Transition Send Mail Action

I have three transitions all named the same.  One Transistion sets the revisions.

The other two send an email based on whether or not a check box variable was checked.

For testing purposes I made each transistion's email go to me.

The problem I only got one of the emails, all transitions should have fired. Is this a quirk of ePDM, that it won't send a email thru two different transitions to the same person? Or am I doing just it wrong?

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