@FlexsolveChris
Hi!
I've talked to the MS support team about this:
They told me custom commands are not being loaded on dashboard load, for performance reasons.
However with the customers approval, they can enable their loading.
We settled on the user clicking the row open into main form, and having the custom command displayed there.
However one thing that i personally noticed, is that if you go to a grid page, where the custom command is being loaded, and then go back to the dashboard, the custom command is displayed on the dashboard - i assume because it got cached when it was loaded in the main grid page.
Hopefully this helps you!