Hi Ana. With simple automations, this is really difficult and isn’t possible without some pretty severe workarounds. For this use case, I’d typically suggest make.com or General Caster.
Some options for avoiding using a third party tool:
If you were doing something like delaying the date each time it’s missed (which is possible) day by day, you could use a number column to keep count of the number of delays (knowing that each delay is only one day) and then use that count column hitting 5 as a trigger for some action.
But if people are just changing that column freely, there’s no way I know of in Monday.com natively to detect, store, or use that value in a way that is meaningfully integrated with automations.
One other alternative is rather than trigger a notification, you could use a formula column as a status indicator.
(You might want to make this more complex to account for situations with no delay or even include the number of delay days in the display)
Once you set this up, you’ll have a really useful column indicating the delay and warning you if something has an “illegal” delay. Also combine this with conditional formatting (set the row to red if column equals “Excessive Delay”) and/or use the result to create a filtered view with only delayed items.
When that’s set up, you might find you don’t need to use notifications at all because you have a really useful monitoring view.
I think people’s first instinct is to create notifications for everything. After a while that can cause them to lose meaning or get lost in a crowd. They certainly have their place, but there are other ways of keeping track too!
Best of luck with your solution. Feel free to reach out if you have questions or need some help.