From c77369bb8ad9adb74b4a0a9e63979d29eef340a4 Mon Sep 17 00:00:00 2001
From: Michael Suchacz <203725896+ibetitsmike@users.noreply.github.com>
Date: Mon, 23 Jun 2025 20:15:21 +0200
Subject: [PATCH 1/4] chore: added latency tooltips on workspaces

---
 App/ViewModels/AgentViewModel.cs        | 126 ++++++++++++++++++++----
 App/ViewModels/TrayWindowViewModel.cs   |  35 +++++--
 App/Views/Pages/TrayWindowMainPage.xaml |   9 +-
 Vpn.Proto/vpn.proto                     |  24 ++++-
 4 files changed, 160 insertions(+), 34 deletions(-)

diff --git a/App/ViewModels/AgentViewModel.cs b/App/ViewModels/AgentViewModel.cs
index cd5907b..0b41fc1 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);
@@ -40,8 +41,11 @@ 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)
     {
+        System.Diagnostics.Debug.WriteLine($"Creating agent: {didP2p} {preferredDerp} {latency} {lastHandshake}");
         return new AgentViewModel(childLogger, coderApiClientFactory, credentialManager, agentAppViewModelFactory,
             expanderHost, id)
         {
@@ -51,6 +55,11 @@ 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 +82,10 @@ public AgentViewModel CreateDummy(IAgentExpanderHost expanderHost, Uuid id,
 
 public enum AgentConnectionStatus
 {
-    Green,
-    Yellow,
-    Red,
-    Gray,
+    Healthy,
+    Unhealthy,
+    NoRecentHandshake,
+    Offline,
 }
 
 public partial class AgentViewModel : ObservableObject, IModelUpdateable<AgentViewModel>
@@ -182,6 +191,75 @@ 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();
+
+            if (DidP2p != null && DidP2p.Value && Latency != null)
+            {
+                description.Append($"""
+                You're connected peer-to-peer.
+
+                You ↔ {Latency.Value.Milliseconds} ms ↔ {WorkspaceName}
+                """
+                );
+            }
+            else if (PreferredDerpLatency != null)
+            {
+                description.Append($"""
+                You're connected through a DERP relay.
+                We'll switch over to peer-to-peer when available.
+
+                Total latency: {PreferredDerpLatency.Value.Milliseconds} ms
+                """
+                );
+
+                if (PreferredDerp != null && Latency != 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");
+                    }
+                }
+            }
+            if (LastHandshake != null)
+                description.Append($"\n\nLast handshake: {LastHandshake?.ToString() ?? "Unknown"}");
+
+            var tooltip = description.ToString().TrimEnd('\n', ' ');
+
+            if (string.IsNullOrEmpty(tooltip))
+                return "No connection information available.";
+
+            return tooltip;
+        }
+    }
+
+
     // 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 +270,7 @@ 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 +363,16 @@ 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 +395,7 @@ 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 +404,7 @@ 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..b43eaa8 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;
@@ -222,12 +224,26 @@ 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;
+
+            // 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 : true;
+            var connectionStatus = AgentConnectionStatus.Healthy;
+            if (lastHandshakeAgo > TimeSpan.FromMinutes(5))
+            {
+                connectionStatus = AgentConnectionStatus.NoRecentHandshake;
+            }
+            else if (!isLatencyAcceptable)
+            {
+                connectionStatus = AgentConnectionStatus.Unhealthy;
+            }
+
+            
             workspacesWithAgents.Add(agent.WorkspaceId);
             var workspace = rpcModel.Workspaces.FirstOrDefault(w => w.Id == agent.WorkspaceId);
+            System.Diagnostics.Debug.WriteLine($"Agent {uuid} LastHandshakeAgo: {lastHandshakeAgo} ConnectionStatus: {connectionStatus} FQDN: {fqdn} Last ping: {agent.LastPing} Last handshake: {agent.LastHandshake}");
 
             agents.Add(_agentViewModelFactory.Create(
                 this,
@@ -236,7 +252,12 @@ 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?.ToDateTime()));
         }
 
         // For every stopped workspace that doesn't have any agents, add a
@@ -253,7 +274,7 @@ private void UpdateFromRpcModel(RpcModel rpcModel)
                 // conflict with any agent IDs.
                 uuid,
                 _hostnameSuffixGetter.GetCachedSuffix(),
-                AgentConnectionStatus.Gray,
+                AgentConnectionStatus.Offline,
                 credentialModel.CoderUrl,
                 workspace.Name));
         }
@@ -268,7 +289,7 @@ 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 +454,7 @@ 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/Views/Pages/TrayWindowMainPage.xaml b/App/Views/Pages/TrayWindowMainPage.xaml
index 9f27fb1..896327e 100644
--- a/App/Views/Pages/TrayWindowMainPage.xaml
+++ b/App/Views/Pages/TrayWindowMainPage.xaml
@@ -137,22 +137,22 @@
                                             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="Healthy">
                                                 <converters:StringToBrushSelectorItem.Value>
                                                     <SolidColorBrush Color="#34c759" />
                                                 </converters:StringToBrushSelectorItem.Value>
@@ -189,6 +189,7 @@
                                         HorizontalAlignment="Right"
                                         VerticalAlignment="Center"
                                         Height="14" Width="14"
+                                        ToolTipService.ToolTip="{x:Bind ConnectionTooltip, Mode=OneWay}"
                                         Margin="0,1,0,0">
 
                                         <Ellipse
diff --git a/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

From 419dcb2aced16db058017688130452c439480668 Mon Sep 17 00:00:00 2001
From: Michael Suchacz <203725896+ibetitsmike@users.noreply.github.com>
Date: Tue, 24 Jun 2025 14:17:57 +0200
Subject: [PATCH 2/4] PR fixes

---
 App/ViewModels/AgentViewModel.cs      | 33 +++++++++++++++++++--------
 App/ViewModels/TrayWindowViewModel.cs |  6 ++---
 2 files changed, 26 insertions(+), 13 deletions(-)

diff --git a/App/ViewModels/AgentViewModel.cs b/App/ViewModels/AgentViewModel.cs
index 0b41fc1..c1ea0fc 100644
--- a/App/ViewModels/AgentViewModel.cs
+++ b/App/ViewModels/AgentViewModel.cs
@@ -45,7 +45,6 @@ public AgentViewModel Create(IAgentExpanderHost expanderHost, Uuid id, string fu
         string? workspaceName, bool? didP2p, string? preferredDerp, TimeSpan? latency, TimeSpan? preferredDerpLatency,
         DateTime? lastHandshake)
     {
-        System.Diagnostics.Debug.WriteLine($"Creating agent: {didP2p} {preferredDerp} {latency} {lastHandshake}");
         return new AgentViewModel(childLogger, coderApiClientFactory, credentialManager, agentAppViewModelFactory,
             expanderHost, id)
         {
@@ -88,6 +87,19 @@ public enum AgentConnectionStatus
     Offline,
 }
 
+public static class AgentConnectionStatusExtensions
+{
+    public static string ToDisplayString(this AgentConnectionStatus status) =>
+        status switch
+        {
+            AgentConnectionStatus.Healthy => "Healthy",
+            AgentConnectionStatus.Unhealthy => "High latency",
+            AgentConnectionStatus.NoRecentHandshake => "No recent handshake",
+            AgentConnectionStatus.Offline => "Offline",
+            _ => status.ToString()
+        };
+}
+
 public partial class AgentViewModel : ObservableObject, IModelUpdateable<AgentViewModel>
 {
     private const string DefaultDashboardUrl = "https://coder.com";
@@ -169,6 +181,7 @@ public string FullyQualifiedDomainName
     [ObservableProperty]
     [NotifyPropertyChangedFor(nameof(ShowExpandAppsMessage))]
     [NotifyPropertyChangedFor(nameof(ExpandAppsMessage))]
+    [NotifyPropertyChangedFor(nameof(ConnectionTooltip))]
     public required partial AgentConnectionStatus ConnectionStatus { get; set; }
 
     [ObservableProperty]
@@ -214,11 +227,12 @@ public string FullyQualifiedDomainName
     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.
+                You're connected peer-to-peer. {highLatencyWarning}
 
                 You ↔ {Latency.Value.Milliseconds} ms ↔ {WorkspaceName}
                 """
@@ -227,7 +241,7 @@ public string ConnectionTooltip { get
             else if (PreferredDerpLatency != null)
             {
                 description.Append($"""
-                You're connected through a DERP relay.
+                You're connected through a DERP relay. {highLatencyWarning}
                 We'll switch over to peer-to-peer when available.
 
                 Total latency: {PreferredDerpLatency.Value.Milliseconds} ms
@@ -247,15 +261,14 @@ public string ConnectionTooltip { get
                     }
                 }
             }
+            else
+            {
+                description.Append(ConnectionStatus.ToDisplayString());
+            }
             if (LastHandshake != null)
-                description.Append($"\n\nLast handshake: {LastHandshake?.ToString() ?? "Unknown"}");
-
-            var tooltip = description.ToString().TrimEnd('\n', ' ');
-
-            if (string.IsNullOrEmpty(tooltip))
-                return "No connection information available.";
+                description.Append($"\n\nLast handshake: {LastHandshake?.ToString()}");
 
-            return tooltip;
+            return description.ToString().TrimEnd('\n', ' '); ;
         }
     }
 
diff --git a/App/ViewModels/TrayWindowViewModel.cs b/App/ViewModels/TrayWindowViewModel.cs
index b43eaa8..3b1e0be 100644
--- a/App/ViewModels/TrayWindowViewModel.cs
+++ b/App/ViewModels/TrayWindowViewModel.cs
@@ -224,12 +224,13 @@ private void UpdateFromRpcModel(RpcModel rpcModel)
             if (string.IsNullOrWhiteSpace(fqdn))
                 continue;
 
-
+#pragma warning disable CS8602 // Protobuf will always set this value, so we can safely dereference them.
             var lastHandshakeAgo = DateTime.UtcNow.Subtract(agent.LastHandshake.ToDateTime());
+#pragma warning restore CS8602
 
             // 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 : true;
+            var isLatencyAcceptable = agent.LastPing == null || agent.LastPing.Latency.ToTimeSpan() < HealthyPingThreshold;
             var connectionStatus = AgentConnectionStatus.Healthy;
             if (lastHandshakeAgo > TimeSpan.FromMinutes(5))
             {
@@ -243,7 +244,6 @@ private void UpdateFromRpcModel(RpcModel rpcModel)
             
             workspacesWithAgents.Add(agent.WorkspaceId);
             var workspace = rpcModel.Workspaces.FirstOrDefault(w => w.Id == agent.WorkspaceId);
-            System.Diagnostics.Debug.WriteLine($"Agent {uuid} LastHandshakeAgo: {lastHandshakeAgo} ConnectionStatus: {connectionStatus} FQDN: {fqdn} Last ping: {agent.LastPing} Last handshake: {agent.LastHandshake}");
 
             agents.Add(_agentViewModelFactory.Create(
                 this,

From d1b2c7d59b7e770d334f0ea449ad13bb8468980f Mon Sep 17 00:00:00 2001
From: Michael Suchacz <203725896+ibetitsmike@users.noreply.github.com>
Date: Tue, 24 Jun 2025 14:46:36 +0200
Subject: [PATCH 3/4] added connecting state and improved the logic on tooltip
 generation

---
 App/ViewModels/AgentViewModel.cs        |  8 +++++--
 App/ViewModels/TrayWindowViewModel.cs   | 30 ++++++++++++++-----------
 App/Views/Pages/TrayWindowMainPage.xaml |  5 +++++
 3 files changed, 28 insertions(+), 15 deletions(-)

diff --git a/App/ViewModels/AgentViewModel.cs b/App/ViewModels/AgentViewModel.cs
index c1ea0fc..0e50b06 100644
--- a/App/ViewModels/AgentViewModel.cs
+++ b/App/ViewModels/AgentViewModel.cs
@@ -82,9 +82,10 @@ public AgentViewModel CreateDummy(IAgentExpanderHost expanderHost, Uuid id,
 public enum AgentConnectionStatus
 {
     Healthy,
+    Connecting,
     Unhealthy,
     NoRecentHandshake,
-    Offline,
+    Offline
 }
 
 public static class AgentConnectionStatusExtensions
@@ -93,6 +94,7 @@ 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",
@@ -224,7 +226,9 @@ public string FullyQualifiedDomainName
     [NotifyPropertyChangedFor(nameof(ConnectionTooltip))]
     public partial DateTime? LastHandshake { get; set; } = null;
 
-    public string ConnectionTooltip { get
+    public string ConnectionTooltip
+    {
+        get
         {
             var description = new StringBuilder();
             var highLatencyWarning = ConnectionStatus == AgentConnectionStatus.Unhealthy ? $"({AgentConnectionStatus.Unhealthy.ToDisplayString()})" : "";
diff --git a/App/ViewModels/TrayWindowViewModel.cs b/App/ViewModels/TrayWindowViewModel.cs
index 3b1e0be..f57947d 100644
--- a/App/ViewModels/TrayWindowViewModel.cs
+++ b/App/ViewModels/TrayWindowViewModel.cs
@@ -224,24 +224,28 @@ private void UpdateFromRpcModel(RpcModel rpcModel)
             if (string.IsNullOrWhiteSpace(fqdn))
                 continue;
 
-#pragma warning disable CS8602 // Protobuf will always set this value, so we can safely dereference them.
-            var lastHandshakeAgo = DateTime.UtcNow.Subtract(agent.LastHandshake.ToDateTime());
-#pragma warning restore CS8602
-
-            // 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 connectionStatus = AgentConnectionStatus.Healthy;
-            if (lastHandshakeAgo > TimeSpan.FromMinutes(5))
+
+            if (agent.LastHandshake != null && agent.LastHandshake.ToDateTime() != default && agent.LastHandshake.ToDateTime() < DateTime.UtcNow)
             {
-                connectionStatus = AgentConnectionStatus.NoRecentHandshake;
+                // 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 (!isLatencyAcceptable)
+            else
             {
-                connectionStatus = AgentConnectionStatus.Unhealthy;
+                // 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);
 
@@ -257,7 +261,7 @@ private void UpdateFromRpcModel(RpcModel rpcModel)
                 agent.LastPing?.PreferredDerp,
                 agent.LastPing?.Latency?.ToTimeSpan(),
                 agent.LastPing?.PreferredDerpLatency?.ToTimeSpan(),
-                agent.LastHandshake?.ToDateTime()));
+                agent.LastHandshake != null && agent.LastHandshake.ToDateTime() != default ? agent.LastHandshake?.ToDateTime() : null));
         }
 
         // For every stopped workspace that doesn't have any agents, add a
diff --git a/App/Views/Pages/TrayWindowMainPage.xaml b/App/Views/Pages/TrayWindowMainPage.xaml
index 17d2eef..3cc21de 100644
--- a/App/Views/Pages/TrayWindowMainPage.xaml
+++ b/App/Views/Pages/TrayWindowMainPage.xaml
@@ -152,6 +152,11 @@
                                                     <SolidColorBrush Color="#ffcc01" />
                                                 </converters:StringToBrushSelectorItem.Value>
                                             </converters:StringToBrushSelectorItem>
+                                            <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" />

From 8fbbff0531065a2c469e323e953d4cac002a5668 Mon Sep 17 00:00:00 2001
From: Michael Suchacz <203725896+ibetitsmike@users.noreply.github.com>
Date: Tue, 24 Jun 2025 14:50:23 +0200
Subject: [PATCH 4/4] PR review

---
 App/ViewModels/AgentViewModel.cs | 6 +++---
 1 file changed, 3 insertions(+), 3 deletions(-)

diff --git a/App/ViewModels/AgentViewModel.cs b/App/ViewModels/AgentViewModel.cs
index 0e50b06..0cf2651 100644
--- a/App/ViewModels/AgentViewModel.cs
+++ b/App/ViewModels/AgentViewModel.cs
@@ -242,17 +242,17 @@ public string ConnectionTooltip
                 """
                 );
             }
-            else if (PreferredDerpLatency != null)
+            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: {PreferredDerpLatency.Value.Milliseconds} ms
+                Total latency: {Latency.Value.Milliseconds} ms
                 """
                 );
 
-                if (PreferredDerp != null && Latency != null)
+                if (PreferredDerpLatency != null)
                 {
                     description.Append($"\nYou ↔ {PreferredDerp}: {PreferredDerpLatency.Value.Milliseconds} ms");
 

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