Thanks for the reply.
On the /libs/cq/workflow/content/console.html i'm not seeing anything unusual on both instances and failures tab.
Should i be checking somewhere else?
In addition, what i found as a workaround
1. Activate the asset
2. Right-click choose Workflow
3. Select DAM Update Asset and Start it.
4. Refresh the whole DAM Admin page
So i'm guessing is that the DAM Update Asset is not being fired automatically?