diff --git a/App/App.csproj b/App/App.csproj
index bd36f38..ca3d3c9 100644
--- a/App/App.csproj
+++ b/App/App.csproj
@@ -17,6 +17,8 @@
         <LangVersion>preview</LangVersion>
         <!-- We have our own implementation of main with exception handling -->
         <DefineConstants>DISABLE_XAML_GENERATED_MAIN;DISABLE_XAML_GENERATED_BREAK_ON_UNHANDLED_EXCEPTION</DefineConstants>
+        <!-- Default version for debug builds, overridden during releases -->
+        <Version>0.1.0.0</Version>
 
         <AssemblyName>Coder Desktop</AssemblyName>
         <AssemblyTitle>Coder Desktop</AssemblyTitle>
@@ -24,6 +26,7 @@
         <Product>Coder Desktop</Product>
         <Copyright>© Coder Technologies Inc.</Copyright>
         <ApplicationIcon>coder.ico</ApplicationIcon>
+        <IncludeSourceRevisionInInformationalVersion>false</IncludeSourceRevisionInInformationalVersion>
     </PropertyGroup>
 
     <PropertyGroup Condition="$(Configuration) == 'Release'">
diff --git a/App/App.xaml.cs b/App/App.xaml.cs
index f4c05a2..a07af43 100644
--- a/App/App.xaml.cs
+++ b/App/App.xaml.cs
@@ -27,7 +27,7 @@
 
 namespace Coder.Desktop.App;
 
-public partial class App : Application, IDispatcherQueueManager
+public partial class App : Application, IDispatcherQueueManager, IDefaultNotificationHandler
 {
     private const string MutagenControllerConfigSection = "MutagenController";
     private const string UpdaterConfigSection = "Updater";
@@ -91,6 +91,7 @@ public App()
         services.AddSingleton<IAgentApiClientFactory, AgentApiClientFactory>();
 
         services.AddSingleton<IDispatcherQueueManager>(_ => this);
+        services.AddSingleton<IDefaultNotificationHandler>(_ => this);
         services.AddSingleton<ICredentialBackend>(_ =>
             new WindowsCredentialBackend(WindowsCredentialBackend.CoderCredentialsTargetName));
         services.AddSingleton<ICredentialManager, CredentialManager>();
@@ -335,4 +336,9 @@ public void RunInUiThread(DispatcherQueueHandler action)
         }
         dispatcherQueue.TryEnqueue(action);
     }
+
+    public void HandleNotificationActivation(IDictionary<string, string> _)
+    {
+        TrayWindow?.Tray_Open();
+    }
 }
diff --git a/App/Assets/coder_icon_32_dark.ico b/App/Assets/coder_icon_32_dark.ico
index 4eaa1bb..dd68b83 100644
Binary files a/App/Assets/coder_icon_32_dark.ico and b/App/Assets/coder_icon_32_dark.ico differ
diff --git a/App/Assets/coder_icon_32_light.ico b/App/Assets/coder_icon_32_light.ico
index 1fc307f..f4dc2a8 100644
Binary files a/App/Assets/coder_icon_32_light.ico and b/App/Assets/coder_icon_32_light.ico differ
diff --git a/App/Services/CredentialManager.cs b/App/Services/CredentialManager.cs
index 6868ae7..c8030c3 100644
--- a/App/Services/CredentialManager.cs
+++ b/App/Services/CredentialManager.cs
@@ -223,8 +223,9 @@ private async Task<CredentialModel> LoadCredentialsInner(CancellationToken ct)
             };
         }
 
-        // Grab the lock again so we can update the state.
-        using (await _opLock.LockAsync(ct))
+        // Grab the lock again so we can update the state. Don't use the CT
+        // here as it may have already been canceled.
+        using (await _opLock.LockAsync(TimeSpan.FromSeconds(5), CancellationToken.None))
         {
             // Prevent new LoadCredentials calls from returning this task.
             if (_loadCts != null)
@@ -242,11 +243,8 @@ private async Task<CredentialModel> LoadCredentialsInner(CancellationToken ct)
                 if (latestCreds is not null) return latestCreds;
             }
 
-            // If there aren't any latest credentials after a cancellation, we
-            // most likely timed out and should throw.
-            ct.ThrowIfCancellationRequested();
-
             UpdateState(model);
+            ct.ThrowIfCancellationRequested();
             return model;
         }
     }
diff --git a/App/Services/UserNotifier.cs b/App/Services/UserNotifier.cs
index 5ad8e38..27f924d 100644
--- a/App/Services/UserNotifier.cs
+++ b/App/Services/UserNotifier.cs
@@ -3,6 +3,7 @@
 using System.Collections.Generic;
 using System.Threading;
 using System.Threading.Tasks;
+using Coder.Desktop.App.Views;
 using Microsoft.Extensions.Logging;
 using Microsoft.Windows.AppNotifications;
 using Microsoft.Windows.AppNotifications.Builder;
@@ -14,23 +15,52 @@ public interface INotificationHandler
     public void HandleNotificationActivation(IDictionary<string, string> args);
 }
 
+// This interface is meant to protect the default
+// notification handler from being overriden by DI.
+public interface IDefaultNotificationHandler : INotificationHandler
+{
+}
+
 public interface IUserNotifier : INotificationHandler, IAsyncDisposable
 {
     public void RegisterHandler(string name, INotificationHandler handler);
     public void UnregisterHandler(string name);
 
     public Task ShowErrorNotification(string title, string message, CancellationToken ct = default);
-    public Task ShowActionNotification(string title, string message, string handlerName, IDictionary<string, string>? args = null, CancellationToken ct = default);
+    /// <summary>
+    /// This method allows to display a Windows-native notification with an action defined in
+    /// <paramref name="handlerName"/> and provided <paramref name="args"/>.
+    /// </summary>
+    /// <param name="title">Title of the notification.</param>
+    /// <param name="message">Message to be displayed in the notification body.</param>
+    /// <param name="handlerName">Handler should be e.g. <c>nameof(Handler)</c> where <c>Handler</c>
+    /// implements <see cref="Coder.Desktop.App.Services.INotificationHandler" />.
+    /// If handler is <c>null</c> the action will open Coder Desktop.</param>
+    /// <param name="args">Arguments to be provided to the handler when executing the action.</param>
+    public Task ShowActionNotification(string title, string message, string? handlerName, IDictionary<string, string>? args = null, CancellationToken ct = default);
 }
 
-public class UserNotifier(ILogger<UserNotifier> logger, IDispatcherQueueManager dispatcherQueueManager) : IUserNotifier
+public class UserNotifier : IUserNotifier
 {
     private const string CoderNotificationHandler = "CoderNotificationHandler";
+    private const string DefaultNotificationHandler = "DefaultNotificationHandler";
 
     private readonly AppNotificationManager _notificationManager = AppNotificationManager.Default;
+    private readonly ILogger<UserNotifier> _logger;
+    private readonly IDispatcherQueueManager _dispatcherQueueManager;
 
     private ConcurrentDictionary<string, INotificationHandler> Handlers { get; } = new();
 
+    public UserNotifier(ILogger<UserNotifier> logger, IDispatcherQueueManager dispatcherQueueManager,
+        IDefaultNotificationHandler notificationHandler)
+    {
+        _logger = logger;
+        _dispatcherQueueManager = dispatcherQueueManager;
+        var defaultHandlerAdded = Handlers.TryAdd(DefaultNotificationHandler, notificationHandler);
+        if (!defaultHandlerAdded)
+            throw new Exception($"UserNotifier failed to be initialized with {nameof(DefaultNotificationHandler)}");
+    }
+
     public ValueTask DisposeAsync()
     {
         return ValueTask.CompletedTask;
@@ -50,6 +80,8 @@ public void RegisterHandler(string name, INotificationHandler handler)
 
     public void UnregisterHandler(string name)
     {
+        if (name == nameof(DefaultNotificationHandler))
+            throw new InvalidOperationException($"You cannot remove '{name}'.");
         if (!Handlers.TryRemove(name, out _))
             throw new InvalidOperationException($"No handler with the name '{name}' is registered.");
     }
@@ -61,8 +93,11 @@ public Task ShowErrorNotification(string title, string message, CancellationToke
         return Task.CompletedTask;
     }
 
-    public Task ShowActionNotification(string title, string message, string handlerName, IDictionary<string, string>? args = null, CancellationToken ct = default)
+    public Task ShowActionNotification(string title, string message, string? handlerName, IDictionary<string, string>? args = null, CancellationToken ct = default)
     {
+        if (handlerName == null)
+            handlerName = nameof(DefaultNotificationHandler); // Use default handler if no handler name is provided
+
         if (!Handlers.TryGetValue(handlerName, out _))
             throw new InvalidOperationException($"No action handler with the name '{handlerName}' is registered.");
 
@@ -90,11 +125,11 @@ public void HandleNotificationActivation(IDictionary<string, string> args)
 
         if (!Handlers.TryGetValue(handlerName, out var handler))
         {
-            logger.LogWarning("no action handler '{HandlerName}' found for notification activation, ignoring", handlerName);
+            _logger.LogWarning("no action handler '{HandlerName}' found for notification activation, ignoring", handlerName);
             return;
         }
 
-        dispatcherQueueManager.RunInUiThread(() =>
+        _dispatcherQueueManager.RunInUiThread(() =>
         {
             try
             {
@@ -102,7 +137,7 @@ public void HandleNotificationActivation(IDictionary<string, string> args)
             }
             catch (Exception ex)
             {
-                logger.LogWarning(ex, "could not handle activation for notification with handler '{HandlerName}", handlerName);
+                _logger.LogWarning(ex, "could not handle activation for notification with handler '{HandlerName}", handlerName);
             }
         });
     }
diff --git a/App/ViewModels/AgentViewModel.cs b/App/ViewModels/AgentViewModel.cs
index cd5907b..0cf2651 100644
--- a/App/ViewModels/AgentViewModel.cs
+++ b/App/ViewModels/AgentViewModel.cs
@@ -1,11 +1,3 @@
-using System;
-using System.Collections.Generic;
-using System.Collections.ObjectModel;
-using System.ComponentModel;
-using System.Linq;
-using System.Threading;
-using System.Threading.Tasks;
-using Windows.ApplicationModel.DataTransfer;
 using Coder.Desktop.App.Services;
 using Coder.Desktop.App.Utils;
 using Coder.Desktop.CoderSdk;
@@ -18,15 +10,24 @@
 using Microsoft.UI.Xaml;
 using Microsoft.UI.Xaml.Controls;
 using Microsoft.UI.Xaml.Controls.Primitives;
+using System;
+using System.Collections.Generic;
+using System.Collections.ObjectModel;
+using System.ComponentModel;
+using System.Linq;
+using System.Text;
+using System.Threading;
+using System.Threading.Tasks;
+using System.Xml.Linq;
+using Windows.ApplicationModel.DataTransfer;
 
 namespace Coder.Desktop.App.ViewModels;
 
 public interface IAgentViewModelFactory
 {
     public AgentViewModel Create(IAgentExpanderHost expanderHost, Uuid id, string fullyQualifiedDomainName,
-        string hostnameSuffix,
-        AgentConnectionStatus connectionStatus, Uri dashboardBaseUrl, string? workspaceName);
-
+        string hostnameSuffix, AgentConnectionStatus connectionStatus, Uri dashboardBaseUrl,
+        string? workspaceName, bool? didP2p, string? preferredDerp, TimeSpan? latency, TimeSpan? preferredDerpLatency, DateTime? lastHandshake);
     public AgentViewModel CreateDummy(IAgentExpanderHost expanderHost, Uuid id,
         string hostnameSuffix,
         AgentConnectionStatus connectionStatus, Uri dashboardBaseUrl, string workspaceName);
@@ -40,7 +41,9 @@ public class AgentViewModelFactory(
 {
     public AgentViewModel Create(IAgentExpanderHost expanderHost, Uuid id, string fullyQualifiedDomainName,
         string hostnameSuffix,
-        AgentConnectionStatus connectionStatus, Uri dashboardBaseUrl, string? workspaceName)
+        AgentConnectionStatus connectionStatus, Uri dashboardBaseUrl,
+        string? workspaceName, bool? didP2p, string? preferredDerp, TimeSpan? latency, TimeSpan? preferredDerpLatency,
+        DateTime? lastHandshake)
     {
         return new AgentViewModel(childLogger, coderApiClientFactory, credentialManager, agentAppViewModelFactory,
             expanderHost, id)
@@ -51,6 +54,11 @@ public AgentViewModel Create(IAgentExpanderHost expanderHost, Uuid id, string fu
             ConnectionStatus = connectionStatus,
             DashboardBaseUrl = dashboardBaseUrl,
             WorkspaceName = workspaceName,
+            DidP2p = didP2p,
+            PreferredDerp = preferredDerp,
+            Latency = latency,
+            PreferredDerpLatency = preferredDerpLatency,
+            LastHandshake = lastHandshake,
         };
     }
 
@@ -73,10 +81,25 @@ public AgentViewModel CreateDummy(IAgentExpanderHost expanderHost, Uuid id,
 
 public enum AgentConnectionStatus
 {
-    Green,
-    Yellow,
-    Red,
-    Gray,
+    Healthy,
+    Connecting,
+    Unhealthy,
+    NoRecentHandshake,
+    Offline
+}
+
+public static class AgentConnectionStatusExtensions
+{
+    public static string ToDisplayString(this AgentConnectionStatus status) =>
+        status switch
+        {
+            AgentConnectionStatus.Healthy => "Healthy",
+            AgentConnectionStatus.Connecting => "Connecting",
+            AgentConnectionStatus.Unhealthy => "High latency",
+            AgentConnectionStatus.NoRecentHandshake => "No recent handshake",
+            AgentConnectionStatus.Offline => "Offline",
+            _ => status.ToString()
+        };
 }
 
 public partial class AgentViewModel : ObservableObject, IModelUpdateable<AgentViewModel>
@@ -160,6 +183,7 @@ public string FullyQualifiedDomainName
     [ObservableProperty]
     [NotifyPropertyChangedFor(nameof(ShowExpandAppsMessage))]
     [NotifyPropertyChangedFor(nameof(ExpandAppsMessage))]
+    [NotifyPropertyChangedFor(nameof(ConnectionTooltip))]
     public required partial AgentConnectionStatus ConnectionStatus { get; set; }
 
     [ObservableProperty]
@@ -182,6 +206,77 @@ public string FullyQualifiedDomainName
     [NotifyPropertyChangedFor(nameof(ExpandAppsMessage))]
     public partial bool AppFetchErrored { get; set; } = false;
 
+    [ObservableProperty]
+    [NotifyPropertyChangedFor(nameof(ConnectionTooltip))]
+    public partial bool? DidP2p { get; set; } = false;
+
+    [ObservableProperty]
+    [NotifyPropertyChangedFor(nameof(ConnectionTooltip))]
+    public partial string? PreferredDerp { get; set; } = null;
+
+    [ObservableProperty]
+    [NotifyPropertyChangedFor(nameof(ConnectionTooltip))]
+    public partial TimeSpan? Latency { get; set; } = null;
+
+    [ObservableProperty]
+    [NotifyPropertyChangedFor(nameof(ConnectionTooltip))]
+    public partial TimeSpan? PreferredDerpLatency { get; set; } = null;
+
+    [ObservableProperty]
+    [NotifyPropertyChangedFor(nameof(ConnectionTooltip))]
+    public partial DateTime? LastHandshake { get; set; } = null;
+
+    public string ConnectionTooltip
+    {
+        get
+        {
+            var description = new StringBuilder();
+            var highLatencyWarning = ConnectionStatus == AgentConnectionStatus.Unhealthy ? $"({AgentConnectionStatus.Unhealthy.ToDisplayString()})" : "";
+
+            if (DidP2p != null && DidP2p.Value && Latency != null)
+            {
+                description.Append($"""
+                You're connected peer-to-peer. {highLatencyWarning}
+
+                You ↔ {Latency.Value.Milliseconds} ms ↔ {WorkspaceName}
+                """
+                );
+            }
+            else if (Latency != null)
+            {
+                description.Append($"""
+                You're connected through a DERP relay. {highLatencyWarning}
+                We'll switch over to peer-to-peer when available.
+
+                Total latency: {Latency.Value.Milliseconds} ms
+                """
+                );
+
+                if (PreferredDerpLatency != null)
+                {
+                    description.Append($"\nYou ↔ {PreferredDerp}: {PreferredDerpLatency.Value.Milliseconds} ms");
+
+                    var derpToWorkspaceEstimatedLatency = Latency - PreferredDerpLatency;
+
+                    // Guard against negative values if the two readings were taken at different times
+                    if (derpToWorkspaceEstimatedLatency > TimeSpan.Zero)
+                    {
+                        description.Append($"\n{PreferredDerp} ms ↔ {WorkspaceName}: {derpToWorkspaceEstimatedLatency.Value.Milliseconds} ms");
+                    }
+                }
+            }
+            else
+            {
+                description.Append(ConnectionStatus.ToDisplayString());
+            }
+            if (LastHandshake != null)
+                description.Append($"\n\nLast handshake: {LastHandshake?.ToString()}");
+
+            return description.ToString().TrimEnd('\n', ' '); ;
+        }
+    }
+
+
     // We only show 6 apps max, which fills the entire width of the tray
     // window.
     public IEnumerable<AgentAppViewModel> VisibleApps => Apps.Count > MaxAppsPerRow ? Apps.Take(MaxAppsPerRow) : Apps;
@@ -192,7 +287,7 @@ public string? ExpandAppsMessage
     {
         get
         {
-            if (ConnectionStatus == AgentConnectionStatus.Gray)
+            if (ConnectionStatus == AgentConnectionStatus.Offline)
                 return "Your workspace is offline.";
             if (FetchingApps && Apps.Count == 0)
                 // Don't show this message if we have any apps already. When
@@ -285,6 +380,16 @@ public bool TryApplyChanges(AgentViewModel model)
             DashboardBaseUrl = model.DashboardBaseUrl;
         if (WorkspaceName != model.WorkspaceName)
             WorkspaceName = model.WorkspaceName;
+        if (DidP2p != model.DidP2p)
+            DidP2p = model.DidP2p;
+        if (PreferredDerp != model.PreferredDerp)
+            PreferredDerp = model.PreferredDerp;
+        if (Latency != model.Latency)
+            Latency = model.Latency;
+        if (PreferredDerpLatency != model.PreferredDerpLatency)
+            PreferredDerpLatency = model.PreferredDerpLatency;
+        if (LastHandshake != model.LastHandshake)
+            LastHandshake = model.LastHandshake;
 
         // Apps are not set externally.
 
@@ -307,7 +412,7 @@ public void SetExpanded(bool expanded)
 
     partial void OnConnectionStatusChanged(AgentConnectionStatus oldValue, AgentConnectionStatus newValue)
     {
-        if (IsExpanded && newValue is not AgentConnectionStatus.Gray) FetchApps();
+        if (IsExpanded && newValue is not AgentConnectionStatus.Offline) FetchApps();
     }
 
     private void FetchApps()
@@ -316,7 +421,7 @@ private void FetchApps()
         FetchingApps = true;
 
         // If the workspace is off, then there's no agent and there's no apps.
-        if (ConnectionStatus == AgentConnectionStatus.Gray)
+        if (ConnectionStatus == AgentConnectionStatus.Offline)
         {
             FetchingApps = false;
             Apps.Clear();
diff --git a/App/ViewModels/TrayWindowViewModel.cs b/App/ViewModels/TrayWindowViewModel.cs
index 8540453..f57947d 100644
--- a/App/ViewModels/TrayWindowViewModel.cs
+++ b/App/ViewModels/TrayWindowViewModel.cs
@@ -3,6 +3,7 @@
 using System.Collections.ObjectModel;
 using System.ComponentModel;
 using System.Linq;
+using System.Security.Principal;
 using System.Threading.Tasks;
 using Coder.Desktop.App.Models;
 using Coder.Desktop.App.Services;
@@ -29,6 +30,7 @@ public partial class TrayWindowViewModel : ObservableObject, IAgentExpanderHost
 {
     private const int MaxAgents = 5;
     private const string DefaultDashboardUrl = "https://coder.com";
+    private readonly TimeSpan HealthyPingThreshold = TimeSpan.FromMilliseconds(150);
 
     private readonly IServiceProvider _services;
     private readonly IRpcController _rpcController;
@@ -222,10 +224,28 @@ private void UpdateFromRpcModel(RpcModel rpcModel)
             if (string.IsNullOrWhiteSpace(fqdn))
                 continue;
 
-            var lastHandshakeAgo = DateTime.UtcNow.Subtract(agent.LastHandshake.ToDateTime());
-            var connectionStatus = lastHandshakeAgo < TimeSpan.FromMinutes(5)
-                ? AgentConnectionStatus.Green
-                : AgentConnectionStatus.Yellow;
+            var connectionStatus = AgentConnectionStatus.Healthy;
+
+            if (agent.LastHandshake != null && agent.LastHandshake.ToDateTime() != default && agent.LastHandshake.ToDateTime() < DateTime.UtcNow)
+            {
+                // For compatibility with older deployments, we assume that if the
+                // last ping is null, the agent is healthy.
+                var isLatencyAcceptable = agent.LastPing == null || agent.LastPing.Latency.ToTimeSpan() < HealthyPingThreshold;
+
+                var lastHandshakeAgo = DateTime.UtcNow.Subtract(agent.LastHandshake.ToDateTime());
+
+                if (lastHandshakeAgo > TimeSpan.FromMinutes(5))
+                    connectionStatus = AgentConnectionStatus.NoRecentHandshake;
+                else if (!isLatencyAcceptable)
+                    connectionStatus = AgentConnectionStatus.Unhealthy;
+            }
+            else
+            {
+                // If the last handshake is not correct (null, default or in the future),
+                // we assume the agent is connecting (yellow status icon).
+                connectionStatus = AgentConnectionStatus.Connecting;
+            }
+
             workspacesWithAgents.Add(agent.WorkspaceId);
             var workspace = rpcModel.Workspaces.FirstOrDefault(w => w.Id == agent.WorkspaceId);
 
@@ -236,7 +256,12 @@ private void UpdateFromRpcModel(RpcModel rpcModel)
                 _hostnameSuffixGetter.GetCachedSuffix(),
                 connectionStatus,
                 credentialModel.CoderUrl,
-                workspace?.Name));
+                workspace?.Name,
+                agent.LastPing?.DidP2P,
+                agent.LastPing?.PreferredDerp,
+                agent.LastPing?.Latency?.ToTimeSpan(),
+                agent.LastPing?.PreferredDerpLatency?.ToTimeSpan(),
+                agent.LastHandshake != null && agent.LastHandshake.ToDateTime() != default ? agent.LastHandshake?.ToDateTime() : null));
         }
 
         // For every stopped workspace that doesn't have any agents, add a
@@ -253,7 +278,7 @@ private void UpdateFromRpcModel(RpcModel rpcModel)
                 // conflict with any agent IDs.
                 uuid,
                 _hostnameSuffixGetter.GetCachedSuffix(),
-                AgentConnectionStatus.Gray,
+                AgentConnectionStatus.Offline,
                 credentialModel.CoderUrl,
                 workspace.Name));
         }
@@ -268,7 +293,7 @@ private void UpdateFromRpcModel(RpcModel rpcModel)
 
         if (Agents.Count < MaxAgents) ShowAllAgents = false;
 
-        var firstOnlineAgent = agents.FirstOrDefault(a => a.ConnectionStatus != AgentConnectionStatus.Gray);
+        var firstOnlineAgent = agents.FirstOrDefault(a => a.ConnectionStatus != AgentConnectionStatus.Offline);
         if (firstOnlineAgent is null)
             _hasExpandedAgent = false;
         if (!_hasExpandedAgent && firstOnlineAgent is not null)
@@ -433,7 +458,7 @@ private static bool ShouldShowDummy(Workspace workspace)
             case Workspace.Types.Status.Stopping:
             case Workspace.Types.Status.Stopped:
                 return true;
-            // TODO: should we include and show a different color than Gray for workspaces that are
+            // TODO: should we include and show a different color than Offline for workspaces that are
             // failed, canceled or deleting?
             default:
                 return false;
diff --git a/App/ViewModels/UpdaterUpdateAvailableViewModel.cs b/App/ViewModels/UpdaterUpdateAvailableViewModel.cs
index 9fd6dd9..4d3c692 100644
--- a/App/ViewModels/UpdaterUpdateAvailableViewModel.cs
+++ b/App/ViewModels/UpdaterUpdateAvailableViewModel.cs
@@ -4,10 +4,12 @@
 using System.IO;
 using System.Linq;
 using System.Threading.Tasks;
+using Coder.Desktop.App.Services;
 using CommunityToolkit.Mvvm.ComponentModel;
 using Microsoft.Extensions.Logging;
 using Microsoft.UI.Xaml;
 using Microsoft.UI.Xaml.Controls;
+using Microsoft.Web.WebView2.Core;
 using NetSparkleUpdater;
 using NetSparkleUpdater.Enums;
 using NetSparkleUpdater.Events;
@@ -174,8 +176,18 @@ public async Task Changelog_Loaded(object sender, RoutedEventArgs e)
         if (sender is not WebView2 webView)
             return;
 
-        // Start the engine.
-        await webView.EnsureCoreWebView2Async();
+        // Start the engine with a custom user data folder. The default for
+        // unpackaged WinUI 3 apps is to write to a subfolder in the app's
+        // install directory, which is Program Files by default and not
+        // writeable by the user.
+        var userDataFolder = Path.Join(SettingsManagerUtils.AppSettingsDirectory(), "WebView2");
+        _logger.LogDebug("Creating WebView2 user data folder at {UserDataFolder}", userDataFolder);
+        Directory.CreateDirectory(userDataFolder);
+        var env = await CoreWebView2Environment.CreateWithOptionsAsync(
+            null,
+            userDataFolder,
+            new CoreWebView2EnvironmentOptions());
+        await webView.EnsureCoreWebView2Async(env);
 
         // Disable unwanted features.
         var settings = webView.CoreWebView2.Settings;
diff --git a/App/Views/Pages/TrayWindowMainPage.xaml b/App/Views/Pages/TrayWindowMainPage.xaml
index 80f557d..3cc21de 100644
--- a/App/Views/Pages/TrayWindowMainPage.xaml
+++ b/App/Views/Pages/TrayWindowMainPage.xaml
@@ -137,22 +137,27 @@
                                             x:Key="StatusColor"
                                             SelectedKey="{x:Bind Path=ConnectionStatus, Mode=OneWay}">
 
-                                            <converters:StringToBrushSelectorItem>
+                                            <converters:StringToBrushSelectorItem Key="Offline">
                                                 <converters:StringToBrushSelectorItem.Value>
                                                     <SolidColorBrush Color="#8e8e93" />
                                                 </converters:StringToBrushSelectorItem.Value>
                                             </converters:StringToBrushSelectorItem>
-                                            <converters:StringToBrushSelectorItem Key="Red">
+                                            <converters:StringToBrushSelectorItem Key="NoRecentHandshake">
                                                 <converters:StringToBrushSelectorItem.Value>
                                                     <SolidColorBrush Color="#ff3b30" />
                                                 </converters:StringToBrushSelectorItem.Value>
                                             </converters:StringToBrushSelectorItem>
-                                            <converters:StringToBrushSelectorItem Key="Yellow">
+                                            <converters:StringToBrushSelectorItem Key="Unhealthy">
                                                 <converters:StringToBrushSelectorItem.Value>
                                                     <SolidColorBrush Color="#ffcc01" />
                                                 </converters:StringToBrushSelectorItem.Value>
                                             </converters:StringToBrushSelectorItem>
-                                            <converters:StringToBrushSelectorItem Key="Green">
+                                            <converters:StringToBrushSelectorItem Key="Connecting">
+                                                <converters:StringToBrushSelectorItem.Value>
+                                                    <SolidColorBrush Color="#ffcc01" />
+                                                </converters:StringToBrushSelectorItem.Value>
+                                            </converters:StringToBrushSelectorItem>
+                                            <converters:StringToBrushSelectorItem Key="Healthy">
                                                 <converters:StringToBrushSelectorItem.Value>
                                                     <SolidColorBrush Color="#34c759" />
                                                 </converters:StringToBrushSelectorItem.Value>
@@ -189,6 +194,7 @@
                                         HorizontalAlignment="Right"
                                         VerticalAlignment="Center"
                                         Height="14" Width="14"
+                                        ToolTipService.ToolTip="{x:Bind ConnectionTooltip, Mode=OneWay}"
                                         Margin="0,1,0,0">
 
                                         <Ellipse
diff --git a/App/Views/TrayWindow.xaml.cs b/App/Views/TrayWindow.xaml.cs
index 6131e25..de944c2 100644
--- a/App/Views/TrayWindow.xaml.cs
+++ b/App/Views/TrayWindow.xaml.cs
@@ -5,17 +5,19 @@
 using Coder.Desktop.App.Views.Pages;
 using CommunityToolkit.Mvvm.Input;
 using Microsoft.UI;
-using Microsoft.UI.Input;
 using Microsoft.UI.Windowing;
 using Microsoft.UI.Xaml;
 using Microsoft.UI.Xaml.Controls;
 using Microsoft.UI.Xaml.Media.Animation;
 using System;
+using System.Collections.Generic;
 using System.Runtime.InteropServices;
+using System.Threading;
 using System.Threading.Tasks;
 using Windows.Graphics;
 using Windows.System;
 using Windows.UI.Core;
+using Microsoft.UI.Input;
 using WinRT.Interop;
 using WindowActivatedEventArgs = Microsoft.UI.Xaml.WindowActivatedEventArgs;
 
@@ -33,25 +35,29 @@ public sealed partial class TrayWindow : Window
     private int _lastWindowHeight;
     private Storyboard? _currentSb;
 
+    private VpnLifecycle curVpnLifecycle = VpnLifecycle.Stopped;
+    private RpcLifecycle curRpcLifecycle = RpcLifecycle.Disconnected;
+
     private readonly IRpcController _rpcController;
     private readonly ICredentialManager _credentialManager;
-    private readonly ISyncSessionController _syncSessionController;
     private readonly IUpdateController _updateController;
+    private readonly IUserNotifier _userNotifier;
     private readonly TrayWindowLoadingPage _loadingPage;
     private readonly TrayWindowDisconnectedPage _disconnectedPage;
     private readonly TrayWindowLoginRequiredPage _loginRequiredPage;
     private readonly TrayWindowMainPage _mainPage;
 
-    public TrayWindow(IRpcController rpcController, ICredentialManager credentialManager,
-        ISyncSessionController syncSessionController, IUpdateController updateController,
+    public TrayWindow(
+        IRpcController rpcController, ICredentialManager credentialManager,
+        IUpdateController updateController, IUserNotifier userNotifier,
         TrayWindowLoadingPage loadingPage,
         TrayWindowDisconnectedPage disconnectedPage, TrayWindowLoginRequiredPage loginRequiredPage,
         TrayWindowMainPage mainPage)
     {
         _rpcController = rpcController;
         _credentialManager = credentialManager;
-        _syncSessionController = syncSessionController;
         _updateController = updateController;
+        _userNotifier = userNotifier;
         _loadingPage = loadingPage;
         _disconnectedPage = disconnectedPage;
         _loginRequiredPage = loginRequiredPage;
@@ -64,9 +70,7 @@ public TrayWindow(IRpcController rpcController, ICredentialManager credentialMan
 
         _rpcController.StateChanged += RpcController_StateChanged;
         _credentialManager.CredentialsChanged += CredentialManager_CredentialsChanged;
-        _syncSessionController.StateChanged += SyncSessionController_StateChanged;
-        SetPageByState(_rpcController.GetState(), _credentialManager.GetCachedCredentials(),
-            _syncSessionController.GetState());
+        SetPageByState(_rpcController.GetState(), _credentialManager.GetCachedCredentials());
 
         // Setting these directly in the .xaml doesn't seem to work for whatever reason.
         TrayIcon.OpenCommand = Tray_OpenCommand;
@@ -117,8 +121,7 @@ public TrayWindow(IRpcController rpcController, ICredentialManager credentialMan
         };
     }
 
-    private void SetPageByState(RpcModel rpcModel, CredentialModel credentialModel,
-        SyncSessionControllerStateModel syncSessionModel)
+    private void SetPageByState(RpcModel rpcModel, CredentialModel credentialModel)
     {
         if (credentialModel.State == CredentialState.Unknown)
         {
@@ -142,19 +145,62 @@ private void SetPageByState(RpcModel rpcModel, CredentialModel credentialModel,
         }
     }
 
-    private void RpcController_StateChanged(object? _, RpcModel model)
+    /// <summary>
+    /// This method is called when the state changes, but we don't want to notify
+    /// the user if the state hasn't changed.
+    /// </summary>
+    /// <param name="rpcModel"></param>
+    private void MaybeNotifyUser(RpcModel rpcModel)
     {
-        SetPageByState(model, _credentialManager.GetCachedCredentials(), _syncSessionController.GetState());
+        var isRpcLifecycleChanged = rpcModel.RpcLifecycle == RpcLifecycle.Disconnected && curRpcLifecycle != rpcModel.RpcLifecycle;
+        var isVpnLifecycleChanged = (rpcModel.VpnLifecycle == VpnLifecycle.Started || rpcModel.VpnLifecycle == VpnLifecycle.Stopped) && curVpnLifecycle != rpcModel.VpnLifecycle;
+
+        if (!isRpcLifecycleChanged && !isVpnLifecycleChanged)
+        {
+            return;
+        }
+
+        var oldRpcLifeycle = curRpcLifecycle;
+        var oldVpnLifecycle = curVpnLifecycle;
+        curRpcLifecycle = rpcModel.RpcLifecycle;
+        curVpnLifecycle = rpcModel.VpnLifecycle;
+
+        var messages = new List<string>();
+
+        if (oldRpcLifeycle != RpcLifecycle.Disconnected && curRpcLifecycle == RpcLifecycle.Disconnected)
+        {
+            messages.Add("Disconnected from Coder background service.");
+        }
+
+        if (oldVpnLifecycle != curVpnLifecycle)
+        {
+            switch (curVpnLifecycle)
+            {
+                case VpnLifecycle.Started:
+                    messages.Add("Coder Connect started.");
+                    break;
+                case VpnLifecycle.Stopped:
+                    messages.Add("Coder Connect stopped.");
+                    break;
+            }
+        }
+
+        if (messages.Count == 0) return;
+        if (_aw.IsVisible) return;
+
+        var message = string.Join(" ", messages);
+        _userNotifier.ShowActionNotification(message, string.Empty, null, null, CancellationToken.None);
     }
 
-    private void CredentialManager_CredentialsChanged(object? _, CredentialModel model)
+    private void RpcController_StateChanged(object? _, RpcModel model)
     {
-        SetPageByState(_rpcController.GetState(), model, _syncSessionController.GetState());
+        SetPageByState(model, _credentialManager.GetCachedCredentials());
+        MaybeNotifyUser(model);
     }
 
-    private void SyncSessionController_StateChanged(object? _, SyncSessionControllerStateModel model)
+    private void CredentialManager_CredentialsChanged(object? _, CredentialModel model)
     {
-        SetPageByState(_rpcController.GetState(), _credentialManager.GetCachedCredentials(), model);
+        SetPageByState(_rpcController.GetState(), model);
     }
 
     // Sadly this is necessary because Window.Content.SizeChanged doesn't
@@ -297,7 +343,7 @@ private void Window_Activated(object sender, WindowActivatedEventArgs e)
     }
 
     [RelayCommand]
-    private void Tray_Open()
+    public void Tray_Open()
     {
         MoveResizeAndActivate();
     }
diff --git a/App/coder.ico b/App/coder.ico
index e13ad3b..b80bdc2 100644
Binary files a/App/coder.ico and b/App/coder.ico differ
diff --git a/Tests.App/Services/CredentialManagerTest.cs b/Tests.App/Services/CredentialManagerTest.cs
index 9f1b0df..3f9c4cb 100644
--- a/Tests.App/Services/CredentialManagerTest.cs
+++ b/Tests.App/Services/CredentialManagerTest.cs
@@ -317,7 +317,10 @@ public async Task SetDuringLoad(CancellationToken ct)
         var loadTask = manager.LoadCredentials(ct);
         // Then fully perform a set.
         await manager.SetCredentials(TestServerUrl, TestApiToken, ct).WaitAsync(ct);
-        // The load should have been cancelled.
-        Assert.ThrowsAsync<TaskCanceledException>(() => loadTask);
+
+        // The load should complete with the new valid credentials
+        var result = await loadTask;
+        Assert.That(result.State, Is.EqualTo(CredentialState.Valid));
+        Assert.That(result.CoderUrl?.ToString(), Is.EqualTo(TestServerUrl));
     }
 }
diff --git a/Vpn.Proto/vpn.proto b/Vpn.Proto/vpn.proto
index bace7e0..11a481c 100644
--- a/Vpn.Proto/vpn.proto
+++ b/Vpn.Proto/vpn.proto
@@ -3,6 +3,7 @@ option go_package = "github.com/coder/coder/v2/vpn";
 option csharp_namespace = "Coder.Desktop.Vpn.Proto";
 
 import "google/protobuf/timestamp.proto";
+import "google/protobuf/duration.proto";
 
 package vpn;
 
@@ -48,10 +49,10 @@ message TunnelMessage {
 message ClientMessage {
 	RPC rpc = 1;
 	oneof msg {
-	StartRequest start = 2;
-	StopRequest stop = 3;
-	StatusRequest status = 4;
-  }
+		StartRequest start = 2;
+		StopRequest stop = 3;
+		StatusRequest status = 4;
+	}
 }
 
 // ServiceMessage is a message from the service (to the client). Windows only.
@@ -131,6 +132,21 @@ message Agent {
 	// last_handshake is the primary indicator of whether we are connected to a peer. Zero value or
 	// anything longer than 5 minutes ago means there is a problem.
 	google.protobuf.Timestamp last_handshake = 6;
+	// If unset, a successful ping has not yet been made.
+	optional LastPing last_ping = 7;
+}
+
+message LastPing {
+	// latency is the RTT of the ping to the agent.
+	google.protobuf.Duration latency = 1;
+	// did_p2p indicates whether the ping was sent P2P, or over DERP.
+	bool did_p2p = 2;
+	// preferred_derp is the human readable name of the preferred DERP region,
+	// or the region used for the last ping, if it was sent over DERP.
+	string preferred_derp = 3;
+	// preferred_derp_latency is the last known latency to the preferred DERP
+	// region. Unset if the region does not appear in the DERP map.
+	optional google.protobuf.Duration preferred_derp_latency = 4;
 }
 
 // NetworkSettingsRequest is based on
diff --git a/Vpn.Service/Manager.cs b/Vpn.Service/Manager.cs
index fdb62af..027a882 100644
--- a/Vpn.Service/Manager.cs
+++ b/Vpn.Service/Manager.cs
@@ -172,6 +172,10 @@ await _tunnelSupervisor.StartAsync(_config.TunnelBinaryPath, HandleTunnelRpcMess
                 if (reply.MsgCase != TunnelMessage.MsgOneofCase.Start)
                     throw new InvalidOperationException("Tunnel did not reply with a Start response");
 
+                // If the tunnel failed to start, stop the subprocess.
+                if (!reply.Start.Success)
+                    await _tunnelSupervisor.StopAsync(ct);
+
                 await BroadcastStatus(reply.Start.Success ? TunnelStatus.Started : TunnelStatus.Stopped, ct);
                 return reply.Start;
             }
diff --git a/Vpn.Service/coder.ico b/Vpn.Service/coder.ico
index e13ad3b..b80bdc2 100644
Binary files a/Vpn.Service/coder.ico and b/Vpn.Service/coder.ico differ
diff --git a/scripts/files/logo.png b/scripts/files/logo.png
index 7d87306..bdb8b9b 100644
Binary files a/scripts/files/logo.png and b/scripts/files/logo.png differ

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