How do I track 401k rollovers in Quicken?
When I did this I sold the stock out of my 401k account.  Then transferred the cash to my rollover IRA account.  No tax event was created for me.  Make sure your rollover IRA account is listed as tax deferred.  If this still doesn't work for you then it could be a bug in Quicken and your best bet is the Quicken forums.  Good luck. You definitely should NOT do what you are doing now (#2) since this is not a reflection of what actually is going on.  (Unless you actually did transfer the equities themselves and not the cash.)    Your first option is correct solution. As noted by mpenrow you need to make sure that the target account is also tax deferred.  If that still doesn't work and there is a bug you should still do it this way anyway. If it messes up your tax planner just make sure to include a comment so that everyone knows what is really going on. When I have had issues like this in the past I always try to stick to whatever is the closest indication of what actually occurred.
That would be my suggestion (and what I've personally done), but I can't tell you what's right for you.   As an aside, you don't usually need to manually fund an IRA (traditional *or* Roth) to open it for a rollover - Just tell them you're doing a rollover, and they'll set you up and tell you where to have the 401k checks sent (and sometimes even arrange it all *for* you). There are several things being mixed up in the questions being asked. The expense ratio charged by the mutual fund is built into the NAV per share of the fund, and you do not see the charge explicitly  mentioned as a deduction  on your 401k statement (or in the statement received from the mutual fund in a non-401k situation). The expense ratio is listed in the fund's prospectus, and should also have been made available to you in the literature about the new 401k plan that your employer is setting up. Mutual fund fees (for things like having a small balance, or for that matter, sales charges if any of the funds in the 401k are load funds, God forbid) are different. Some load mutual funds waive  the sales charge load for 401k participants, while some may not. Actually, it all depends on how hard the employer negotiates with the 401k administration company who handles all the paperwork and the mutual fund company with which the 401k administration company negotiates.  (In the 1980s, Fidelity Magellan (3% sales load) was a hot fund, but my employer managed to get it as an option in our plan with no sales load: it helped that my employer was large and could twist arms more easily than a mom-and-pop outfit or Solo 401k plan could). A long long time ago in a galaxy far far away, my first ever IRA contribution of $2000 into a  no-load mutual fund resulted in a $25 annual maintenance fee, but the law allowed the payment of this fee separately from the $2000 if the IRA owner wished to do so. (If not, the $25 would reduce the IRA balance (and no, this did  not count as a premature distribution from the IRA). Plan expenses are what the 401k administration company charges the employer for running the plan (and these expenses are not necessarily peanuts; a 401k plan is not something that needs just a spreadsheet -- there is lots of other paperwork that the employee never gets to see). In some cases, the employer pays the entire expense as a cost of doing business; in other cases, part is paid by the employer and the rest is passed on to the employees.  As far as I know, there is no mechanism for the employee to pay these expenses outside the 401k plan (that is, these expenses are (visibly) deducted from the 401k plan balance). Finally, with regard to the question asked: how are plan fees divided among the investment options? I don't believe that anyone other than the 401k plan administrator or the employer can answer this. Even if the employer simply adopts one of the pre-packaged plans offered by a big 401k administrator (many brokerages and mutual fund companies offer these), the exact numbers depend on which pre-packaged plan has been chosen. (I do think the answers the OP has received are rubbish). I currently do not have an IRA (other than a rollover IRA from my 401k from a previous employer) The source is irrelevant. You have an IRA.  The reason to keep contributing is that at some point, you might transfer the pretax dollars into a 401(k) and the post tax dollars can be converted to Roth.  Other than the above, investing in a standard brokerage account (a non-retirement account) has its positives. Gains can see long term cap gain treatment, and the assets see a step-up in basis when you die. I'd argue that you should be focusing on avoiding taxation and maximizing employer matching funds as your first objective.  Over a longer period, quality of investment options and fees will both drive your account value. A personal IRA account is usually a better value over time -- so contribute as much as possible to your IRA, and rollover 401k accounts whenever you have an opportunity to do so. http://www.irs.gov/pub/irs-pdf/f5498.pdf see the instructions for box 2, it's used to report incoming rollover/transfers. The receiving broker should be acknowledging the transfer with the 5498.  If you read the PDF carefully, any incoming money is reported this way. I found a way to do this, but it's slightly backwards. Quicken does not allow you to make a graph of just your income, probably because that would be a fairly boring graph for most people.  But it does allow you to do a graph of your expenses.  Doing so, while including income categories, will produce the graph I want, but with negative numbers (savings is negative spending). This will show a bar graph of overall spending, counting income as Negative Spending.  So, having negative bars is good in this case. I can't give you a detailed answer because I'm away from the computer where I use kMyMoney, but IIRC to add investments you have to create new transactions on the 'brokerage account' linked to your investment account. You can also roll money from prior 401ks into current 401ks. Call the administrator of the 401k you prefer (i.e., Fidelity/Schwab, whoever the financial institution is). Explain you don't work there anymore and ask if you can roll money into it. Some plans allow this and some don't. So either, 1) You  can roll all your prior 401ks into your current 401k. 2) You might be able to roll all prior 401ks into the prior 401k of your choice if they will accept contributions after you've left. You can't move the amount in your current employer's 401k until you separate or hit a certain age. 3) Like mentioned above, you can roll all prior 401ks into an IRA at any financial institution that will let you set up an IRA. Process: -Call the financial institutions you want to move the money from. Tell them you want a direct rollover. Have them write the check to the financial institution you are rolling into with your name mentioned but not the beneficiary (i.e., check written to Schwab FBO: John Doe account #12345) Tax implications: -If you are rolling from a pre-tax 401k to a pre-tax 401k or IRA, and the money goes directly from institution to institution, you are not liable for taxes. You can also roll from a Roth type (already taxed) account into another Roth type account with no tax implications. If they write a check to YOU and you don't put the money in an IRA or 401k within 60 days you will pay ~20% tax and a 10% early withdrawal penalty. That's why it's best to transfer from institution to institution. 401k vs IRA: -This is a personal decision. You could move all your prior 401ks into an IRA you set up for yourself. Generally the limitations of a 401k are the lack of funds to invest in that fit your retirement strategy, or high expense ratios. Be sure to investigate the fees you would pay for trades in an IRA (401k are almost always free) and the expense ratio for funds in your 401k vs funds you might invest in at a broker for your IRA. Best of both: -You can roll all your 401ks into a single 401k and still set up an IRA or Roth IRA (if your income qualifies) that you can contribute to separately. This could give you flexibility in fund choices if your 401k fees tend to be cheaper while keeping the bulk of your nest egg in low cost mutual funds through an employer account. Last advice: Even if you don't like the options in your current 401k, make sure you are contributing at least enough to get any employer match.