I have a DB plan which mailed its 6/30/99 contribution to the investment fund on 3/14/2000. The contribution was sent 2nd day, and therefore was not received by the investment fund until 3/16/2000. Was this deposited timely?

I'd take the position it was, assuming the check actually was received within a reasonable time after the date written. When an individual writes checks on 12/31, to a charity for example, she gets to take a tax deduction for that amount. Now if the check does not reach its destination until 4/1, that could raise a fact issue about when it was in fact written/mailed.

I agree.

Jim Holland of the IRS gave a verbal opinion where he basically agreed with the prior two responses. Namely, the IRS is flexible as long as the contribution is received within a day or two of the date of the check.