diff --git a/CHANGELOG.md b/CHANGELOG.md
index 64bd5ea6e..58634d8c3 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -9,7 +9,7 @@
 - TUI: migrate key handling to the updated pi-tui Key matcher API.
 - macOS: prefer gateway config reads/writes in local mode (fall back to disk if the gateway is unavailable).
 - macOS: local gateway now connects via tailnet IP when bind mode is `tailnet`/`auto`.
-- macOS: Connections removes the sidebar toggle from the Settings toolbar to avoid overflow.
+- macOS: Connections settings now use a custom sidebar to avoid toolbar toggle issues, with rounded styling and full-width row hit targets.
 - macOS: drop deprecated `afterMs` from agent wait params to match gateway schema.
 - Auth: add OpenAI Codex OAuth support and migrate legacy oauth.json into auth.json.
 - Docs: clarify auth storage, migration, and OpenAI Codex OAuth onboarding.
diff --git a/apps/macos/Sources/Clawdbot/ConnectionsSettings+View.swift b/apps/macos/Sources/Clawdbot/ConnectionsSettings+View.swift
index 3fb1bc0fd..0527394fb 100644
--- a/apps/macos/Sources/Clawdbot/ConnectionsSettings+View.swift
+++ b/apps/macos/Sources/Clawdbot/ConnectionsSettings+View.swift
@@ -2,13 +2,11 @@ import SwiftUI
 
 extension ConnectionsSettings {
     var body: some View {
-        NavigationSplitView {
+        HStack(spacing: 0) {
             self.sidebar
-        } detail: {
             self.detail
         }
-        .navigationSplitViewStyle(.balanced)
-        .toolbar(removing: .sidebarToggle)
+        .frame(maxWidth: .infinity, maxHeight: .infinity, alignment: .topLeading)
         .onAppear {
             self.store.start()
             self.ensureSelection()
@@ -20,27 +18,30 @@ extension ConnectionsSettings {
     }
 
     private var sidebar: some View {
-        List(selection: self.$selectedProvider) {
-            if !self.enabledProviders.isEmpty {
-                Section("Configured") {
+        ScrollView {
+            LazyVStack(alignment: .leading, spacing: 8) {
+                if !self.enabledProviders.isEmpty {
+                    self.sidebarSectionHeader("Configured")
                     ForEach(self.enabledProviders) { provider in
                         self.sidebarRow(provider)
-                            .tag(provider)
                     }
                 }
-            }
 
-            if !self.availableProviders.isEmpty {
-                Section("Available") {
+                if !self.availableProviders.isEmpty {
+                    self.sidebarSectionHeader("Available")
                     ForEach(self.availableProviders) { provider in
                         self.sidebarRow(provider)
-                            .tag(provider)
                     }
                 }
             }
+            .padding(.vertical, 10)
+            .padding(.horizontal, 10)
         }
-        .listStyle(.sidebar)
-        .frame(minWidth: 220, idealWidth: 240, maxWidth: 280)
+        .frame(minWidth: 220, idealWidth: 240, maxWidth: 280, maxHeight: .infinity, alignment: .topLeading)
+        .background(
+            RoundedRectangle(cornerRadius: 12, style: .continuous)
+                .fill(Color(nsColor: .windowBackgroundColor)))
+        .clipShape(RoundedRectangle(cornerRadius: 12, style: .continuous))
     }
 
     private var detail: some View {
@@ -81,18 +82,41 @@ extension ConnectionsSettings {
     }
 
     private func sidebarRow(_ provider: ConnectionProvider) -> some View {
-        HStack(spacing: 8) {
-            Circle()
-                .fill(self.providerTint(provider))
-                .frame(width: 8, height: 8)
-            VStack(alignment: .leading, spacing: 2) {
-                Text(provider.title)
-                Text(self.providerSummary(provider))
-                    .font(.caption)
-                    .foregroundStyle(.secondary)
+        let isSelected = self.selectedProvider == provider
+        return Button {
+            self.selectedProvider = provider
+        } label: {
+            HStack(spacing: 8) {
+                Circle()
+                    .fill(self.providerTint(provider))
+                    .frame(width: 8, height: 8)
+                VStack(alignment: .leading, spacing: 2) {
+                    Text(provider.title)
+                    Text(self.providerSummary(provider))
+                        .font(.caption)
+                        .foregroundStyle(.secondary)
+                }
             }
+            .padding(.vertical, 4)
+            .padding(.horizontal, 6)
+            .frame(maxWidth: .infinity, alignment: .leading)
+            .background(isSelected ? Color.accentColor.opacity(0.18) : Color.clear)
+            .clipShape(RoundedRectangle(cornerRadius: 10, style: .continuous))
+            .background(Color.clear) // ensure full-width hit test area
+            .contentShape(Rectangle())
         }
-        .padding(.vertical, 4)
+        .frame(maxWidth: .infinity, alignment: .leading)
+        .buttonStyle(.plain)
+        .contentShape(Rectangle())
+    }
+
+    private func sidebarSectionHeader(_ title: String) -> some View {
+        Text(title)
+            .font(.caption.weight(.semibold))
+            .foregroundStyle(.secondary)
+            .textCase(.uppercase)
+            .padding(.horizontal, 4)
+            .padding(.top, 2)
     }
 
     private func detailHeader(for provider: ConnectionProvider) -> some View {
diff --git a/apps/macos/Sources/Clawdbot/SettingsRootView.swift b/apps/macos/Sources/Clawdbot/SettingsRootView.swift
index da53a3c5c..c99e88bab 100644
--- a/apps/macos/Sources/Clawdbot/SettingsRootView.swift
+++ b/apps/macos/Sources/Clawdbot/SettingsRootView.swift
@@ -75,7 +75,6 @@ struct SettingsRootView: View {
         }
         .padding(.horizontal, 28)
         .padding(.vertical, 22)
-        .background(SettingsToolbarCleaner())
         .frame(width: SettingsTab.windowWidth, height: SettingsTab.windowHeight, alignment: .topLeading)
         .frame(maxWidth: .infinity, maxHeight: .infinity, alignment: .topLeading)
         .onReceive(NotificationCenter.default.publisher(for: .clawdbotSelectSettingsTab)) { note in
diff --git a/apps/macos/Sources/Clawdbot/SettingsToolbarCleaner.swift b/apps/macos/Sources/Clawdbot/SettingsToolbarCleaner.swift
deleted file mode 100644
index a209c89c8..000000000
--- a/apps/macos/Sources/Clawdbot/SettingsToolbarCleaner.swift
+++ /dev/null
@@ -1,23 +0,0 @@
-import AppKit
-import SwiftUI
-
-struct SettingsToolbarCleaner: NSViewRepresentable {
-    func makeNSView(context: Context) -> NSView {
-        NSView()
-    }
-
-    func updateNSView(_ nsView: NSView, context: Context) {
-        DispatchQueue.main.async {
-            guard let toolbar = nsView.window?.toolbar else { return }
-            let items = toolbar.items
-            for (index, item) in items.enumerated().reversed() {
-                let isSidebarToggle =
-                    item.itemIdentifier == .toggleSidebar
-                        || item.itemIdentifier.rawValue == "com.apple.NSToolbarShowSidebarItem"
-                if isSidebarToggle {
-                    toolbar.removeItem(at: index)
-                }
-            }
-        }
-    }
-}