Can you put the wood shingle siding over metal siding, and how?

Hi Jane! I wouldn't. I think you will end up with moisture problems, your windows will not be at the right level with the new siding, and you are going to create new or worsening problems down the road. Remove the metal siding, apply sheathing, etc. and you will end up with a nice look. I can always tell when someone has covered old siding, because if you look down the side of the building, you will see wavy areas and bumps. It was a lot of work, but, when we replaced our siding, we removed all of the old stuff, put new sheathing on with insulation and a moisture barrier. Makes it snug and long lasting. Our neighbor put new siding over the old stuff, and it's sad when you see the uneven spots, since they just put theirs on. Ours has been on for years and still looks good.

Cynthia's answer is SPOT ON. You will trap moisture between a metal and a natural product and the long term results will be miserable. I would use a good house wrap like Tyvek, but many brands are out there. You are also inviting moisture nightmares around every window and door, if you go over metal. Look at some U-tubes about proper window rough-in procedure and you will see why you are building water traps at every sill. Yup. Strip it and take the aluminum to the recycle and go on vacation with the money you get!