Hello, i have a workflow Trigger that is not working. Can someone tell me what i am doing wrong or if When trigger is not working when you select two options. its seams like to me when two options are selected and "any" of above it selected it never runs the workflow when the second When option is called on?

Module - Opportunity/ Deals 

workflow Issue - emblem status doesn't trigger workflow to run when picklist is changed

Example - 

1st pic - workflow "When" showing emblem status on change and Any are satisfied 

2nd pic - showing emblem status - when changed to "emblem Approved"

3rd pic - timeline showing Emblem Status was changed to - Emblem approved but the workflow was not called on (screen shot was taken 30 minutes after Emblem Status was changed incase workflows are taking a long time to run, time stamp 11:55am)