Do you keep track of original 401k contributions?

Yes, I do keep track of this. I've been using Quicken since 1996, the year I started contributing to my 401k. I've entered every paycheck as a Split Transaction, transferring my contribution and my employers contribtion to a 401k account. I don't enter Buy or Sell transactions. At the end of every quarter I enter a Gain or a Loss Transaction to reflect my earnings/losses for the quarter. If I don't want to wait until the end of the quarter, I can just add a transaction with today's date and put the gain/loss in. Next week, I'll just change the date on that same transaction and the gain/loss amount. Eventually, when the end of the quarter comes, I'll make a permanent transaction that I leave in the register for future reference. Now that I have several years worth of transactions, I can easily view the register and scroll back over the last few quarters or years and see my losses and gains at a glance. You could also create a report for the 401k account that lists just contributions and compare that with your ending balance.

At one time I tried to get granular and enter all the buy/sell transactions, but my 401k funds aren't traded publicly, so it wasn't so easy to download updates each day and see an accurate balance at any given time. At another time I tried connecting with Vanguard online to download my buy/sell transactions and that was a nightmare. What Vanguard displays on the website to the 2nd decimal place is not exactly equal to what Vanguard pushes down via Quicken WebConnect. So my balances were never accurate anyway.

In the end, I reverted back to the way I had been doing things, (the way I described in the first paragraph).

Does your company provide you with a statement (perhaps quarterly) that describes what you paid, what they paid, market gains, etc? Mine does, and I use that to do all of what you asked about. It would be a real pain to split the way you infer you have to if you need this info and your company (or website) can't produce it!

Yes, I have a split item in my paycheck for the contribution, and purchase, each time. Then each week I update the unit value for each fund.

Thus with little effort on my part by selecting the Value view in Quicken's Summary for the account I see my cost basis as well as the current market value of each fund.

Bernie

Yes, I have checked this on occassion out of curiosity. By proper selection of customizing criteria, QW can give you this figure quite easily - total, sub-total by year, etc. A Banking > Transaction Report, customized for appropriate accounts and categories, can be created to give you the info. It helps/simplifies the procedure if you include a unique memo in your paycheck entry, e.g., 'Employee Contribution' as you can include this in the customization criteria - all transactions in which Memo Contains....

My case was complicated slightly by the fact that I have made both pre-tax and after-tax contributions to the 401k. I differentiated between these by creating classes - PT and AT - and appending the class to the 'category'; e.g., an after tax contribution is indicated by '[401k Acct]/AT'. An alternative is to include this info in the memo, e.g., 'Emplyee Contribution - AT' or 'Employee Contribution - PT'.