I have been preparing taxes for a very long time and, up to last year, have been a site manager with the AARP's Tax-Aide program.
Regarding penalties - The IRS wants to receive 90% of your tax due before you submit your return. There are 2 exceptions - the tax due is less than $1,000 or the tax due is greater than the previous year.
Regarding Withholding - Yes, a simple phone call to Social Security can start withholding from your monthly payments. You can give them a dollar amount or a percentage to deduct. These deductions are Withholding not Estimated Payments. The total annual withholding will appear on Form 1099-SSA.
For Qualified Retirement Accounts - IRA, 403(B), 401(k), Pensions, etc. the company is required to deduct withholding unless you direct them not to. You can specify an amount or a percentage. The same is true for Non-Qualified Accounts - Annuities.
For Capital Gains and Dividends - It is not recommended that withholding be taken every time you have a Capital Gain. There are two reasons for this. First, Capital Gains and Dividends get a favorable tax rate and the brokerage cannot determine what your particular rate would be - some of your gain or dividends may not be taxed at all. Second, why take withholding when you may have a Capital loss to offset any gain.
For most people who have a large tax due when they file, the very first thing to do is to review every 1099-R to make sure there is an entry in Box 4. If so, is it between 10% and 15% of the amount shown in Box 2a? If not, call the company and increase the withholding. Then, use the Estimated Tax Worksheet to calculate what your tax might be for the following year. Remember to exclude events that are you unique to the current year - you had to surrender an annuity or an IRA for medical expenses, etc.
Hope this helps.
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