Hello there Michelle!
Will here from Shopify to help out with your shipping.
Currently, our default system only allows one label to be purchased with each Order - as it's essentially assuming that it's being shipped together. In the case where you might need two or more, I'd suggest checking out an App called Shippo, or even our App Store for other shipping apps. There's lots of options available that allow you to purchase outside of Shopify :)
I hope that helps you! If you need further assistance, definitely let us know. Thanks for taking the time to reach out to us.
Guru @ Shopify
Will. Is it me or do you guys not update your system anymore to accomodate customers? I'm experiencing numerous drawbacks with Shopify that can easily be fixed and in the several times that I had reached out in the forum, I'm simply told that you guys don't do that. Using this situation for example, requiring multiple shipping labels for the same order is not common nor uncommon but you guys just don't offer it and advise that we create another account with another vendor. I'm not sure about everyone else but even as a small business owner, we have so many vendors to deal with and opening another account is the last solution we care for, especially for a minor issue as multiple shipping labels. If you can put this on the queue to perhaps look at, that'd be great.
Thanks Shopfiy Team.