From your description, you are evaluating VSTA 1.0.
You need to unload the 'release' add-in, build a 'release' of the add-in and reload new add-in before the changes can be reflected.
This is demonstrated by the AdvancedShapeApp samples with macro recording. The IDE/debug version makes things confusing.
This might be a helpful hint:
There is a bug in the ShapeApp MacroManager samples which by default prevents the list of macros from being populated without first recording a macro or opening and building the macro project. If you are using the ShapeApp sample’s MacroManager and the code associated with this in the extension class, you are probably having the same problem. To check if this is the same problem, try starting the shape app sample, then record a macro or open and build the macro project - once either of these are done the macro list should be populated.
If the above check works, then try changing the line in the Connect method of the Extension class (line 61, see below) that assigns the macroAddInPath using “bin\debug” to use “bin\release” instead. The folder used to create the macroAddInPath should match the build output of your macro project.
//Change this to match the build output of the macro project
//this.macroAddInPath = System.IO.Path.Combine(this.macroProjectPath, @"bin\debug");
this.macroAddInPath = System.IO.Path.Combine(this.macroProjectPath, @"bin\release");
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The simplest minimal sample would be Testcon (http://www.summsoft.com/files/folders/vsta_samples/entry248.aspx)