What the rule asks of a seller. Rule 144 sets five conditions, and which ones apply depends on whether the seller is an affiliate of the issuer.
Current public information, at 230.144(c). For a reporting company this generally means it has been subject to Exchange Act reporting for at least 90 days and has filed all required reports for the preceding 12 months, "other than Form 8-K reports". For a non-reporting company it means specified information about the business, its officers and directors and its financials is publicly available.
Holding period, at 230.144(d)(1). If the issuer is, and has been for at least 90 days, an Exchange Act reporting company, "a minimum of six months must elapse" between acquiring the securities from the issuer or an affiliate and reselling them under the rule. If it is not, the minimum is one year. Paragraph (d)(1)(iii) adds that when the acquirer buys the securities, the clock does not start "until the full purchase price or other consideration is paid". Paragraph (d)(3) then handles the awkward cases, including stock splits and recapitalizations, conversions and exchanges, pledges, gifts, trusts and estates, generally by tacking the earlier holder's period.
Volume limitation, at 230.144(e), which applies only to sales for an affiliate's account. Sales in any three months, aggregated with the prior three months' sales of the same class, may not exceed the greatest of one percent of the shares outstanding as shown by the issuer's most recent report; the average weekly reported volume on all national securities exchanges and through a registered securities association's automated quotation system during the four calendar weeks preceding the Form 144 filing; or the average weekly volume reported under an effective transaction reporting plan or national market system plan over the same four weeks.
Manner of sale, at 230.144(f). Affiliate sales must be brokers' transactions, transactions directly with a market maker, or qualifying riskless principal transactions, and the seller may not solicit buy orders or pay anyone other than the executing broker. The paragraph does not apply to debt securities or to securities sold for a non-affiliate estate.
Notice, at 230.144(h). If more than 5,000 shares, or more than $50,000 worth, will be sold in any three-month period, a notice on Form 144 must be filed, transmitted concurrently with placing the order, and the filer must have a bona fide intention to sell within a reasonable time.
The two paths, side by side. Under 230.144(b)(1), a person who is not an affiliate and has not been one for three months may resell restricted securities of a reporting company once the holding period is satisfied and the current-public-information condition is met, and that information condition falls away entirely "provided a period of one year has elapsed" since acquisition. For a non-reporting company, the only condition for such a person is the one-year holding period. An affiliate, by contrast, is covered by 230.144(b)(2) and must meet all of the conditions on every sale, which is the practical reason an executive's selling is slow and documented even years after the shares were acquired.
The legend, and who can lift it. Because the shares cannot be resold freely, the certificate or book-entry position normally carries a restrictive legend. The SEC's own investor publication is unusually direct about what follows: even after the Rule 144 conditions are satisfied, "you can't sell your restricted securities to the public until you've gotten the legend removed from the certificate", only a transfer agent can remove it, and the transfer agent will not act "unless you've obtained the consent of the issuer, usually in the form of an opinion letter from the issuer's counsel". If a dispute arises, the SEC "will not intervene"; removal "is a matter solely in the discretion of the issuer", and any dispute is governed by state law. For a shareholder in a private company that has soured, this is often a more binding constraint than the holding period.
Two limits on the safe harbor. Rule 144 "is not an exclusive safe harbor", so a seller who cannot meet its conditions may still claim another available exemption; and the safe harbor is unavailable "to any person with respect to any transaction or series of transactions that, although in technical compliance with Rule 144, is part of a plan or scheme to evade the registration requirements". Paragraph (i) separately makes the rule unavailable for the resale of securities initially issued by shell companies with no or nominal operations, a provision aimed squarely at a recurring fraud pattern.