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Workflow Assistance

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Hi I've been struggling getting a workflow off the ground it never quite seems to perform the way i want. 

my conditions of this are related to products and their licensing information contained in dynamics

I want to check when a product licence renewal is 60 days away from expiration, for this i need to verify the product type and the expiration date

is the best way to start this 

If Product Licence:Expiration Date equals [ 2 Months Before Product Licence:Expiration Date] AND Product Licence:Product equals [****], 

Then i want to send an email as a reminder of product expiration

i then need to check values of whether or not customer has purchased and their licence renewed (which needs to check any change in renewal date and do this at at different intervals 30 days then 15 days for which i have included timeouts and i also send respective emails based on countdown of days and subsequent none renewal of product subscription. If they renew i need to capture this and end the workflow

Are there any good guides on this sort of this, some of the time my 60 day check gets skipped and moves to day 30 sometimes it sits in a constant waiting phase in system jobs. i have had varying results depending how i have modified the workflow.

i guess I'm just looking at the best way to create such a workflow any guidance much appreciated 


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