Chrysler decided to revamp their online bill payment system. The web site still looks like the same crappy website, but they’re forcing all their customers to complete a new registration process. This is how they decided to inform users of the process: User attempts to log in, and fails. Your old password no longer works, and you’re directed to a “Registration” screen if you read the message that says:
Please proceed to the Registration Page if you are a first-time or existing user who has not yet completed the new registration process.
Also missing from their new database, is my SSN, (as evidenced by the error message received when I follow the “forgot password” link) which might otherwise be used to validate my request to “register” under their new system.
In order to register for their new system, Chrysler is requesting my account number and the VIN for the vehicle I’m currently leasing. Since I pay all of my bills online, I don’t have that information handy. (In)conveniently, I receive e-Bills (which should contain both the account number and the VIN), but the e-Bills are locked behind the 128-bit encryption of a system to which I apparently no longer have access.
Other companies with whom I do business have, in the past, felt it was necessary to upgrade something in their system, which required users to update information or re-register. Typically, they will allow you to access your account using your existing credentials, at which point you are prompted to update whatever it is that needs updating, prior to proceeding. This happened quite recently with my mortgage servicer and the transition was seamless.
Chrysler, on the other hand, is a disaster. You literally have to re-register because you no longer exist in their system.
Since I don’t exist in their system, perhaps my payment for the month of September doesn’t exist in their system.

I woudln't be surprised if it's missin hahaha. Chrysler's IT sucks the big one..trust me
Everything is fucking up left and right.
Kunstler has an article that touches on this over on his site.
Alltel pulled this shit on me 3 years ago with a cellphone, but it was much worse than you described with Chrysler.
I tried to deal with them but they were unreasonable, so after 3 months of back n forth I told them to stick it. In their opinion I owe them $242. but in my opinion I don't as I didn't have a fully working phone during that duration. Their system is fucked and to hell with the customer.
Well I got news for them. That was at the exact time that I decided to pull completely out of ALL systems and all of them can shove it straight up their collective asses. Their lame threats to damage my credit falls on deaf ears. I don't use credit anymore. Fuck all of them. I don't owe anybody anything and intend to keep it that way.
We're doing everything we can to get to that point. Aside from the mortgage locked at 5.5%, and student loans, practically no debt. Paid cash for a used car a few months back, and will do the same when the wife needs to replace her lease.
The less you rely on the system, the freer you are; not a slave to your possessions, not a slave to the creditors. And once you get that freedom, you don't need them any more.