Sensitivity button grayed out

[Taen keren]

Hi 

Previously the Sensitivity button was working fine in word 8latest ProPlus) - now its grayed out. 

Classifications Labels are defined and scoped/re-published to an O365 group/members through the compliance center - however, the button remains grayed out - got E3 licenses. 
The group also has a 'Team' and therefor SharePoint site where there are files that need to be classified

Why is this suddenly stopped working? - how to troubleshoot this? 
 

[#2]

Happy New Year @Taen keren,

1)  Has it ever worked?

2)  What about in Outlook Web Access?

3)  If you have more than one mailbox setup on your profile, like a Shared mailbox.  Make sure you are not trying to send from it.  It may not have a license and may not have a Security forms.

4)  If you have more than one mailbox setup on your profile such as a shared mailbox.  Make sure that the Primary Office file "OST" file matches the account sending the email from.

As this has been a couple months since you posted your question, hopefully you found an answer already.

Take Care,

Kevin

[#3]

@Taen keren I found that there is a "new feature" in the Office 365 admin portal under the Compliance Center > Information Protection section. You have to create a new Sensitivity label that sets it for files & emails to encrypt, let user decide on the options, and let any authenticated user open them. You then have to create a label policy to publish it to all users. This worked great for us.