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Home/ Questions/Q 894587
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Editorial Team
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Editorial Team
Asked: May 15, 20262026-05-15T14:24:57+00:00 2026-05-15T14:24:57+00:00

I’m trying to debug an ASP.NET web application in this environment: Windows Server Standard

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I’m trying to debug an ASP.NET web application in this environment:

  • Windows Server Standard 2008 SP2 x64
  • Single-core CPU
  • 4GB RAM
  • Visual Studio 2008 with Remote Debugger SP1
  • .NET 3.5 Web Application running in IIS in 64-bit mode

The code I am trying to debug is a simple event handler with some basic sequential code.
What I observe is that breakpoints get randomly ignored and VS often exits debug mode when I try to step through the code.
The code is compiled in debug mode.

EventViewer shows no warning or error messages that would relate to this. I am certain that this is not caused by IIS app pool recycle/reset.

I’ve tried all the usual steps: iisreset, reboot VM, rebuild solution, reinstall Visual Studio.

Any ideas?

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  1. Editorial Team
    Editorial Team
    2026-05-15T14:24:58+00:00Added an answer on May 15, 2026 at 2:24 pm

    Could not find a solution.

    Worked around this behaviour by using a combination of Debug.Print() and Sysnternals DebugView

    Hope this helps.

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