Every once in a while I see something like this posted in the Microsoft Entourage newsgroup:
Is there a way to set a rule so that certain signatures are sent to certain recipients? For example, a rule that would send “signature 1” to recipients of “domain-X” and “signature 2” to everyone else. The first would be for internal use and the second for external?
While Entourage can’t set different signatures automatically on new messages, you can apply a few tricks to make it automatically select the appropriate signature for replies. The following instructions will walk you through how I set up one of my POP E-mail accounts to select the best signature for family & friends, business contacts and mailing lists. (These instructions can not be used for IMAP nor Exchange accounts.)
Why can’t I just use a rule to change my signature?
In my examples below I use rules to accomplish part of the process but keep in mind that rules are only applied when mail is Sent or Received. Entourage can apply rules to an Outgoing message but it will apply them only after it has been sent, not before. Therefore, you can’t use an Outgoing rule to set your signature. And that’s a good thing, Martha!
You want to maintain control of your message up to the point that you send it. If Entourage allowed Outgoing rules to change your message then a faulty rule could easily send your message to the wrong person (an ex-girlfriend, for example, instead of your current girlfriend) or apply an inappropriate signature (“Go Jets!” instead of “We aim to please everyone!”)

Create signatures
For my one E-mail address I create three signatures using Tools --> Signatures... To easily identify them I prepend the name of my Gmail account to each one.
- talkingmoose - family & friends
--
bill
Forever frozen in Minneapolis!
(612) 555-5555 - talkingmoose - business
--
William Smith
GladCo Corporation
“We’re here to help. We aim to please.”
work: (651) 577-7775
mobile: (612) 555-5555 - talkingmoose - mailing lists
--
William Smith, Microsoft Interop MVP - Mac/Windows
http://entourage.mvps.org
http://blog.entourage.mvps.org
Set up an account
Next, I create one account using Tools --> Accounts... Because I use this account mostly for family and friends I append that designation to the end of the account name in the Account Settings pane to more easily identify it later. Take note that by default Include this account in my “Send & Receive All” schedule is selected.

I also set the default signature for this account to my talkingmoose - family & friends signature in the Options pane.

Set up additional dummy accounts
For each additional signature I create a new dummy account. These accounts will be similar to the first except for a couple of differences:
- These accounts will have the Include this account in my “Send & Receive All” schedule option disabled.
That means it can still send E-mail but it won’t receive new E-mail. The first account is already doing that and we don’t need to duplicate efforts.
- Each dummy account will be dedicated to one of the secondary signatures.
Using Tools --> Accounts... I create two new POP accounts with identical settings as my first account. In the Account Settings pane I append my secondary designation to the end of the account name to more easily identify it later. I disable Include this account in my “Send & Receive All” schedule.

And I set the appropriate signature for the account in the Options pane.

The glue that binds everything together — Rules

I now have my signatures and my accounts created.
When a specific account is used to reply to someone then its signature is automatically used in the message. The final task is to get Entourage to know when to use each account.
Remember, only the first account is receiving mail but any of these three accounts can send mail.
Using rules on incoming messages, we can make Entourage think it’s receiving “friends & family” mail from the first account, receiving “business” mail on the second account and receiving “mailing list” mail on the third account.
Since I have three signatures and three accounts then I’ll also create three rules, right? Nope, just two—one for each of my dummy accounts. I do this using Tools --> Rules...
Under the Mail (POP) tab of the Rules window I make a new rule. To easily identify my rules I’m using the same account names as my dummy accounts.
For my business mail I identify three possible criteria that tell me a message is a business message and I set the rule to fire if any of these three criteria are met:
- From Contains acme.com
- Category is Work
- Specific header X-MimeOLE contains Exchange
Then I set an action to:
- Change account Talking Moose (Gmail) - business
Because I have my business contacts already listed in my Address Book and labeled with the Work category and I have my preferences set to Automatically match message categories to senders’ categories under Entourage menu --> Preferences... --> General Preferences --> Address Book --> Messages, new messages from my business contacts will be correctly identified.
I added the Exchange header to identify mail from users who would be sending from Exchange accounts, which are typically used more for business.

My mailing list rule is simpler. Because I have Mailing List Manger rules already set up to manage my mailing lists, I set my rule to identify messages from a mailing list as well as include the address of a mailing list that I don’t manage with a Mailing List Manager rule. Again, it will fire if any of these criteria is met.
- Is from a mailing list
- From Contains Entourage-Talk@lists.letterrip.com
I set an action to:
- Change account Talking Moose (Gmail) - mailing lists

The criteria you use to identify incoming mail as either business, family, friend, mailing list or something else will be unique to you.
Now what happens?
Let’s assume I now receive a message from my friend Diane (diane@example.org) through my Gmail account. I have her address in my Address Book and her contact record is in my "Friends" category. Her message will trigger neither the business rule nor the mailing list rule. Her message will appear to have come through my Talking Moose (Gmail) - friends & family account.
When I reply to Diane’s message I will reply with my friends & family account, which uses my friends & family signature. She will see:
bill Forever frozen in Minneapolis!
(612) 555-5555
Next, I have a business client with whom I exchange several messages a day. He is in my Address Book and his contact record is in my "Work" category. All messages from him will trigger my Talking Moose (Gmail) - business rule and they will appear to have come through my Talking Moose (Gmail) - business account.
When I reply to him my business signature will appear in my message. He will see:
William Smith
GladCo Corporation
“We’re here to help. We aim to please.”
work: (651) 577-7775
mobile: (612) 555-5555
Finally, I have subscribed to a mailing list and I have a mailing list manager rule set to manage all E-mail messages and put them into certain folders. These messages will also be identified by my new rule as mailing list messages and will trigger my Talking Moose (Gmail) - mailing lists rule. They will appear to have come through my Talking Moose (Gmail) - mailing lists account.
When I reply to any of those messages my mailing lists signature will appear in my message and other subscribers will see:
William Smith, Microsoft Interop MVP - Mac/Windows
http://entourage.mvps.org
http://blog.entourage.mvps.org
A quick tip for sending new messages with the appropriate signatures
Again, new messages can not trigger Outgoing rules to apply the signature you wish. However, because you have your three accounts created and each account can send mail, you can use them to quickly change your signature in new messages.
Because my default account is Talking Moose (Gmail) - family & friends, my friends & family signature will always appear in new messages. But if I want to send my new messages to either a business contact or a mailing list then all I need to do is select that account in the From drop-down menu at the top of my new message.

And my signature changes automatically!

For more information about using signatures in Entourage have a look at:
Signatures on The Entourage Help Page
Signature Blocks and Netiquette on The Entourage Help Blog
Don’t waste time with unbusinesslike signatures on The Entourage Help Blog

Comments (8)
For a signature at the end of my e-mail, I've gone through all the steps, but how does it get inserted? Does it just show up at the end of my letter, or do I have to press a special key to insert my Signature?
Open your Accounts window under Tools in the Menu bar. Open the account and click on the Options tab. You will see Default Signature popup. Select the sig you want in the popup. Click OK and your sig will automatically be inserted using the preference you set in Entourage preferences.
Signature reply options
I have my signature set up but I also want my email to come from the business name, that is, mary.smith@businessname.com and not mary.smith@gmail.com. I can do this in Gmail where I can nominate the email address I want to use but can't see where I set this up in Entourage 2008.
Hi Cathie!
I'm not quite sure I understand your question. My instructions above tell you to create multiple accounts in Entourage, one of which should be your mary.smith@businessname.com address. Your rules should be set to look for your "business" contacts and therefore reply with your "business" account. The From drop down menu a the top of your reply should indicate you're sending from mary.smith@businessname.com.
Let me know if I've misunderstood your question or which part of the instructions above are unclear to you.
Thanks for the prompt reply! When I try to set up the new dummy account for my mary.smith@businessname.com in Entourage 2008, it won't let me deselect the Include this account in my “Send & Receive All” schedule.
Be sure that you have the Receiving mail and Sending mail fields filled with something. The SMTP server should be a valid server but the POP server field can be a bogus or real address.
My signatures go at the very bottom (under the orignal email) when replying or forwarding emails. Is there a way so the signatures get inserted right above the original email when replying or forwarding?
See the examples and instructions here:
Switch my reply/signature placement in a message