A Canadian was recently denied a weekend visit from Toronto to NY due to two previous overstays for about a year.
- What is the the penalty for this overstay?
- How does he correct this so the next planned weekend doesn't get denied?
On his previous entries when he overstayed, did he receive an I-94 (paper or electronic) upon entry? Canadian visitors are usually not given I-94s. One generally only starts accruing "unlawful presence" after staying beyond the date on the I-94. If he did not get an I-94 (as is usual for Canadian visitors), then he does not automatically accrue "unlawful presence" even if he overstays. If he has no unlawful presence, then he has no ban. (There is a 3-year or 10-year ban for accruing 180 days or 1 year, respectively, of "unlawful presence", and then departing the U.S.)
Just because he has no ban does not mean they have to let him in. It just means he is not automatically denied entry. But the immigration officer at the border always has the discretion to deny entry to a visitor, especially one who has overstayed in the past. Since he has no ban, he does not file a waiver (because there is no ban to "waive"). He can just hope that they will let him in. There is no way to guarantee him entry.
The penalty for an overstay of six months to a year is a ban on entry for 3 years. The penalty for more than a year is a ban on entry for 10 years. That's why it's important to be precise about the time of overstay. I don't know how a second offence would be viewed. You can apply for a waiver of this period, but with two offences I wouldn't hold out much hope.
Your friend should probably be reconciled to staying home for a while, or if that's not possible, getting professional legal advice.