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Gary11112 asks:" The funds are in a brokerage account and writing a check directly on the account is not an option. For private school
tuition due in December, would I withdraw the funds for myself and then
write a check from my account to the school, or would I write the check to the school first and then reimburse myself from the UGMA account? Or
does the sequence matter? Can I reimburse myself for tuition paid in June of this year? What about expenses from last year? What about expenses from five years ago?"

IMHO the sequence of writing the checks or withdrawing the funds is of not that much importance. The documentation to support your actions will be of importance. Now for how many years you go back may be rely on the date that the UGMA started. Certaimly you can be reimbursed for expenses incurred in Junes. Going back many years may be looked on as manipulative.

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