Visual Studio Remote Debugger and PDB files
When I tried to remote debug a windows service I was wondering why VisualStudio kept telling me that my BreakPoints wouldn't be hit because the symbols haven't been loaded, although the PDB files where on the remote host. Turns out there are a few cases where you need the PDB files both on the remote host and on the client. Here is a brief excerpt from MSDN about this:
The symbol files for native applications must be located on the Visual Studio host computer.
The symbol files for managed applications must be located on the remote computer.
The symbol files for mixed (managed and native) applications must be located on both the Visual Studio host computer and the remote computer.
Apart from that, I've noticed that a ClickOnce application can provide the .pdb files but only if the application to deploy is not an Office AddIn. As soon as the project is an Office AddIn, the option to specify the files you want deployed is gone. Due to this limitation I switched most setup projects from ClickOnce to Wix#. This allows me to programmatically create and deploy a MSI which can include .pdb files, that then can be picked up by VS when remote debugging. For this to work simply add the remote folder path to your symbols location list.