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.
"Before anything, I see that no one mentioned the one thing about 401(k) accounts that's just shy of magic - The matching deposit. In 2015, 42% of companies offered a dollar for dollar match on deposits. Can't beat that.  (Note - to respond to Xalorous' comment, the $18K OP deposits can be nearly any percent of his income. The typical match is 'up to' 6% of gross income. If that's the case, the 401(k) deposits are doubled. But say he makes $100K. The $18K deposit will see a $6K match. This adds a layer of complexity to the answer that I preferred to avoid, as I show with no match at all, and no change in tax brackets, the deferral alone shows value to the investor.) On to the main answer - Let's pull out a spreadsheet -  We start with $10,000, and assume the 25% bracket. This gives a choice of $10,000 in the 401(k) or $7500 in the taxable account. Next, let 20 years pass, with 10% return each year. The 401(k) sees the full 10% and after 20 years, $67K. The taxable account owner waits to get the 15% cap gain rate and adjusts portfolio, thus seeing an 8.5% return each year and carrying no ongoing gains. After 20 years of 8.5% returns, he has $38K net. The 401(k) owner on withdrawal pays the 25% tax and has $50K, still more than 25% more money that the taxable account. Because transactions within the account were all tax deferred.  EDIT - With respect to davmp's comment, I'll offer the other extreme -  In his comment, he (rightly) objected that I chose to trade every year, although I did assign the long term 15% cap gain rate, he felt the annual trade was my attempt to game the analysis. Above, I offer his extreme case, a 10% return each year, no trade, no dividend. Just a cap gain at the end. The 401(k) still wins. I also left the tax (on the 401(k)) at withdrawal at 25%, when in fact, much, if not all will be taxed at 15% or lower, which would put the net at $57K or 30% above the taxable account final withdrawal.  The next issue I'd bring up is that the 401(k) is taken out at the top (marginal) tax rate, e.g. a single filer with taxable income over $37,650 (in 2016) would save 25% on that 401(k) deduction. Of course if the deduction pulls you under that line, I'd go Roth or taxable. But, withdrawals start at zero. Today, a single retiree has a standard deduction ($4050) and exemption ($6300) for a total $10,350 ""zero bracket"" with the next $9275 taxed at 10%. This points to needing $500K in pre tax accounts before withdrawals each year would get you past the 10% bracket. (This comes from the suggestion of using 4% as an annual withdrawal rate).  Last - the tax discussion has 2 major points in time, deposit and withdrawal, of course. But, the answers here all ignore all the time in between.  In between, you see that for any number of reasons, you'll drop from the 25% bracket to 15% that year. That's the time to convert a bit of money to Roth and 'top off' the 15% bracket. It can happen due to job loss, marriage with new spouse either not working or having lower income, new baby, house purchase, etc.  Or in-between, a disability put you out of work. That permits you to take money out with no penalty, and little chance of paying even the 25% that you paid going in. This, from personal experience with a family member, funded a 401(k) with 28% money. Then divorced and disabled, able to take the $10K/yr to supplement worker's comp (non taxed) income." Post-86 After tax contributions to a 401k are after tax.   The earnings on that money is taxable, but not the contributions. This means: You'll have $15,000 in the 401k and $10,000 is considered after-tax and $5,000 is considered pre-tax. The after-tax portion can be converted to a Roth IRA without paying taxes or penalties. New in September 2014 The IRS has made substantial changes that now enable this to happen.   You can request a distribution from your 401k provider where they divide the money into pre-tax and after-tax funds.  In my example, you'd get a check for $10,000 that you could send to a Roth IRA and a check for $5,000 you could add to a traditional Roll-over IRA. Neither of those would be taxable events and you'd end with a Roth IRA with $10K and a Traditional, Rollover IRA with $5K in it. Notes: "Because you've sold something you've received cash (or at least an entry on your brokerage statement to say you've got cash) so you should record that as a credit in your brokerage account in GnuCash. The other side of the entry should go into another account that you create called something like ""Open Positions"" and is usually marked as a Liability account type (if you need to mark it as such). If you want to keep an accurate daily tally of your net worth you can add a new entry to your Open Positions account and offset that against Income which will be either negative or positive depending on how the position has moved for/against you. You can also do this at a lower frequency or not at all and just put an entry in when your position closes out because you bought it back or it expired or it was exercised. My preferred method is to have a single entry in the Open Positions account with an arbitrary date near when I expect it to be closed and each time I edit that value (daily or weekly) so I only have the initial entry and the current adjust to look at which reduces the number of entries and confusion if there are too many." Former pension/retirement/401(k) administrator here.  1.  If you don't want to bother with maintaining your own investments, you can 'roll-over' your existing 401(k) into *your new company's 401(k) plan*.  Then you will choose your investments in the new plan, you will be 100% vested in 'rollover account'.  2.  If you want control over your own investments (recommended!) you can roll over your existing 401(k) into an IRA (Individual Retirement Account).  Then *your entire account* will go into your new IRA.  3.  You can take part, or all, of your existing account as cash, paid directly to you.  Note that this will trigger *20% mandatory Federal Withholding* on whatever goes straight to you.  So some of your money is going to the IRS. Don’t do anything that causes taxes or penalties, beyond that it’s entirely personal choice and other posters have already done a great job enumerating then.  I recently switched jobs in June and rolled over a 401k from my old company to new company and the third party managing the account at the new company was much more professional and walked me through all the required steps and paperwork. "As far as I can tell there are no ""out-of-the-box"" solutions for this.  Nor will Moneydance or GnuCash give you the full solution you are looking for.  I imaging people don't write a well-known, open-source, tool that will do this for fear of the negative uses it could have, and the resulting liability.  You can roll-you-own using the following obscure tools that approximate a solution: First download the bank's CSV information: http://baruch.ev-en.org/proj/gnucash.html That guy did it with a perl script that you can modify. Then convert the result to OFX for use elsewhere: http://allmybrain.com/2009/02/04/converting-financial-csv-data-to-ofx-or-qif-import-files/" You should never roll a 401(k) to a Roth IRA. If the intention is to do so, you are better off rolling to a traditional IRA, and then converting. (Per the comment below, I should add - if the 401(k) contained post tax money, this portion rolls to a Roth, not a Tradition IRA. You then have the exercise of converting/recharacterizing just the TIRA money, as the Roth stands aside) This preserves the ability to recharacterize back to a traditional IRA. You might wish to do this if: The answers so far are great, but I'll add what I see missing - I would check to see what the fee schedule is on your previous employer's 401k. Depending on how it was setup, the quarterly/annual maintenance fee may be lower/higher than your current employer. Another reason to rollover/not-rollover is that selection of funds available is better than the other plan. And of course always consider rolling over your old plan into a standard custodial rollover IRA where the management company gives you a selection of investment options. At least look at the fees and expense ratios of your prior employer's plan and see if anything reaches a threshold of what you consider actionable and worth your time. Note: removed reference to self directed IRA as vehicle is more complicated account type allowing for more than just stocks, bonds, and mutual funds. Not for your typical retail investor. You'll want to roll the 401k over to a specifically designated rollover IRA. Rollover IRAs differ from an ordinary IRA account because they have NO contribution limit per year. Also Rolling over a 401k to a Roth IRA has consequences. There won't be a penalty but you will have to pay taxes on the amount being rolled over. The choice of Roth or Traditional IRA depends on your current tax situation as well as your expected taxes at retirement. Typically if you are in a low tax bracket and expect to be in a higher tax bracket at retirement a Roth IRA is suggested as withdrawals are tax free. With a rollover conversion you will have to evaluate whether paying taxes now outweighs the potential benefits of tax free withdrawals when you retire. rollover funds only mean the funds one was foolish enough to first roll into this 401(k). With no matching, and need for cash, I'd stop depositing to that account. But, from details you gave, you can't withdraw that money. Perhaps you should use your own tracking software, such as GnuCash, Quicken, Mint, or even Excel.  The latter would work given you say you're manually putting in your transactions.   There's lots of pre-done spreadsheets for tracking investments if you look around.    I'm hoping that a web search gets you help on migrating transaction data, but I've yet to run into any tools to do the export and import beyond a manual effort.  Then again, I haven't checked for this lately. Not sure about your other questions, but I'd recommend you edit the question to only contain what you're asking about in the subject. As to the rollover question.  Only rollover to a ROTH if you have other funds you can use to pay the taxes you will be hit with if you do that.  DO NOT pay the taxes out of the funds in the 401k. If you don't have a way to pay the taxes, then roll it to a traditional IRA.  You never want to pay the government any taxes 'early' and you don't want to reduce the balance. beyond that, A lot depends on how long you figure you will be with that company.  If it's only a few years, or if you and other employees can make enough of a fuss that they move the fund to someplace decent (any of the big no-load companies such as Vanguard would be a better custodian), then I'd go ahead and max it out. If you figure to be there for a long while, and it looks like someone is in bed with the custodian and there's no way it will be changed, then maybe look to max out a Roth IRA instead. It's really boring and you should automate it. Most front office guys worth their salt have built something that will normally calculate what they should have in their portfolios.  Basically we own X units of stock K, stock K pays dividend D on date M, you check on date M that we have received X*D for all K's.  When trades are made you also need to verify that the dollar amounts are correct, for equity its usually automatic but for fixed income and OTC products you can build a tool to check it. "I'm not sure what you mean by ""receive retirement benefits"". If the company had a 401k, that probably is the retirement plan. Few companies have both a 401k and an old-style pension plan, you typically have one or the other. So if your 401k was rolled over into some other account, you have already received your retirement benefits. If you mean that the 401k was rolled over into an IRA and you are asking if you can now start withdrawing from the IRA, see Excel Strategies answer. Short answer: Yes you can, but there's a 10% penalty unless you meet one of the exceptions." Similar to the lawn care you mentioned: if you have space, you could have the kids create a mini-farmstand. They could grow flowers for cutting, some vegetables, etc. It would be a different twist on the classic lemonade stand. If the kids are into animals and space and zoning allows, you could keep chickens and add eggs to your mini-farmstand. Upfront costs for the garden would be small enough that they can learn about how investing in a business works at a very small scale. Along with learning about money, they also learn responsibility because it requires commitment and daily attention. It's also seasonal in a way that meshes well with school (though having animals is a constant year-round responsibility).