Having trouble getting 'Share an issue' to consistently work Edited

I have a Service Desk project that I create issues in via a portal. I'd like to be share the issue I created with others. When I go to my requests and look at a specific issue I see the share icon, and I can manually type in userid and they show up in the user's list, select one and share. The problem is that only seemingly random users actually have the share take effect. In many, but  not all, cases the selected user doesn't show up in the 'shared with' list on the issue, and the user doesn't get an email indicating share was done. However, in other cases it works as I would expect. I can't see any difference in groups/organization/user definitions between users that do work and those who don't. This problem both in the case where the selected user is just a customer and also when it has some licenses(core, confluence, etc) assigned to them.

Can anyone give me a clue on where I should be looking to find the difference between working and non-working share userids?

I'm using the cloud version

Thanks,

Jay

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