Can the transfer get held up at the bank?

It can, and the reason is usually not tax. Banks classify incoming transfers by reading the payment description alongside the relationship between the parties. Money arriving from a company you own does not automatically read as a dividend. A single word in the description can have the transfer treated as a loan or a capital movement and held for weeks. A description that reflects what the payment actually is, backed by a documented distribution resolution, is what moves it fastest.