Automated Workflow - Condition Blocks


I'm trying to create an automated workflow where if certain conditions are met, a request is sent to a contact person to update information. The issue is that I would like separate emails to be sent if (1) condition 1 is met => update closing date

(2) condition 2 is met => upload information

(3) condition 1 and 2 are met update closing date and upload information.

Below is how I've attempted to incorporate it. My issue is that I never seem to get to condition (3).

action for conditions (1) and (2):