diff --git a/src/PowerShellEditorServices/Services/DebugAdapter/Handlers/ConfigurationDoneHandler.cs b/src/PowerShellEditorServices/Services/DebugAdapter/Handlers/ConfigurationDoneHandler.cs
index 2cfc24a2d..14bd5389e 100644
--- a/src/PowerShellEditorServices/Services/DebugAdapter/Handlers/ConfigurationDoneHandler.cs
+++ b/src/PowerShellEditorServices/Services/DebugAdapter/Handlers/ConfigurationDoneHandler.cs
@@ -102,14 +102,17 @@ public Task<ConfigurationDoneResponse> Handle(ConfigurationDoneArguments request
             return Task.FromResult(new ConfigurationDoneResponse());
         }
 
-        private async Task LaunchScriptAsync(string scriptToLaunch)
+        // NOTE: We test this function in `DebugServiceTests` so it both needs to be internal, and
+        // use conditional-access on `_debugStateService` and `_debugAdapterServer` as its not set
+        // by tests.
+        internal async Task LaunchScriptAsync(string scriptToLaunch)
         {
             PSCommand command;
             if (System.IO.File.Exists(scriptToLaunch))
             {
                 // For a saved file we just execute its path (after escaping it).
                 command = PSCommandHelpers.BuildDotSourceCommandWithArguments(
-                    string.Concat('"', scriptToLaunch, '"'), _debugStateService.Arguments);
+                    string.Concat('"', scriptToLaunch, '"'), _debugStateService?.Arguments);
             }
             else // It's a URI to an untitled script, or a raw script.
             {
@@ -135,7 +138,7 @@ private async Task LaunchScriptAsync(string scriptToLaunch)
                     // on each invocation, so passing the user's arguments directly in the initial
                     // `AddScript` surprisingly works.
                     command = PSCommandHelpers
-                        .BuildDotSourceCommandWithArguments("$args[0]", _debugStateService.Arguments)
+                        .BuildDotSourceCommandWithArguments("$args[0]", _debugStateService?.Arguments)
                         .AddArgument(ast.GetScriptBlock());
                 }
                 else
@@ -148,7 +151,7 @@ private async Task LaunchScriptAsync(string scriptToLaunch)
                             "{" + System.Environment.NewLine,
                             isScriptFile ? untitledScript.Contents : scriptToLaunch,
                             System.Environment.NewLine + "}"),
-                            _debugStateService.Arguments);
+                            _debugStateService?.Arguments);
                 }
             }
 
@@ -156,7 +159,8 @@ await _executionService.ExecutePSCommandAsync(
                 command,
                 CancellationToken.None,
                 s_debuggerExecutionOptions).ConfigureAwait(false);
-            _debugAdapterServer.SendNotification(EventNames.Terminated);
+
+            _debugAdapterServer?.SendNotification(EventNames.Terminated);
         }
     }
 }
diff --git a/test/PowerShellEditorServices.Test.E2E/DebugAdapterProtocolMessageTests.cs b/test/PowerShellEditorServices.Test.E2E/DebugAdapterProtocolMessageTests.cs
index 7505ad89e..553024856 100644
--- a/test/PowerShellEditorServices.Test.E2E/DebugAdapterProtocolMessageTests.cs
+++ b/test/PowerShellEditorServices.Test.E2E/DebugAdapterProtocolMessageTests.cs
@@ -305,9 +305,8 @@ public async Task CanStepPastSystemWindowsForms()
         [Fact]
         public async Task CanLaunchScriptWithCommentedLastLineAsync()
         {
-            string script = GenerateScriptFromLoggingStatements("a log statement") + "# a comment at the end";
-            Assert.Contains(Environment.NewLine + "# a comment", script);
-            Assert.EndsWith("at the end", script);
+            string script = GenerateScriptFromLoggingStatements("$($MyInvocation.Line)") + "# a comment at the end";
+            Assert.EndsWith(Environment.NewLine + "# a comment at the end", script);
 
             // NOTE: This is horribly complicated, but the "script" parameter here is assigned to
             // PsesLaunchRequestArguments.Script, which is then assigned to
@@ -317,8 +316,13 @@ public async Task CanLaunchScriptWithCommentedLastLineAsync()
 
             ConfigurationDoneResponse configDoneResponse = await PsesDebugAdapterClient.RequestConfigurationDone(new ConfigurationDoneArguments()).ConfigureAwait(true);
             Assert.NotNull(configDoneResponse);
+            // We can check that the script was invoked as expected, which is to dot-source a script
+            // block with the contents surrounded by newlines. While we can't check that the last
+            // line was a curly brace by itself, we did check that the contents ended with a
+            // comment, so if this output exists then the bug did not recur.
             Assert.Collection(await GetLog().ConfigureAwait(true),
-                (i) => Assert.Equal("a log statement", i));
+                (i) => Assert.Equal(". {", i),
+                (i) => Assert.Equal("", i));
         }
 
         [SkippableFact]
diff --git a/test/PowerShellEditorServices.Test/Debugging/DebugServiceTests.cs b/test/PowerShellEditorServices.Test/Debugging/DebugServiceTests.cs
index b58997005..eef37f1ca 100644
--- a/test/PowerShellEditorServices.Test/Debugging/DebugServiceTests.cs
+++ b/test/PowerShellEditorServices.Test/Debugging/DebugServiceTests.cs
@@ -10,6 +10,7 @@
 using System.Threading;
 using System.Threading.Tasks;
 using Microsoft.Extensions.Logging.Abstractions;
+using Microsoft.PowerShell.EditorServices.Handlers;
 using Microsoft.PowerShell.EditorServices.Services;
 using Microsoft.PowerShell.EditorServices.Services.DebugAdapter;
 using Microsoft.PowerShell.EditorServices.Services.PowerShell.Host;
@@ -521,6 +522,40 @@ await debugService.SetCommandBreakpointsAsync(
             Assert.Equal("\"True > \"", prompt.ValueString);
         }
 
+        [SkippableFact]
+        public async Task DebuggerBreaksInUntitledScript()
+        {
+            Skip.IfNot(VersionUtils.PSEdition == "Core", "Untitled script breakpoints only supported in PowerShell Core");
+            const string contents = "Write-Output $($MyInvocation.Line)";
+            const string scriptPath = "untitled:Untitled-1";
+            Assert.True(ScriptFile.IsUntitledPath(scriptPath));
+            ScriptFile scriptFile = workspace.GetFileBuffer(scriptPath, contents);
+            Assert.Equal(scriptFile.DocumentUri, scriptPath);
+            Assert.Equal(scriptFile.Contents, contents);
+            Assert.True(workspace.TryGetFile(scriptPath, out ScriptFile _));
+
+            await debugService.SetCommandBreakpointsAsync(
+                new[] { CommandBreakpointDetails.Create("Write-Output") }).ConfigureAwait(true);
+
+            ConfigurationDoneHandler configurationDoneHandler = new(
+                NullLoggerFactory.Instance, null, debugService, null, null, psesHost, workspace, null, psesHost);
+
+            Task _ = configurationDoneHandler.LaunchScriptAsync(scriptPath);
+            AssertDebuggerStopped(scriptPath, 1);
+
+            VariableDetailsBase[] variables = GetVariables(VariableContainerDetails.CommandVariablesName);
+            VariableDetailsBase myInvocation = Array.Find(variables, v => v.Name == "$MyInvocation");
+            Assert.NotNull(myInvocation);
+            Assert.True(myInvocation.IsExpandable);
+
+            // Here we're asserting that our hacky workaround to support breakpoints in untitled
+            // scripts is working, namely that we're actually dot-sourcing our first argument, which
+            // should be a cached script block. See the `LaunchScriptAsync` for more info.
+            VariableDetailsBase[] myInvocationChildren = debugService.GetVariables(myInvocation.Id);
+            VariableDetailsBase myInvocationLine = Array.Find(myInvocationChildren, v => v.Name == "Line");
+            Assert.Equal("\". $args[0]\"", myInvocationLine.ValueString);
+        }
+
         [Fact]
         public async Task DebuggerVariableStringDisplaysCorrectly()
         {