I have successfully created a Custom Keyboard with Swift on iOS 8 simulator.
Although it worked well, but I could not debug it. It is a contained target and was installed through Settings->General. Placing a bookmark in XCode not work.
I am able to debug a custom keyboard using the simulator via Xcode 6.
Select the keyboard (and not it's container) as the scheme.
"Run" and then select on of the apps on your simulator to debug the extension with.
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