Does “cash in lieu of dividend” incur any tax consequences in an IRA?
In a (not Roth) IRA, withdrawals are generally already taxed as regular income. So there should be no tax disadvantage to earning payment in lieu of dividends.  It's possible that there is an exception for IRAs but I was unable to find one and I cannot see the reason for one since the dividend tax rate is usually lower than the income tax rate (which is why some company owners elect to receive part of the company profits via dividend rather than all through their salary).
"People often have the wrong idea about how taxes apply to their money.  There's not really any such thing as ""pre-tax"" or ""post-tax"" income, only pre-tax and post-tax **uses** of your income.  This is somewhat hidden by the fact that we pay income tax based on our income for the year; but if you look a bit closer, you'll notice that come April 15th, (almost) every dollar you get to *subtract* from your gross income isn't defined by where it comes from, but rather, where it *went* (there are a few special cases there, like qualified dividends, that that's an entirely different issue).  Perhaps the most clear example of this is a traditional IRA that you self-fund from your savings account on April 14th, for the prior tax year - You're putting dollars you've already taken home, into a pre-tax account, *after* the end of the calendar tax-year; and yet it all works out exactly the same (tax-liability wise - There's certainly an opportunity cost there) as if you had contributed those dollars via a weekly payroll deduction.  So when you manually fund a Roth IRA, it has *no* effect on your tax liability (except insofar as you *don't* get to deduct it from your taxable income, which you wouldn't if you had left it in a savings account, etiher).  In the year you earned that money, you paid taxes on it; when you take it out, you won't." Yes, you may make non-deductible contributions to an IRA. The main benefit of a non-deductible IRA is tax-deferred earnings. If the investment pays out dividends, they will be kept in the IRA (whether you take them in cash and put them in a Cash Management Account, or you automatically reinvest them). You do not get taxed on these earnings until you withdraw from the IRA during retirement. If your income at that time is significantly lower than your income while you're working, you will be in a lower tax bracket (unless tax rates change drastically between now and then), so the taxes you pay on these earnings will be lower than if you'd invested outside the IRA and paid taxes along the way. You also get the benefit of compounding of the tax-deferred earnings. There's one caveat -- when you withdraw from the IRA, all the growth is treated as ordinary income. Even if some of it is capital gains, it will be taxed at your ordinary income rate, not your capital gains rate. So this is most beneficial for investments that produce dividends.  If you have a mix of deductible and non-deductible contributions to your IRA, the tax on the principle portion of your withdrawals is pro-rated based on the ratio of deductible to total contributions. This ensures that you eventually get taxed for the deductible portion (it's not really tax-free, it's tax-deferred), but don't get taxed twice for the non-deductible portion. Another option, if your 401(k) plan allows it, is to make after-tax contributions to the 401(k). At the end of the year, you can make an in-service distribution of these contributions and their earnings from the 401(k) to a Roth Conversion IRA. This allows you to contribute to a Roth IRA even if you're above the income limit for normal Roth IRA contributions. You can also do this even if you're also making non-deductible contributions to your regular IRA. Advantages of Gold IRA (regardless of where you're holding it): Disadvantages of Gold IRA: Instead, you can invest in trust funds like SLV (The ETF for silver) or GLD in your regular brokerage IRA. These funds negotiate their prices of storage, are relatively liquid, and shield you from the dangers of owning physical metal while providing opportunity to invest in it at market prices. The Brokerage firm will purchase shares for the dividend paid in a omnibus account for the security of the issuer and then they will distribute fractional shares among all their clients that chose Div Reinvest.  They will only have to buy 1 extra share to account for the fractional portion of what they allocate.  The structure of the market does not permit trading of fractional shares. There is generally not any impact to the market place for Div Reinvest with the exception of certain securities that pay large dividends that are not liquid. sometimes this occurs in  preferred securities where a large amount of Div reinvestment could create a large market order that has market impact.  Most brokers place market orders for the opening on the day following the payment of the dividend. When you sell the fractional portion same process as full shares are sold into the market and the fractional if traded between you and the brokers omnibus account.  if it creates a full share for the broker (omnibus has .6 shares and you sell him .5 they would likely flip that out to the street with the full share portion of your order. This would not have impact to outstanding shares and all cost are operational and with the broker handling the Div reinvestment service. There are no immediate tax-related benefits to putting money into a Roth IRA. You are investing after-tax money in the hope that the rules won't change and you'll be able to take out the money tax-free when you retire. Under current rules, you can take out your contributions at any time without penalties or taxes. You can't take out earnings without penalties until you retire. You said you don't have any debt (great!). So if you have cash that you don't have other uses for, and you don't mind possibly tying it up for a long time, you can put money into a Roth IRA. I'd argue that if you have, say, $25-50/month to put into long term savings, it's a good habit to start. When you move into a job that gives you more disposable income, you can increase this amount. The earlier you start, the lower the monthly amount you'll need to contribute towards a comfortable retirement. Once you get started putting a little bit away, you'll never miss it. "Some investment trusts have ""zero dividend preference shares"" which deliver all their gains as capital gains rather than income, even if the trust was investing in income yielding stocks. They've rather gone out of fashion after a scandal some years ago (~2000).  Good 2014 article on them here includes the quote  ""Because profits from zero dividend preference shares are taxed as   capital gains, they can be used tax efficiently if you are smart about   how you use your annual capital gains tax allowance.""" "You withdrew the 'cash' portion, and will pay tax on it. How was the check ""another for move remaining to B"" issued? Was it payable to you? If so, it's too late, it's your money and the whole account was cashed out.  If it was payable to B, you should have had it sent directly to their custodian, are you saying you still have that check? You might need to ask A to reissue the check to you, since you are no longer in the US. I'm not sure if you can roll it to an IRA at this point." No. As a rule, the dividends you see in the distribution table are what you'll receive before paying any taxes. Tax rates differ between qualified and unqualified/ordinary dividends, so the distribution can't include taxes because tax rates may differ between investors. In my case I hold it in an Israeli account but the tax treaty between our countries still specifies 25% withheld tax This is another example of why tax rates differ between investors. If I hold SPY too, my tax rate will be very different because I don't hold it in an account like yours, so the listed dividend couldn't include taxes. "Taxes are triggered when you sell the individual stock.      The IRS doesn't care which of your accounts the money is in.  They view all your bank and brokerage accounts as if they are one big account mashed together.   That kind of lumping is standard accounting practice for businesses. P/L, balance sheets, cash flow statements etc. will clump cash accounts as ""cash"".  Taxes are also triggered when they pay you a dividend.  That's why ETFs are preferable to mutual funds; ETFs automatically fold the dividends back into the ETF's value, so it doesn't cause a taxable event.  Less paperwork.  None of the above applies to retirement accounts.  They are special.  You don't report activity inside retirement accounts, because it would be very hard for regular folk to do that reporting, so that would discourage them from taking IRAs.   Taxes are paid at withdrawal time (or in Roth's, never.)" Now assume these shares are vested, held for at least 1 year, and are   then sold for $5 each. Everything I've read implies that the grantee   now owes long-term capital gains taxes on the difference, which would   be 10k * ($5 - $1). No. That's exactly what the SO is NQ for. Read more on the differences between ISO and NQSO here. Now assume these shares are vested, held for at least 1 year, and are   then sold for $5 each. Everything I've read implies that the grantee   now owes long-term capital gains taxes on the difference, which would   be 10k * ($5 - $1). At this point you no longer have NQSO, you have RSU. If you filed 83(b) when  you exercised, then you pay capital gains tax when they vest. If you didn't - its ordinary income to you. NQSO is a red herring here since once exercised they no longer exist. If you didn't file 83(b), then when the stock vests the difference between the FMV at vest and the money you spent on it when exercising (if any) is considered wages and taxed as ordinary income (+FICA etc). From that point the RSU becomes a regular stock investment and the capital gains clock starts ticking. The answer to this question requires looking at the mathematics of the Qualified Dividends and Capital Gains Worksheet (QDCGW). Start with Taxable Income which is the number that appears on Line 43 of Form 1040.  This is after the Adjusted Gross Income has been reduced by the Standard Deduction or Itemized Deductions as the case may be, as well as the exemptions claimed.   Then, subtract off the Qualified Dividends and the Net Long-Term Capital Gains (reduced by Net Short-Term  Capital Losses, if any) to get the non-cap-gains part of the Taxable Income. Assigning somewhat different meanings to the numbers in the OPs' question, let's say that the Taxable Income is $74K of which $10K is Long-Term Capital Gains leaving $64K as the the non-cap-gains taxable income on Line 7 of the QDCGW.   Since $64K is smaller than $72.5K (not $73.8K as stated by the OP) and this is a MFJ return, $72.5K - $64K = $8.5K of the long-term capital gains are taxed at 0%. The balance $1.5K is taxed at 15% giving $225 as the tax due on that part.   The 64K of non-cap-gains taxable income has a tax of $8711 if I am reading the Tax Tables correctly, and so the total tax due is $8711+225 = $8936.  This is as it should be; the non-gains income of $64K was assessed the tax due on it, $8.5K of the cap gains were taxed at 0%, and $1.5K at 15%. There are more complications to be worked out on the QDCGW for high earners who attract the 20% capital gains rate but those are not relevant here. "While @JB's ""yes"" is correct, a few more points to consider: There is no tax penalty for withdrawing any time from a taxable investment, that is, one not using specific tax protections like 401k/IRA or ESA or HSA. But you do pay tax on any income or gain distributions you receive from a taxable investment in a fund (except interest on tax-exempt aka ""municipal"" bonds),  and any net capital gains you realize when selling (or technically redeeming for non-ETF funds). Just like you do for dividends and interest and gains on non-fund taxable investments. Many funds have a sales charge or ""load"" which means you will very likely lose money if you sell quickly typically within at least several months and usually a year or more, and even some no-load funds, to discourage rapid trading that makes their management more difficult (and costly), have a ""contingent sales charge"" if you sell after less than a stated period like 3 months or 6 months.  For funds that largely or entirely invest in equities or longer term bonds, the share value/price is practically certain to fluctuate up and down, and if you sell during a ""down"" period you will lose money; if ""liquid"" means you want to take out money anytime without waiting for the market to move, you might want funds focussing on short-term bonds, especially government bonds, and ""money market"" funds which hold only very short bonds (usually duration under 90 days), which have much more stable prices (but lower returns over the longer term)." "The answer to your first question is true. No tax on withdrawls. Under these circumstances, the withdrawl is ""qualified"". To your second question, as long as the withdrawl is qualified, it is not taxed, regardless of your additional income. http://www.investopedia.com/articles/retirement/03/030403.asp?lgl=rira-baseline-vertical has a very comprehensive, plain English, description of the IRS rules (as of today, anyway)." I am not a lawyer but I do not see a legal problem here. However, if the puts in the Roth IRA are not purchased at fair market value that could be a problem. For example, if your traditional IRA sold puts to the Roth IRA below fair market value that would not be allowed. However, from your post, it appears that you will be buying the puts from a third party so that will not be an issue. There is something else that just cross my mind. Imagine that you own 100 shares of the XYZ stock in your traditional IRA and 100 shares of the XYZ stock outside of an IRA. Now, you buy a put on the XYZ stock inside your Roth IRA. Are the dividends on the XYZ stock still qualified? I do not know but my guess is the answer is no. "If a company earns $1 Million in net profit (let's say all cash, which is not entirely realistic), it can do one of three things with it: On the balance sheet - profits that have not been distributed show up as ""retained earnings"".  When dividends are paid, Retained Earnings and cash are reduced. None of the other options change the fact that it is still ""profit"" - they all just affect the balance sheet, not the income statement: Note that when a company issues dividends, it reduces its per-share value since cash is leaving the door with nothing in return.   In Apple's case, since a significant amount of its profit was earned in other countries (where it was not taxed by the US), it would pay a significant amount in US corporate tax by bringing it back to the US by investing it or paying dividends. They are betting that at some point, the US will change the rules to make it more favorable to ""repatriate"" the money and reduce their tax significantly."