diff --git a/apps/macos/Sources/Clawdis/GeneralSettings.swift b/apps/macos/Sources/Clawdis/GeneralSettings.swift
index 6e47ea752..2d59ea29b 100644
--- a/apps/macos/Sources/Clawdis/GeneralSettings.swift
+++ b/apps/macos/Sources/Clawdis/GeneralSettings.swift
@@ -330,14 +330,34 @@ private enum RemoteStatus: Equatable {
 
 extension GeneralSettings {
     private var healthRow: some View {
-        HStack(spacing: 10) {
-            Circle()
-                .fill(self.healthStore.state.tint)
-                .frame(width: 10, height: 10)
-            Text(self.healthStore.summaryLine)
-                .font(.callout)
-                .lineLimit(1)
-                .frame(maxWidth: .infinity, alignment: .leading)
+        VStack(alignment: .leading, spacing: 6) {
+            HStack(spacing: 10) {
+                Circle()
+                    .fill(self.healthStore.state.tint)
+                    .frame(width: 10, height: 10)
+                Text(self.healthStore.summaryLine)
+                    .font(.callout)
+                    .frame(maxWidth: .infinity, alignment: .leading)
+            }
+
+            if let detail = self.healthStore.detailLine {
+                Text(detail)
+                    .font(.caption)
+                    .foregroundStyle(.secondary)
+                    .fixedSize(horizontal: false, vertical: true)
+            }
+
+            HStack(spacing: 10) {
+                Button("Retry now") {
+                    Task { await HealthStore.shared.refresh(onDemand: true) }
+                }
+                .disabled(self.healthStore.isRefreshing)
+
+                Button("Open logs") { self.revealLogs() }
+                    .buttonStyle(.link)
+                    .foregroundStyle(.secondary)
+            }
+            .font(.caption)
         }
     }
 
diff --git a/apps/macos/Sources/Clawdis/HealthStore.swift b/apps/macos/Sources/Clawdis/HealthStore.swift
index 7b576c3fd..d2492a930 100644
--- a/apps/macos/Sources/Clawdis/HealthStore.swift
+++ b/apps/macos/Sources/Clawdis/HealthStore.swift
@@ -149,6 +149,21 @@ final class HealthStore: ObservableObject {
         return "linked · auth \(auth) · socket ok"
     }
 
+    /// Short, human-friendly detail for the last failure, used in the UI.
+    var detailLine: String? {
+        if let error = self.lastError, !error.isEmpty {
+            let lower = error.lowercased()
+            if lower.contains("connection refused") {
+                return "The relay control port (127.0.0.1:18789) isn’t listening — restart Clawdis to bring it back."
+            }
+            if lower.contains("timeout") {
+                return "Timed out waiting for the control server; the relay may be crashed or still starting."
+            }
+            return error
+        }
+        return nil
+    }
+
     private func describeFailure(from snap: HealthSnapshot, fallback: String?) -> String {
         if !snap.web.linked {
             return "Not linked — run clawdis login"