Bob is an employee of Company A who is a third party service provider for Company B.
Company B decide to do that service themselves so they TUPE over Bob.
Company B don't need Bob so there's a tripartite settlement agreement between Bob + Company A + Company B.
As part of that settlement, Company B make a termination payment to Bob consisting of redunancy + notice + a £30k ex-gratia payment.
Can Bob also receive a £30k ex-gratia payment from Company A?
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The parties may do whatever they wish but would need to take tax advice to ensure the payments were appropriately dealt with by payer(s) and payee.
When asking a question on an open internet forum such as this, it is wise to be quite clear and specific as to what you are asking. It is then also wise to make sure that any answers you receive provide you with sufficient information to enable you to make a sound judgement, rather than simply relying on some unknown person's say so.
Is this an entirely legal question? Most that start with "can" are.
Even were this a legal forum (it's not), I don't see how anyone could answer with any certainty. You haven't told us much. For one thing, Company A is governed by its constitution (Articles etc) as well as by company law.
But (in case you still haven't grasped the point) the question you asked is - presumably - not the question you intended to ask. I think the answer to that is almost certainly no. But you really haven't told us much. The answer may well be no and no.
Perhaps 3 questions
"When" and "how "to take ex-gratia on termination
.......
Can Bob also receive a £30k ex-gratia payment from Company A?
Though no ? in the titular summary so perhaps not.
The answer is, of course, if you have an issue where tens of thousands of pounds of tax are at stake, pay for professional advice.
The issue is not who pays, but what for? This is a payment in connection with Bob's employment, so the first question to ask is what are the terms of his employment by Company A? Is he entitled to pay in lieu of notice{PILON] under the terms of that contract. If so it is more difficult to persuade HMRC that the payment is in fact ex gratia.
Just to be clear whether the payment is made by company A or Company B is immaterial