When are payroll taxes due in the US?
It depends on the size of the payroll, not on the number of employees.  Probably you need to file Form 941 quarterly under this scenario.  You may or may not need to deposit taxes more frequently.  If you must deposit, then you need to do it electronically. I excerpted this from the instructions for Form 941: If your total taxes (line 10) are less than $2,500 for   the current quarter or the preceding quarter, and you   did not incur a $100,000 next-day deposit obligation   during the current quarter. You do not have to make a deposit. To avoid a penalty, you must pay the amount in full with a timely filed return or you must deposit the amount timely. ... If you are not sure your total tax liability for the current quarter will be less than $2,500 (and your liability for the preceding quarter was not less than $2,500), make deposits using the semiweekly or monthly rules so you won't be subject to failure to deposit penalties. If your total taxes (line 10) are $2,500 or more for the   current quarter and the preceding quarter.  You must   make deposits according to your deposit schedule. See   section 11 of Pub. 15 (Circular E) for information and rules   about federal tax deposits. I would say that probably for two employees, you need to deposit by the 15th of each month for the prior month, but you really need to check the limits above and the deposit schedule in Pub 15 (as referenced above) based on your actual payroll size. Note that if you have a requirement to deposit, that must be done either through EFTPS or by wire-transfer.  The former is free but requires registration in advance of your first payment (they snail-mail you a PIN that you need to log-in) and it requires that you get your payment in by the night before.  The latter does not incur a charge from the IRS, but your bank will likely charge you a fee.  You can do the wire-transfer on the due date, however, so it's handy if don't get into ETFPS in time. This is all for federal.  You may also need to deposit for your state, and then you'll need to check the state's rules.
"Be careful of the other answers here. Many are wrong or partially wrong. The question implies that you knew this, but for everyone else's benefit, you can keep you LLC organization and still elect to be treated as a S-Corp by the IRS just for tax purposes.  You do this by filing Form 2553 with the IRS. (You can also, by the way, elect to be taxed as a ""regular"" C-Corp if you want, although that's probably not advantageous.  See Form 8832.) The advantage of electing to be treated as an S-Corp is that income beyond what constitutes a ""reasonable salary"" are not subject to social security and medicare taxes as they would when paid was wages or counted as self-employment income on Schedule C.  Depending on what you need to pay yourself to meet the ""reasonable salary"" test, your overall income, and other factors about your business, this could result in tax savings. Contrary to other answers here, making this election will not force you to create a board of directors.  You are still an LLC for all purposes except taxes, so whatever requirements you had in organization and governance at the state level will not change.  You will have to file a ""corporate"" tax return on Form 1120S (and likely some corresponding state tax form), so that is additional paperwork, but this ""corporate"" return does not mean the S-Corp pays taxes itself. With a couple of exceptions, the S-Corp pays no taxes directly (and therefore does not pay at the corporate tax rate). Instead the S-Corp apportions its income, expenses, and deductions to the owner(s) on Schedule K.  The owners get their portion reported from the S-Corp on Schedule K1 and then include that on their personal Form 1040 to pay tax at their personal rate. In addition to filing Form 1120S, you will have to handle payroll taxes, which will create some additional administrative work and/or cost. Using a payroll service for this will likely be your best option and not terribly expensive. You've also got the issue of determining your reasonable salary within the rules, which is the subject of other questions on this site and other IRS guidance." Are you obligated to do what they ask? Probably not, with one big caveat discussed below. Your employer sent your money and their money after every paycheck to the 401K management company. Then after a while the 401K management company followed your instructions to roll it over into an IRA. Now the IRA management company has it. Pulling it out of the IRA would be very hard, and the IRA company would be required to report it to the IRS as a withdraw. Here is the caveat. If the extra funds you put in allowed you to exceed the annual contribution amount set by the law, or if it allowed you to put more than 100% of your income into the fund, then this would be an excess contribution, and you and your employer would have to resolve or face the excess contribution penalties. Though if the 401K company and HR allowed you to exceed the annual limit they have a much more complex problem with their payroll system. The bigger concern is why they want you to pull out your $27.50 and their $27.50. Unless you were hitting the maximum limit, your $27.50 could have been invested by adjusting the percentage taken out of each check.  You could have picked a percentage to reach a goal. That money is yours because you contributed it and unless you exceed the IRS set limits it is still pre-tax retirement money. The return of matching funds may be harder to calculate. The returns for 2013 were very good. Each $1.06 of matching funds each paycheck purchased a fraction of some investment. That investment went up and down, ok mostly up, if it was invested in the broad market. I guess you should be glad they aren't asking for more due to the increase in value.  It would be very hard to calculate what happened if you have moved it around since then. Which of course you did when you moved it into an IRA. If the average employee was also given a $55 gift last year, then the suggestion to the employer is that the tax complexity you and your fellow employees face would exceed the cost of the extra funds. They should chalk it up to an expensive lesson and move on. "The big difference is that you get your money earlier at the start. Suppose you start on a random day with payday on the last day of the month (monthly), or on every 2nd wednesday (biweekly), and it takes 3 days for payroll to ""ramp up"" (ie, if payday is within 3 days on your start date, your next paycheck is not on the next payday, but on the one after). If we assume every month has 30 days (to keep things simple), it is an average of 4+5+...+33 days until you get your first paycheck with monthly pay, an average of 18.5 days. For weekly it is a bit trickier Assuming you get hired at a random date here, with * being a paydate: time until you get paid: an average of 10.5 days. So you get your first pay an average of 8 days earlier. Later on, that 3 day thing no longer occurs, and now the company holds an average of 6.5 days of your pay ""due to you"" with biweekly paychecks, and about 14.5 days with weekly paychecks if you have monthly pay. So with monthly pay, on average your bank account has 8 fewer days of  your pay in it at all times.  This happens when  you are first hired, and persists over the length of your employment. Now suppose you save that extra money (on average): Suppose you have an investment at 4% (after inflation).  Over 40 years those 8 days of pay invested at 4% grow to 38 days of pay, a free month. What more, if the company has problems making payroll, you'll get a warning (to, say, look for another job) an average of 8 days sooner, and/or have the money in your account.  Having someone owe you money is usually worse than having the money in your bank account." The rebate amount is a non-qualified distribution: IRS Pub 969 describes how the HSA works: Reporting Distributions on Your Return How you report your distributions depends on whether or not you use the distribution for qualified medical expenses (defined earlier). If you use a distribution from your HSA for qualified medical expenses, you do not pay tax on the distribution but you have to report the distribution on Form 8889. However, the distribution of an excess contribution taken out after the due date, including extensions, of your return is subject to tax even if used for qualified medical expenses. Follow the instructions for the form and file it with your Form 1040 or Form 1040NR. If you do not use a distribution from your HSA for qualified medical expenses, you must pay tax on the distribution. Report the amount on Form 8889 and file it with your Form 1040 or Form 1040NR. If you have a taxable HSA distribution, include it in the total on Form 1040 or Form 1040NR, line 21, and enter “HSA” and the amount on the dotted line next to line 21. You may have to pay an additional 20% tax on your taxable distribution. I looked at several plans regarding how to handle mistaken distributions: example A What if I accidentally use my HSA Visa debit card for a non-qualified expense?   To fix this problem, just bring that same amount into any local branch and tell us it was a Mistaken Distribution. We can then put the funds back into your HSA and correct the problem.  example B  You’re allowed to correct mistaken   HSA withdrawals when there is clear and convincing   evidence that amounts were distributed from an HSA   because of a mistake of fact due to reasonable cause. You   can correct the mistake by repaying the withdrawal   no later than April 15 following the first year that you   knew or should have known that the withdrawal was   a mistake. When a correction is made, the mistaken   withdrawal does not have to be included in gross   income or be subject to the 6 percent additional tax, and   the repayment does not count as an excess contribution.   If an error is made by SelectAccount in its role as the   administrator, SelectAccount will be responsible for   taking appropriate corrective action. Check with your plan trustee on their procedure to fix the mistaken withdrawal. According to TurboTax: You report the income in the year you received it... Therefore, since you received payment in 2017, you will report it on your 2017 tax return. Do you have any insight on average *effective* rates paid by SE owners?  As a counterpoint to your (very valid) links, filing as S-corp allows for taxes on distributions to be exempt from payroll tax and taxed at much lower rates. Also, being SE allows for various deductions not possible for wage earners. There's probably other examples not immediately coming to mind.  Also, SE taxes equal taxes otherwise paid by employer + employee. It's just that those employer taxes don't appear on the employee's paystub so not everyone realizes this. "New York will want to you to pay taxes on income from ""New York sources"". I'm not sure what this means to a freelance web developer.  If your wife is doing freelance web development under the same business entity as she did in New York (ie. a New York sole proprietor, corporation, etc), you probably do need to file. From nonresident tax form manual: http://tax.ny.gov/pdf/2011/inc/it203i_2011.pdf If you were a nonresident of New York State, you are subject to New   York State tax on income you received from New York State sources in   2011. If you were a resident of New York State for only part of 2011, you are subject to New York State tax on all income you received while   you were a resident of the state and on income you received from New   York State sources while  you were a nonresident.  To compute the amount of tax due, use Form IT-203, Nonresident and   Part-Year Resident Income Tax Return. You will compute a base tax as   if you were a full-year  resident, then determine the percentage of   your income that is subject to New York State tax and the amount of   tax apportioned to New York State." In Singapore, this is sufficiently common that the Singapore IRS has a page on their website dedicated to informing employers of how to properly pay this under Responsibilites of an Employer.   Specifically, tax paid by employer is taxable income for the employee (as it's really the employee's responsibility), so they must pay tax for that tax.  A tax-on-tax is computed for the tax paid, which also would be owed by the employer if they were paying the full tax rate for the employee. As a clarification, this is not the employer being truly responsible for the employee's income; this is the employer compensating the employee further to offset their taxable income.  This is effectively a fringe benefit, although it may be particularly useful in countries where either tax evasion is common (and thus an employer must compete with employers willing to pay under the table) or where employers are competing with others in nearby countries with lower tax rates.  It is not the same thing as the employer making your income nontaxable, though, and has implications for your tax filing. Significantly, it is likely that if you have additional income beyond income from that employer, it is likely to be taxed at your highest tax rate, as the employer will likely calculate the tax due based on their income being the only income you have in that year. *Edit based on emphasis in question: I'm not from Singapore nor am I a lawyer, but based on my reading of the IRAS website, it looks like you do not have to file if you have no other source of income, because they have a No-Filing Service which takes income information from your employer automatically and generates a tax bill, which presumably would be fully paid in your case.  This only aplies if you have no other sources of income, however; you still have to file if you have other sources of income since your employer would not know about them. If you are eligible for this service, you should get a letter informing you as such.  They also have a tool to check your filing status on their website.