diff --git a/src/PowerShellEditorServices/Services/DebugAdapter/DebugService.cs b/src/PowerShellEditorServices/Services/DebugAdapter/DebugService.cs
index 383ecf4fa..7a1f4764e 100644
--- a/src/PowerShellEditorServices/Services/DebugAdapter/DebugService.cs
+++ b/src/PowerShellEditorServices/Services/DebugAdapter/DebugService.cs
@@ -7,6 +7,7 @@
 using System.Linq;
 using System.Management.Automation;
 using System.Management.Automation.Language;
+using System.Management.Automation.Runspaces;
 using System.Reflection;
 using System.Threading;
 using System.Threading.Tasks;
@@ -263,7 +264,30 @@ public VariableDetailsBase[] GetVariables(int variableReferenceId)
                 VariableDetailsBase parentVariable = variables[variableReferenceId];
                 if (parentVariable.IsExpandable)
                 {
-                    childVariables = parentVariable.GetChildren(_logger);
+                    // PERFORMANCE: Because of ToString calls that might be PS script properties, we want this
+                    // to run on the pipeline thread to avoid retry timeouts
+                    // TODO: Cancellation Token Maybe?
+                    // TODO: Maybe pass
+                    childVariables = _psesHost.InvokeDelegate<VariableDetailsBase[]>
+                    (
+                        representation: "GetChildren",
+                        ExecutionOptions.Default,
+                        (_) =>
+                        {
+                            var existingRunspace = Runspace.DefaultRunspace;
+                            try
+                            {
+                                Runspace.DefaultRunspace = _psesHost.CurrentRunspace.Runspace;
+                                return parentVariable.GetChildren(_logger);
+                            }
+                            finally
+                            {
+                                Runspace.DefaultRunspace = existingRunspace;
+                            }
+                        },
+                        CancellationToken.None
+                    );
+
                     foreach (var child in childVariables)
                     {
                         // Only add child if it hasn't already been added.
diff --git a/test/PowerShellEditorServices.Test.Shared/Debugging/VariableTest.ps1 b/test/PowerShellEditorServices.Test.Shared/Debugging/VariableTest.ps1
index e8c23d9a0..8a327506d 100644
--- a/test/PowerShellEditorServices.Test.Shared/Debugging/VariableTest.ps1
+++ b/test/PowerShellEditorServices.Test.Shared/Debugging/VariableTest.ps1
@@ -51,3 +51,21 @@ $sortedDictionary['blue'] = 'red'
 
 # This is a dummy function that the test will use to stop and evaluate the debug environment
 function __BreakDebuggerDerivedDictionaryPropertyInRawView{}; __BreakDebuggerDerivedDictionaryPropertyInRawView
+
+
+class CustomToString {
+    [String]$String = 'Hello'
+    [String]ToString() {
+        return $this.String.ToUpper()
+    }
+}
+$SCRIPT:CustomToStrings = 1..1000 | ForEach-Object {
+    [CustomToString]::new()
+}
+$SCRIPT:Small = $SCRIPT:CustomToStrings[1..10]
+$SCRIPT:Medium = $SCRIPT:CustomToStrings[1..50]
+$SCRIPT:Large = $SCRIPT:CustomToStrings[1..100]
+
+
+# This is a dummy function that the test will use to stop and evaluate the debug environment
+function __BreakDebuggerToStringShouldMarshallToPipeline{}; __BreakDebuggerToStringShouldMarshallToPipeline
diff --git a/test/PowerShellEditorServices.Test/Debugging/DebugServiceTests.cs b/test/PowerShellEditorServices.Test/Debugging/DebugServiceTests.cs
index 00996db96..bd3988d9c 100644
--- a/test/PowerShellEditorServices.Test/Debugging/DebugServiceTests.cs
+++ b/test/PowerShellEditorServices.Test/Debugging/DebugServiceTests.cs
@@ -905,6 +905,26 @@ await debugService.SetLineBreakpointsAsync(
             Assert.Equal("73", childVars[1].ValueString);
         }
 
+        /// <summary>
+        /// Verifies Issue #1686
+        /// </summary>
+        [Fact]
+        public async Task DebuggerToStringShouldMarshallToPipeline()
+        {
+            CommandBreakpointDetails breakpoint = CommandBreakpointDetails.Create("__BreakDebuggerToStringShouldMarshallToPipeline");
+            await debugService.SetCommandBreakpointsAsync(new[] { breakpoint }).ConfigureAwait(true);
+
+            // Execute the script and wait for the breakpoint to be hit
+            Task _ = ExecuteVariableScriptFile();
+            AssertDebuggerStopped(commandBreakpointDetails: breakpoint);
+
+            VariableDetailsBase variableArray = Array.Find(
+                GetVariables(VariableContainerDetails.ScriptScopeName),
+                v => v.Name == "$CustomToStrings"
+            );
+            Assert.NotNull(variableArray);
+        }
+
         // Verifies fix for issue #86, $proc = Get-Process foo displays just the ETS property set
         // and not all process properties.
         [Fact(Skip = "Length of child vars is wrong now")]