It sounds like all you need to do is refill the hole with joint compound, let it dry completely and redo just that side. Unless I'm not understanding the problem correctly.

I am hoping that is the answer. I guess my concern is whether or not the holes, once patched with joint compound, will be able to take another (probably longer) anchor in the same exact spot. If I have to move this one even just a little bit, I'll probably have to move the others for consistency's sake.

URSpider-
I've been hanging things on walls for over 35 years using all kinds of brackets and fasteners and I can tell you that I'm no fan of plastic anchors. If there is any weight on them, and particularly if they're subject to stress (such as curtains being moved), they'll usually loosen up. I recommend you use either: 1) moly bolts (these are the metal plugs that spread out behind the sheetrock when you screw into them). They are a little tricky to remove in the future without damaging the wall, but there are ways to do it; 2) a new type of fastener I've seen which has a large diameter helical thread that you screw into the wall, and then put your metal fastener into the center hole (these are almost as good as moly bolts). Your question about wall repair depends on how much of a hole you have now. If you get a big enough version of either of the two fasteners I've suggested so that there is a reasonably tight fit when it goes in, then you can use the existing holes. If the holes are too big, you'll need to repair them and then install the fasteners. However, a patched hole is not going to be quite as strong as it was before, so you may have to move the holes if you have a lot of damage.

I have to agree about the plastic anchors. I just hope that I can re-use those holes or I have a whole lot of work ahead of me this weekend.

Here is a picture of the drywall 'damage,' as yet unrepaired.

Here is a link that might be useful: This is how the drywall looks

I've had the same problem before. I would fill the holes with Bondo and let dry for 24 hours. I'd then use molly bolts as has been sugested. I'd drill the new holes carefully for the molly bolts.

I would just run out and buy some of the screw in type anchors, they are superior to the typical plastic anchors. I bought a large kit of them at lowes for about $10. I now through away the cheapies that normall come with shelves, hooks, etc. and use these. They are larger so the small hole you have wont be a problem just screw them in and reattach the screws. I have linked a picture of the anchors below:

Here is a link that might be useful: Drywall anchor

You guys are great. Thanks for the picture. I patched it today and I'll pick up the new hardware tonight. If I see those plastic anchors again, I'm going to save myself future trouble by replacing them out of the gate with molly bolts or the larger plastic type.

Actually, I think toggle bolts may be the best solution. See the link below.

Here is a link that might be useful: Wall Fasteners

Take a look at Toggler brand toggle bolts.

Here is a link that might be useful: Snaptoggle Toggle Bolts

Here is a link that will show you how to solve your problem
Go to Google or Yahoo and search www.smithfasteners.com
These plastic toggles have no sharp edges to cut or damage walls. They will not pull out. Will carry 100 pound wall load but a safety factor of 30 is about right. The original holes would have worked great without making new holes. Add an extra one close to excessive load points.

From the looks of the picture, don't be surprised if this pulls out again - the center area is comprimised and patching compound will not hold up well. It looks like a bit of weight is on this as well.

If this repair does fail on you, I would cut out a square of drywall around the area you are securing, place backing plywood behind, and fasten in a new square of drywall in the area. Finish and paint this and then you will have solid plywood behind your drywall to fasten into and you can simply use screws. To get an idea how this patching process works, go to the link below.

Here is a link that might be useful: Patching Drywall Holes

I am designing a solution for a series of holes that are responsible for protecting my grandchildren from falling down a long flight of stairs by anchoring a child gate. It is extremely important to me to protect them, so I would love to hear your ideas. I am designing this solution to be 3DPrinted, so once I have a solution, I would be glad to mail some out to any of you as a beta-tester to provide feedback.

Start a new thread. sheesh!