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DILE is so excellent utility and I can debug some .NET apps mostly situation. But sometimes I want to set breakpoint at Main() or .ctor in entry class, it can't work on!
Within the next release, more debug options could be supported? Like: Break on process initialization, break on thread start, break when DllMain called? etc., and so on...
I'm sorry for answering only now but I didn't spend the weekend at home.
Actually some of the options that you mention are already available. In the Project Explorer right-click on the project name and choose Properties. In the displayed window choose "Debugging" from the list and you'll get several options that can be selected as "breaking event". For example, if you check the CreateThread event then whenever a new thread is created DILE will break the execution of the debuggee. I think this is what you're looking for...
In the next release, you'll also be able to start debugging by stepping (F10/F11/F12) and then DILE will break on the first instruction of the entry method.
And about the breakpoint issue, yes, I know it's a little bit confusing and uncomfortable to use. I also often set breakpoint on 3-4 consecutive instructions and hope that one of them will be hit. However, this is rather a CLR problem. But I'll try to somehow make it more convenient...