diff --git a/clients/windows/src/app/connect.rs b/clients/windows/src/app/connect.rs
index f450bc05..98a71c77 100644
--- a/clients/windows/src/app/connect.rs
+++ b/clients/windows/src/app/connect.rs
@@ -36,7 +36,9 @@ pub(crate) fn initiate_waking(
     set_screen: &AsyncSetState<Screen>,
     set_status: &AsyncSetState<String>,
 ) {
-    crate::wol::wake(&target.mac, target.addr.parse().ok());
+    if ctx.settings.lock().unwrap().auto_wake {
+        crate::wol::wake(&target.mac, target.addr.parse().ok());
+    }
     initiate_opts(ctx, target, set_screen, set_status, true)
 }
 
@@ -291,9 +293,13 @@ fn connect_spawn(
                             *shared.target.lock().unwrap() = target.clone();
                             ss.call(Screen::Pair);
                         }
-                        Some((_, false)) if wake_on_fail => {
+                        Some((_, false))
+                            if wake_on_fail && ctx2.settings.lock().unwrap().auto_wake =>
+                        {
                             // The dial-first attempt to a non-advertising host failed — it
-                            // may genuinely be asleep. NOW wake and wait.
+                            // may genuinely be asleep. NOW wake and wait. Skipped entirely
+                            // when auto-wake is off: the wait is only worth showing if we
+                            // are actually sending magic packets to end it.
                             wake_and_connect(&ctx2, target.clone(), &ss, &st);
                         }
                         Some((msg, false)) => {
diff --git a/clients/windows/src/app/settings.rs b/clients/windows/src/app/settings.rs
index 11404eca..ccf2697b 100644
--- a/clients/windows/src/app/settings.rs
+++ b/clients/windows/src/app/settings.rs
@@ -162,7 +162,10 @@ fn described(control: impl Into<Element>, caption: &str) -> Element {
             .font_size(12.0)
             .foreground(ThemeRef::SecondaryText)
             .wrap()
-            .max_width(420.0),
+            .max_width(420.0)
+            // Stretch (the TextBlock default) CENTRES a MaxWidth-capped block in the leftover
+            // width — the caption must be pinned left or it drifts away from its control.
+            .horizontal_alignment(HorizontalAlignment::Left),
     ))
     .spacing(5.0)
     .into()
@@ -182,6 +185,7 @@ fn group(header: Option<&str>, fields: Vec<Element>, footer: Option<&str>) -> Ve
                 .font_size(12.0)
                 .foreground(ThemeRef::SecondaryText)
                 .wrap()
+                .horizontal_alignment(HorizontalAlignment::Left)
                 .margin(edges(2.0, 6.0, 0.0, 0.0))
                 .into(),
         );
@@ -267,6 +271,9 @@ pub(crate) fn settings_page(
     let comp_combo = setting_combo(ctx, "Host compositor", comp_names, comp_i, |s, i| {
         s.compositor = COMPOSITORS[i].0.to_string();
     });
+    let auto_wake_toggle = setting_toggle(ctx, "Auto-wake on connect", s.auto_wake, |s, on| {
+        s.auto_wake = on
+    });
     let fullscreen_toggle = setting_toggle(
         ctx,
         "Start streams fullscreen",
@@ -577,10 +584,19 @@ pub(crate) fn settings_page(
         _ => {
             let mut out = group(
                 Some("Session"),
-                vec![described(
-                    fullscreen_toggle,
-                    "Go fullscreen when a session starts; F11 or Alt+Enter switches back live.",
-                )],
+                vec![
+                    described(
+                        fullscreen_toggle,
+                        "Go fullscreen when a session starts; F11 or Alt+Enter switches back \
+                         live.",
+                    ),
+                    described(
+                        auto_wake_toggle,
+                        "Connecting to a saved host that\u{2019}s offline sends Wake-on-LAN and \
+                         waits for it to boot. Turn off if hosts behind a VPN look offline when \
+                         they aren\u{2019}t.",
+                    ),
+                ],
                 None,
             );
             out.extend(group(
@@ -634,9 +650,16 @@ pub(crate) fn settings_page(
     //
     // The content column (not the NavigationView — the sidebar must stay put) carries the
     // section-switch entrance: fade + slide-up from the root-driven tween.
-    let content = page(vec![vstack(groups).spacing(10.0).with_key(section).into()])
-        .opacity(progress)
-        .margin(edges(0.0, (1.0 - progress) * 22.0, 0.0, 0.0));
+    // No max-width cap here (unlike the other pages): the NavigationView already spends the
+    // left third on its pane, so a 640-wide column left the cards as a narrow ribbon.
+    let content = scroll_view(
+        vstack(groups)
+            .spacing(10.0)
+            .margin(edges(24.0, 20.0, 28.0, 40.0))
+            .with_key(section),
+    )
+    .opacity(progress)
+    .margin(edges(0.0, (1.0 - progress) * 22.0, 0.0, 0.0));
     NavigationView::new(items, content)
         .pane_title("Settings")
         .header(title)
diff --git a/crates/pf-client-core/src/trust.rs b/crates/pf-client-core/src/trust.rs
index 2d2c6f11..d6a2a3c8 100644
--- a/crates/pf-client-core/src/trust.rs
+++ b/crates/pf-client-core/src/trust.rs
@@ -526,6 +526,13 @@ pub struct Settings {
     /// Experimental: the game-library browser ("Browse library…" on saved cards) —
     /// mirrors the Apple client's "Show game library" toggle, default off.
     pub library_enabled: bool,
+    /// Send Wake-on-LAN before connecting to a saved host and wait for it to boot (the
+    /// Apple client's "Auto-wake on connect"). Default ON — that was the unconditional
+    /// behavior before this became a setting. Off is for hosts reached over a VPN, where
+    /// an offline-looking host is really just unreachable by broadcast and the wake +
+    /// wait only adds a delay.
+    #[serde(default = "default_true")]
+    pub auto_wake: bool,
     /// Match-window resolution policy (design/midstream-resolution-resize.md D1): the
     /// stream mode follows the session window — the connect asks for the window's pixel
     /// size and a mid-session resize renegotiates the host's virtual display + encoder
@@ -614,6 +621,7 @@ impl Default for Settings {
             stats_verbosity: None,
             fullscreen_on_stream: true,
             library_enabled: false,
+            auto_wake: true,
             match_window: false,
             last_window_w: 0,
             last_window_h: 0,