Are these scenarios considered as taxable income?
For case 1, there is no tax due as you sold the book for less than your cost basis. If you had sold for more than $100, then you would have had a profit. For case 2, that depends on the value of the gift card with respect to the value of your fare. Most likely that gift card is less than the cost of the fare. And in that case it would generally be treated as a reduction in the purchase price. The same way that rebates and cash back on credit card are treated. Note if for some reason a 1099 was generated that would change the situation and you would need to consult a tax professional. Since that would indicate that the other party to the transaction had a different view of the situation. You can always reduce the income by the direct expenses required to earn it, and figure out whether it is ultimately a net profit or loss.   The net profit is taxable income.  The loss may be tax deductible if the underlying thing is tax deductible.    For the book, the $50 revenue required a $100 expense, so that's a $50 net loss.  You don't owe any income tax since it's a loss.  You could take the loss as a tax deduction if you have a business trading books, or if buying the book would be tax deductible for some reason.  Note that in the latter case you can only deduct the $50 not the $100.  For the airline ticket, it is to compensate you for the losses you took as a result if the delayed flight. So you tally up the $22 meal you had in the airport waiting for news, the $110 on the motel room you rented or forfeited, any other way you can peg a cash value to any losses you took.  Total them up, again, a net loss is only deductible if the travel is already deductible. Note that if the actual expenses (book, flight) were tax deductible for some reason, the cash-back reduces the amount of your tax deduction, so it has the same effect as the sale/gift being taxable income.
Typically, the discount is taxable at sale time But what about taxes?  When the company   buys the shares for you, you do not   owe any taxes. You are exercising your   rights under the ESPP. You have bought   some stock. So far so good. When you sell the stock, the discount   that you received when you bought the   stock is generally considered   additional compensation to you, so you   have to pay taxes on it as regular   income. Source: Turbotax.   Second source. Your pretax rate of return would be: 17% (100/85) In your scenario where the stock price is fixed at $100. Your tax rate would be your marginal rate.   If the stock stayed at 100, you would still be taxed as income on $15/share (the discount) and would receive no benefit for holding the stock one year. Assuming you are in the 25% tax bracket, your after tax rate of return would be 13% ((15*.75)+85)/85) "Do I need to pay taxes in India in this scenario? For India tax purposes, you would still qualify as ""Resident Indian"". As a resident Indian you have to pay taxes on Global income. It is not relevant whether you transfer the money back to India to keep in US. The income is generated and taxable.  Depending on your contract, presumably you are working as a free lance; certain expenses are allowed to be deducted from your income, for example if you purchase equipment to help carry out the work, stay / entertainment costs, etc. Consult a professional CA who should be able to guide you on what is eligible and what is not. The balance along with your other income will be taxed as per tax brackets. There is exemption for certain category of workers, mostly in entertainment industry where such income is not taxable. This does not apply to your case." If you buy foreign currency as an investment, then the gains are ordinary income. The gains are realized when you close the position, and whether you buy something else go back to the original form of investment is of no consequence. In case #1 you have $125 income. In case #2 you have $125 income. In case #3 you have $166 loss. You report all these items on your Schedule D. Make sure to calculate the tax correctly, since the tax is not capital gains tax but rather ordinary income at marginal rates. Changes in foreign exchange between a transaction and the conversion of the proceeds to USD are generally not considered as income (i.e.: You sold a property in Mexico, but since the money took a couple of days to clear, the exchange rate changed and you got $2K more/less than you would based on the exchange rate on the day of the transaction - this is not a taxable income/loss). This is covered by the IRC Sec. 988. There are additional rules for contracts on foreign currency, TTM rules, etc. Better talk to a licensed tax adviser (EA/CPA licensed in your State) for anything other than trivial. I'm a series 24 securities principle and have explained and trained people on questions like these more times than I can count. Although, my first recommendation is to speak to a qualified tax professional for the appropriate answer for each individual scenario.  Disclosure aside, the source of truth for these questions is always the IRS publications. In this case it's IRS pub 590b: When Must You Withdraw Assets? (Required Minimum Distributions).  IRA stands for Individual Retirement Arrangement. Basically it's an arrangement between you a the government to encourage retirement savings. Tax payers(up to a define taxable income amount) agree to receive a deduction during your working years lowering your taxable income in the present. Your taxable income should drop in retirement because you're not working anymore and any withdraws would most likely be taxed at a lower rate. To be clear the require minimum distribution is based on a life expectancy factor and the ending balance of your pre-tax retirement accounts from the prior year(for ex. 2016 ending balance for a 2017 rmd). The rmd works out to be somewhere around 3-4% of your total balance.  Most retirement account providers(if not all) have established several conveniences to automate the withdraw process. I've believe that moving funds directly to bank deposits or moving the funds to another taxable investment account are most common.  Retirement account providers are required by law to give you notifications about RMDs. Some big firms allow you to setup an auto-distribution a year before you turn 70.5 to start when they need to. Because of the 50% penalty you're given so many notifications about an RMD that it's hard to forget about it. "The decision whether this test is or is not met seems to be highly dependent on the specific situation of the employer and the employee.  I think that you won't find a lot of general references meeting your needs. There is such a thing as a ""private ruling letter,"" where individuals provide specific information about their situation and request the IRS to rule in advance on how the situation falls with respect to the tax law.  I don't know a lot about that process or what you need to do to qualify to get a private ruling.  I do know that anonymized versions of at least some of the rulings are published.  You might look for such rulings that are close to your situation. I did a quick search and found two that are somewhat related: As regards your situation, my (non-expert) understanding is that you will not pass in this case unless either (a) the employer specifies that you must live on the West Coast or you'll be fired, (b) the employer would refuse to provide space for you if you moved to Boston (or another company location), or (c) you can show that you could not possibly do your job out of Boston.  For (c), that might mean, for example, you need to make visits to client locations in SF on short-notice to meet business requirements.  If you are only physically needed in SF occasionally and with ""reasonable"" notice, I don't think you could make it under (c), although if the employer doesn't want to pay travel costs, then you might still make it under (a) in this case." There is a moral and legal obligation to file the earnings. Not doing so is tax fraud. You should keep a ledger or some record of your earnings, helpful guidelines here. Records are required by the CRA: According to the law, your responsibilities include: (source) You could get in trouble if one of your pupils report the expense at their tax filing, and the CRA finds no matching statement on your filing report. Tutoring are eligible for tax credit in case of disability: Tutoring services that are supplementary to the primary education of a person with a learning disability or an impairment in mental functions, and paid to a person in the business of providing these services to individuals who are not related to the person. A medical practitioner must certify in writing that these services are necessary. So if one of your pupils fall under that provision, you will get tax trouble sooner or later. Bottom line: start making records now, and report your earnings. Collect your tax as any lawful citizen is required to. Ethically, you and your landlord should always report both income and expense as there technically exists a service and a rent. So it is subject to taxation. On the other hand, it can be considered an exchange of a simple favour and if it doesn't involve a money exchange or any profits (I am assuming that you are not selling what you or your landlord produce on the market) no value can be calculated thus no taxation can be applied. This changes though if a contract is involved, as a legal value can be estimated. Caution: These subjects can vary on an extreme level of specificity, of what can and cannot be claimed as income and expense, which can vary per country, state, province and even per judge, as well as the nature and sector of the work. Also, if you intend to formalize this relationship, the type of contract and reporting forms do vary per state as well. So it might be best to confirm it with a local legal advisor to avoid unfortunate surprises. You need to fill out form 8606.  It's not taxable, but you still need to report it