Please note that if both elements have the same attributes this is expected behavior and Test Studio will always find the first element in the tree. In order to be able to differentiate both elements they must have something unique which the find logic of test studio will use.
In general that's what the IDs are used for, to differentiate elements which is quite helpful in automation cases like this one. Having multiple elements with the same ID makes no sense of using an ID at all.
The best practice of using different IDs will repay in a long term.
If you are not able to change the IDs for the elements in the application you are using you will need to use a coded step in order to find the right element. Please check this article
for more information on how you can proceed. In your case since all the attributes of the elements are the same you can use TagIndex which searches for an element using its tag name occurrence index.
@ Matt Thanks for your input. I have updated your telerik points accordingly.