Paying estimated taxes in a quarter with losses
Yes, if you're caught up you can skip the quarter.
The GuruFocus Link is just reporting the high and low price of the quarter.  Price Range (Average) – The estimated trade prices. The average price   is calculated from the time weighted average during the period. If no   price range is shown, the trade prices are estimated trade prices,   which are more accurate estimates. AAPL: $420.05 - $549.03 ($467.26) The numbers for the high and low match what I found for AAPL on Yahoo Finance. Keep in mind their definition uses estimate 3 times. &gt; 1 funny how you picked the highest estimate for the US and the lowest estimate for the UK  Mea culpa. It appears average cost for the US is [$30K](https://www.medigo.com/blog/medigo-guides/coronary-angioplasty-cost-guide/) (my personal family experience with it is $50K though). This means the US costs would have to come down by only 80% to be affordable by US families. I still strongly disagree that this could be accomplished by deregulation of any kind. And that's not even considering the loss in quality that would likely accompany such a move.  &gt;2 if anyone expresses wishful thinking it's you  Sources man. Sources. There is no argument without facts.   &gt;I live in a country with UH.   Well then we're both operating from a position of ignorance. I don't know what it's like with UH and you don't know what it's like without it. In that case - all I can do is look at the money the US spends vs everyone else - and then look at our national health outcomes vs. everyone else (e.g. heart health, maternity health, life span, etc.). America sucks at both.   &gt;You'll still have the same problems, except that you get a hefty tax increase on top and end up shoving 50-60% of your income down the state's throat in addition.  There are a handful of countries that charge that much income tax. But the bottom line is that those countries, on the whole, *still spend less on healthcare than the US*. So while that 10 or 15% of your check that goes towards UH sucks - remember that if you were in the US you'd be paying 20 to 30% to an outside company for insurance. Plus you'd have to deal with pre-existing conditions and finding doctors in network and jumping all the bullshit hurdles Americans do on a daily basis without any of the convenience of having *one single system* to coordinate those resources.   So you're either paying down the government's throat - or your paying twice that down a private company's throat. It sucks either way - but UH mitigates how bad it sucks.  And one interesting note - I thought you were full of shit about paying 60% in taxes - but some places actually do charge [that much](http://www.worldatlas.com/articles/countries-with-the-highest-taxes-in-the-world.html). So you could be right. But two interesting correlations about those countries is that they all have UH - and they all dominate the top spots in the UN's [happiest places in the world](https://www.theguardian.com/world/2017/mar/20/norway-ousts-denmark-as-worlds-happiest-country-un-report).   Don't underestimate the stress of living as a regular citizen without the benefit of a strong social safety net. Yes, you can do what you are contemplating doing, and it works quite well. Just don't get the university's payroll office too riled by going in each June, July, August and September to adjust your payroll withholding! Do it at the end of the summer when perhaps most of your contract income for the year has already been received and you have a fairly good estimate for what your tax bill will be for the coming year. Don't forget to include Social Security and Medicare taxes (both employee's share as well as employer's share) on your contract income in estimating the tax due. The nice thing about paying estimated taxes via payroll deduction is that all that tax money can be counted as having been paid in four equal and timely quarterly payments of estimated tax, regardless of when the money was actually withheld from your university paycheck. You could (if you wanted to, and had a fat salary from the university, heh heh) have all the tax due on your contract income withheld from just your last paycheck of the year! But whether you increase the withholding in August or in December, do remember to change it back after the last paycheck of the year has been received so that next year's withholding starts out at a more mellow pace. First off, some companies do something like this.  Microsoft for example was well-known for consistently hitting earnings estimates every quarter - nearly never missed them, and most of the time didn't exceed by much either.  In order to do this and not be prosecuted for accounting fraud, you typically have to be a service or nontangible good company (like Microsoft used to be) where you can manipulate the amount of product on hand and move costs fairly easily from one quarter to the next.  A company like, say, Home Depot or Caterpillar - both of which have tangible goods they're either retailing or producing - has less flexibility there, although they will still try to move profits around to match earnings estimates more closely. However, you have to be consistently doing well to be able to do this.  You can't manufacture additional total revenue; so if you have one 'down' quarter, you have to either have moved some revenue into it from the previous quarter, or you have to be able to move some into it from the next quarter.  That obviously doesn't work consistently unless you're a fast-growing company, or have an extremely stable base.  It's also hard to do this in a legal-seeming fashion - technically this sort of manipulation is illegal, so decisions have to be justifiable.  Companies (like Microsoft) that are expanding can also do things to encourage slightly lower expectations.  A company in need of a stock price bump issues press releases touting its inventions and products as amazing things that will drive profits through the roof and an aggressive profit forecast - just as easy to issue a press release with a conservative forecast, meaning the bar will be lower to hit.   It's also not really necessary to manipulate earnings to have a consistently well-performing stock.  This article for example shows that companies who miss earnings estimates don't really suffer much (when controlling for their actual earnings changes, of course) in the long run.  Your price might drop a bit, but if your company is otherwise sound, it will recover. Finally, companies do sometimes come out with information ahead of earnings that cause expectations to be lowered.  7-Eleven for example just lowered its earnings expectations due to various reasons.  Some companies choose to do this in order to dilute the effect on the market.  I'm not sure if this is ever required, but it seems to me that some companies are much quicker to restate earnings expectations than others. There is a shortcut you can use when calculating federal estimated taxes.  Some states may allow the same type of estimation, but I know at least one (my own--Illinois) that does not. The shortcut: you can completely base your estimated taxes for this year on last year's tax return and avoid any underpayment penalty.  A quick summary can be found here (emphasis mine): If your prior year Adjusted Gross Income was $150,000 or less, then   you can avoid a penalty if you pay either 90 percent of this year's   income tax liability or 100 percent of your income tax liability from   last year (dividing what you paid last year into four quarterly   payments). This rule helps if you have a big spike in income one year,   say, because you sell an investment for a huge gain or win the   lottery. If wage withholding for the year equals the amount of tax you   owed in the previous year, then you wouldn't need to pay estimated   taxes, no matter how much extra tax you owe on your windfall. Note that this does not mean you will not owe money when you file your return next April; this shortcut ensures that you pay at least the minimum allowed to avoid penalty. You can see this for yourself by filling out the worksheet on form 1040ES.  Line 14a is what your expected tax this year will be, based on your estimated income.  Line 14b is your total tax from last year, possibly with some other modifications.  Line 14c then asks you to take the lesser of the two numbers.  So even if your expected tax this year is one million dollars, you can still base your estimated payments on last year's tax. "The IRS rules are actually the same.  26 U.S. Code § 1091 - Loss from wash sales of stock or securities In   the case of any loss claimed to have been sustained from any sale or   other disposition of shares of stock or securities where it appears   that, within a period beginning 30 days before the date of such sale   or disposition and ending 30 days after such date, the taxpayer has   acquired (by purchase or by an exchange on which the entire amount of   gain or loss was recognized by law), or has entered into a contract or   option so to acquire, substantially identical stock or securities,   then no deduction shall be allowed... What you should take away from the quote above is ""substantially identical stock or securities."" With stocks, one company may happen to have a high correlation, Exxon and Mobil come to mind, before their merger of course. With funds or ETFs, the story is different. The IRS has yet to issue rules regarding what level of overlap or correlation makes two funds or ETFs ""substantially identical.""  Last month, I wrote an article, Tax Loss Harvesting, which analyses the impact of taking losses each year. I study the 2000's which showed an average loss of 1% per year, a 9% loss for the decade. Tax loss harvesting made the decade slightly positive, i.e. an annual boost of approx 1%." You add the wash sale loss to your cost basis for the other transaction so you would have two entries in your schedule d reporting 1.) Listing the $2000 loss as a wash 2.) The cost basis for your second transaction is thus $1000+$2000 = $3000 so when it was sold for $2000 you now have a reportable loss of $1000. For more information see here.... http://www.ehow.com/how_5313540_calculate-wash-sale.html "This doesn't make sense to me. Writing a covered call gives him a long delta position - the exact opposite of what he wants. And the tax losses won't turn a losing position into a winning one.  Is there something I'm missing?  Edit: Also, doesn't ""shorting against the box"" mean he has to have a long position, and short against that? That means you've got zero net delta, which isn't very useful at all..."