@ Adam
That rotation issue is weird… never seen that before… Oh wait, I see… it is confusing but does make perfect sense. The image was shot “sideways”. The photographer turned the camera, instead of holding it upright, they rotated the camera -90ccw. This orientation is saved in the actual image, it’s called EXIF. Windows/OSX will auto orient the image so it appears upright even though it is still sideways. The thumbnail is created of the actual image as it is, ignoring the EXIF. Actually I do not attempt to read it all because it is hit or miss if the server supports reading that data from the image in the first place. Well, one exception which is new to 8.1.6. On image upload, the image will be scaled down, if larger than 1920×1080 to 1920×1080. This new code will check the server to see if it can read EXIF orientation and apply the orientation to the new 1920×1080 image.
What makes this even more confusing is… it seems, and throw me for a bit, both Chrome and Firefox appears to read the EXIF orientation so when you view just the image in the browser, they too will auto orient the image. It seems IE11 does not read the orientation and display the image just as it is, sideways.
Here’s a nifty page you test this for yourself:
http://metapicz.com/
Drag the original image of Bill on the page. After it uploads it’ll show you the EXIF data. Look for Orientation. You’ll see it says Rotate 90 CW. This is what Windows/OSX and the browsers are doing, rotating the image 90cw to counter the -90ccw orientation the image was shot in.
Does that make sense?
It seems the best way to avoid this whole orientation issue, is to save a PNG of the image and upload that instead.
As for the cropping … I can not duplicate that. I changed my logo settings to match, pulled down the original of Anthony and Christopher and they scaled down and added the border as they should.
Can you enable the Debug option on the Settings admin page under the Advanced tab and re-upload the image for Anthony? Right after you add the new image, after the page refreshes, at the top of the page there will be a log of events that occurred when processing the logo. Can you paste that log here?