Fix for e-mailing from iPhoto '11 using Microsoft Outlook 2011

When Apple released the iPhoto '11 version 9.1.1 update, one of the included features was to allow Microsoft Outlook users to send photos via e-mail through that program. Apple has in the past supported the use of Entourage, but the new Outlook e-mail client has a few different protocols and features and needed specific support. Unfortunately even though iPhoto is supposed to send e-mails through Outlook, a number of people are finding the feature broken.

Luckily the problem is not with iPhoto's coding, which would require Apple to recompile the program, but instead is with a crude implementation of the applescripts used to send photos to external e-mail clients. Apple apparently quickly changed the Entourage script to point to Outlook, and while it will launch Outlook, it will not manage the program properly and therefore results in an error.

Being a matter of scripting, you can edit the scripts to allow Outlook to be used. There are several approaches you can take, with some being quick ways to get Outlook working, and some extended steps to the same fix for cosmetic purposes, which allow iPhoto to properly display the "Microsoft Outlook" name in the program's settings.

The fixes will require editing of a couple of files within iPhoto, so first be sure to back them up. Right-click the iPhoto application and choose "Show package contents" to see the program's resource structure. Then copy the following three items to the Desktop or another safe location from within the program's package:

/Contents/Resources/ClientAppSignatures.plist
/Contents/Resources/Scripts/Microsoft Entourage.scpt
/Contents/Resources/Scripts/Microsoft Entourage.tif

Once these files are backed up, you can perform the basic fix to get Outlook working, and you can then optionally perform additional steps to get the "Microsoft Outlook" name to appear properly in iPhoto.

The basic fix

This is the basic fix to get Outlook working, and it will involve modifying the current Entourage script to properly handle the Outlook application by adding one missing line and modifying another. Unfortunately by default the program's permissions are set to not allow users to edit these files, so we must first alter the permissions of the script and its enclosing folder (this will not harm the program).

1. Go to the /Resources/Scripts/ folder and get information on it (select it and press Command-I).

2. Click the lock at the bottom of the information window, and then click the plus button to add your username to the list

3. Give your username both read and write permissions, and close the window.

4. Do the same for the "Microsoft Entourage.scpt" file within this folder

Now that the script is editable, we will modify it with the following steps to properly handle Microsoft Outlook 2011:

1. Open the "Microsoft Entourage.scpt" file (should open with Script Editor).

2. Locate the line at the top that reads:

   set the new_message to make new draft window with properties {subject:email_subject}

3. Replace the words "draft window" with "outgoing message"

4. Next locate the lines that look like the following (they are about two-thirds down the script):

   set the content to content & sig
   end tell
   end tell

5. Add the line "open new_message" between the two "end tell" lines so it looks like the following:

   set the content to content & sig
   end tell
   open new_message
   end tell

6. Save the file and quit applescript editor.

When this s done, relaunch iPhoto and ensure Entourage is chosen in the e-mail preferences. Then try e-mailing a photo again and the program should properly launch Outlook and create a message containing the photo.

Extended fix option 1: Change the name in iPhoto from "Entourage" to "Outlook"

At this point e-mailing photos with Outlook should work, even though in iPhoto the program is still referred to as "Entourage." To change this, you will have to edit the script again and change all references of "Microsoft Entourage" to "Microsoft Outlook" and save the file. Then rename the file and its corresponding .tif file to "Microsoft Outlook," followed by editing the /Contents/Resources/ClientAppSignatures.plist file (located up one directory from the scripts) and changing the "Microsoft Entourage" reference in there to "Microsoft Outlook," so the entry in this file looks like the following:

<key>Microsoft Outlook</key>
<string>OPIM</string>

With these changes implemented and saved, relaunch iPhoto, and the program should now properly show the "Microsoft Outlook" name as the e-mail client it is using in the preferences.

Extended fix option 2: Re-enable an "Entourage" option in iPhoto

With the Extended fix option 1 implemented, the program will refer to the name "Microsoft Outlook;" however, it will not have an option for the Entourage program anymore. If you are using Outlook, then it is likely you are no longer using Entourage, but if you want the option to select and use Entourage, then perform the following additional steps:

1. Locate the backed up files on your Desktop, and copy the script and its corresponding .tif file back to the "Scripts" folder in the iPhoto application package (these files should be called "Microsoft Entourage").

2. Ensure you have read and write permissions on the script file, and then open it

3. Locate the line at the top that reads:

   tell application "Microsoft Outlook"

4. Change the words "Microsoft Outlook" to "Microsoft Entourage" and save the file

5. Now go up one directory from the "Scripts" folder and open the file "ClientAppSignatures.plist"

6. In this file, duplicate the lines that read as follows so the file contains two of them:

   <key>Microsoft Outlook</key>
   <string>OPIM</string>

7. Change the name of one of these entries to "Microsoft Entourage" so these entries look something like the following:

   <key>Microsoft Outlook</key>
   <string>OPIM</string>
   <key>Microsoft Entourage</key>
   <string>OPIM</string>

8. Save and close the file.

At this point when you relaunch iPhoto the "Entourage" option should now be available for use if you have the program installed, so you can switch between these two e-mail clients if you would like.

Questions? Comments? Have a fix? Post them below or e-mail us!
Be sure to check us out on Twitter and the CNET Mac forums.