Hi, to me it seems you try to send a message on a date before the workflow actually runs: Workflow Context - Current Date is the moment that the workflow is running. If you calculate the previous date from it, you get yesterday's date or further down the past....... So what I guess that you try to do is to that you have a Leave Date that you should use, extract 1 day from that and compare if it is equal to Current Date (I think this sentence's syntax/symantecs suck...). If so then send the email. And I assume it is a Scheduled Site Workflow.

Assume you are doing this as a site workflow?  Have you looked at this example:

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