In the first scenario, CUC is operating as designed. The calls comes into CUC and is treated with the "Forwarded Routing Rules". If you have the default rule configuration, then the first rule is "Attempt Forward" and this rule will attempt to send all calls forward from a user extension to the user's mailbox greeting. This is a key point, calls are sent directly to the greeting and the mailbox transfer rules are completely bypassed.
In your second scenario, you are creating a direct routing rule and specifically sending the call to the transfer rules.
Going back to your first scenario. I suppose you could try the following:
1. Go to the standard greeting on 2461640
2. Config the "Callers Hear" setting to Nothing and uncheck "Play the "record your message at the tone" Prompt"
3. Check "Ignore Caller Input"
4. Config the "After Greeting" setting to send the call to a "User with Mailbox". Select the same mailbox for 2461640, but select "Attempt Transfer".
Then, ensure that your transfer settings are configured to send the call to 8881611.
This setup worked in my lab. Now, you have to careful with the configurations in CUC. If you put the wrong configuration in place, you have a chance of creating a loop. For example, if the transfer setting is sending the call to the 2461640 extension which is configured forward all to voicemail then you would have a loop. Also, there is another loop if the transfer setting is set to send to the greeting for 2461640.
But, if you set it up correctly it will do exactly what you need it to.
Just to add something to the great advise from Bill.
The transfer settings work for transfers within CUC (attempt transfer, dial from a call handler, select user from directory handler, etc). That's why it doesn't work.
An alternative for what you're doing if the user doesn't need a mailbox as you will send his calls to someone else is to create a call routing rule and set the attempt transfer to the call handler or subscriber where the target is 8881611.
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