Now that I have withdrawn twice from my daughter's 529 plan, I wanted to share some timing issues I've experienced. I withdrew (check payable to my daughter since that is the recommended approach) both in July and early December to pay 1st and 2nd semester bills for the 2015-2016 school year. Because when paying to the beneficiary the relevant 529 Plan will only send a check, I had to deal with a 5-10 business day delay before receipt of the check. After receipt, endorsement by student, and deposit, there is then another couple of days delay b/c the bank won't immediately make the funds available due to the large dollar amount. It all worked out okay in July although ultimately, our tuition payment was late. For December, we received permission from the bursar on a one-time basis to just endorse the check over to them for payment so that we didn't risk the payment being made in January instead of December, thus screwing up our "matching" of payments. Fortunately my daughter's small college is willing to work with us. They recommended that we send the check directly to them in the future - it does not impact financial aid in their case. I just find it very nerve-wracking that we can't guarantee matching of withdrawal and payment in the same year in December especially when issuance of that check and ultimate payment is in the hands of others. Of course if we had cash available in the amount of semester bills we could pay with that and then reimburse ourselves, but we don't (thus the whole reason for having a 529). Is the solution just to withdraw very early each year? I am reluctant to do that just b/c you never know what could happen. What if my daughter decided to not go back to school or something like that? I realize I may be worrying too much, but curious how others have dealt with this timing issue.