diff --git a/src/PowerShellEditorServices/Services/Extension/ExtensionService.cs b/src/PowerShellEditorServices/Services/Extension/ExtensionService.cs
index f4284f934..028fe0f19 100644
--- a/src/PowerShellEditorServices/Services/Extension/ExtensionService.cs
+++ b/src/PowerShellEditorServices/Services/Extension/ExtensionService.cs
@@ -104,10 +104,11 @@ internal Task InitializeAsync()
             // This is constant so Remove-Variable cannot remove it.
             PSVariable psEditor = new(PSEditorVariableName, EditorObject, ScopedItemOptions.Constant);
 
-            // Register the editor object in the runspace
+            // NOTE: This is a special task run on startup! Register the editor object in the
+            // runspace. It has priority next so it goes before LoadProfiles.
             return ExecutionService.ExecuteDelegateAsync(
                 $"Create ${PSEditorVariableName} object",
-                executionOptions: null,
+                new ExecutionOptions { Priority = ExecutionPriority.Next },
                 (pwsh, _) => pwsh.Runspace.SessionStateProxy.PSVariable.Set(psEditor),
                 CancellationToken.None);
         }
diff --git a/src/PowerShellEditorServices/Services/PowerShell/Execution/ExecutionOptions.cs b/src/PowerShellEditorServices/Services/PowerShell/Execution/ExecutionOptions.cs
index 83de5301c..dbcab3a9c 100644
--- a/src/PowerShellEditorServices/Services/PowerShell/Execution/ExecutionOptions.cs
+++ b/src/PowerShellEditorServices/Services/PowerShell/Execution/ExecutionOptions.cs
@@ -15,12 +15,15 @@ public enum ExecutionPriority
     // Generally the executor will do the right thing though; some options just priority over others.
     public record ExecutionOptions
     {
+        // This determines which underlying queue the task is added to.
         public ExecutionPriority Priority { get; init; } = ExecutionPriority.Normal;
+        // This implies `ExecutionPriority.Next` because foreground tasks are prepended.
         public bool RequiresForeground { get; init; }
     }
 
     public record PowerShellExecutionOptions : ExecutionOptions
     {
+        // TODO: Because of the above, this is actually unnecessary.
         internal static PowerShellExecutionOptions ImmediateInteractive = new()
         {
             Priority = ExecutionPriority.Next,
diff --git a/src/PowerShellEditorServices/Services/PowerShell/Host/PsesInternalHost.cs b/src/PowerShellEditorServices/Services/PowerShell/Host/PsesInternalHost.cs
index 8b2fd79ad..bf3382b85 100644
--- a/src/PowerShellEditorServices/Services/PowerShell/Host/PsesInternalHost.cs
+++ b/src/PowerShellEditorServices/Services/PowerShell/Host/PsesInternalHost.cs
@@ -1,4 +1,4 @@
-// Copyright (c) Microsoft Corporation.
+// Copyright (c) Microsoft Corporation.
 // Licensed under the MIT License.
 
 using System;
@@ -277,6 +277,8 @@ public void SetExit()
         public Task<T> InvokeTaskOnPipelineThreadAsync<T>(
             SynchronousTask<T> task)
         {
+            // NOTE: This causes foreground tasks to act like they have `ExecutionPriority.Next`.
+            // TODO: Deduplicate this.
             if (task.ExecutionOptions.RequiresForeground)
             {
                 // When a task must displace the current foreground command,
@@ -296,6 +298,7 @@ public Task<T> InvokeTaskOnPipelineThreadAsync<T>(
                 return task.Task;
             }
 
+            // TODO: Apply stashed `QueueTask` function.
             switch (task.ExecutionOptions.Priority)
             {
                 case ExecutionPriority.Next:
@@ -404,14 +407,10 @@ public void InvokePSDelegate(string representation, ExecutionOptions executionOp
 
         internal Task LoadHostProfilesAsync(CancellationToken cancellationToken)
         {
-            // TODO: Why exactly does loading profiles require the foreground?
+            // NOTE: This is a special task run on startup!
             return ExecuteDelegateAsync(
                 "LoadProfiles",
-                new PowerShellExecutionOptions
-                {
-                    RequiresForeground = true,
-                    ThrowOnError = false
-                },
+                new PowerShellExecutionOptions { ThrowOnError = false },
                 (pwsh, _) => pwsh.LoadProfiles(_hostInfo.ProfilePaths),
                 cancellationToken);
         }
@@ -625,7 +624,10 @@ private void RunTopLevelExecutionLoop()
         {
             try
             {
-                // Make sure we execute any startup tasks first
+                // Make sure we execute any startup tasks first. These should be, in order:
+                // 1. Delegate to register psEditor variable
+                // 2. LoadProfiles delegate
+                // 3. Delegate to import PSEditModule
                 while (_taskQueue.TryTake(out ISynchronousTask task))
                 {
                     task.ExecuteSynchronously(CancellationToken.None);
@@ -990,6 +992,8 @@ private void OnPowerShellIdle(CancellationToken idleCancellationToken)
                 while (!cancellationScope.CancellationToken.IsCancellationRequested
                     && _taskQueue.TryTake(out ISynchronousTask task))
                 {
+                    // NOTE: This causes foreground tasks to act like they have `ExecutionPriority.Next`.
+                    // TODO: Deduplicate this.
                     if (task.ExecutionOptions.RequiresForeground)
                     {
                         // If we have a task that is queued, but cannot be run under readline
diff --git a/src/PowerShellEditorServices/Services/Workspace/Handlers/ConfigurationHandler.cs b/src/PowerShellEditorServices/Services/Workspace/Handlers/ConfigurationHandler.cs
index 43a341191..f0020f122 100644
--- a/src/PowerShellEditorServices/Services/Workspace/Handlers/ConfigurationHandler.cs
+++ b/src/PowerShellEditorServices/Services/Workspace/Handlers/ConfigurationHandler.cs
@@ -97,7 +97,8 @@ public override async Task<Unit> Handle(DidChangeConfigurationParams request, Ca
                 }
             }
 
-            // TODO: Load profiles when the host is already running
+            // TODO: Load profiles when the host is already running? Note that this might mess up
+            // the ordering and require the foreground.
             if (!_cwdSet)
             {
                 if (!string.IsNullOrEmpty(_configurationService.CurrentSettings.Cwd)
@@ -124,6 +125,11 @@ await _psesHost.SetInitialWorkingDirectoryAsync(
                 _cwdSet = true;
             }
 
+            // This is another place we call this to setup $psEditor, which really needs to be done
+            // _before_ profiles. In current testing, this has already been done by the call to
+            // InitializeAsync when the ExtensionService class is injected.
+            //
+            // TODO: Remove this.
             await _extensionService.InitializeAsync().ConfigureAwait(false);
 
             // Run any events subscribed to configuration updates
diff --git a/src/PowerShellEditorServices/Services/Workspace/RemoteFileManagerService.cs b/src/PowerShellEditorServices/Services/Workspace/RemoteFileManagerService.cs
index 6c0b9bd1c..1229951de 100644
--- a/src/PowerShellEditorServices/Services/Workspace/RemoteFileManagerService.cs
+++ b/src/PowerShellEditorServices/Services/Workspace/RemoteFileManagerService.cs
@@ -645,9 +645,10 @@ private async void HandlePSEventReceivedAsync(object sender, PSEventArgs args)
             }
         }
 
+        // NOTE: This is a special task run on startup!
         private Task RegisterPSEditFunctionAsync()
             => _executionService.ExecuteDelegateAsync(
-                "Register psedit function",
+                "Register PSEdit function",
                 executionOptions: null,
                 (pwsh, _) => RegisterPSEditFunction(pwsh.Runspace),
                 CancellationToken.None);
@@ -673,7 +674,7 @@ private void RegisterPSEditFunction(Runspace runspace)
             }
             catch (Exception e)
             {
-                logger.LogException("Could not create psedit function.", e);
+                logger.LogException("Could not create PSEdit function.", e);
             }
             finally
             {