Windows 7

Windows 7 File Transfer Issue (Destination Path Too Long)

One of my friends reported the error while trying to copy several files from an external USB drive using Windows 7 x64 OS.

Randomly the user gets an error that the Desination Path is Too Long.

To be able to solve this you will have to simplify folders and titles because of the Operating System limitation.

Windows 2000 has a 254 character limit.
Windows XP has a 255 character limit.
Windows Vista and Windows 7 has a 260 character limit.

Path+Filename limit is 260 characters.

Exceeding either will result in the error mentioned.
So, to solve this simplify your folders and titles.

More info...

Each application/API handles long filenames differently, so be careful:

For instance, Nero 6 could only handle 108 characters, but that isn't mentioned. Instead, it burned the disc and truncated the filename resulting in garbage.
QuickTime 2006 could only handle 63 characters. Oops to all those podcasts titles.
Even Mac systems advertised 255 characters, but the shell could only handle 31 characters until OS X.

While there are a few workarounds, they are limited in how they can be used and becomes somewhat inconvenient if you are handling lots of files:
From the command prompt only.
May overwrite other data in the filename record resulting in loss of information: (ie. attributes, creation date, starting location for file, etc.)

"What should I do?"

The answer was already proposed: Simplify your titles.