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To: gdb@sourceware.org
From: meator <meator.dev@gmail.com>
Subject: Re: How can I reload a pretty printer?
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List-Id: <gdb.sourceware.org>

Of course right after I send the email, I find the solution. Passing 
replace=True to register_pretty_printer() solves my problem. I have 
asked the same question on the IRC and was bit impatient. They have 
solved my problems.