Why do I have to manually type in cash balance when reconciling?

Sometime this year the behavior of my many investing accounts changed to where I need to manually type in the ending cash balance when reconciling the account. 

I have been using Quicken since 1992 and at no time has Quicken ever filled in the current cash balance for an investment reconcile.

It has been requested a few times (including by me) but has never been a feature in Quicken.

(Note in a lot of cases the "online balance" for non-investment accounts has been wrong/a problem, so it is highly likely that if they provided this option for the investment accounts, it probably would have similar problems. As in, it is dependent on the financial institution to send the right number, and they don't always do that right).

The "invalid date" problem is a different problem that comes up from time to time, and I'm not entirely sure what triggers it.

@Boatnmaniac it might sound strange but, at least in Chase's case it is the security information that lags, but not the cash balance (and the more I thought about it this should be true in the real world too).

Let me go through my process which shows this. I have "compare securities" off, mostly for this very reason. So, I have three action button setups in my register. The first one, is the Security compare (as it turns out I'm currently in this situation so I can even show it):

The next action button is "Update Cash Balance". Why this one? Because it shows what the financial institution downloaded for the cash balance (it also shows the amount that Quicken has, and that first text box does default to what the financial institution downloaded, which I copy for the next step).

EDIT I need to point out that I always cancel out of this Update Cash Balance dialog. I don't want to change the cash balance in Quicken, just get the amount that the financial institution sent.

The last action button I have is Reconcile (I already.

This is where I would paste in what I copied from the last step. And finish the "cash" reconcile. And this will work with the value from the financial institution.

When the transaction(s) close I will get another indication that transactions have downloaded but see no new transactions. That is when I know that they have in fact closed and I will do another compare of the securities to make sure everything is correct (and short of some mistake they will compare). It has been a while since I switched to Chase, but I also remember it working similarly with other financial institutions with the exception that some financial institutions don't have the lag in updating the security positions in the "summary information" that is downloaded.

On the subject of whether this violates "reconcile accounting rules", well I don't think so.

If I sell I security today, I can turn around and use the cash to buy another security. So, that cash is "in my account". Now mind you have to be very careful about doing this, but it is possible. What's more if I buy a security, that cash is immediately no longer available.

So, in summary, securities have the waiting period, but the cash doesn't.

And another thing that occurs to me is that "Reconcile" is a "Cash Reconcile", it says nothing about the securities. That has to be reconciled separately. That is the reason for comparing the number of shares of each of your securities in Quicken to the number of shares at the financial institution. It is quite easy to have the cash amount reconciled and have the securities completely wrong.

The reconcile problem started somewhere in the past 3-6 months, and it is possible that it started when I changed some setting in each account, such as checking the box in online settings for "Reconcile using online balance". 

Should I uncheck that box in every investment account where I have this problem?

I didn't realize that you had this setting on!

The history as I remember it is this. Even though that setting has been in there for a very long time, it didn't do anything in an investment account.

Then like you said about a while back it started "working". Working in the sense that it did something, but not in the sense that it properly did an automatic reconcile, so I ended up turning it off on all of my accounts (I had turned it on when I saw something in the release notes that suggested it would work.)

I don't remember all the details, but I remember it would do it in the first account, but not any others, I believe that the very fact that "Reconcile" doesn't really reconcile both the securities and the cash, just the cash it caused more problems than it was worth. (actually I shouldn't speculate on that because I can't remember the details, it might even be I ran into the same kind of problems you are reporting.)

So, it seems that different investment companies treat the cash settlement differently.

And that is what lead me to believe that is it a "false hope" to ever have automatic reconcile in an investment account. Give that there are problems just with the "Online Balance" of banking accounts, it is extremely unlikely that it would ever be possible to get automatic reconciling working for investment accounts.

It would be nice though if when you brought up the reconcile dialog the ending amount defaulted to what the financial institution downloaded.

I think your summary is pretty much what I remember it was when I tried it before some months ago when I saw that release notes that suggested it would work. I don't know if it changed in between times since I just turned it off since it wasn't really working right.

I will mentionmention that it has been my experience that if you have automatic transaction entry mode on Quicken ignores the setting to do the compare of the securities.

Yes, that is the conclusion too and the main reason why I didn't pursue trying to get this fixed when I found it.

Note I'm more talking about the proper procedure than the bug in Quicken for how Automatic transaction entry mode works.

First some history on the bug. A long time ago before they had the feature to decide if you wanted to do comparing of securities selectable at the account level there was a complaint that automatic transaction entry mode would always create placeholders if any share amount didn't agree. They "fixed" that by turning off comparing of security positions while in automatic transaction entry mode.

When they got around to adding the feature for deciding if you wanted comparing of securities at the account level, they never went back and did the same for automatic transaction mode. I will also note that there seems to be an inconsistency in whether to ask the user about adding the placeholders or doing it automatically. I see some complaints about it on here. To me the default should always be to ask, and maybe have an option to do it automatically. When I kick it off manually it always just displays what I showed above and as such you can just cancel it.

That is the "current bug" for automatic transaction mode in this regard.

Now on to the process.

One might consider that the proper "automatic" process would be to first do the security compare and if it matches, then do the cash reconcile with the online balance and if all of that passes then mark the transactions reconciled. But two things really stood out when I tried this. The first is that is much more complicated flow, and I doubted that they could make it work reliably. The other is that this could be happening for multiple accounts, and not only would that be even more complicated it might be very confusing when the securities don't match and/or the cash balance doesn't reconcile. Like I said before I think currently it will only do one account and stop.

This brings me to a much broader statement. Automatic transaction entry mode and Automatic reconcile should NEVER be allowed both in investment accounts and in banking accounts. At least not the way it is implemented in Quicken Windows (Quicken Mac does it differently). In banking accounts, the reason these two options should be mutually exclusive is because reconcile checks amounts, not payees/categories/tags. The user should always review the downloaded transactions to make sure the transactions have the correct payee/category/tag because if they don't and the automatic reconcile kicks in the status New/New Match will go away and you will have no way of knowing when transactions are new and need to be checked for payee/category/tag. Note that for Quicken Mac, reconciling doesn't change the New/New Match status so they can do this check after the automatic reconcile.

And the reason not to do this for investments is all of the above, plus the fact that I don't even recommend using it in investment accounts unless you are quite familiar with the bugs in the process that have never been fixed (mostly because there aren't enough people using the mode and complaining about the bugs for them to ever get fixed). The main one being that when the situation of "close match" comes up, it is buried in a hidden "Downloaded Transactions tab" and the user has to know the signs of when this has happened and how to fix it. Note this comes up mostly when you manually enter transactions, which I don't do, and as such I can get away with it. There might be other situations where Quicken "prompts" by putting something in the hidden Downloaded Transaction tab.

That brings me to given all of this could automatic reconcile be used if the user isn't using automatic transaction entry mode?

My guess would be that it is "possible", but I haven't tested it. Note I also believe that turning off of the security compare and turning on automatic reconcile should be mutually exclusive.