
-                            .text_color(gpui::rgb(theme::text_muted()))
-                            .child(count_label),
-                    )
                     .into_any_element()
             }
             None => div().into_any_element(),
@@ -2657,15 +2687,16 @@ impl Sidebar {
             .flex()
             .items_center()
             .gap_1p5()
-            .w_full()
-            .pl_4()
+            .w_auto()
+            .mx_2()
+            .my(px(1.))
+            .pl_2()
             // Room for the new-project button, which sits over this end.
-            .pr(px(46.))
+            .pr(px(38.))
             .py_1()
-            .rounded(theme::RADIUS_SM)
+            .rounded(ROW_RADIUS)
             .text_sm()
-            .font_weight(gpui::FontWeight::MEDIUM)
-            .text_color(gpui::rgb(theme::text_primary()))
+            .text_color(gpui::rgb(theme::text_sidebar()))
             .hover(|style| {
                 style
                     .bg(gpui::rgb(theme::bg_sidebar_row_hover()))
@@ -2937,9 +2968,16 @@ impl Sidebar {
         let pin_id = row.pin_id.clone();
         let rename_field = self.task_rename_field(&row.id, cx);
         let renaming = rename_field.is_some();
+        let hover_bg = if is_selected {
+            theme::bg_sidebar_row_selected_hover()
+        } else {
+            theme::bg_sidebar_row_hover()
+        };
         div()
             .relative()
-            .w_full()
+            .w_auto()
+            .mx_2()
+            .my(px(1.))
             .id(row.element_id.clone())
             .role(gpui::Role::ListBoxOption)
             .accessibility_id(row.id.to_string())
@@ -2951,25 +2989,20 @@ impl Sidebar {
             .flex()
             .items_center()
             .gap_1p5()
-            .when(archived, |row| row.pl_6())
-            .when(!archived, |row| row.pl_8())
-            .pr_6()
+            .when(archived, |row| row.pl_4())
+            .when(!archived, |row| row.pl_6())
+            .pr_4()
             .py_1()
-            .rounded(theme::RADIUS_MD)
+            .rounded(ROW_RADIUS)
             .text_sm()
             .when(is_selected, |row| {
                 row.bg(gpui::rgb(theme::bg_sidebar_row_selected()))
-                    .font_weight(gpui::FontWeight::MEDIUM)
             })
-            .text_color(gpui::rgb(theme::text_primary()))
+            .text_color(gpui::rgb(theme::text_sidebar()))
             // A row being renamed is a text field: no hover highlight and
             // no hover actions over it, so the edit is plain to see.
             .when(!renaming, |el| {
-                el.hover(|style| {
-                    style
-                        .bg(gpui::rgb(theme::bg_sidebar_row_hover()))
-                        .cursor_pointer()
-                })
+                el.hover(|style| style.bg(gpui::rgb(hover_bg)).cursor_pointer())
             })
             .on_click(cx.listener(move |_this, _event, _window, cx| {
                 cx.emit(SidebarEvent::Select(session_id.to_string()));
@@ -3035,16 +3068,14 @@ impl Sidebar {
                         .bottom_0()
                         .when(is_pinned, |overlay| overlay.right(px(26.)))
                         .when(!is_pinned, |overlay| {
-                            overlay.right_0().rounded_r(theme::RADIUS_MD)
+                            overlay.right_0().rounded_r(ROW_RADIUS)
                         })
                         .flex()
                         .items_center()
                         .gap_1p5()
                         .pl_2()
-                        .pr_6()
-                        .group_hover(row.group.clone(), |style| {
-                            style.bg(gpui::rgb(theme::bg_sidebar_row_hover()))
-                        })
+                        .pr_4()
+                        .group_hover(row.group.clone(), |style| style.bg(gpui::rgb(hover_bg)))
                         .child(self.task_menu_trigger(row, task, window, cx))
                         .child(row_action(
                             row.rename_id.clone(),
@@ -3139,7 +3170,7 @@ impl Render for Sidebar {
                             .flex()
                             .items_center()
                             .child(
-                                wordmark(WORDMARK_HEIGHT, theme::text_primary())
+                                wordmark(WORDMARK_HEIGHT, theme::text_sidebar())
                                     .debug_selector(|| "sidebar-wordmark".to_string()),
                             ),
                     ),
@@ -3302,6 +3333,105 @@ fn remote_root_display_name(root: &str) -> String {
 mod tests {
     use super::{remote_root_display_name, root_display_name};
 
+    #[gpui::test]
+    fn sidebar_remeasures_an_offscreen_heading_when_its_gap_changes(cx: &mut gpui::TestAppContext) {
+        use super::*;
+        cx.executor().allow_parking();
+        let backend =
+            Arc::new(AgentBackend::for_test("http://127.0.0.1:9".into(), String::new()).unwrap());
+        let chat = cx.new(|cx| ChatScreen::new_without_start(backend, "user".into(), cx));
+        let sidebar = chat.update(cx, |chat, _| chat.sidebar.clone());
+        sidebar.update(cx, |sidebar, cx| {
+            sidebar.application_vim_enabled = true;
+            sidebar.list = gpui::ListState::new(0, gpui::ListAlignment::Top, px(0.));
+            let sessions = (0..102)
+                .map(|ix| AgentSessionSummary {
+                    id: format!("s{ix}"),
+                    title: format!("Task {ix}"),
+                    project_root: "/tmp/proj".into(),
+                    created_ms: 0,
+                    updated_ms: 0,
+                    message_count: 1,
+                    model: None,
+                    web_enabled: true,
+                    state: if ix == 101 {
+                        AgentTaskState::Settled
+                    } else {
+                        AgentTaskState::Active
+                    },
+                    acp: false,
+                })
+                .collect();
+            sidebar.pinned_tasks = (0..100).map(|ix| format!("s{ix}")).collect();
+            sidebar.set_sessions(sessions, cx);
+        });
+        let list = sidebar.update(cx, |sidebar, _| sidebar.list.clone());
+        struct Host(Entity<Sidebar>);
+        impl Render for Host {
+            fn render(&mut self, _: &mut Window, _: &mut Context<Self>) -> impl IntoElement {
+                div()
+                    .w(px(300.))
+                    .h(px(400.))
+                    .flex()
+                    .flex_col()
+                    .child(self.0.clone())
+            }
+        }
+        let (_host, cx) = cx.add_window_view(|_, _| Host(sidebar.clone()));
+        cx.simulate_resize(gpui::size(px(300.), px(400.)));
+        let settled = |cx: &mut gpui::VisualTestContext| {
+            sidebar.update(cx, |sidebar, _| {
+                sidebar
+                    .entries
+                    .iter()
+                    .position(|entry| *entry == SidebarEntry::SectionLabel(SidebarSection::Settled))
+                    .unwrap()
+            })
+        };
+        let row = settled(cx);
+        sidebar.update(cx, |sidebar, cx| {
+            sidebar.list.scroll_to(gpui::ListOffset {
+                item_ix: row,
+                offset_in_item: px(0.),
+            });
+            cx.notify();
+        });
+        cx.run_until_parked();
+        let height = list.bounds_for_item(row).unwrap().size.height;
+        for expanded in [false, true] {
+            sidebar.update(cx, |sidebar, cx| {
+                sidebar.list.scroll_to(gpui::ListOffset::default());
+                cx.notify();
+            });
+            cx.run_until_parked();
+            let row = settled(cx);
+            assert!(list.item_is_below_viewport(row).unwrap());
+            assert!(list.bounds_for_item(row).is_some());
+            sidebar.update(cx, |sidebar, cx| {
+                sidebar.toggle_section_expanded(SidebarSection::Active, cx);
+            });
+            let row = settled(cx);
+            assert!(
+                list.bounds_for_item(row).is_none(),
+                "discard the off-screen heading's old measurement"
+            );
+            sidebar.update(cx, |sidebar, cx| {
+                sidebar.list.scroll_to(gpui::ListOffset {
+                    item_ix: row,
+                    offset_in_item: px(0.),
+                });
+                cx.notify();
+            });
+            cx.run_until_parked();
+            let measured = list.bounds_for_item(row).unwrap().size.height;
+            if expanded {
+                assert_eq!(measured, height);
+            } else {
+                assert!(measured < height, "adjacent headings lose the section gap");
+            }
+        }
+    }
+
     #[test]
     fn remote_project_labels_use_the_owners_path_syntax() {
         assert_eq!(remote_root_display_name(r"C:\Users\Alex\Maple"), "Maple");
diff --git a/apps/maple-agent/app/src/ui/chat/sidebar_computers.rs b/apps/maple-agent/app/src/ui/chat/sidebar_computers.rs
index 26e7c5cb0..7e0077475 100644
--- a/apps/maple-agent/app/src/ui/chat/sidebar_computers.rs
+++ b/apps/maple-agent/app/src/ui/chat/sidebar_computers.rs
@@ -1183,6 +1183,11 @@ impl Sidebar {
         selected: bool,
         cx: &mut Context<Self>,
     ) -> AnyElement {
+        let hover_bg = if selected {
+            theme::bg_sidebar_row_selected_hover()
+        } else {
+            theme::bg_sidebar_row_hover()
+        };
         match entry {
             SidebarEntry::ComputerMore(index) => {
                 let action = self.group_pages.more[index].clone();
@@ -1192,8 +1197,11 @@ impl Sidebar {
                     .id(SharedString::from(format!("computer-page-{index}")))
                     .role(gpui::Role::Button)
                     .aria_label(label.clone())
-                    .px_8()
+                    .mx_2()
+                    .my(px(1.))
+                    .px_6()
                     .py_2()
+                    .rounded(ROW_RADIUS)
                     .text_xs()
                     .text_color(gpui::rgb(theme::text_secondary()))
                     .when(selected, |row| {
@@ -1201,10 +1209,7 @@ impl Sidebar {
                             .bg(gpui::rgb(theme::bg_sidebar_row_hover()))
                     })
                     .when(!loading, |row| {
-                        row.hover(|s| {
-                            s.cursor_pointer()
-                                .bg(gpui::rgb(theme::bg_sidebar_row_hover()))
-                        })
+                        row.hover(|s| s.cursor_pointer().bg(gpui::rgb(hover_bg)))
                     })
                     .on_click(cx.listener(move |this, _, _, cx| {
                         if !loading {
@@ -1221,9 +1226,12 @@ impl Sidebar {
                     .id(project.id.clone())
                     .role(gpui::Role::Button)
                     .aria_label(project.label.clone())
+                    .mx_2()
+                    .my(px(1.))
                     .mt_3()
-                    .px_4()
+                    .px_2()
                     .py_1p5()
+                    .rounded(ROW_RADIUS)
                     .flex()
                     .gap_2()
                     .items_center()
@@ -1233,10 +1241,7 @@ impl Sidebar {
                         row.aria_active_descendant()
                             .bg(gpui::rgb(theme::bg_sidebar_row_hover()))
                     })
-                    .hover(|s| {
-                        s.bg(gpui::rgb(theme::bg_sidebar_row_hover()))
-                            .cursor_pointer()
-                    })
+                    .hover(|s| s.bg(gpui::rgb(hover_bg)).cursor_pointer())
                     .on_click(cx.listener(move |_, _, _, cx| {
                         cx.emit(SidebarEvent::Navigate(request.clone()))
                     }))
@@ -1262,23 +1267,22 @@ impl Sidebar {
                     .role(gpui::Role::ListBoxOption)
                     .aria_label(task.title.clone())
                     .aria_selected(false)
-                    .pl_8()
-                    .pr_6()
+                    .mx_2()
+                    .my(px(1.))
+                    .pl_6()
+                    .pr_4()
                     .py_1()
                     .flex()
                     .gap_2()
                     .items_center()
-                    .rounded(theme::RADIUS_MD)
+                    .rounded(ROW_RADIUS)
                     .text_sm()
-                    .text_color(gpui::rgb(theme::text_primary()))
+                    .text_color(gpui::rgb(theme::text_sidebar()))
                     .when(selected, |row| {
                         row.aria_active_descendant()
                             .bg(gpui::rgb(theme::bg_sidebar_row_hover()))
                     })
-                    .hover(|s| {
-                        s.bg(gpui::rgb(theme::bg_sidebar_row_hover()))
-                            .cursor_pointer()
-                    })
+                    .hover(|s| s.bg(gpui::rgb(hover_bg)).cursor_pointer())
                     .on_click(cx.listener(move |_, _, _, cx| {
                         cx.emit(SidebarEvent::Navigate(request.clone()))
                     }))
@@ -1308,18 +1312,18 @@ impl Sidebar {
                     .id(SharedString::from(format!("computer-{index}")))
                     .role(gpui::Role::Button)
                     .aria_label(computer.label.clone())
+                    .mx_2()
+                    .my(px(1.))
                     .mt_3()
-                    .px_4()
+                    .px_2()
                     .py_2()
+                    .rounded(ROW_RADIUS)
                     .flex()
                     .flex_col()
                     .gap_1()
                     .text_xs()
                     .text_color(gpui::rgb(theme::text_secondary()))
-                    .hover(|s| {
-                        s.bg(gpui::rgb(theme::bg_sidebar_row_hover()))
-                            .cursor_pointer()
-                    })
+                    .hover(|s| s.bg(gpui::rgb(hover_bg)).cursor_pointer())
                     .on_click(cx.listener(move |_, _, _, cx| {
                         cx.emit(SidebarEvent::Navigate(request.clone()))
                     }))
diff --git a/apps/maple-agent/app/src/ui/theme.rs b/apps/maple-agent/app/src/ui/theme.rs
index 0551fef9f..81f367c7c 100644
--- a/apps/maple-agent/app/src/ui/theme.rs
+++ b/apps/maple-agent/app/src/ui/theme.rs
@@ -203,6 +203,8 @@ tokens! {
     // Dark body is Pebble 200 (~12:1 on the well), not Pebble 50, so
     // Regular and SemiBold stay distinct. Headings sit one step brighter.
     text_primary: 0xd1d2dc, 0x171717;
+    /// Sidebar text stays softer than body text in both themes.
+    text_sidebar: 0xbcbdc8, 0x45454b;
     text_heading: 0xe8e8ed, 0x171717;
     text_secondary: 0xbabccb, 0x525252;
     /// Captions. Light sits between neutral-500 and 600: neutral-400 was
@@ -242,6 +244,7 @@ tokens! {
     bg_sidebar_chrome: 0x1e1e24, 0xffffff;
     bg_sidebar_row_hover: 0x32323a, 0xe8e8ed;
     bg_sidebar_row_selected: 0x3a3a44, 0xd1d2dc;
+    bg_sidebar_row_selected_hover: 0x43434e, 0xc5c6d1;
 
     /// Display headings (Array face): pebble-300 on dark, pebble-800 on
     /// light, as the brand kit sets its section titles.