The results of my ongoing learning experience with Caltrain and Clipper... Checking online, asking conductors, and calling on-line help never provides the whole truth. I'm given fragmented information, partially true, partially wrong. Yet I continue to chip away at that vague thing we call reality. That hyperdimensional fractal volume whose surface can never be perfectly realized, only approximated to ever-increasing resolution...
Here's my understanding for how Clipper Direct works with monthly passes on Caltrain:
1. Each month you deposit via Clipper Direct at least sufficient pre-tax dollars into your "account".
2. Using the website, you can then purchase "transit products". These can be one-time or recurring orders. In my case, I have a recurring order for a monthly pass between zones 1 and 3.
3. This monthly pass will get you on the train for the first nine days of the month (at least this worked for me this month).
4. If at some point during those nine days you "tag" on or off within your passe's zones, the monthly pass is activated. If the trip took you outside those zones, "zone upgrades" will be purchased to cover any zones outside the monthly pass zones. If you forget to tag off during this trip, it will be assumed you were traveling to the most expensive destination, typically Gilroy (zone 5) but perhaps San Francisco (zone 1). If you tag on outside the zones of your monthly pass and forget to tag off, I would guess it registers this most expensive trip, and activates the monthly pass only if this trip enters the monthly pass region, but this is speculation.
5. Starting on the 10th of the month, if there has been no tagging, the monthly pass is "returned". You now have no pass on your card. You've been riding Caltrain for free for the first nine days of the month.
6. At this point you have have "credit" with Clipper Direct, and can purchase "one-time" products to ride the rest of the month. For example, yesterday I purchased an 8-ride ticket on-line. Upon purchase, this 8-ride is claimed to be available by the "first of the benefit month". I don't know what this means: I want it to be available immediately. Presently (the next morning) it is indicated as "ordered".
7. As with any monthly pass, if the pass is active, and you get on the train without tagging on, you are fine unless you leave your zones or if your cash balance is less than $1.25, in which case you are cited. I have no idea why you need a $1.25 balance if you didn't tag on, since in this case there is no way to spend the $1.25 anyway.
8. If you tag on with a monthly pass you are fine as long as you have at least $1.25 balance, even if you leave your pass's zones. In this case if you tag off you will be charged for any additional zones entered during the trip. If you forget to tag off, I believe you will be charged for the most expensive trip. However, I do not know if expense in this case is simply most zones, or the most zones outside of your pass's zones.
Still learning my way around Clipper. Presently I have an 8-ride ticket "ordered". I really don't know what that means. Hopefully it's active before my next monthly pass kicks in on 01 June, or else I just flushed that money down the digital toilet.
I told the woman on customer support that this was the "most pathologically complex transit system ticketing procedure I'd ever experienced", and that is easily the case. The problem is it's trying to do too much with the simple tagging process. It's like trying to program a computer with only a push-button, without the contribution of Samuel Morse. At some point they need touch-screens in the stations so these things can be managed more directly.