At Vanguard, can I transfer shares from regular investment account to a Roth IRA?
No, IRA contributions can only be made in the form of cash (rollovers and conversions are different). You'd have to sell the investments in your taxable account, incurring capital gains or losses, then transfer the proceeds to your IRA in cash. Note that the amount you can transfer is subject to the limits on how much one can contribute to the IRA each year. You could look into Vanguard Target Retirement funds, which have a lower $1,000 minimum investment, or Vanguard ETFs. Since you are paying taxes on the distributions from your mutual funds anyway, instead of reinvesting the distributions back into the mutual funds, you could receive them as cash, then contribute them to your Roth IRA once you are able to open one.
Whether or not you can deposit to a Roth IRA, you are able to convert those deposits to A Roth account. In effect, you pay the tax going in (as with the regular brokerage account) but no tax on growth when withdrawn.  The non-deductible IRA, on its own, holds little appeal, in comparison. "Good question.  And it depends a bit on your current plan, your future income, and the plan you are moving too. Mostly you want to roll out of your existing 401K.  There will likely be a fee, and your investment choices are limited.  You will want to do a direct transfer, and going with a quality company such as Fidelity or Vanguard.  Both of those have zero fees for accounts and pretty good customer service. However, if your future income is likely to be high there is something else to consider.  If you are over the limits do a ROTH, and are considering doing a ""Backdoor ROTH"" a key success for this strategy is keeping your roll over IRA balance low (or zero).   So you may want to either leave the 401K where it is, or roll it to your new 401K plan.  In that case you will have to call the two 401K custodians, and select the best choice as far as fees and fund choice." All the answers that show the equivalency of 401(k) pre-tax and Roth 401(k) post-tax using equivalent contributions are correct assuming equivalent tax rates upon withdrawal. There is some potential gain if your tax rate upon retirement is higher than your working tax rate, but often people calculate a smaller percentage of their working income for their retirement income, which may offset a higher tax-rate anyway. In my mind, the primary advantage of a Roth 401(k) is that it effectively allows you to contribute more for retirement if you are currently maxing out your contributions in a regular 401(k) and IRA and want to contribute more. Doing so can be a big advantage when you are young and can benefit from those additional dollars being put into your retirement account early. This is effectively what is illustrated by the Fidelity calculation, and is something to consider if you are of the mind to aggressively save early for retirement. The reason Roth allows you to contribute more is because traditional IRA contributions are capped. Suppose the cap is $5500. Suppose also you immediately rollover your traditional IRA to a Roth IRA. This is a post-tax contribution, and growth on that is tax-free. If you maxed out your employer pre-tax 401(k) to $17500 and maxed out your IRA, you have maxed out your retirement contributions to $23000. Suppose two doublings, then the 401(k) has grown to $70000, and the IRA has grown to $22000. However, the withdrawal from the 401(k) is taxed, so assuming 25%, the total is $74500 after tax. Now, suppose instead you maxed out your employer Roth 401(k) post-tax instead, so you have put in $17500 post tax. And now, also max out your IRA. Now, all of your $23000 grows tax-free. So upon two doublings, you walk away with $92000. This is because you maxed out your contribution post-tax, meaning it was as if you were allowed to contribute $23333 to your pre-tax 401(k). So if you intend to max out your retirement account contributions, and are looking to contribute even more to retirement accounts, one way is two change over to contributing into the employer Roth 401(k). Conversion of after-tax 401K into a Roth is known (on Bogleheads for instance) as a Mega Backdoor Roth IRA.  Recent tax rulings seem to allow for this kind of transfer more cleanly. After conversions, the money is treated as a normal Roth - you don't pay any taxes or penalties on contributions.  For investment earnings, the Roth IRA has the standard five-year rule: most commonly - you must hold the account for five years and be 59.5  years old (there are other criteria). Otherwise, you may pay taxes plus a 10% penalty on the earnings portion of your distribution.  There are other reasons you can withdraw early - spelled out in IRS Publication 590B Figure 2-1. You can contribute to a Traditional IRA instead of a Roth.  The main difference is a contribution to a Roth is made with after tax money but at retirement you can withdraw the money tax free.  With a Traditional IRA your contribution is tax-deductible but at retirement the withdrawal is not tax free.  This is why most people prefer a Roth if they can contribute. You can also contribute to your work's 401k plan assuming they have one.  And you can always save for retirement in a regular account. I have managed two IRA accounts; one I inherited from my wife's 401K and my own's 457B.  I managed actively my wife's 401 at Tradestation which doesn't restrict on Options except level 5 as naked puts and calls. I moved half of my 457B funds to TDAmeritrade, the only broker authorized by my employer, to open a Self Directed account.  However, my 457 plan disallows me from using a Cash-secured Puts, only Covered Calls.  For those who does not know investing, I resent the contention that participants to these IRAs should not be messing around with their IRA funds.  For years, I left my 401k/457B funds with my current fund custodian, Great West Financial.  I checked it's current values once or twice a year. These last years, the market dived in the last 2 quarters of 2015 and another dive early January and February of 2016.  I lost a total of $40K leaving my portfolio with my current custodian choosing all 30 products they offer, 90% of them are ETFs and the rest are bonds. If you don't know investing, better leave it with the pros - right?  But no one can predict the future of the market.  Even the pros are at the mercy of the market. So, I you know how to invest and choose your stocks, I don't think your plan administrator has to limit you on how you manage your funds. For example, if you are not allowed to place a Cash-Secured Puts and you just Buy the stocks or EFT at market or even limit order, you buy the securities at their market value. If you sell a Cash-secured puts against the stocks/ETF you are interested in buying, you will receive a credit in fraction of a dollar in a specific time frame.  In average, your cost to owning a stock/ETF is lesser if you buy it at market or even a limit order.  Most of the participants of the IRA funds rely too much on their portfolio manager because they don't know how to manage. If you try to educate yourself at a minimum, you will have a good understanding of how your IRA funds are tied up to the market.  If you know how to trade in bear market compared to bull market, then you are good at managing your investments.  When I started contributing to my employer's deferred comp account (457B) as a public employee, I have no idea of how my portfolio works.  Year after year as I looked at my investment, I was happy because it continued to grow.  Without scrutinizing how much it grew yearly, and my regular payroll contribution, I am happy even it only grew 2% per year.  And at this age that I am ready to retire at 60, I started taking investment classes and attended pre-retirement seminars.  Then I knew that it was not totally a good decision to leave your retirement funds in the hands of the portfolio manager since they don't really care if it tanked out on some years as long at overall it grew to a meager 1%-4% because they managers are pretty conservative on picking the equities they invest.  You can generalize that maybe 90% of IRA investors don't know about investing and have poor decision making actions which securities/ETF to buy and hold. For those who would like to remain as one, that is fine.  But for those who spent time and money to study and know how to invest, I don't think the plan manager can limit the participants ability to manage their own portfolio especially if the funds have no matching from the employer like mine. All I can say to all who have IRA or any retirement accounts, educate yourself early because if you leave it all to your portfolio managers, you lost a lot.  Don't believe much in what those commercial fund managers also show in their presentation just to move your funds for them to manage.  Be proactive.  If you start learning how to invest now when you are young, JUST DO IT! No, the reinvestment is done as a courtesy. Consider, one can have, say, 100 shares of a $50 stock. A 2% dividend is $100/yr or $25/quarter. It would be a pretty bad deal if brokers charged you even $5 for that trade. When cap gains and dividends are grouped as you suggest, it refers to Mutual Funds. My funds will have a year end dividend and cap gain distribution. In a non-retirement account, one has to pay the tax due, and be sure to add this to your cost basis, as it's money you are effectively adding to your account. It does not mean cap gain the same as when you sell your shares of Apple for a huge gain.  Those check boxes seem to offer you a chance to put all your holding on the same reinvestment plan for div/cap gain. You should also be able to choose one by one what you'd like to do. "One other thing to consider, particularly with Vanguard, is the total dollar amount available.  Vanguard has ""Admiralty"" shares of funds which offer lower expense ratios, around 15-20% lower, but require a fairly large investment in each fund (often 10k) to earn the discounted rate.  It is a tradeoff between slightly lower expense ratios and possibly a somewhat less diverse holding if you are relatively early in your savings and only have say 20-30k (which would mean 2 or 3 Admiralty share funds only)."