Please ensure the pending email is configured to be sent BEFORE payment. At any other point in time the password becomes encoded and would no longer substitute.

If I set the Plan User Email Confirmation: to [Yes, Before Payment], the password is now being sent with the Pending email. But, now they are not being presented with the payment plan until after first log-in.

This would be working as intended.

Is that the way this is intended? It seems to me that this process delays payment and gives the user a chance to back out of the transaction, but their user registration information remains in the system if they do and creates additional administrative tasks. This work flow doesn't make sense from a user's or administrator's standpoint.

Always always the registration is completed BEFORE CBSubs will do anything. This means if you try to send the password AFTER payment, which is far after the registration process then the password has already become encrypted and it's too late to send cleartext. You MUST send it BEFORE payment. This doesn't apply though when using random generated passwords as it will re-generate a password whenever necessary.

Another option is to simply use incubator project CB Emails to send the email (it handles cleartext passwords at the appropriate triggers) using the after registration trigger and the to address as [email]. This would allow you to send the user a custom email after they've registered. I've no idea if the [CONFIRM] substitution will work appropriately with CB Emails, but it's worth a try.

Side note: It might be a big help to have a "Pre-Flight" checklist on all of the options available in CB and CB Subs. Juuust sayin'.

We've a couple workflows explained in the documentation, but there are just soo many to document with new workflows showing up sometimes daily or weekly as users find them. Very hard to predict every outcome with such a complex system. Hopefully when we've provided a better platform for offering documentation we'll be able to update it more and more often with new information.