I used Garmin Express 4.1.5.0 for Mac to update my Garmin Nuvi 58. Both the software and the map needed to be updated. The program updated the software first and then told me to disconnect the device. I disconnected it and got an OS (Yosemite 10.10.5) warning that the device wasn't safely ejected before disconnecting. I restarted the device and installed the map successfully. But then I checked the filesystem with Disk Utility and found some issues that needed to be fixed.
I believe Garmin Express should always eject the device before telling the user to disconnect it. Failing that, Garmin Express should tell the user to eject the device .
I'm actually surprised that Nuvi 58 exposes FAT filesystem to Mac OS. Most modern gadgets use MTP, which doesn't require a safe eject. Moreover, I believe my older Garmin Nuvi 2555 was using MTP (but I used it with Windows). The need for safe eject is not self-explanatory these days, please don't blame users!