If an already existing fleet (737-800 and 900 without winglets) is thinking of a winglet modification, is that possible without regulations? Or what are the regulations?

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    $\begingroup$ Aircraft modifications in general are subject to airworthiness update. CAA (UK) // FAA (US). $\endgroup$ – mins Oct 28 '15 at 9:24
  • $\begingroup$ Are you referring to the regulatory approval process that declares the plane (type) is airworthy with the addition of the winglet, or the physical installation on an existing plane of a previously approved winglet? $\endgroup$ – FreeMan Oct 28 '15 at 12:53

In the U.S., changing anything on the wing is considered to be a "Major Repair/Alteration" according to the FAA (FAR Part 43 - Appendix A)

To make those changes, this form - http://www.faa.gov/documentLibrary/media/Form/Form_337.pdf needs to be completed.

As you can see, it requires a certified mechanic to handle the work after which a person with Inspection Authorization would approve the aircraft for return to service.

A little extra reading - Who can perform different maintenance checks?.

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    $\begingroup$ It's more than checking the change has been done properly. You need to renew the type certificate if a winglet is added, which includes structural tests and flight testing before a mechanic can attach the winglet to the next plane of the same type. Legally, that is. $\endgroup$ – Peter Kämpf Oct 28 '15 at 16:48

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