diff --git a/src/PowerShellEditorServices/Server/PsesDebugServer.cs b/src/PowerShellEditorServices/Server/PsesDebugServer.cs
index b3bf2edba..860dbc845 100644
--- a/src/PowerShellEditorServices/Server/PsesDebugServer.cs
+++ b/src/PowerShellEditorServices/Server/PsesDebugServer.cs
@@ -24,6 +24,8 @@ public class PsesDebugServer : IDisposable
 
         private IJsonRpcServer _jsonRpcServer;
 
+        private PowerShellContextService _powerShellContextService;
+
         public PsesDebugServer(
             ILoggerFactory factory,
             Stream inputStream,
@@ -42,8 +44,14 @@ public async Task StartAsync(IServiceProvider languageServerServiceProvider)
                 options.Reciever = new DapReciever();
                 options.LoggerFactory = _loggerFactory;
                 ILogger logger = options.LoggerFactory.CreateLogger("DebugOptionsStartup");
+
+                // We need to let the PowerShell Context Service know that we are in a debug session
+                // so that it doesn't send the powerShell/startDebugger message.
+                _powerShellContextService = languageServerServiceProvider.GetService<PowerShellContextService>();
+                _powerShellContextService.IsDebugServerActive = true;
+
                 options.Services = new ServiceCollection()
-                    .AddSingleton(languageServerServiceProvider.GetService<PowerShellContextService>())
+                    .AddSingleton(_powerShellContextService)
                     .AddSingleton(languageServerServiceProvider.GetService<WorkspaceService>())
                     .AddSingleton(languageServerServiceProvider.GetService<RemoteFileManagerService>())
                     .AddSingleton<PsesDebugServer>(this)
@@ -85,6 +93,7 @@ public async Task StartAsync(IServiceProvider languageServerServiceProvider)
 
         public void Dispose()
         {
+            _powerShellContextService.IsDebugServerActive = false;
             _jsonRpcServer.Dispose();
         }
 
diff --git a/src/PowerShellEditorServices/Services/DebugAdapter/DebugService.cs b/src/PowerShellEditorServices/Services/DebugAdapter/DebugService.cs
index c8d566b12..dbde29254 100644
--- a/src/PowerShellEditorServices/Services/DebugAdapter/DebugService.cs
+++ b/src/PowerShellEditorServices/Services/DebugAdapter/DebugService.cs
@@ -1191,7 +1191,7 @@ private string TrimScriptListingLine(PSObject scriptLineObj, ref int prefixLengt
         /// </summary>
         public event EventHandler<DebuggerStoppedEventArgs> DebuggerStopped;
 
-        private async void OnDebuggerStopAsync(object sender, DebuggerStopEventArgs e)
+        internal async void OnDebuggerStopAsync(object sender, DebuggerStopEventArgs e)
         {
             bool noScriptName = false;
             string localScriptPath = e.InvocationInfo.ScriptName;
diff --git a/src/PowerShellEditorServices/Services/DebugAdapter/Handlers/ConfigurationDoneHandler.cs b/src/PowerShellEditorServices/Services/DebugAdapter/Handlers/ConfigurationDoneHandler.cs
index 03cdf7fde..addf829a1 100644
--- a/src/PowerShellEditorServices/Services/DebugAdapter/Handlers/ConfigurationDoneHandler.cs
+++ b/src/PowerShellEditorServices/Services/DebugAdapter/Handlers/ConfigurationDoneHandler.cs
@@ -73,9 +73,18 @@ public Task<ConfigurationDoneResponse> Handle(ConfigurationDoneArguments request
 
                 if (_debugService.IsDebuggerStopped)
                 {
-                    // If this is an interactive session and there's a pending breakpoint,
-                    // send that information along to the debugger client
-                    _debugEventHandlerService.TriggerDebuggerStopped(_debugService.CurrentDebuggerStoppedEventArgs);
+                    if (_debugService.CurrentDebuggerStoppedEventArgs != null)
+                    {
+                        // If this is an interactive session and there's a pending breakpoint,
+                        // send that information along to the debugger client
+                        _debugEventHandlerService.TriggerDebuggerStopped(_debugService.CurrentDebuggerStoppedEventArgs);
+                    }
+                    else
+                    {
+                        // If this is an interactive session and there's a pending breakpoint that has not been propagated through
+                        // the debug service, fire the debug service's OnDebuggerStop event.
+                        _debugService.OnDebuggerStopAsync(null, _powerShellContextService.CurrentDebuggerStopEventArgs);
+                    }
                 }
             }
 
diff --git a/src/PowerShellEditorServices/Services/PowerShellContext/PowerShellContextService.cs b/src/PowerShellEditorServices/Services/PowerShellContext/PowerShellContextService.cs
index c0effd3be..f46b5cfba 100644
--- a/src/PowerShellEditorServices/Services/PowerShellContext/PowerShellContextService.cs
+++ b/src/PowerShellEditorServices/Services/PowerShellContext/PowerShellContextService.cs
@@ -137,6 +137,10 @@ public RunspaceDetails CurrentRunspace
         /// </summary>
         public string InitialWorkingDirectory { get; private set; }
 
+        internal bool IsDebugServerActive { get; set; }
+
+        internal DebuggerStopEventArgs CurrentDebuggerStopEventArgs { get; private set; }
+
         #endregion
 
         #region Constructors
@@ -2296,6 +2300,15 @@ private void StartCommandLoopOnRunspaceAvailable()
 
         private void OnDebuggerStop(object sender, DebuggerStopEventArgs e)
         {
+            // We maintain the current stop event args so that we can use it in the DebugServer to fire the "stopped" event
+            // when the DebugServer is fully started.
+            CurrentDebuggerStopEventArgs = e;
+
+            if (!IsDebugServerActive)
+            {
+                _languageServer.SendNotification("powerShell/startDebugger");
+            }
+
             if (CurrentRunspace.Context == RunspaceContext.Original)
             {
                 StartCommandLoopOnRunspaceAvailable();
@@ -2361,6 +2374,9 @@ private void OnDebuggerStop(object sender, DebuggerStopEventArgs e)
                     e.ResumeAction = localDebuggerStoppedTask.GetAwaiter().GetResult();
                     this.logger.LogTrace("Received debugger resume action " + e.ResumeAction.ToString());
 
+                    // Since we are no longer at a breakpoint, we set this to null.
+                    CurrentDebuggerStopEventArgs = null;
+
                     // Notify listeners that the debugger has resumed
                     this.DebuggerResumed?.Invoke(this, e.ResumeAction);
 
@@ -2398,6 +2414,9 @@ private void OnDebuggerStop(object sender, DebuggerStopEventArgs e)
                         this.PromptNest,
                         this.CurrentRunspace.Runspace))
                     {
+                        // Since we are no longer at a breakpoint, we set this to null.
+                        CurrentDebuggerStopEventArgs = null;
+
                         if (this.CurrentRunspace.Context == RunspaceContext.DebuggedRunspace)
                         {
                             // Notify listeners that the debugger has resumed
@@ -2436,8 +2455,7 @@ private void OnBreakpointUpdated(object sender, BreakpointUpdatedEventArgs e)
 
         private void ConfigureRunspaceCapabilities(RunspaceDetails runspaceDetails)
         {
-            // TODO: Bring this back
-            //DscBreakpointCapability.CheckForCapability(this.CurrentRunspace, this, this.logger);
+            DscBreakpointCapability.CheckForCapability(this.CurrentRunspace, this, this.logger);
         }
 
         private void PushRunspace(RunspaceDetails newRunspaceDetails)