Using version: 2016.1.113.40
If i upload a file using the upload button found in the image manager and the file that is uploaded doesn't appear on the first page of results, then the image isn't pre-selected after upload. This is an issue if there are a lot of files and/or pages of files to choose from. in almost all cases when a user uploads an image they want to insert that image, so having to go find it in the file list is an inconvenience. everything works fine if the image that is uploaded appears on the current page of file results. It is only when there are multiple pages of files and the image uploaded appears to appear at the end of the list that the image isn't pre-selected after upload. The only other thing of interest to note is that we use the EditorDialogs files because we have some minor customizations that we've made in the default dialogs.
I've created a video that you can watch that demonstrates this issue.