If you have an agreement that the shares will be gifted back to you after a period of time then that is going to be problematic too.
The only way you could avoid being caught under this kind of arrangement is by demonstrating that the original transaction was a commercial one and therefore not even a settlement in the first place, in which case the whole thing is outside the scope of settlements legislation and retained interest doesn't matter anyway.
I only mention this because it is quite possible to have a commercial arrangement whereby an investor invests £x for y% with an agreement to return a proportion of their shareholding if a business meets certain targets. The settlements legislation is specifically not designed to catch genuine commercial agreements like this.
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