Rule 144 sale checklist: 8 phases to work through before the trade.

• Identify the security type: restricted securities (acquired in a private transaction), control securities (freely tradeable shares held by an affiliate), or both. The conditions that apply depend on this distinction.¹
• Determine affiliate status: are you a current executive officer, director, or 10%+ shareholder? If you left any of those roles, when was your last day? The 90-day former-affiliate look-back counts — if you left less than 90 days ago, you still must comply with full affiliate conditions.¹

  See affiliate sale plan or non-affiliate guide depending on your status.

• Confirm issuer reporting status: is the issuer a current Exchange Act filer (listed on NYSE, Nasdaq, or otherwise current on 10-K/10-Q filings)? The answer changes the required holding period and, for non-affiliates past 6 months, whether current public information is still required.

• Find the original acquisition date: pull the stock purchase agreement, option exercise confirmation, grant agreement, vesting schedule, or cap table record showing exactly when shares were acquired and fully paid for.
• Check for tacking events: if shares were received as a gift, through inheritance, in a conversion, or via a private transfer from a non-affiliate, you may be able to add the prior holder's period to your own. Confirm with counsel if any tacking applies.

  See Rule 144 holding period guide for tacking rules and common clock-reset traps.

• Calculate days held against the Rule 144 safe harbor:

  Issuer type	Affiliate minimum hold	Non-affiliate minimum hold
  Reporting company (SEC filings current)	6 months	6 months + current public info After 12 months: freely resell
  Non-reporting or delinquent filer	12 months	12 months

• Run the separate IRS long-term capital gains clock: the Rule 144 holding period and the IRS 12-month LTCG threshold are independent. Meeting the Rule 144 period does not mean long-term rates apply. If the LTCG period has not run, weigh whether waiting weeks or months changes your effective tax rate materially.

  For 2026 rates see Phase 8. The gap between 37% ordinary income and 20% + 3.8% NIIT is 19.8 percentage points — on a $2M gain that is roughly $400K in federal tax.

Volume limits apply to affiliates on every sale — not just restricted securities. Open-market shares you purchased are also subject to the cap while you remain an affiliate.

• Pull shares outstanding: use the cover page of the issuer's latest Form 10-K or 10-Q, or a current market-data source. The number changes quarterly; stale data can cause an inadvertent violation.¹
• Get average weekly trading volume: the four calendar weeks immediately preceding the date of sale (for exchange and Nasdaq securities). OTC securities are limited to the 1% cap only — the volume alternative is not available.
• Calculate the 3-month ceiling: the greater of (a) 1% of shares outstanding or (b) the 4-week average weekly reported trading volume. That number is the maximum you can sell in any rolling 3-month window.

  Use the Rule 144 volume limit calculator to run the numbers. Remember: the window is rolling, not calendar-quarter — sales from the previous 89 days count against the current cap.

• Map a multi-quarter cadence if needed: if the position requires more than one quarter to exit at an acceptable rate, sketch the quarters now. The volume limit resets at the start of each rolling 3-month window from the date of the last sale.

  See the affiliate sale plan guide for a worked example of multi-year cadence planning with tax-year allocation.

• Contact the general counsel or chief compliance officer: issuers almost always have an insider trading policy, and most require pre-clearance for any insider trade before execution. The Rule 144 conditions are separate from — and in addition to — issuer policy requirements.
• Confirm you are in an open trading window: most issuers allow trading only during the 2–4 weeks following a quarterly earnings release, when the market is assumed to have all material information. Selling during a blackout period violates issuer policy regardless of Rule 144 compliance.
• Confirm no material non-public information (MNPI): Rule 144 is a safe harbor from the registration requirements — it is not a safe harbor from insider trading liability. You must be clear of MNPI at the time of the order. If a 10b5-1 plan is in place, the plan provides an affirmative defense; without one, the MNPI question rests on the circumstances at the time of the trade.
• Ask about advance notice requirements: some companies require 48–72 hours of advance notice before an insider submits a sell order. Others require the sale to be made through a designated broker. Confirm both.

• Issuer counsel: the company's outside securities lawyers. They typically provide the opinion letter that allows the transfer agent to remove the restrictive legend. Get their name and usual turnaround time early — opinion letters on complex situations can take 2–4 weeks.
• Personal securities counsel (if needed): for unusual tacking situations, SPAC-related restricted stock, Section 4(a)(1) vs. Rule 144 questions, or cases where issuer counsel will not represent you directly. Often a one-time engagement — budget $1,500–$5,000 for a clean opinion.
• CPA / tax advisor: should be engaged before the first sale executes, not after. Lot selection, estimated tax payments, year-end allocation, and state tax implications are all decisions made before (or immediately after) the trade, not at tax time.
• Restricted-stock broker: not every brokerage desk handles restricted stock or coordinates with transfer agents. Confirm the broker has experience with Rule 144 transactions, knows the transfer agent, and can process the paperwork without unnecessary delays. The legend removal broker process guide covers what the broker needs to know.
• Transfer agent: identify the issuer's transfer agent (AST, Computershare, Equiniti, Broadridge, etc.) and get direct contact information. Confirm whether shares are held as physical certificates or in book-entry/DRS form — the legend removal process differs.
• Financial advisor: for positions worth $1M+, a financial advisor who understands concentrated stock can help sequence the sale cadence, model reinvestment options, coordinate estimated tax payments with the CPA, and build the post-sale portfolio plan.

  Get matched with a Rule 144 advisor who has done this workflow before.

• Affidavit of seller status: a written representation that you are (or are not) an affiliate, signed under penalty of perjury. The broker typically provides a standard form. This is the document that unlocks the non-affiliate path; affiliates substitute their Form 144.
• Holding period evidence: trade confirmation, grant agreement, vesting schedule, or cap table record showing the acquisition date and basis for each lot being sold. The transfer agent and broker need a clear audit trail to the original acquisition.
• Opinion letter from counsel: for affiliates, this typically comes from issuer counsel and confirms the sale meets Rule 144 conditions. Some transfer agents also require it for non-affiliates selling shares of private or thinly-traded issuers. Request it early — the letter is typically specific to the transaction size and date range.
• Broker account details: provide the broker's DTC participant number to the transfer agent so the freed shares can be moved electronically (DWAC). Shares held as physical certificates require surrender and a medallion signature guarantee — allow extra time for certified mail and the guarantee process.
• Physical certificate (if certificated): if shares are represented by a paper certificate with a restrictive legend printed on its face, the certificate must be surrendered to the transfer agent before a clean certificate or book-entry position is issued. Locate and secure the certificate before starting the process — replacing a lost certificate adds weeks.

• Form 144 affiliates only: required when the sale amount in any rolling 3-month period exceeds both 5,000 shares and $50,000 in aggregate sale price.² The form must be filed concurrently with — not before — the sell order. Electronic filing through EDGAR is now required; paper filing is no longer accepted.

  See the Form 144 filing guide for the line-by-line instructions, the EDGAR process, and the distinction between Form 144 and Form 4.

• Form 4 Section 16 insiders only: executive officers and directors (Section 16 persons) must report every change in beneficial ownership within 2 business days of the transaction. Form 4 is filed on EDGAR separately from Form 144 and is not optional. Late Form 4 filings are disclosed in the company's proxy statement.³

  Engage your securities counsel or the company's general counsel to handle Form 4 filing. Some companies file on behalf of their insiders; confirm who is responsible before the trade executes.

• Calculate gain per lot: for each lot being sold, identify the cost basis (purchase price, option exercise price, or FMV at vesting for RSUs), the holding period, and whether it qualifies for long-term capital gains treatment (held >12 months under IRC § 1222).
• Apply 2026 federal LTCG rates:

  Rate	Single filer taxable income	MFJ taxable income
  0%	Up to $49,450	Up to $98,900
  15%	$49,451 – $545,500	$98,901 – $613,350
  20%	Above $545,500	Above $613,350

• Add 3.8% NIIT if MAGI exceeds the threshold: the Net Investment Income Tax applies to capital gains for single filers with MAGI above $200,000 and MFJ filers above $250,000.⁴ These thresholds are not inflation-adjusted. Most founders and executives selling meaningful positions will owe NIIT on the full gain.
• Factor state capital gains tax: California and New York tax LTCG as ordinary income (no preferential rate). Other states vary. A California resident selling a $3M gain owes ~13.3% state tax in addition to 23.8% federal — effective rate above 37%. State allocation matters if you moved states between grant and sale.
• Decide whether to spread recognition across tax years: if you have volume-limit headroom and multiple years of sales planned, compare the all-in tax rate of selling this year versus waiting to January. Crossing from the 15% to the 20% LTCG bracket plus NIIT is a 8.8% difference. On a $5M gain, that is $440K — a decision worth modeling before you place the order.
• Schedule estimated tax payments: a large capital gain in Q1 or Q2 will likely require a revised estimated payment in the same quarter to avoid underpayment penalties (IRC § 6654). Work with your CPA to calculate and schedule the payment within 15 days of the sale. Do not wait until April of the following year.
• Set a concentration target: before the sale, define an endpoint — e.g., reduce this single-stock exposure from 65% of net worth to below 20% over three years. Work backward to the annual sale quantity and confirm volume limits support that timeline. Having an explicit target prevents "I'll sell when it feels right" drift that often means never selling.

  See concentrated stock tax strategies for tools that can reduce concentration without triggering full immediate recognition — DAFs, charitable remainder trusts, exchange funds, and hedging strategies.

• Document the reinvestment policy for proceeds: what asset allocation receives the cash? Having a written investment policy statement prevents analysis paralysis after the sale — and ensures the after-tax proceeds actually get invested rather than sitting in a money market account for two years.

• Evaluate whether a 10b5-1 plan makes sense: for executive officers and directors who want to sell a material quantity over multiple quarters, a properly structured 10b5-1 plan provides an affirmative defense against insider trading allegations and reduces the scrutiny of each individual trade. Without one, every order is subject to a MNPI question at the time of execution.
• Adopt the plan during an open trading window: the plan must be adopted (signed and in effect) while you are in an open window and are not aware of any MNPI.
• Observe the cooling-off period before the first trade: for officers and directors, the later of (a) 90 days after plan adoption, or (b) two business days after the next 10-Q or 10-K filing, subject to a maximum of 120 days.⁵ For other affiliates (e.g., large shareholders who are not officers or directors): 30 days. The first trade cannot occur before the cooling-off period expires.
• Build volume limits into the plan: each trade under the plan must still comply with Rule 144 volume limits for affiliates. The 10b5-1 plan does not override Rule 144 — it only addresses the timing and MNPI question.

  See the 10b5-1 trading plan guide for the 2022 SEC rule changes, the single-plan rule, good-faith certification, and how the plan interacts with Form 144.