diff --git a/CodeConverter/CSharp/VBToCSConversion.cs b/CodeConverter/CSharp/VBToCSConversion.cs
index d6b6bce1d..9452e8243 100644
--- a/CodeConverter/CSharp/VBToCSConversion.cs
+++ b/CodeConverter/CSharp/VBToCSConversion.cs
@@ -202,7 +202,7 @@ public List<SyntaxNode> FindSingleImportantChild(SyntaxNode annotatedNode)
 
     public async Task<Document> SingleSecondPassAsync(Document doc)
     {
-        var simplifiedDocument = await doc.SimplifyStatementsAsync<UsingDirectiveSyntax>(UnresolvedNamespaceDiagnosticId, _cancellationToken);
+        var simplifiedDocument = await _vbToCsProjectContentsConverter.OptionalOperations.SimplifyStatementsAsync<UsingDirectiveSyntax>(doc, UnresolvedNamespaceDiagnosticId);
 
         // Can't add a reference to Microsoft.VisualBasic if there's no project file, so hint to install the package
         if (_vbToCsProjectContentsConverter.SourceProject.AssemblyName == FabricatedAssemblyName) {
diff --git a/CodeConverter/Common/OptionalOperations.cs b/CodeConverter/Common/OptionalOperations.cs
index b1365d089..99a805825 100644
--- a/CodeConverter/Common/OptionalOperations.cs
+++ b/CodeConverter/Common/OptionalOperations.cs
@@ -48,4 +48,19 @@ public SyntaxNode Format(SyntaxNode node, Document document)
             return node.NormalizeWhitespace();
         }
     }
+
+    public async Task<Document> SimplifyStatementsAsync<T>(Document doc, string unresolvedNamespaceDiagnosticId) where T : SyntaxNode
+    {
+        using var cts = CancellationTokenSource.CreateLinkedTokenSource(_wholeTaskCancellationToken);
+        var token = cts.Token;
+        cts.CancelAfter(_abandonTasksIfNoActivityFor);
+        try {
+            // This sometimes gets stuck in an infinite loop within the CodeAnalysis library - https://github.com/icsharpcode/CodeConverter/issues/877#issuecomment-1221519204
+            return await doc.SimplifyStatementsAsync<T>(unresolvedNamespaceDiagnosticId, token);
+        } catch (OperationCanceledException) {
+            _progress.Report(new ConversionProgress($"Timeout expired - abandoning simplification for {doc.FilePath}. If within Visual Studio you can adjust the timeout in Tools -> Options -> Code Converter.", 1));
+            return doc;
+        }
+        
+    }
 }
\ No newline at end of file
diff --git a/CodeConverter/VB/CSToVBConversion.cs b/CodeConverter/VB/CSToVBConversion.cs
index af0d33da9..3cf34a3de 100644
--- a/CodeConverter/VB/CSToVBConversion.cs
+++ b/CodeConverter/VB/CSToVBConversion.cs
@@ -1,5 +1,6 @@
 using System.Globalization;
 using System.Text;
+using ICSharpCode.CodeConverter.CSharp;
 using Microsoft.CodeAnalysis.CSharp;
 using Microsoft.CodeAnalysis.CSharp.Syntax;
 using Microsoft.CodeAnalysis.VisualBasic.Syntax;
@@ -28,7 +29,7 @@ public async Task<IProjectContentsConverter> CreateProjectContentsConverterAsync
     }
     public async Task<Document> SingleSecondPassAsync(Document doc)
     {
-        return await doc.SimplifyStatementsAsync<ImportsStatementSyntax>(UnresolvedNamespaceDiagnosticId, _cancellationToken);
+        return await _csToVbProjectContentsConverter.OptionalOperations.SimplifyStatementsAsync<ImportsStatementSyntax>(doc, UnresolvedNamespaceDiagnosticId);
     }
 
     public SyntaxNode GetSurroundedNode(IEnumerable<SyntaxNode> descendantNodes,