@DHClem Have you figured out your problem(s) yet?
I believe there are two problems that have been identified here. They are related.
1) Quicken is reporting a -$0- balance in the online account. Here, Quicken is talking about the Cash Balance, not the Market Value, of the account.
This is as it should be. All of your investment at TIAA is in mutual funds or other securities. There is no free cash laying around, so the cash balance for the account should be -$0-.
2) Quicken is reporting a negative Cash Balance in your Quicken account records.
Reviewing the screenshots you posted earlier, I notice the reconcile window shows
- Cash Outs of $ -94,399.73
So, there appear to be Buy or Withdrawal transactions in the amount of $-94,339.73. You should be able to find these transactions in the reconcile window. Can you? You might try sorting by the Cash Out column to help.
- Cash Ins of $ 726.77
Can you find the transactions - Deposits and Sells - that contribute to the Cash In amount? Try sorting by the Cash In column.
Difference: $ -93,672.96
This difference is the same negative Quicken Balance reported in the header of the reconciliation window.
So, now, why is the Cash Balance so hugely negative? Because more cash was taken out of the account than was put into the account over the period of the reconcile. That is true at least if the account Cash Balance was $0 at the beginning of the reconciliation period.
The likely cause of this problem is that a large chunk of cash was used to buy securities, but there were no deposits or other sources of cash to supply that cash. So the balance went negative.
For a 401k, the usual source of cash for purchases is payroll deductions and employer matching funds. Are there Deposit transactions in the account to account for this cash?
PS: you might want to try reconciling the account for a shorter period. Most retirement accounts issue statements at least quarterly, so try reconciling for a 3-month period corresponding to the first statement for the account. This should make it easier to see what is going on.