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Agreements randomly not generating Booking Dates

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We've had agreements setup in our 365 environment since launch - 2019.  And have always randomly had problems where booking dates aren't generated.  Say an agreement is setup for an Annual Fire Inspection.  There are 3 past booking dates out there for 3/2/2020, 3/2/2021, 3/2/2022 .... the 3/2/2023 booking date didn't get generated .. but the 3/2/2024 booking date did get generated.  

Sometimes that 3/2/2024 booking date doesn't get generated either .. we would have to deactivate the agreement and the booking setup, and reactivate it to get the dates generated.  There is no end date set on the Agreement on these, its set to 1/1/2079.

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