scalecrop.swift

import UIKit

// Swift rewrite challenge
// Starting point: https://gist.github.com/jkereako/200342b66b5416fd715a#file-scale-and-crop-image-swift

func scaleAndCropImage(
    image: UIImage,
    toSize size: CGSize,
    fitImage: Bool = true
    ) -> UIImage {
    
    // Return original when cropping is not needed
    guard !CGSizeEqualToSize(image.size, size) else { return image }
    
    // Calculate scale factor for fit or fill
    let (widthFactor, heightFactor) = (size.width / image.size.width, size.height / image.size.height)
    let fitFillTest = fitImage ? widthFactor < heightFactor : widthFactor > heightFactor
    let scaleFactor = fitFillTest ? widthFactor : heightFactor
    
    // Establish drawing destination, which may start outside the drawing context bounds
    let (scaledWidth, scaledHeight) = (image.size.width * scaleFactor, image.size.height * scaleFactor)
    let drawingOrigin = CGPoint(
        x: (size.width - scaledWidth) / 2.0,
        y: (size.height - scaledHeight) / 2.0)
    
    // Perform drawing and return image
    UIGraphicsBeginImageContextWithOptions(size, false, 0.0)
    let scaledImage: UIImage
    do {
        // Fill background
        UIColor.blackColor().setFill(); UIRectFill(CGRect(origin: .zero, size: size))
        
        // Draw scaled image
        let drawingRect: CGRect = CGRect(
            origin: drawingOrigin,
            size: CGSize(width: scaledWidth, height: scaledHeight))
        image.drawInRect(drawingRect)
        
        // Fetch image
        scaledImage = UIGraphicsGetImageFromCurrentImageContext()!
    }
    UIGraphicsEndImageContext()
    return scaledImage
}

// Test with some basic placeholder data
guard let url = NSURL(string: "http://placehold.it/300x150") else { fatalError("Bad URL") }
guard let data = NSData(contentsOfURL: url) else { fatalError("Bad data") }
guard let img = UIImage(data: data) else { fatalError("Bad data") }

let outImageFit = scaleAndCropImage(img, toSize: CGSize(width: 200, height: 200))
let outImageFill = scaleAndCropImage(img, toSize: CGSize(width: 200, height: 200), fitImage: false)

I did not have a guard to prevent needless scaling in my version of this code. Good Stuff!

But I think you will like this defer : (had not refreshed the page to see your new comments...)

UIGraphicsBeginImageContextWithOptions(newSize, false, 0.0)
defer { UIGraphicsEndImageContext() }

And maybe this bit :

func scale(toSize newSize: CGSize, fit: Bool) -> CGSize {
  let test : (CGFloat,CGFloat) -> CGFloat = fit ? { max($0, $1) } : { min($0, $1) }
  let scale : CGFloat = test(width / newSize.width, height / newSize.height)
  return CGSize(width: (width / scale), height: (height / scale))
}

my version

I would recommend to split into several functions (size calculations, image cropping, glue) for unit testing support.

my version

Add asserts for size.width and size.height > 0.0 or some minimum point size as desired. See: http://twitter.com/deadbeefa/status/737722278608142345

Enjoyed the light challenge.
Here's my full rewrite (FWIW), it doesn't add the functionality you added.
I like your use of do and tuples.
My preference is for an extension of UIImage.
I still maintained an if/else/else.

also re: "http://placehold.it/300x150" … i heard angels sing (new to me and quite useful!)

extension UIImage {
  func scaleAndCrop(size: CGSize) -> UIImage {
    guard CGSizeEqualToSize(self.size, size) == false else {
      return self
    }

    let widthFactor = size.width / self.size.width
    let heightFactor = size.height / self.size.height
    let scaleFactor = max(widthFactor, heightFactor)
    let scaledWidth = self.size.width * scaleFactor
    let scaledHeight = self.size.height * scaleFactor

    var scaledRect: CGRect
    if widthFactor > heightFactor {
      scaledRect = CGRect(x: 0.0, y: (size.height - scaledHeight) / 2.0,
                          width: scaledWidth, height: scaledHeight)
    } else if widthFactor < heightFactor {
      scaledRect = CGRect(x: (size.width - scaledWidth) / 2.0, y: 0,
                          width: scaledWidth, height: scaledHeight)
    } else {
      scaledRect = CGRect(x: 0, y: 0,
                          width: scaledWidth, height: scaledHeight)
    }

    UIGraphicsBeginImageContextWithOptions(size, false, 0.0)
    self.drawInRect(scaledRect)
    let scaledImage = UIGraphicsGetImageFromCurrentImageContext()!
    UIGraphicsEndImageContext()

    return scaledImage
  }
}

Useful method for performing drawing in the resulting context
Using calculation of x, y in both branches instead of checking for if widthFactor > heightFactor

import UIKit

extension UIImage {

    /**
     Creates image of specified size and perfomrs drawing commands

     - parameter size:    result image size
     - parameter drawing: closure that contains deawing operations

     - returns: image with the drawing operation
     */
    func drawingWithSize(size:CGSize, @noescape drawing:()->()) -> UIImage {
        UIGraphicsBeginImageContextWithOptions(size, false, 0.0)
        drawing()
        let image = UIGraphicsGetImageFromCurrentImageContext()!
        UIGraphicsEndImageContext()
        return image
    }

    /**
     Scales image to specified size, savin aspect ratio
     Crops parts of image that out of provided size 
     Works as UICntentModeAspectFill

     - parameter size: result image size

     - returns: scaled image
     */
    func scaleAndCrop(toSize size:CGSize) -> UIImage {

        // Skip unneeded scaling
        guard CGSizeEqualToSize(self.size, size) == false else {
            return self
        }

        let scaleFactor = max(size.width / self.size.width,
                              size.height / self.size.height)

        let (scaledWidth, scaledHeight) = (self.size.width * scaleFactor,
                                           self.size.height * scaleFactor)

        let drawingRect = CGRectMake(
            (size.width - scaledWidth) / 2.0,
            (size.height - scaledHeight) / 2.0,
            scaledWidth,
            scaledHeight)

        let scaledImage = drawingWithSize(size) {
            self.drawInRect(drawingRect)
        }
        return scaledImage
    }
}

@PaulTaykalo

In my real world code, I use code that passes a context. You can always get context from a valid drawing session and UIKit supports a context stack, so you can push the context, perform drawing, and then pull an image to return and pop the context.