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I am applying for Schengen Visa, I'll be ticking the “Multiple entry visa” as I have some plan to go back to Schengen zone after a month but that is not finalized yet. I will be only showing my current trip which I have booked completely.

Reg the Insurance, do i need to buy some annual trip insurance as I am ticking “Multiple entry visa”, or just insurance for the current concrete trip?

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    Note that, depending on your situation, simply checking the box might not be enough to get a multiple-entry visa. The consulate can still decide to issue a single entry visa. But it won't be because you don't have insurance. – Relaxed Apr 14 '16 at 6:24
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As someone who did the same as you did, you only need proof of insurance for the first trip (the trip whose details you provide as part of your visa application).

The insurance must have a minimum 30,000 EUR policy and cover the dates of your trip. I have used https://www.axa-schengen.com/en and found it to be easy and quick.

Assuming you get your multiple entry visa, for your second trip - you will need to obtain insurance again and carry proof of the same with you (along with other documents pertaining to the nature of your visit). You won't be visiting the embassy (since you already have a visa) but the immigration officer may ask for further documentation regarding the nature and purpose of your visit.

To be honest, I have yet to be asked for proof of medical insurance; I have been asked for hotel/ticket/purpose of visit etc. questions, but never "please show me proof of medical insurance"; however as the cost is trivial compared to the cost of the overall trip, it doesn't hurt to keep the paper with you; and hope you never have to need it during your trip :)

  • That is a very good answer . BTW A friend travelling with me was indeed asked for the insurance at the immigration counter . Also note that the duration of each stay in the visa will match the duration of the insurance you present ( or at least it used to ) – Obmerk Kronen Apr 16 '16 at 10:03
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You only need to submit proof that you have insurance for your first trip, cf. article 15(2) of the Schengen visa code:

Applicants for a uniform visa for more than two entries (multiple entries) shall prove that they are in possession of adequate and valid travel medical insurance covering the period of their first intended visit.

You probably also need insurance for each subsequent trip but you don't need to prove that in advance when applying; you only need to have it when presenting yourself at the border (and I don't think they check in practice).

Incidentally, this paragraph does not cover visas for two entries as those were originally intended for people from outside Europe who would visit the UK in the middle of a trip in the Schengen area. In that case, you are expected to have insurance for the whole journey, and not only for the first part of your stay in the Schengen area.

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