diff --git a/src/appcontext.cpp b/src/appcontext.cpp
index e6b36e4..293b11c 100644
--- a/src/appcontext.cpp
+++ b/src/appcontext.cpp
@@ -72,9 +72,9 @@ void AppContext::cachePairedDevices()
         if (!fileData) {
             continue;
         }
-        plist_print(fileData);
         const std::string wifiMacAddress =
             PlistNavigator(fileData)["WiFiMACAddress"].getString();
+        // FIXME: free ?
         // plist_free(fileData);
         bool isCompatible = !wifiMacAddress.empty();
         // TODO: !important invalidate expired pairing files
@@ -98,13 +98,11 @@ void AppContext::cachePairedDevices()
     auto conn = UsbmuxdConnection::default_new(0);
     if (conn.is_err()) {
         qDebug() << "ERROR: Failed to connect to usbmuxd!";
-        // return 1;
     }
 
     auto devices = conn.unwrap().get_devices();
     if (devices.is_err()) {
         qDebug() << "ERROR: Failed to get device list!";
-        // return 1;
     }
 
     for (const auto &device : devices.unwrap()) {
@@ -142,11 +140,14 @@ void AppContext::cachePairedDevices()
                             if (mac_address) {
                                 qDebug() << "Adding to cache"
                                          << QString::fromUtf8(mac_address);
+                                QString path = QString::fromStdString(
+                                    "/var/db/lockdown/" + udid.unwrap() +
+                                    ".plist");
+                                SettingsManager::sharedInstance()
+                                    ->setIdeviceDefaultPairingFile(
+                                        QString::fromUtf8(mac_address), path);
                                 m_pairingFileCache[QString::fromUtf8(
-                                    mac_address)] =
-                                    QString::fromStdString("/var/db/lockdown/" +
-                                                           udid.unwrap() +
-                                                           ".plist");
+                                    mac_address)] = path;
                                 free(mac_address);
                             }
                         }
@@ -155,12 +156,6 @@ void AppContext::cachePairedDevices()
                     }
                     free(plist_data);
                 }
-                // qDebug() << "Wireless device UDID:"
-                //          << QString::fromStdString(udid.unwrap())
-                //          << "Pairing file retrieval"
-                //          << (error == nullptr
-                //                  ? "succeeded"
-                //                  : QString::fromStdString(error->message));
                 // Clean up
                 // idevice_pairing_file_free(pairing_file.unwrap().raw());
             }
@@ -172,6 +167,19 @@ void AppContext::cachePairedDevices()
             }
         }
     }
+
+    // sometimes macOS doesn't find the network iDevice even tho we can connect
+    // if we know the ip address
+    QMap<QString, QString> cachedPairingFiles =
+        SettingsManager::sharedInstance()->getAllIdeviceDefaultPairingFiles();
+
+    for (const QString &mac : cachedPairingFiles.keys()) {
+        const QString path = cachedPairingFiles.value(mac);
+        qDebug() << "Using pairing file for MAC:" << mac
+                 << "cached from settings";
+        m_pairingFileCache[mac] = path;
+    }
+
 #endif
 }
 
@@ -181,6 +189,7 @@ void AppContext::addDevice(QString udid,
                            QString ipAddress)
 {
 
+    emit initStarted(udid);
     try {
         // iDescriptorInitDeviceResult initResult;
         auto initResult = std::make_shared<iDescriptorInitDeviceResult>();
diff --git a/src/appcontext.h b/src/appcontext.h
index 40f8c17..52cd902 100644
--- a/src/appcontext.h
+++ b/src/appcontext.h
@@ -75,6 +75,7 @@ signals:
     // only fired on wireless devices when we have no pairing file for them
     void noPairingFileForWirelessDevice(const QString &macAddress);
     void initFailed(const QString &udid);
+    void initStarted(const QString &udid);
 
     void systemSleepStarting();
     void systemWakeup();
diff --git a/src/networkdevicestoconnectwidget.cpp b/src/networkdevicestoconnectwidget.cpp
index cecd186..3c89b96 100644
--- a/src/networkdevicestoconnectwidget.cpp
+++ b/src/networkdevicestoconnectwidget.cpp
@@ -32,6 +32,7 @@
 #include <QLabel>
 #include <QPalette>
 #include <QPushButton>
+#include <QTimer>
 
 NetworkDeviceCard::NetworkDeviceCard(const NetworkDevice &device,
                                      QWidget *parent)
@@ -117,6 +118,25 @@ void NetworkDeviceCard::failed()
     });
 }
 
+void NetworkDeviceCard::noPairingFile()
+{
+    // TODO: add a button or hint to explain how to create a pairing file for
+    // this device
+    m_connectButton->setText("No pairing file");
+    m_connectButton->setEnabled(false);
+
+    QTimer::singleShot(5000, this, [this]() {
+        m_connectButton->setText("Connect");
+        m_connectButton->setEnabled(true);
+    });
+}
+
+void NetworkDeviceCard::initStarted()
+{
+    m_connectButton->setText("Connecting...");
+    m_connectButton->setEnabled(false);
+}
+
 NetworkDevicesToConnectWidget::NetworkDevicesToConnectWidget(QWidget *parent)
     : QWidget(parent)
 {
@@ -147,6 +167,8 @@ NetworkDevicesToConnectWidget::NetworkDevicesToConnectWidget(QWidget *parent)
             &NetworkDevicesToConnectWidget::onNoPairingFileForWirelessDevice);
     connect(AppContext::sharedInstance(), &AppContext::initFailed, this,
             &NetworkDevicesToConnectWidget::onDeviceInitFailed);
+    connect(AppContext::sharedInstance(), &AppContext::initStarted, this,
+            &NetworkDevicesToConnectWidget::onDeviceInitStarted);
 }
 
 NetworkDevicesToConnectWidget::~NetworkDevicesToConnectWidget()
@@ -284,7 +306,11 @@ void NetworkDevicesToConnectWidget::onWirelessDeviceRemoved(
 void NetworkDevicesToConnectWidget::onNoPairingFileForWirelessDevice(
     const QString &macAddress)
 {
-    // m_deviceCards.
+    NetworkDeviceCard *deviceCard = m_deviceCards[macAddress];
+    if (deviceCard) {
+        qDebug() << "Calling noPairingFile() on device card for" << macAddress;
+        deviceCard->noPairingFile();
+    }
 }
 
 // udid or mac address
@@ -295,4 +321,13 @@ void NetworkDevicesToConnectWidget::onDeviceInitFailed(const QString &udid)
         qDebug() << "Calling failed() on device card for" << udid;
         deviceCard->failed();
     }
+}
+
+void NetworkDevicesToConnectWidget::onDeviceInitStarted(const QString &udid)
+{
+    NetworkDeviceCard *deviceCard = m_deviceCards[udid];
+    if (deviceCard) {
+        qDebug() << "Calling initStarted() on device card for" << udid;
+        deviceCard->initStarted();
+    }
 }
\ No newline at end of file
diff --git a/src/networkdevicestoconnectwidget.h b/src/networkdevicestoconnectwidget.h
index 5536495..90959c9 100644
--- a/src/networkdevicestoconnectwidget.h
+++ b/src/networkdevicestoconnectwidget.h
@@ -20,6 +20,8 @@
 #ifndef NETWORKDEVICESTOCONNECTWIDGET_H
 #define NETWORKDEVICESTOCONNECTWIDGET_H
 
+#include "iDescriptor-ui.h"
+
 #ifdef __linux__
 #include "core/services/avahi/avahi_service.h"
 #else
@@ -45,6 +47,8 @@ private:
 
 public:
     void failed();
+    void noPairingFile();
+    void initStarted();
 };
 
 class NetworkDevicesToConnectWidget : public QWidget
@@ -60,6 +64,7 @@ private slots:
     void onWirelessDeviceRemoved(const QString &deviceName);
     void onNoPairingFileForWirelessDevice(const QString &macAddress);
     void onDeviceInitFailed(const QString &udid);
+    void onDeviceInitStarted(const QString &udid);
 
 private:
     void setupUI();
diff --git a/src/servicemanager.cpp b/src/servicemanager.cpp
index dc4a3d7..c2c089e 100644
--- a/src/servicemanager.cpp
+++ b/src/servicemanager.cpp
@@ -180,7 +180,7 @@ IdeviceFfiError *ServiceManager::mountImage(const iDescriptorDevice *device,
 void ServiceManager::getCableInfo(const iDescriptorDevice *device,
                                   plist_t &response)
 {
-    executeOperation<void>(
+    executeVoidOperation(
         device, [device, &response]() { _get_cable_info(device, response); });
 }
 
diff --git a/src/servicemanager.h b/src/servicemanager.h
index f1af482..541f9ca 100644
--- a/src/servicemanager.h
+++ b/src/servicemanager.h
@@ -146,6 +146,31 @@ public:
         operation();
     }
 
+    static void
+    executeVoidOperation(const iDescriptorDevice *device,
+                         std::function<void()> operation,
+                         std::optional<AfcClientHandle *> altAfc = std::nullopt)
+    {
+        if (!device) {
+            return;
+        }
+
+        std::lock_guard<std::recursive_mutex> lock(device->mutex);
+
+        // Double-check device is still valid after acquiring lock
+        if (!device->afcClient) {
+            return;
+        }
+
+        if (altAfc && !*altAfc) {
+            // altAfc was explicitly provided but is null, which is an
+            // invalid state.
+            return;
+        }
+
+        operation();
+    }
+
     static IdeviceFfiError *executeAfcOperation(
         const iDescriptorDevice *device,
         std::function<IdeviceFfiError *(AfcFileHandle *handle)> operation,
diff --git a/src/settingsmanager.cpp b/src/settingsmanager.cpp
index 65c688b..cbfee40 100644
--- a/src/settingsmanager.cpp
+++ b/src/settingsmanager.cpp
@@ -442,4 +442,37 @@ void SettingsManager::setShowV4L2(bool show)
     m_settings->setValue("showV4L2", show);
     m_settings->sync();
 }
+#endif
+
+/*
+    only needed on macOS because
+    we cannot read /var/db/lockdown without root perm
+    so caching must be implemented
+*/
+#ifdef __APPLE__
+void SettingsManager::setIdeviceDefaultPairingFile(const QString &macAddress,
+                                                   const QString &pairingFile)
+{
+    m_settings->setValue("_macos_idevice_" + macAddress, pairingFile);
+    m_settings->sync();
+}
+
+QString
+SettingsManager::getIdeviceDefaultPairingFile(const QString &macAddress) const
+{
+    return m_settings->value("_macos_idevice_" + macAddress, "").toString();
+}
+
+QMap<QString, QString> SettingsManager::getAllIdeviceDefaultPairingFiles() const
+{
+    QMap<QString, QString> macAddresses;
+    QStringList allKeys = m_settings->allKeys();
+    for (const QString &key : allKeys) {
+        if (key.startsWith("_macos_idevice_")) {
+            QString macAddress = key.mid(QString("_macos_idevice_").length());
+            macAddresses[macAddress] = m_settings->value(key, "").toString();
+        }
+    }
+    return macAddresses;
+}
 #endif
\ No newline at end of file
diff --git a/src/settingsmanager.h b/src/settingsmanager.h
index 372ddff..153282a 100644
--- a/src/settingsmanager.h
+++ b/src/settingsmanager.h
@@ -119,6 +119,14 @@ public:
     bool showV4L2() const;
     void setShowV4L2(bool show);
 #endif
+
+#ifdef __APPLE__
+    void setIdeviceDefaultPairingFile(const QString &macAddress,
+                                      const QString &pairingFile);
+    QString getIdeviceDefaultPairingFile(const QString &macAddress) const;
+    QMap<QString, QString> getAllIdeviceDefaultPairingFiles() const;
+#endif
+
 signals:
     void favoritePlacesChanged();
     void recentLocationsChanged();