Hello LGabbard -
We are not aware of any issues where images would fail to reach eBay if they are added to listings as expected, so it sounds like we will need to have a look in your account at some of the listings in question to be able to know what is going on for you.
If you have not already, please file a support case that includes some example listings where this issue has occurred so our support agents can have a look into it and assist you. If you have already filed a case, please be aware that our support team replies to cases in the order that they arrive and will assist you as soon as they are able.
- Craig