diff --git a/src/Cli/dotnet/Program.cs b/src/Cli/dotnet/Program.cs
index 71feefd8e7f9..077d46aa615a 100644
--- a/src/Cli/dotnet/Program.cs
+++ b/src/Cli/dotnet/Program.cs
@@ -306,19 +306,19 @@ internal static int ProcessArgs(string[] args, TimeSpan startupTime)
         {
             // If we didn't match any built-in commands, and a C# file path is the first argument,
             // parse as `dotnet run --file file.cs ..rest_of_args` instead.
-            if (parseResult.GetValue(Parser.DotnetSubCommand) is { } unmatchedCommandOrFile
-                && VirtualProjectBuildingCommand.IsValidEntryPointPath(unmatchedCommandOrFile))
+            if (parseResult.GetResult(Parser.DotnetSubCommand) is { Tokens: [{ Type: TokenType.Argument, Value: { } } unmatchedCommandOrFile] }
+                && VirtualProjectBuildingCommand.IsValidEntryPointPath(unmatchedCommandOrFile.Value))
             {
                 List<string> otherTokens = new(parseResult.Tokens.Count - 1);
                 foreach (var token in parseResult.Tokens)
                 {
-                    if (token.Type != TokenType.Argument || token.Value != unmatchedCommandOrFile)
+                    if (token != unmatchedCommandOrFile)
                     {
                         otherTokens.Add(token.Value);
                     }
                 }
 
-                parseResult = Parser.Parse(["run", "--file", unmatchedCommandOrFile, .. otherTokens]);
+                parseResult = Parser.Parse(["run", "--file", unmatchedCommandOrFile.Value, .. otherTokens]);
 
                 InvokeBuiltInCommand(parseResult, out var exitCode);
                 return exitCode;
diff --git a/test/dotnet.Tests/CommandTests/Run/RunFileTests.cs b/test/dotnet.Tests/CommandTests/Run/RunFileTests.cs
index 72c7f082d9b4..06d59a59bed2 100644
--- a/test/dotnet.Tests/CommandTests/Run/RunFileTests.cs
+++ b/test/dotnet.Tests/CommandTests/Run/RunFileTests.cs
@@ -264,6 +264,17 @@ Release config
                 Hello from Program
                 Release config
                 """);
+
+        // https://github.com/dotnet/sdk/issues/52108
+        new DotnetCommand(Log, "Program.cs", "Program.cs")
+            .WithWorkingDirectory(testInstance.Path)
+            .Execute()
+            .Should().Pass()
+            .And.HaveStdOut("""
+                echo args:Program.cs
+                Hello from Program
+                Release config
+                """);
     }
 
     /// <summary>