Automatic downloads for iTunes on mac

I am having trouble with the automatic downloads on my Mac's iTunes. Recently I have purchased 2 songs on my iPhone and successfully downloaded them on my iPhone, however today when I went to my laptop to listen to them there, they were not there. Additionally, they are not available via the check for available downloads option. I have the automatic download option turned on for both my iPhone and Mac, and have never had an issue before. The iTunes store does acknowledge that I've purchased them but, again, will not allow me to download them. I also just recently updated to OS Mavericks as well, but I wouldn't think that, that update would have thrown it off, or be causing any issues. Any help would be greatly appreciated.