I've tried getEnabled and getVisible callbacks in Ribbon.xml file, but they are not called every time an email is opened. I've also tried subscribing to Outlook NewInspector event, but is executes only at the first time an email is opened. Is there any other method I could try?
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Inspectors.NewInspector event fires every time an item is opened as long as you keep the object that fires the events (Inspectors) in a global/class variable to make sure it stays alive. Please show your code that does not work for you.

Dmitry Streblechenko
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Thanks! Storing inspector reference helped. – user2508051 Feb 15 '14 at 19:07