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Hang on... is this user group a group of admins? And by that I mean users who are assigned an SP admin role? If so then they don't have a 'real' user group as their permissions are global and blanket. and it makes no difference what WP role they have as that has no relevance. So is this the case?

OK. .So let's backtrack. I may be wrong here but I wasn't aware that WordPress allowed for multiple roles for a single user. It's natural and standard state as I understand it is one user/one role. So what plugin are you using that allows for this? And perhaps you need to talk to the plugin authors about firing the right hooks.

So - a few things first. SP allows for users to belong to multiple user groups (although you can turn that off).

When you use the explicit 'map users to user group option' - SP will trawl through the users and the roles they are associated with and implement the mapping rules you have set. This is always going work.

I do not know how fully you understand WP action and filter hooks so excuse me if I cover ground you are familiar with. When an action occurs - such as a user is assigned to a  WP role - an action is triggered. Think of it like a message being broadcast and all your plugins can pick up that message and they know if they have to do something in response.

SP knows it might have to adapt the users role/user group mappings on a WP role change or assignment. But only if that message is sent.

When a plugin takes over responsibility for a task then it is supposed to trigger the same actions - i.e., send out the same messages for plugins to pick up. This is where some plugins have been seen to go astray. They fail to replicate standard WP API behaviour as they are supposed to. The net result is, of course, that plugins like SP do not get the message and hence - do not respond as expected.

I am, of course, merely speculating at this juncture. But this is, as I have said above, something we have encountered before wth a membership plugin and it is possible that this was the one - I just don't recall the name and frankly, searching for the term 'Members' through the forum topics is going to yield a very high result count!

Which lead to my suggestion that perhaps asking the plugin authors if they do correctly call all of the WP filter and action hooks as expected - might be a good idea. Especially in the area of role assignment and role change.