Messages can get stuck in the Outbox for different reasons, but most commonly it’s due to an attachment that’s too big. Entourage doesn’t have a limit but your ISP does.

Entourage 2008 is better about handling “send” when there is a problem message, but sometimes this can lock up Entourage until you remove the message.

Starting with Entourage 2004, you can start Entourage from default settings – i.e. with Send & Receive All schedule OFF (Manual only) – by holding down the Shift key at startup – like “Extensions Off” when starting up your Mac. This allows Entourage to launch without crashing in situations like this. You should now be able to delete the message from the Outbox.

So, how do you deal with attachments?

Size Allowed

  • While your ISP might allow you to send a 10MB attachment your recipient’s e-mail server might reject the message.
  • Recipient’s mailbox quoto could be maxed out blocking them from receiving other messages.
  • When you attach a file it has to be encoded. This can cause the file to become 1.37 times larger. For example, if you send a 10MB file through e-mail, you’ll actually send 13MB of data.

How “green” are your attachments?

I using the term “green” here to indicate frugality and consideration for your recipients. Are your attachments clogging up their database with unnecessary attachments? I would consider that pollution.

  1. Do you send a link to a website, or do you forward the entire page?
  2. Do you send a signature with a graphic?
  3. Do you edit those joke messages that contain multiple copies of the same message as attachments?

Keeping your database lean

When sending large files is necessary.

I’ve seen reports especially from graphic designers that their databases are enormous as a result of attachments they receive. Even ordinary users can have huge database with lots of attachments that can contribute to instability in your database, result in large file that has to be backed up and cause Entourage to be slow because of bloated size.

  • Use a script to remove attachments
  • Use one of the online services to share attachments

Use a script: Scripts can help deal with attachments.

Removing incoming attachments with one of the “remove attachment” scripts. They will save, remove and link the saved files to the message, so you can open the file directly from the message.

Friendlier Claris it! By: Rob Buckley
Save Attachments By: Paul Berkowitz
Remove Attachments By: Jolly Roger

Create a message with attachment:

Send Attachment Droplet 1.3.1 By: jswenson

Drag a file on this droplet and a new message will be created with that file as an attachment and the subject will be the file name. Then simply enter the recipient(s) address and press send. Supports multiple files and email accounts. Also runs when double clicked. Now compatible with filevault.

Remove Outgoing attachments: Remove your outgoing attachments with a rule. This is assuming your outgoing attachments are stored elsewhere on your computer. No need to have them duplicated and filling up your database.
Create an Outgoing rule. Go to Tools -> Rules / Outgoing tab:

Use online service to share files Accepts up to 300MB.
DropBox Offers 2GB free. Use this link to get an account and we’ll both get free extra space. You can send large files with Dropbox. I use it for clients to send me their databases for recovery. The largest one I did was 11 GB.

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