When an ESOP repurchases shares from departing employees, does this have an impact on Section 415 (individual annual addition) or Section 404 (corporate deduction) limits?
If the ESOP uses its own existing cash to buy back shares, then there are no 404 or 415 issues because there are no contributions being made. Cash goes out of employee accounts, where it has already been allocated, and is replaced by shares. If the company contributes additional cash to the ESOP to repurchase shares, then this too is an additional contribution that would affect both 415 and 404.
Link to this FAQ Topic: Distributions & Repurchase