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dshook
Task workflow rule not sending outbound message
Steps to reproduce:
1) Create a Task workflow rule that runs every time a record is created or edited and have the criteria be an all encompassing one (I have 1=1) 2) Have the workflow rule send an outbound message. 3) Send an email from a contact or custom object that relates to contacts. 4) No outbound message is sent. However, if you edit the email in salesforce it will then send an outbound message.
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This and many other similar actions don't trigger workflow rules. Basically, there are some actions that when are not done by the user directly they wont trigger WF rules. In this case you are not really creating a task directly, you are sending an email and the system is then creating a task. I am pretty sure this is standard behaviour and there is not much you can do other than re-thinking your design.
You can confirm this by looking at the debug log.
This behavior is very counter-intuitive, it shouldn't matter how or who the task is created by when the workflow rule is set to run "Every time a task is created or updated".
Are there any workarounds for this problem? Sychronizing emails with an external application was a big part of the draw of salesforce for us.