Import obj, files not selectable

More often than not, the dialog will show the name of my obj file but it's greyed out. I click cancel and on the second try the file is selectable. This happens randomly but often, more than half the time on m2 macbook pro with latest updates. Don't know if it's the cause but I export from the same file every time and overwrite the previous obj to reduce the amount of files on my desktop.