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Hi, I've had a go. As you say, it's tricky because you need to wrap around an object with an ever decreasing view. I tried a couple of times to warp and this was the best I came up with. In terms of replacing the image, if you place it in a group and have your layer mask group's folder instead of the image layer, you can simply replace the picture layer in the group with the new one. Un-link your layer mask from the group folder (click the paperclip icon between layer and mask) to move and position the image without moving the layer mask. All you have to do then is transform/warp it and then save your new image. It is possible to record a transform/warp as an action, but even so, you might need to make further adjustments depending on each image. This particular one isn't so bad because very little hard colours touch the edges of the jug, which helps.

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