There are also other problems with reconciling investment accounts.  Note that although it does keep track of the date of the last reconciliation, it does NOT change "C"leared transactions to "R"econciled.  I suspect this is because reconciliation was designed to handle changes to the cash balance of the account.  Investment accounts do not have any cash in them, just numbers of shares and current value.  I've been thinking about this for a long time, and have still not come up with how this really should work.  In the meantime, perhaps it would be worth adding a warning pop-up that reconciling an investment account probably does not do what you expect.

Quicken just disallows reconcile on an investment account whose cash balance is in a different (linked) account, and pops up a message saying you should reconcile the cash account instead. KMM could do the same. 

I have wondered if when reconciling the cash account, if the linked transaction in the investment account could also be automatically marked somehow - maybe with a 'C' ?.  The investment transaction is not really reconciled, as only the cash amount has been verified, not the number of shares, etc. But it seems useful to be able to see that the cash amount was reconciled while trying to verify the investment account ledger.  You would still need to manually verify the transaction and change the C to R. And transactions like "Reinvest Dividend" would not be affected by a cash account reconcile.

When you change the state of a transaction (such as in a checking account) it only changes it for that account - not for the account at the other end of the transaction.  That makes me lean against automatically marking cleared the brokerage account part of an investment transaction just because you mark cleared the investment part.

However, on the issue of reconciling the investment account itself - I do actually use that to mark that I have confirmed the number of shares of all equities in the account.  I do it manually, and although I suppose I could file a wishlist bug for KMM to do it automatically, I know that would be very low on the priority list of wishes.  I do agree that it should warn you in some way - but whether it just refuses to do so, or actually marks all cleared transactions as reconciled I'm still not decided about.

Maybe I'm missing something, but how it should work seems pretty obvious to me. It should work just like a cash account, but act on investment value instead of cash balance. Working on cash balance obviously doesn't make sense, since investment accounts don't have a cash balance, and working on shares doesn't work, since an investment account can have multiple securities (if you wanted to reconcile share numbers, we would need to be able to select individual securities from the ledger view) so investment value is the only option. It's also what you would expect from a UI perspective, since the share value appears in the bottom-right corner of the ledger, where the cash balance and reconciliation difference normally appear.

Whether or not that's simple to implement is a different matter, but it seems obvious to me how it *should* work.

Unfortunately, that isn't a realistic approach.  Remember, reconciling cash is pretty exact - starting amount plus deposits minus withdrawals equals ending amount.  That could be done for securities - but yes, it would have to be done separately for each security.  The investment value doesn't just change by adding or removing shares. It changes suddenly when you enter or download new prices for the securities.  Everyone doesn't always update prices on a daily or even regular basis, and matching the value in the ledger to the value on a printed statement would require having prices valid on the day the statement value was calculated.

It would definitely be considered good practice to update your prices before you reconcile, but for thoroughness I suppose it would be a good idea to add warning dialogues to the update prices and add price dialogues that say something like "Warning: The dates of some of the downloaded prices have already been reconciled. [Cancel] [Continue]"

For Investment accounts, it seems to me the only reasonable Reconciliation is the number of shares. My investment statements always starts with that info. The share price changes daily, so it is not reasonable to Reconcile by value. I use the Reconcile field to indicate that the number of shares in KMM matches the number of shares in the statement.
The Investment Cash account can be Reconciled by value, like any bank account.

To Rick's comment from 2015, the statement uses prices on the last day of the period covered.  I suspect most users reconcile some days later, so unless you happened to download prices on the right date, you are unlikely to match values.  This is all clearly part of what needs to be more fully discussed before any major changes to investment accounts are made.

Glenn - I agree with you on using the number of shares.  I'm also changing this to a wishlist, as things currently work as designed, even if this is not the most useful behavior.  I will likely also change the title, as I'm not sure what "difference" is not being updated.