If you have ever had to fight with a list of image file names in a folder that wouldn’t stay sorted, you have to blame Bill Gates.

When Bill was writing the DOS operating system for the first PC, to save time he used the old “8.3″ file naming specification: eight characters (no punctuation or spaces), a period, and three characters on the end to tell you what kind of file it was. So for years, files could only have names like Lotus.exe (an executable program) or data.dbf (a database file). If you tried to name a file Aunt Millie’s 80th Birthday Picture #2, the computer would refuse to open the file.

But the worst part of 8.3 file names was that PCs sorted files according to a strange rule where numbers came before letters, and “11″ came before “2″. For example, say you had four files on your computer in the order you want them printed in LabPrints:

1. Page 1.jpg
2. 2.jpg
3. 11.jpg
4. Back page.jpg

LabPrints will store them alpha-numerically, so what you will get is this:

1. 11.jpg
2. 2.jpg
3. Back page.jpg
4. Page 1.jpg

Notice on the screen on the right. I made this as an experiment. You can see four files alphabetically sorted in Windows on top, and the exact same four files sorted alphabetically in DOS on the bottom - both on my PC! Although Mac people have never had this limitation, us PC folks have been fighting with it for years.

If you are a Mac user, you have a different set of problems that you don’t even know about. Mac files are stored in 2 parts: the file itself, and a hidden file that has the real file name, the extension, what program opens it, etc. That’s why when you copy just the image file from a Mac to a PC, the PC can’t open it. Newer Macs have solved this problem by including a check box that you should use that makes sure the files can be read by both Windows and Mac.

So what’s the solution? My suggestion is, when naming lots of images, put a number in front, and pad it with zeros so they line up. Then the rest of the file name can describe the image. For example:

1. 001 Front cover.jpg
2. 002 First page.jpg
3. 003 Mother Father.jpg
4. 004 Bride.jpg

Obviously, you only need the extra zero if you have more than 99 pages. However, these images will always sort correctly, no matter which computer (or CD or DVD) you save them on.

A couple of other “rules” for file naming that will make your life simpler:

• Keep file names short. “Katrina and Jeremy Dompulskis Wedding on December 12 2009-001.jpg” is so long it will always be abbreviated when it  is viewed.
• Don’t use punctuation. “Bill and Martha’s Wedding @ 1:00p.m.” will work on a Mac, but not a PC.

So what’s an easy way to rename files? Both ROES and LabPrints have automatic file renaming built into them. If you’re looking for something that can batch process images, try Bulk-rename. I was able to rename this sample group of four DSC files automatically less than 10 minutes after I installed the utility. Best of all, the basic version is free.

Need to share a great full-res digital photo, a PDF proof book or Adobe PSD layout? Attaching files larger than 1Mb to an email has a 50-50 chance of getting through. Either the receiving mail server mysteriously deletes the email, or it locks up the other person’s computer while they wait for the file attachment to download. Even if it finally gets through, it isn’t polite to lock up someone else’s computer.

Here are three FREE solutions:

Dropbox. Up to 2GB of file space for free, but you need to register and install the application. Works on Mac or PC. Betsy Flinn has started using this service, and she really likes it. Read her review.

Sendspace. Free version allows files up to 300Mb. You upload a file, copy and paste the link in an e-mail, and send. File stays up for 30 days, no registration required, no software to install. Here’s a test image I uploaded in less than 10 seconds for you to try. Note the ugly ads you have to look at, which is how they offer the service for free.

Drop.io is very popular with the online community. The free version only allows files up to 100Mb, but you don’t need to register or install any software. Click this link to see what your customer would see - again same image, much cleaner look.

After trying all three,

• I recommend the free version of Drop.io for sharing an image or two with customers.
• I recommend Dropbox for collaborating on images or sharing with family and friends.
• If you just need to send a large file to a non-client quickly, Sendspace is worth remembering.

Of course, when sending images to JD, always use ROES, LabPrints or our FTP service.