diff --git a/apps/macos/Sources/Clawdis/Bridge/BridgeServer.swift b/apps/macos/Sources/Clawdis/Bridge/BridgeServer.swift
index e3c536fd2..37a901729 100644
--- a/apps/macos/Sources/Clawdis/Bridge/BridgeServer.swift
+++ b/apps/macos/Sources/Clawdis/Bridge/BridgeServer.swift
@@ -307,6 +307,9 @@ enum BridgePairingApprover {
             """
             alert.addButton(withTitle: "Approve")
             alert.addButton(withTitle: "Reject")
+            if #available(macOS 11.0, *), alert.buttons.indices.contains(1) {
+                alert.buttons[1].hasDestructiveAction = true
+            }
             let resp = alert.runModal()
             cont.resume(returning: resp == .alertFirstButtonReturn)
         }
diff --git a/apps/macos/Sources/Clawdis/NodePairingApprovalPrompter.swift b/apps/macos/Sources/Clawdis/NodePairingApprovalPrompter.swift
index f09c752ad..d072205a3 100644
--- a/apps/macos/Sources/Clawdis/NodePairingApprovalPrompter.swift
+++ b/apps/macos/Sources/Clawdis/NodePairingApprovalPrompter.swift
@@ -80,6 +80,9 @@ final class NodePairingApprovalPrompter {
         alert.addButton(withTitle: "Approve")
         alert.addButton(withTitle: "Reject")
         alert.addButton(withTitle: "Later")
+        if #available(macOS 11.0, *), alert.buttons.indices.contains(1) {
+            alert.buttons[1].hasDestructiveAction = true
+        }
 
         let response = alert.runModal()
         Task { [weak self] in