The deadline is the most important thing to every trucker while operating heavy vehicles on public roads. The IRS recommends heavy vehicle owners file the 2290 tax by the 2290 form due date or on time. For Truckers who file annual returns, the tax season begins on July 1 and ends on August 31. The tax year starts on July 01 and ends on June 30 for the following year. Therefore, never be late filing your HVUT tax return.