diff --git a/src/components/tbc.core/Socket/Abstractions/IRemoteEndpoint.cs b/src/components/tbc.core/Socket/Abstractions/IRemoteEndpoint.cs
index ba83343..0157ad0 100644
--- a/src/components/tbc.core/Socket/Abstractions/IRemoteEndpoint.cs
+++ b/src/components/tbc.core/Socket/Abstractions/IRemoteEndpoint.cs
@@ -5,5 +5,5 @@ namespace Tbc.Core.Socket.Abstractions;
 
 public interface IRemoteEndpoint
 {
-    public Task<TResponse> SendRequest<TRequest, TResponse>(TRequest request, CancellationToken canceller = default);
+    public Task<TResponse?> SendRequest<TRequest, TResponse>(TRequest request, CancellationToken canceller = default);
 }
\ No newline at end of file
diff --git a/src/components/tbc.core/Socket/SocketServer.cs b/src/components/tbc.core/Socket/SocketServer.cs
index 7dc0fb9..83f5dc8 100644
--- a/src/components/tbc.core/Socket/SocketServer.cs
+++ b/src/components/tbc.core/Socket/SocketServer.cs
@@ -149,7 +149,7 @@ private async Task<ReceiveResult> ReceiveAndHandle(CancellationToken ct = defaul
         }
     }
 
-    public async Task<TResponse> SendRequest<TRequest, TResponse>(TRequest request, CancellationToken ct = default)
+    public async Task<TResponse?> SendRequest<TRequest, TResponse>(TRequest request, CancellationToken ct = default)
     {
         if (request == null) throw new ArgumentNullException(nameof(request));
 
@@ -158,7 +158,7 @@ private async Task<ReceiveResult> ReceiveAndHandle(CancellationToken ct = defaul
             _log("ignoring attempt to send message on finished socket server, please find the caller " +
                  "who did this and prevent them from doing this >:)");
 
-            return default!;
+            return default;
         }
 
         var responseMessageId =
diff --git a/src/components/tbc.host/Components/FileEnvironment/FileEnvironment.cs b/src/components/tbc.host/Components/FileEnvironment/FileEnvironment.cs
index bcacf8b..05a7d9e 100644
--- a/src/components/tbc.host/Components/FileEnvironment/FileEnvironment.cs
+++ b/src/components/tbc.host/Components/FileEnvironment/FileEnvironment.cs
@@ -93,6 +93,9 @@ private async Task TryLoadLoadContext()
                 var ctx = JsonConvert.DeserializeObject<PersistedContext>(
                     await File.ReadAllTextAsync($"{_loadContext}.json"));
 
+                if (ctx is null)
+                    return;
+
                 foreach (var file in ctx.WatchedFiles.Select(x => new ChangedFile { Path = x, Contents = File.ReadAllText(x) }))
                     IncrementalCompiler.StageFile(file, silent: true);
 
@@ -122,6 +125,8 @@ public async Task SetupReferenceTracking()
 
             var tempFilePath = FileSystem.Path.GetTempFileName();
             var targetHello = await Client.Hello(new HostHello { SharedHostFilePath = tempFilePath });
+            if (targetHello is null)
+                throw new Exception("Remote disconnected");
 
             var sharedFilesystem = targetHello.CanAccessSharedHostFile;
             var existingReferences = new List<AssemblyReference>();
@@ -344,7 +349,7 @@ private async Task AddSharedFilesystemReference(TargetHello targetHello, List<As
                 var reference = new AssemblyReference
                 {
                     AssemblyLocation = f,
-                    ModificationTime = FileSystem.FileInfo.FromFileName(f).LastWriteTime,
+                    ModificationTime = FileSystem.FileInfo.New(f).LastWriteTime,
                     PeBytes = await FileSystem.File.ReadAllBytesAsync(f)
                 };
 
diff --git a/src/components/tbc.host/Components/GlobalUsingsResolver/GlobalUsingsResolver.cs b/src/components/tbc.host/Components/GlobalUsingsResolver/GlobalUsingsResolver.cs
index 1fd362a..7cc74bc 100644
--- a/src/components/tbc.host/Components/GlobalUsingsResolver/GlobalUsingsResolver.cs
+++ b/src/components/tbc.host/Components/GlobalUsingsResolver/GlobalUsingsResolver.cs
@@ -76,7 +76,7 @@ source.Kind switch
 
         var (search, mask) = GetFilePathAndMask(path);
         var matches = _fileSystem.Directory.GetFiles(search, mask, SearchOption.AllDirectories)
-           .OrderByDescending(x => _fileSystem.FileInfo.FromFileName(x).LastWriteTime)
+           .OrderByDescending(x => _fileSystem.FileInfo.New(x).LastWriteTime)
            .ToList();
 
         var usings = matches
diff --git a/src/components/tbc.host/Components/IncrementalCompiler/IncrementalCompiler.cs b/src/components/tbc.host/Components/IncrementalCompiler/IncrementalCompiler.cs
index 0d1eedc..aaeeac3 100644
--- a/src/components/tbc.host/Components/IncrementalCompiler/IncrementalCompiler.cs
+++ b/src/components/tbc.host/Components/IncrementalCompiler/IncrementalCompiler.cs
@@ -244,13 +244,13 @@ public void WriteEmittedAssembly(EmittedAssembly emittedAssembly)
         {
             Logger.LogInformation("Writing emitted assembly {@Assembly}", emittedAssembly);
             
-            var peOut = _fileSystem.Path.Combine(_options.WriteAssembliesPath, $"{emittedAssembly.AssemblyName}.dll");
-            var pdOut = _fileSystem.Path.Combine(_options.WriteAssembliesPath, $"{emittedAssembly.AssemblyName}.pdb");
+            var peOut = _fileSystem.Path.Combine(_options.WriteAssembliesPath!, $"{emittedAssembly.AssemblyName}.dll");
+            var pdOut = _fileSystem.Path.Combine(_options.WriteAssembliesPath!, $"{emittedAssembly.AssemblyName}.pdb");
 
             _fileSystem.File.WriteAllBytes(peOut, emittedAssembly.Pe);
 
-            if (_options.EmitDebugInformation)
-                _fileSystem.File.WriteAllBytes(pdOut, emittedAssembly.Pd);
+            if (_options.EmitDebugInformation && emittedAssembly.Pd is {} pdb)
+                _fileSystem.File.WriteAllBytes(pdOut, pdb);
         }
 
         public void AddMetadataReference(AssemblyReference asm)
diff --git a/src/components/tbc.host/Components/TargetClient/ITargetClient.cs b/src/components/tbc.host/Components/TargetClient/ITargetClient.cs
index e73851d..8ebe91b 100644
--- a/src/components/tbc.host/Components/TargetClient/ITargetClient.cs
+++ b/src/components/tbc.host/Components/TargetClient/ITargetClient.cs
@@ -14,7 +14,7 @@ public interface ITargetClient : IDisposable
     Task WaitForTerminalState();
     IObservable<CanonicalChannelState> ClientChannelState { get; }
 
-    Task<TargetHello> Hello(HostHello hello);
+    Task<TargetHello?> Hello(HostHello hello);
     Task<IAsyncEnumerable<AssemblyReference>> AssemblyReferences(List<AssemblyReference> existing);
     Task<IAsyncEnumerable<ExecuteCommandRequest>> CommandRequests();
     Task<Outcome> RequestClientExecAsync(ExecuteCommandRequest req);
diff --git a/src/components/tbc.host/Components/TargetClient/SocketTargetClient.cs b/src/components/tbc.host/Components/TargetClient/SocketTargetClient.cs
index b6b8ade..3d7b769 100644
--- a/src/components/tbc.host/Components/TargetClient/SocketTargetClient.cs
+++ b/src/components/tbc.host/Components/TargetClient/SocketTargetClient.cs
@@ -83,8 +83,8 @@ public async Task WaitForConnection()
         }
     }
 
-    public Task<TargetHello> Hello(HostHello hello) =>
-        Target!.SendRequest<HostHello, TargetHello>(hello);
+    public Task<TargetHello?> Hello(HostHello hello)
+    => Target!.SendRequest<HostHello, TargetHello>(hello);
 
     public Task<IAsyncEnumerable<AssemblyReference>> AssemblyReferences(List<AssemblyReference> assemblyReferences)
     {
@@ -99,15 +99,18 @@ public Task<IAsyncEnumerable<AssemblyReference>> AssemblyReferences(List<Assembl
     public Task<IAsyncEnumerable<ExecuteCommandRequest>> CommandRequests()
         => Task.FromResult(_incomingCommandRequests.ToAsyncEnumerable());
 
-    public Task<Outcome> RequestClientExecAsync(ExecuteCommandRequest req)
-        => Target!.SendRequest<ExecuteCommandRequest, Outcome>(req);
+    public async Task<Outcome> RequestClientExecAsync(ExecuteCommandRequest req)
+    {
+        var result = await Target!.SendRequest<ExecuteCommandRequest, Outcome>(req);
+        return result ?? new Outcome { Success = false, Messages = new() { new() { Message = "Socket disconnected" } } };
+    }
 
     public async Task<Outcome> RequestClientLoadAssemblyAsync(LoadDynamicAssemblyRequest req)
     {
         var sw = Stopwatch.StartNew();
         var result = await Target!.SendRequest<LoadDynamicAssemblyRequest, Outcome>(req);
         Logger.LogInformation("Round trip for LoadAssembly with primary type {PrimaryTypeName}, {Duration}ms", req.PrimaryTypeName, sw.ElapsedMilliseconds);
-        return result;
+        return result ?? new Outcome { Success = false, Messages = new() { new() { Message = "Socket disconnected" } } };
     }
 
     public Task WaitForTerminalState() =>