Is there a penalty if Form 8288-A is filed late?
There is exposure, and it does not sit where sellers expect. The statement is prepared on the buyer's side of the transaction, so lateness is a default by the party with the withholding obligation, and penalties of this kind are measured by reference to the form and the length of the delay rather than to anybody's tax bill. That is why a sale on which no tax was ultimately due can still be expensive for the party that had to file. The amount depends on the year involved, so check the schedule that applied to that year rather than working from a figure you remember.
What happens to my refund if the statement arrives late?
Usually it waits. The credit for the withholding has to be traced to the disposition it came from, and the statement is what does the tracing, so a claim filed without it tends to sit in correspondence rather than be paid. The practical approach is to file on time with the evidence you hold, being the settlement statement, the remittance confirmations and the correspondence requesting the statement, and to send the statement in when it arrives. That keeps your own filing position clean, which matters more than the wait, because a late statement is somebody else's default and a late return would be yours.
Can I claim the withholding without the statement while I wait?
You can report the disposition and claim the credit, and you should not miss a filing date waiting for a document you do not control. What you cannot do is expect the claim to be paid on assertion. Put the evidence you hold in the file: the settlement statement showing the amount held back, the remittance confirmation, and a note of who was asked for the statement and when. Then expect a query, and expect to answer it with the statement once it exists. Filing with the weaker evidence and improving it later is a better position than filing late with perfect papers.
Who gets penalised for a late statement, me or the buyer?
The default belongs to the party that had to prepare and furnish it, which is on the buyer's side of the transaction. Your loss from the delay is different in kind: the money is already with the tax authority, and what lateness costs you is the time your refund claim spends in correspondence. That asymmetry is worth understanding before you spend effort on the wrong problem. Chasing the document firmly and in writing serves you. Worrying about a penalty charged to somebody else does not, unless you were also the party that handled the withholding.
Does it help that no tax was owed on the sale?
Not to the filing question. The obligation to produce the statement follows the disposition, not the outcome of the seller's return, so a sale that ended in a loss still had withholding remitted and still needs the paperwork that evidences it. If anything the no-tax case is the one where the paperwork matters most, because the whole amount withheld is coming back and the claim for it has to be traceable. Sellers who conclude that nothing is owed and therefore nothing needs doing are the ones who write to us later about an unpaid refund.
The sale was years ago and I never claimed it, too late?
Maybe not, but it is a question decided by dates rather than by when you discovered the problem. A claim for refund of tax withheld is available for a limited period measured from the filing dates for the year of the disposition, so the first step is to establish the year, the closing date and what was remitted. Then look at the earliest year still open and work forward. Do not start by chasing the document: start by working out which years can still produce a refund, because that decides whether the chasing is worth doing.
Is my foreign pension taxable?
Usually in at least one country, and which one depends on the treaty article covering pensions — some give the taxing right to the country paying it, others to where you live, and several treat government service pensions differently again. Withholding at source is common and often reducible by treaty, with an elective return recovering an over-deduction. See the pensions article.
Can I set up a trust that works in two countries?
You can, but the two systems classify and tax trusts differently enough that a structure which is efficient in one is often a reporting problem in the other — a Canadian family trust with a US beneficiary, or a US revocable trust holding Canadian property, are the classic pairs. Canada's twenty-one-year deemed disposition, the US grantor rules and each country's reporting have to be read together, before drafting rather than after. See cross-border wills and trusts.