Evade e-mail exasperation

If you’re like 99.7 percent of computer users, your e-mail client gets more of a workout than any other software you use. And given the amount of time you spend with this particular software, it’s not surprising that minor annoyances you’d forgive in other programs become a Big Deal when you encounter them hour after hour, day after day. I’ve rounded up some common e-mail problems and provided solutions to help you keep them under control.

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Decipher winmail.dat files

Most people who have used e-mail for longer than the lifespan of a fruit fly have received messages with winmail.dat attachments, which typically won’t open on a Mac. The source of these files is Microsoft Outlook, Windows’ omnipresent e-mail program. They’re generated when an Outlook user on a PC formats the e-mail message (and any attachments) in Outlook’s Rich Text Format (RTF). This is not the universal RTF we Mac users know and love; rather, it’s a proprietary format that’s compatible with Outlook but not with other e-mail clients. When an e-mail client other than Outlook receives the message, it finds the inscrutable winmail.dat files enclosed.

There are a couple of things you can do to get at the attachments. If you know the correspondent well enough to make the suggestion, ask that he or she send messages either as plain text or as HTML (Outlook offers both options). Either format works with the Mac (and with every other e-mail client in the universe), and attachments won’t get mucked up.

Alternatively, you can deal with the issue by taking steps on your end. Just drop a winmail.dat file on a utility such as Josh Jacob’s TNEF’s Enough (free), for instance, and the utility will offer to extract the file’s inner goodness. You can also try Christopher Atlan’s Omic ($30), an Apple Mail plug-in that converts these files into their original, readable form, and identifies the attachments properly in a Mail message’s attachments area. Note, however, that as I write this, neither of these utilities has yet been updated for Mac OS X 10.5 (Leopard).

Kick-start a sluggish e-mail client

If your e-mail client runs as slow as molasses, it’s likely jammed with messages. Thankfully, you can speed things up by archiving old messages and then deleting the originals, and by stripping out old attachments.

To do this in the Leopard version of Apple’s Mail, create a smart mailbox that seeks out messages more than a certain number of days old. Just choose Mailbox: New Smart Mailbox and create a rule that reads Date Received Is Not In The Last 365 Days .

A new mailbox will appear under the Smart Mailboxes heading in the Mailboxes pane. Control-click on the smart mailbox you created and choose Archive Mailbox from the contextual menu to save the contents of that mailbox as an mbox file (a common file format for archiving e-mail) that you can store for safekeeping. Once you’ve created the archive and saved it to a secure place on your Mac, feel free to select all the messages in the smart mailbox and delete them. After deleting them, control-click on Mail’s Trash icon and choose Erase Deleted Messages. To strip only attachments from messages, select everything in a mailbox and choose Message: Remove Attachments.

Microsoft Entourage 2004 ( ) and 2008 ( ) both lack a smart mailbox feature. However, you can do the job, using Custom Views (in Entourage 2004) or Saved Searches (in Entourage 2008). To gather old messages in Entourage 2004, choose File: New: Custom View. In the window that appears, name the view (Old E-mail, for example) and use the pop-up menus to configure the criteria to read Date Received Is Greater Than 365 Days Old . Click on OK. In Entourage 2008, choose File: New: Saved Search, click on the All Messages button to search all your mailboxes, configure the search criteria as above, and then click on Save. In the dialog box that appears, name your search and click on Save.

You’ll see an entry for Old E-mail under the header Mail Views in Entourage’s Folders list. Drag this item to the desktop to save the messages within a single mbox archive. (Depending on the number of messages you have, this might take a while.) Once you’ve archived the messages, you can select and delete them in Entourage. Then empty Entourage’s Deleted Items folder by control-clicking on it and choosing Empty Deleted Items from the contextual menu.

If you just want to remove attachments from old messages, you can follow a similar path. Create the same custom view or saved search, but instead of deleting the messages, select them all and choose Message: Remove All Attachments. (For some other ways to speed up a lagging e-mail client, see “Fix Mac Slowdowns”.)

Send messages when you’re out and about

If you’ve tried in vain to send e-mail messages through a café’s or hotel’s Internet connection, you understand that public access points can be picky about what they will and won’t allow through. In particular, they routinely deny outgoing mail server (SMTP) connections to prevent the relaying of spam. You can tell that you have been denied when a message refuses to leave your e-mail client’s outbox.

Public facilities often block SMTP port 25, the port (or network channel) most ISPs use to send e-mail messages. That means you can work around this problem by assigning an alternate port—usually port 587—to the SMTP server. To edit the SMTP port in the Leopard version of Apple’s Mail, choose Mail: Preferences and click on the Accounts tab. Select an e-mail account from the list at the left of the window and make sure the Account Information tab to the right is selected. From the Outgoing Mail Server (SMTP) pop-up menu, choose Edit Server List. In the sheet that appears, select an SMTP server. Click on the Advanced tab at the bottom of the sheet. In the Server Port field, you’ll likely see the number 25 . Change this to 587 and click on OK to dismiss the sheet (see “Unblock Outgoing Messages”). Finally, close the Mail Preferences window.

Unblock Outgoing Messages: If a café’s or hotel’s router is blocking your outgoing e-mail messages, choose an SMTP port designed to work around blocked ports.

In Entourage 2004 and 2008, select Tools: Accounts and double-click on your preferred SMTP account in the Accounts window that appears. In the resulting Edit Account window, ensure that the Account Settings tab is selected and, in the Sending Mail section of the window, click on Click Here For Advanced Options. In the window that appears, type 587 in the Override Default SMTP Port field.

Note that some ISPs create an alternate port for the purposes of working around SMTP port blocking—Port 2525, for example. Check with your ISP to see if it does this and, if so, configure your SMTP settings accordingly.

Transfer Outlook messages to your Mac

You’ve made the switch to the Mac from Windows. You’d like your e-mail messages—currently entombed within your old PC’s copy of Microsoft Outlook—to come along for the ride. Unfortunately, Outlook doesn’t appear to offer an export option compatible with Mail or Entourage. What can you do?

The trick to exporting e-mail messages is to get that data into a form other e-mail clients can read. In this case, that format is our old friend, mbox. Regrettably, Outlook doesn’t export its messages in this otherwise ubiquitous format, so you need to employ an intermediary e-mail client that can import Outlook messages and save those messages in an mbox archive. Mozilla’s free Thunderbird 2 is that client.

You’ll do the heavy lifting on the computer that’s running Windows and Outlook. Download the Windows version of Thunderbird, launch it, and choose Tools: Import. In the Import window that appears, enable the Mail option and click on Next. In the subsequent window, select Outlook or Outlook Express (depending on which version you’re using), and click on Next again. Thunderbird will import your Outlook mail.

Now navigate to your user folder on the Windows machine and follow this path: \Application Data\Thunderbird\ Profiles. You’ll see a folder name made up of a hodgepodge of characters (g9mr6ux8.default, for example). Within this folder you’ll follow this path: \Mail\ Local Folders\Outlook Mail\Personal Folders.sbd. This folder contains the messages from your Outlook mailboxes—Inbox, Sent Items, and Junk E-mail, for example.

Those files without the .msf extension are the mbox files. Copy them to your Mac and use your e-mail client’s Import command (found in the File menu in Entourage and Mail) to import them. Your client will create a mailbox for these messages and tell you its name.

Stop running out of server space

Send Big Files: Tired of your old ISP gateway’s rejection of today’s massive e-mail messages? Keep your old address, but use a modern service with a much bigger transfer limit to configure your account to send messages.
You may be proud that you’ve maintained the same e-mail address for over a decade, but out-of-date standards may be hampering that old POP e-mail account. Specifically, your ISP may offer very little e-mail storage and a skimpy transfer limit— as low as 10MB. The narrow gateway on such an account can cause problems—messages you send with large attachments will be refused passage, and anyone sending you similarly massive attachments will see their mail bounce right back with a “mailbox full” error (see “Send Big Files”).

The simplest solution is to get a different e-mail account. Apple’s $99 per annum .Mac service, Google’s free Gmail, and Yahoo’s free Yahoo Mail offer over 1GB of e-mail storage. But suppose all your friends know your old address and you’re loath to make them switch? No worries. With one of these services, you can configure your old account so that it sends mail for your new address through the SMTP server while maintaining the same old return address. To set up that configuration, open the old e-mail account in Mail’s or Entourage’s Accounts area (in Mail, it’s in Preferences; in Entourage, it’s in the Tools menu). Then change the outgoing (SMTP) server to .Mac, Gmail, or Yahoo. Your recipients will see your old address as the sender. Unless they examine the message headers, they’ll never know you sent your mail via a different service’s SMTP server.

As for receiving mail, the old e-mail account’s space limits still restrict you. However, you can make things easier by automatically deleting messages from the server once you’ve received them. In Leopard’s Mail, go to Mail: Preferences, click on Accounts, choose a POP account, and then click on the Advanced tab. Here you can enable the Remove Copy From Server After Retrieving A Message option, and then choose Right Away from the Remove pop-up menu. In Entourage 2004 and 2008, choose Tools: Accounts, open a POP account, click on the Options tab, and make sure the Leave A Copy Of Each Message On The Server option is not selected.

[Senior Editor Christopher Breen is the author of The iPhone Pocket Guide and The iPod and iTunes Pocket Guide, third edition (both Peachpit Press, 2007).]

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