Hi,
Thank you for reaching us!
You'll need to use two rules using schedule and cron expression:
This cron below will make your rule run every 1st day of each month:
The cron will fire your rule every first day of each month at 08:00 AM.
0 0 8 1 1/1 ? *
This cron will make rule run every 15th day of each month:
The cron will fire your rule every month at day 15 at 08:00 AM.
0 0 8 15 1/1 ? *

Note: Automation for Jira Could use UTC-0. So you need to calculate based on this UTC if you would like to fire on the right hour.
Furthermore, if would like to change your cron you can use cronmaker:
http://www.cronmaker.com/
Also, you can see the next time that it'll run.
Can you give a try with this cron above and let me know how it goes?
Cheers,
Cristiano
[Automation for Jira Support]
Thanks for such detailed answer!
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hello @Rob .
The easiest way to do this would be to go for and add-on such as the scheduler.
There is no solution out of the box in jira.
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