OS X asking for admin login for every email sent in Apple Mail

I am having an issue where I am getting the administrator prompt for every email I send through Apple Mail (Yosemite 10.10.2). Not to be confused with the email account specific password issues that are common... Here is the prompt:
I get this prompt with every email I attempt to send. I am assuming that this is a Keychain issue, but I ran Keychain First Aid which didn't find any issues and also Reset my Default Keychain and that hasn't cured the issue. The only other thing I am wondering is if it might have something to do with an old install of Server that was on this machine from Mavericks.
Any ideas?

Turns out this was related to a preference I hadn't seen before that was on after upgrading to Yosemite. Each email was set to send with a digital signature and as soon as I turned that off, the prompt went away.
Follow up question: was that the expected behavior for that setting? Should it have been prompting me for each email sent if I did indeed want to sign each email?

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