In the context of Regulation D. A private purchaser wishes to invest directly in an issuer but hopes to acquire unrestricted securities. Through arrangements and understandings with the issuer, a stockholder with shares that are either restricted securities currently eligible for sale under Rule 144 or unrestricted securities sells the shares to the private purchaser. At about the same time, the issuer sells an equivalent number of shares to the stockholder. The Securities & Exchange Commission's view is that the shares taken by the private purchaser from the stockholder will be restricted securities within the meaning of Rule 144(a)(3). The holding period will date to the private acquisition. A public resale of the shares acquired from the stockholder without regard to the conditions of Rule 144 would raise serious issues under Section 5 of the Securities Act for all parties to the transactions.
A swap in which the legs are common stock and restricted stock. A gypsy swap generally occurs when an investor wishes to liquidate a position in a publicly-traded company. That is, because a restricted stock may only be sold under certain circumstances, an investor holding one may exchange it for a more liquid investment.