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Can't really find an example exactly like mine, so sorry if this is duplicative.

The user needs to have the ability to assign 1 or many users to an account as an owner. The user needs the ability to assign 1 or many users to many accounts.

The problem comes with bulk actions. Let's say I select 5 accounts, and each account has a unique owner. How do I represent that in the UI so that the user doesn't think that they need to add the unique owner as well as the new owner they want to add.

I have three solutions

1.) This allows you to add users to multiple accounts. However, this is confusing since this doesn't show that some users have already been added.

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This solution is tagging, while allowing them to create a template with any of the accounts and apply all. Seems complicated.

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This solution shows that there are mixed values, but not very intuitive in how you add.

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You can handle this situation without any communication with the user of your program.

From your example (I'm the user of your program):

I select 5 accounts from the account list.
I hit the button "add owner/owners".
The program displays a list of owners.
I select one person.
I hit the "add" button.
The program goes to the first account and checks if that person exists in the owners list of this account.
If yes, it does nothing.
If not, it adds the person to the owners list of the account.
Then, the program, goes to the second account...

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