Depending on my experience in Silverlight following these steps keep your project debug-gable.
Condition 1>
Firstly we need to be ensure that in Web Project's properties there is a Web section, as you see below Silverlight checkbox must be checked.
Condition 2> Follow In Menu Debug => Attach Debugger>
Visual Studio sometimes can't attach debugging platform you need to lead the way :) . By this way you may debug other platforms,(also you may debug your product platform but pdb files must be sync and don't forget you may suspend your product platform using this).
Condition 3> Your default web browser may be Firefox,Chrome or other than IE.By Visual Studio default try to attach to IE. But when you run VS calls default browser,so you need to have a manual attachment in Condition 2 or set your default browser by right clicking on default page > Browse with .
Condition 4> There is xap file generally located in web project\ClientBin directory. Sometimes after build operations this file can't be replaced and your ProjectDll and your Project PDB files not be sync. This cause wrong line match while debugging or can't find a debugging file attached caution. I strongly suggest delete all generated files in Bus project and delete Clientbin\ProjectName.xap file. After rebuild all it must be ok!
Hope helps.
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