Mac OS X may be the greatest operating system in the world, but somehow that news hasn’t reached most of the planet. The sad fact is that most of us are surrounded by Windows PCs. And while it’s easier than ever to share files and networks with Windows systems, Mac users still often feel like strangers in a strange land.
When it comes to sending files between Macs and PCs, you have to be careful about the names and tools you use.
Problem: Windows users can’t open the files you send them.
Solution 1: Fix the file name.
Windows is essentially stupid: the only way it knows which application opens a file is to look at the three-character extension at the end of the file’s name. When it sees .doc, it opens Microsoft Word; when it sees .xls, it turns to Microsoft Excel; and so on.
So when you send a file to a Windows user, you have to give the file name the right extension. For starters, set Mac OS X to display file extensions. Select Preferences in the Finder menu, select Advanced, and then select the Show All File Extensions option.
The next step is to make sure your files have Windows-legal file names. If you don’t follow Windows naming conventions, the recipients might not be able to open your files; in some cases, they won’t even be able to see your attachments.
In Windows file names you can’t use square brackets ([ and ]), slashes (/ and ), the equal sign (=), the plus sign (+), angle brackets (If you have a lot of files that you want to rename to conform to these conventions, simplify the job with Sig Software’s
NameCleaner ($35) and Public Space’s
A Better Finder Rename ($20). These utilities can rename and remove illegal characters from batches of files.
Solution 2: Check your encoding.
E-mailing files to Windows users presents its own set of challenges. If the recipients can’t open a file you’ve sent, check your encoding settings.
In Apple’s Mail, when you’re adding an attachment, select the Send Windows Friendly Attachments option. In Microsoft Entourage, open the Preference pane, select Compose under Mail & News Preferences, and then click on the Encode For menu. Your best option here is Windows (MIME/Base64). While you’re there, turn off compression by making sure None is selected in the Compression drop-down menu. (Mail doesn’t compress attachments when you elect to make them Windows-friendly.)
Problem: You can’t open files you receive from Windows users.
Solution: Convert Winmail.dat files.
Occasionally, you’ll receive an unopenable e-mail attachment named Winmail.dat from one of your Windows friends, and he or she will insist that the attachment was a Word file.
Don’t blame your Mac. The fault lies in Exchange Server and Outlook for Windows. When Outlook sends an e-mail message in Rich Text Format over the Internet, Exchange Server sometimes creates an attachment called Winmail.dat, containing the message and some encoding data.
One fix is to download and install
TNEF’s Enough ( ), a free Mac utility that can extract a Mac-usable file from a Winmail.dat attachment in a few seconds.
If your correspondents frequently send you Winmail.dat files and you find it wearisome to keep extracting them, ask them to turn off RTF in Outlook for Windows. (To do this, they would choose Tools: Options, select the Mail Format tab, specify Plain Text in the Send In This Message Format list, and click on OK.) Or just tell them to point their network administrators to the Microsoft Knowledge Base article
How to Prevent the Winmail.dat File from Being Sent to Internet Users.
Problem: Fonts in your Mac documents don’t show up properly when viewed in Windows, or vice versa.
Solution: Keep fonts simple.
If your Windows-based recipients don’t have the fonts in your document, their PCs will substitute other fonts. This isn’t a problem with plain text and other simple documents. But if you’ve arranged the pages of your document just so, font substitution can ruin your layout.
The easiest fix is to stick with the fonts common to Mac OS X and Windows. These include Arial, Century Gothic, Comic Sans MS, Courier, Courier New, Georgia, Tahoma, Times, Times New Roman, Trebuchet MS, Verdana, and Wingdings.
Problem: PowerPoint presentations created on a Mac don’t play correctly on PCs.
Solution 1: Convert your QuickTime movies to a Windows-friendly format.
If you’re planning to send a PowerPoint file to a Windows user, you should convert any QuickTime movies (MOV files) to AVI or MPEG format (but not MPEG-1) before adding them to the presentation. You can use Apple’s
QuickTime Pro ($30); just open the movie, choose File: Export, and pick the desired format.
To make sure PowerPoint presentations play correctly on different platforms, follow these tips, too:
If you have PowerPoint X or earlier, don’t use QuickTime transitions: they won’t play on Windows. (PowerPoint 2004 doesn’t give you the option of using QuickTime transitions.)
If your Windows friends are sending you PowerPoint files, tell them to convert any WMV movies they want to include to AVI or MPEG format before adding them to presentations.
Flash movies in either Mac or Windows presentations won’t play when moved to the other platform. You can get a Flash movie to play only by reinserting it into the presentation after you move it.
If you are recording a narration (Slide Show: Record Narration), deselect the Link Narrations option. Otherwise, PowerPoint will save your narration as an AIFF file, which Windows can’t play.
Solution 2: Link Word and Excel tables.
PowerPoint also has problems displaying embedded Word tables and Excel spreadsheets when you move presentations between platforms. Either redo tables using PowerPoint’s native table engine, or create a link to the Word or Excel document.
A utility such as A Better Finder Rename makes it easier to rename groups of Mac files using Windows-safe syntax.
When you’re sending e-mail to Windows users from Entourage, you need to adjust the way it encodes attachments.
For years now, Mac users have been using the SIT or SITX file-compression formats used by Allume’s StuffIt. But Windows can’t handle them natively—it prefers the ZIP format. The Finder has been able to deal with ZIP files since OS X 10.3, so if you need to compress files before sending them to PC users, use ZIP. In the Finder, select the file, folder, or group you want to compress, then select File: Create Archive. To decompress a ZIP archive, double-click on its icon.
If you must send a SIT or SITX archive to a Windows user, make sure that person has a copy of
StuffIt Expander for Windows (free). If you will be trading compressed files regularly, your Windows friend should get the Windows version of
StuffIt Standard ($25) or
StuffIt Deluxe ( ). (StuffIt can also create and decompress encrypted ZIP archives; Mac OS X cannot.)
If your Windows buddy sends you a self-extracting EXE file, the Mac version of both StuffIt Standard and StuffIt Deluxe can open it.
Finally, much as you might like to send OS X DMG disk images to your Windows pals, it just won’t work. Windows uses an entirely different format (ISO) for virtual disks. So avoid DMGs when moving files between Macs and PCs.
[ John Rizzo is the publisher of