Do I have to file at home while living in Italy?
It depends on residence, not on address — except for US citizens and green-card holders, for whom the answer is yes regardless of where they live. We settle the residence question first, because every other answer follows from it.
Is there a treaty between my country and Italy?
Possibly, and the version in force for your year is the one that matters — protocols and multilateral-instrument positions change what a treaty does without changing its name. We check it against the authority rather than a summary. Where no treaty applies, domestic relief takes over.
I own property in Italy. Where is the rent taxed?
In Italy, because that is where the property sits. The complication is the base: gross-rent withholding takes no account of mortgage interest, tax or repairs, so a leveraged property can face tax on turnover. An election onto net profit, where it exists, is what fixes that — and it has its own timing.
Can I keep my Canadian job if I live in Italy?
Usually yes as a matter of tax, but it is not a neutral act for either you or your employer. Employment income is generally taxed where the duties are physically performed, so once you are sitting in Italy doing the work, Italy has a claim on it, regardless of where the employer is, where the contract was signed or which bank pays you. Your employer may also acquire obligations of its own in Italy, which is the part employees rarely raise before they go. The conversation to have with the employer belongs before the move, not after the first payslip.
Does my employer have to register in Italy if I work from there?
Possibly, and the exposure is not limited to payroll. Two distinct questions arise. First, whether the employer must operate Italian payroll withholding and social contributions for someone working in the country. Second, whether the employee's presence and activity create a taxable presence for the business itself. That second one turns on what the person actually does there, particularly whether they conclude contracts or play the principal role leading to their conclusion. A support role and a sales role in the same chair produce different answers, which is why employers are entitled to take a view before agreeing to the arrangement.
Which country takes payroll tax if I am paid from abroad but living in Italy?
The two do not have to match, and frequently do not. Where the salary is paid from is largely irrelevant. What matters is where the work is done, where you are resident, and which social security system you belong to. It is entirely possible to have income tax due in Italy while contributions continue in your home system, or the reverse. Treating the payslip as the answer is the common error. The order we work in is residence first, then the taxing right over the employment income, then social security, because each of those is decided by a different rule.
Am I self-employed in Italy if I invoice a company back home?
Invoicing does not by itself make you self-employed, and calling yourself a contractor does not settle it either. Both countries look at the substance of the relationship: who controls how and when the work is done, whether you bear any real business risk, whether you work for others. If the substance is employment, the arrangement can be recharacterised, with consequences for both sides. If it genuinely is independent work, you take on registration, invoicing and contribution obligations in the country where you carry it on. Which of the two it is should be settled before the first invoice, not after an enquiry.
Do I keep paying social security at home while working from Italy?
That is decided by the social security agreement between the two countries, separately from the income tax answer. Those agreements exist to stop a worker paying into two systems for the same work, and they generally allow a person posted abroad for a limited period to stay in the home system, with the home authority issuing documentation to prove it to the host country. Whether you qualify depends on how the move is structured, since a posting by an employer and a self-directed relocation are not the same thing. Resolve it before departure: the cover is easier to establish in advance than to reconstruct.
I worked from Italy for a few months, do I have to file there?
Possibly. A short stay does not automatically create an Italian filing obligation, and it does not automatically avoid one. Two things decide it: how the Italian residence test falls for that calendar year, and whether the income has an Italian source because the work was physically done there. Treaties contain a rule limiting the host country's claim over short assignments, but it carries conditions about who pays the salary and who ultimately bears its cost, and it is not a blanket exemption for anyone staying under a certain length of time. It has to be read against your own facts.
Can I revoke the foreign earned income exclusion, and what happens if I do?
You can stop claiming it, but a revocation is not a free toggle: having revoked, you are locked out of electing it again for a period of years unless the IRS consents to an earlier return. That is why switching from the exclusion to the credit is a modelled decision — it can be right, particularly where local tax is high or where you need earned income for retirement contributions or the refundable child credit, but it should be made once and deliberately. See exclusion against credit.
Can I move my 401(k) or IRA into an RRSP?
In limited circumstances, and rarely without cost. Canada allows a transfer of certain US plan proceeds into an RRSP with additional room for that purpose, but the withdrawal is a taxable distribution on the US side first, with withholding and potentially an additional charge for taking it early. Whether the Canadian credit fully absorbs that US tax is the calculation that decides it. Often leaving the plan where it is and drawing later is the better answer. See RRSP against 401(k) and IRA.
