ive had issues with waking up with leaks too (only had 3 cycles with it though so im still getting used to it?)
but i sleep kinda weirdly, and depending on how my legs are positioned i actually hear/feel the seal breaking! i sleep like this except the top leg a lil more bent and the bottom leg is straight and not bent under the pillow. so maybe your sleep position might be affecting it too.
all i can suggest is getting cloth pads as backup for when you sleep.

Sounds like that might be my best bet!

I'd second a cloth pad or liner for overnight backup. If you're not up to making your own, etsy.com has lots of cute ones. Also, I had trouble with leaks for awhile, and the problem turned out to be that the cup hadn't fully opened after insertion, even though I had been twisting and pulling and what have you. Now, I make sure to feel all the way around it, just to make sure that it's not still a little folded. If it is, I can pinch it open--it works better for me than trying to twist. I don't know if that's helpful or if it even makes sense, but I hope you get everything figured out! :D

Thanks for the ideas... I'm gonna keep trying! woo hoo.

One thing that may be effecting you is that the cup either isn't opening up all the way, or that the cup isn't opening under your cervix. This is also possibly why it feels strange or awkward to you. When my cup isn't opened fully, it feels uncomfortable. I just know it's *there*. When it is opened properly, I can't feel it at all. There are a couple of different methods that you can try to make this work a bit easier for you!

First, what some girls do is insert the cup halfway and allow it to pop open. Then gently push it in the rest of the way until it is at the comfortable spot. You'll know when it's good if you can stand up and sit down and nothing pinches or aches. You should note that there will be a bit of a pressure for the first few minutes after changing it, but that should gradually disappear as you get used to it.

The second method is to insert the cup, and then run your finger around the outside. Check for dips or dents in the cup. If there are none, then your cup is fully open and you are ready to go. If there are some, then you can either take it out and try again, or you can pull it down and then push it back up. Sometimes that will effectively allow the cup to pop open. But of course, sometimes you'll just have to try again.

The third method is to insert the cup, and then gently tug on the bottom until you feel some sort of resistence. The resistence means that your cup has sealed and that it's not going anywhere. If the cup slides out easily, it means it wasn't sealed and that you need to try a second time.

Next, what sort of insertion method are you using? Some girls find it's a lot easier to use something aside from the C-fold. Here are a couple of links to some different folds within this community: http://community.livejournal.com/menstrual_cups/453392.html?thread=3998224 and http://community.livejournal.com/menstrual_cups/769444.html. Experiment with each one until you find one that works well for your needs. Personally, I use a combination of the Punchdown and Origami fold that works wonderfully. But every girl is different, so of course, every girl will need something a little different.

Finally, you should look at the various tags around here. A lot of girls have trouble like you [only a select few don't, and yes, I was jealous, too] and a lot of great advice has been offered over the years. Good luck!

Thank you for all of the information and advice! Looks like I have some more practice to do!

Just so you know, the average learning curve is around three months, and up to half a year before you're really comfortable with it. ;) So it takes most girls more than just one or two cycles to get the hang of it. You're definitely not alone! Until you do feel more comfortable, you may look into wearing a back-up, such as cloth pads. That would prevent you from dealing with a flood, but would still be moderately comfortable. Good luck!