Bringing two laptops from UK to EU and back, one bought in UK and one in EU Pre-Brexit

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They are for personal use, and you are starting your round trip with them. It will be fine.

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What are the rules now?

If you would buy a laptop in Italy now, you would need to declare it when entering the UK and pay VAT. Those are the rules now and the main change brought about by Brexit to the scenario you mentioned.

Do I need to declare the one I bought in Italy to British Customs before I take any flights?

No, that's not how Brexit works, the laptop been grandfathered in if you will. I don't have a clear citation at hand (and there are a few annoying issues for stuff that was, e.g. bought just before the end of the transition period but returned afterwards) but you can easily see that coming back and collecting duty and import tax for everything that was traded since the UK joined the EU is not workable.

Various new rules are being phased in gradually but generally apply only to goods traded after the end of the transition period.

Even if it's for personal use and I intend to bring it back?

In theory, that doesn't make a difference. Either it was properly imported and taxed in the first place (which is the case here) and you have no problem or it hasn't and it's perfectly possible to get caught on a subsequent trip (we even had a question from someone who experienced this a few years back).

In practice, carrying some personal electronic equipment is so common that customs officers rarely seem to go to the trouble of checking anything (certainly one laptop and a phone, but usually a couple of devices of each category would be fine as well), even if they do challenge you or take a look at your bags (alcohol, on the other hand…).

In any case, the fact it's for personal use is not enough to completely circumvent customs rules and most laptops would need to be declared when you bring them into the country (current threshold for tax-free imports for personal use is Β£390).

The only relevant fact is therefore the date you bought and imported the laptop. If you really want to document something out of an abundance of caution it has to be this (receipt from the laptop and any proof you resided in the UK should be enough).

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