Send email from email

Hi,

I want to send an email from plugin, but if some of the contacts don't have email, I want to send another email to the manager to tell him that some contacts don't have email.

So I do it like that:

I added a boolean field named "corectEmail" to email entity .

In the plugin I create an email record and I check that each user has mail. if not - I update the "corectEmail" to be true.
I add a workflow that happens when "corectEmail" is change. this workflow check if "corectEmail" eq true, if true it send an email to the manager.
The problem is that the workflow doesn't work :(
What am I doing wrong?

Thanks!