I would suggest making sure that you make sure that the log shows the emails as sent.  Sometimes it looks like they went but at the end it will say "0 of 4 emails sent".  I had a problem recently where some Windows updates were preventing the emails from going out.  I don't recall exactly which updates they were.  Has this always been an issue or is it relatively recent?

I would suggest making sure that you make sure that the log shows the emails as sent.  Sometimes it looks like they went but at the end it will say "0 of 4 emails sent".  I had a problem recently where some Windows updates were preventing the emails from going out.  I don't recall exactly which updates they were.  Has this always been an issue or is it relatively recent?

Could they have gone to the recipients spam folder?  You might try sending a copy to yourself.

This is our first time billing with Timeslips 2014.  We have been sending them to ourselves to test it, but it's not working.  There is nothing in the spam folder either.

What's your macro security in Outlook? Try turning it off.

Beyond that, might need to hands on.