diff --git a/src/PowerShellEditorServices/Services/DebugAdapter/DebugService.cs b/src/PowerShellEditorServices/Services/DebugAdapter/DebugService.cs
index 5d32451ed..906b9fe4d 100644
--- a/src/PowerShellEditorServices/Services/DebugAdapter/DebugService.cs
+++ b/src/PowerShellEditorServices/Services/DebugAdapter/DebugService.cs
@@ -497,10 +497,22 @@ public async Task<VariableDetails> EvaluateExpressionAsync(
             bool writeResultAsOutput)
         {
             PSCommand command = new PSCommand().AddScript(expressionString);
-            IReadOnlyList<PSObject> results = await _executionService.ExecutePSCommandAsync<PSObject>(
-                command,
-                CancellationToken.None,
-                new PowerShellExecutionOptions { WriteOutputToHost = writeResultAsOutput, ThrowOnError = !writeResultAsOutput }).ConfigureAwait(false);
+            IReadOnlyList<PSObject> results;
+            try
+            {
+                results = await _executionService.ExecutePSCommandAsync<PSObject>(
+                    command,
+                    CancellationToken.None,
+                    new PowerShellExecutionOptions { WriteOutputToHost = writeResultAsOutput, ThrowOnError = !writeResultAsOutput }).ConfigureAwait(false);
+            }
+            catch (Exception e)
+            {
+                // If a watch expression throws we want to show the exception.
+                // TODO: Show the exception as an expandable object.
+                return new VariableDetails(
+                    expressionString,
+                    $"{e.GetType().Name}: {e.Message}");
+            }
 
             // Since this method should only be getting invoked in the debugger,
             // we can assume that Out-String will be getting used to format results
diff --git a/src/PowerShellEditorServices/Services/PowerShell/Debugging/PowerShellDebugContext.cs b/src/PowerShellEditorServices/Services/PowerShell/Debugging/PowerShellDebugContext.cs
index 36aaad0e2..236403e5a 100644
--- a/src/PowerShellEditorServices/Services/PowerShell/Debugging/PowerShellDebugContext.cs
+++ b/src/PowerShellEditorServices/Services/PowerShell/Debugging/PowerShellDebugContext.cs
@@ -6,6 +6,7 @@
 using System.Threading;
 using System.Threading.Tasks;
 using Microsoft.Extensions.Logging;
+using Microsoft.PowerShell.EditorServices.Services.PowerShell.Context;
 using Microsoft.PowerShell.EditorServices.Services.PowerShell.Host;
 using Microsoft.PowerShell.EditorServices.Services.PowerShell.Utility;
 
@@ -145,15 +146,27 @@ public void SetDebugResuming(DebuggerResumeAction debuggerResumeAction)
                 // TODO: We need to assign cancellation tokens to each frame, because the current
                 // logic results in a deadlock here when we try to cancel the scopes...which
                 // includes ourself (hence running it in a separate thread).
-                Task.Run(() => _psesHost.UnwindCallStack());
+                _ = Task.Run(() => _psesHost.UnwindCallStack());
                 return;
             }
 
             // Otherwise we're continuing or stepping (i.e. resuming) so we need to cancel the
             // debugger REPL.
-            if (_psesHost.CurrentFrame.IsRepl)
+            PowerShellFrameType frameType = _psesHost.CurrentFrame.FrameType;
+            if (frameType.HasFlag(PowerShellFrameType.Repl))
             {
                 _psesHost.CancelIdleParentTask();
+                return;
+            }
+
+            // If the user is running something via the REPL like `while ($true) { sleep 1 }`
+            // and then tries to step, we want to stop that so that execution can resume.
+            //
+            // This also applies to anything we're running on debugger stop like watch variables.
+            if (frameType.HasFlag(PowerShellFrameType.Debug | PowerShellFrameType.Nested))
+            {
+                _psesHost.ForceSetExit();
+                _psesHost.CancelIdleParentTask();
             }
         }
 
diff --git a/src/PowerShellEditorServices/Services/PowerShell/Execution/SynchronousPowerShellTask.cs b/src/PowerShellEditorServices/Services/PowerShell/Execution/SynchronousPowerShellTask.cs
index 0661ce962..2fdefbfdc 100644
--- a/src/PowerShellEditorServices/Services/PowerShell/Execution/SynchronousPowerShellTask.cs
+++ b/src/PowerShellEditorServices/Services/PowerShell/Execution/SynchronousPowerShellTask.cs
@@ -382,7 +382,7 @@ internal void MaybeAddToHistory()
 
         private void CancelDebugExecution()
         {
-            if (_pwsh.Runspace.RunspaceStateInfo.IsUsable())
+            if (!_pwsh.Runspace.RunspaceStateInfo.IsUsable())
             {
                 return;
             }