have you made the 475(f) election? if so you are not subject to wash sales rules.
if you sell 10 shares of XYZ at a loss, properly taking into a/c prior wash sales within the 31 days of buying 10 shares of XYZ in the IRA a/c the wash sale rule will apply you will lose the benefit of the loss.
example: 12/2 buy 10 shares of XYZ for $1,000. this is within 31 days of selling 10 shares of XYZ at a loss. thus the wash sale rule applies. if the loss was $99,000, your new basis is $100,000. you sell these shares on 12/3 for $1,000. now you have a $99,000 loss. on 12/31 you buy 10 shares of XYZ in your IRA a/c. this also invokes the wash sale rules. this results in a $99,000 wash sale loss in your taxable a/c. because the shares purchased were in your IRA there is no adjustment to those IRA shares and the $99,000 wash sale loss disappears.
The wash sale rule says you lose your deduction for stock sold at a loss if you buy identical shares (note that purchase quantity creating the wash sale must also be equal to the number of shares sold at a loss - buy 100 shares when 10 shares are sold at a loss only 10 shares of the purchase get their basis adjusted) within 30 days before or after the sale. There’s ample authority for the notion that a purchase of replacement shares by a related person will prevent you from deducting a loss. The IRA is, of course, a related “person.” to specifically clarify the situation the IRS published Rev. Rul. 2008-5 that lays down the law: you lose your capital loss deduction. Note that if you have a spouse and you sell shares of XYZ at a loss in your investment a/c and your spouse buys XYZ in their IRA a/c within the 31 day period, the wash sales rules apply
The ruling specifies, in addition, that you do not obtain an adjustment to the basis of your traditional or Roth IRA when the rule applies. That means the result is worse than a normal wash sale, because the loss is permanently disallowed rather than being added to the basis of the replacement shares.
This rule will continue to be difficult for the IRS to enforce. Purchases and sales occurring within an IRA are not reported on Form 1099-B and will not show up in your individual brokerage account statement. Yet the ugly consequence — permanent disallowance of the deduction — may serve as a deterrent even for people who might otherwise be inclined to play the audit lottery. in the worst-case scenario, if caught, prosecution for tax evasion is possible.
https://www.irs.gov/pub/irs-drop/rr-08-05.pdf
