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I have a USB flash drive that's almost always plugged in. I need to synchronize the contents of a folder on my hard drive with the contents of the flash drive, so that on the rare occasion of me unplugging the flash drive, the flash drive's contents match the current contents of the folder. How do I do that?

I know how to synchronize one folder on my hard drive with another folder on my hard drive, but I don't see how this is applicable in my situation. Is there any guarantee that when I plug in a particular flash drive, the letter assigned to it will always be the same (at least in the context of my computer)?

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If you unplug the flash drive, you can create orphaned files.

Microsoft likes to have a folder owner and client. This can create issues for removable drives.

The way I solve this is with a synchronizing App that treats both sides as real physical files, synchronizes and identifies conflicts, if any, coming from disconnection.

I use Sync Back Pro for this as I find it to very reliable.

(2brightsparks.com)

There are other third party sync tools - Allway Sync comes to mind.

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Keeping the same drive-letter for backup devices is important, and Windows does a good job of remembering them. You should ensure that the drive-letters of your devices do not conflict, by assigning them in with Disk Management. Assure also that the labels of the devices are different in Explorer.

Windows keeps the information about devices and drive-letters in the registry, and will assign the same drive-letter when the device is connected later on, as long as it doesn't conflict with another device, even from long ago.

In case you do not trust Windows, there exist also third-party software that remembers drive-letters. Here are some that I know:

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