An IRA custodian will always report on Form 1099-R a check written on an IRA that has check-writing privileges, treating this a distribution and rollover, not a trustee-to-trustee transfer. To make it a trustee-to-trustee transfer you would have to either convince the IRA custodian not to include this on Form 1099-R or convince the IRS that the Form 1099-R is incorrect because you did not have constructive receipt of the funds. It would be challenging to convince either of these entities, so moving money from one IRA to another in this manner should be avoided unless you intend it to be a distribution and rollover.
