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Problems with Requiring Time Spent on Status Transitions Edited

I have my sub-task workflow setup with a validator that requires Time Spent when transitioning between In Progress and Completed that launches a screen with the Log Work field. 

 

The scenario when someone enters a value for Time Tracking and attempts to make the transition from In Progress to Completed is problematic. The Log Work screen launches, but it doesn't pre-populate the Time Spent field with the value previously entered by the user.

Screen Shot 2020-06-24 at 2.24.22 PM.pngScreen Shot 2020-06-24 at 2.25.10 PM.png

I tried replacing the validator with a condition that checks that Time Spent !=0, but the user experience is less than ideal/not intuitive because the transition from In Progress to Completed isn't shown when the user clicks the status transition button. 

Screen Shot 2020-06-24 at 2.22.28 PM.png

 

Any ideas on how to set this up?

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