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I did this several time before, without any problem. But somehow, this time it simply doesn't work.

Systems:

Remote PC: VPS, Guest Win2008R2 x64 dual core (hosted on VMWare Server), VS 2008 remote debug x64 Sp1, application ASP.NET 2.0, isolated in own classic app pool. All updates applied. Host (if matters): AMD Phenom quad core

Develop PC - Win7 x64, VS 2008, all updates applied

I can connect to remote PC with Attach to Process. If I stop and start the app pool while "Attach to process" is open in VS, I can see the process and (apparently) I can attach to it. However, the breakpoint briefly get activated (red, filled) then immediately gets deactivated (red empty circle) and of course it doesn't stop the application.

I searched on google and found very few references. One suggested to copy the *.PDB in asp.net temporary files, and even if there there are lot of dirs with subdirs (one for each dll) I copied all PDB in temp folder with the dll. No success.

I'm running out of ideas. Does anyone feced similar issue? Any thoughts?

Thanks

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You need pdb files for the same. Copy the actual pdb files of the dll from the development project. It will be inside the bin/debug/ directory of your original project (source code one not the deployed). Then copy the pdb file to remote directory where the dlls resides and then attach the debugger. Also for that , you need Remote Debugger.

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Thanks, but I did all this: I published the app (with bin and all dll's and pdb) to remote pc - all dll's and PDB were there. I started the remote debugger on remote pc, as Admin, (I was logged ion remote pc with same user as on dev pc). Then I attached VS to remote debugger (as I said I did this lot of time before and it worked everytime).
Use visual studio remote debugger.
And also check if vs ide is in release or debug mode. If its in release change it to debug
Yes. the project was built in debug mode. VS is in debug mode. I attached to VS to VS remote debugger on remote pc.
no not the development one. the one which you are using for debugging must be in debug mode.
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