I have a homebrew item called Magic's Annoyance, for months it has worked fine then, suddenly as of may 14th it stopped being able to roll damage, all my other homebrew still work. 

Are you using any extensions or VPNs?

Can you provide a screen shot from the homebrew editor showing how you set up the item?

just beyond 20, but that still works for my other homebrew.

screenshot. https://imgur.com/a/rbXIpIn

Can you test by disabling Beyond20 and see if the dice roll?

If they do, Beyond20 is the reason (and most often is). 

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See, thing is, mine works perfectly but I don't use Beyond20 anymore (partly because I'm not playing right now and partly because Beyond20, while useful, is very buggy). If it was a D&D Beyond thing it wouldn't be so inconsistent and we'd be seeing a lot of similar complaints which we aren't. So that leaves the extension or how you set up the modifier (your screenshot doesn't show the modifier set up only the list of them). 

Since 99% of the time it's the extension, I'm gonna wager it's that. So please disable it and see if you can roll the dice with D&D Beyond's dice roller. 

it is beyond 20, that is very annoying as it used to work, it's not even that complicated an item just +1 and a d4 with a little text after the d4.

update. works if there is no text after the d4, o well.