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Safeguard outlook add-in

I have a synchronized encryption policy set up and everything appears to be installed and working correctly except for the outlook add-in. On x64 systems with 32bit Office installed I can see the add-in is installed but when sending an encrypted file to an email address outside of our organization I do not get a prompt to decrypt the file. On my windows 10 x64 machine with 32bit Office I do get the prompt and everything seems to work great. Is there something I am missing? Below is the picture from my outlook on the machine that isn't working showing version number and 32bit.

 



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