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. 

[#4]

@FarmhouseNetworking 

For the version I have installed for the full software installed client (not Web version):Outlook Version 2205 (Build 15225.20288 Click-to-Run), Current Channel.

I found in the Message Ribbon, command: Tags (pop out for dialog box), This opens the message properties box. There I found in the upper left a Settings area. That contains a Sensitivity Drop down box. The labels I found appear the same as they have been since the late 1990's: Normal, Personal, Private, and Confidential.

I hope this helps in some way.

Best regards.

[#5]

@Taen keren 

I figured out, that sensitivity label settings that have enforced encryption (encrypt only, do not forward) settings included are greyed out when having Outlook settings for signing or encrypting mails via SMIME activated.

When deactivating encryption or signing via. SMIME the sensitivity labels are not greyed out anymore.

Maybe this solves your problem?