Every Form 4 that Cloudastructure, Inc. (CSAI) has filed with the SEC in the last 12 months is listed below, newest first, and each one links through to the document itself with the summary and the scores our analysis gives it.
A Form 4 covers the transactions officers, directors and large holders report, so if you follow CSAI and want that one kind of document rather than the whole filing history, this is the page to keep. The company's other filings, of every form, are on the full CSAI filings page.
CLOUDASTRUCTURE, INC. (CSAI) reported that Chief Financial Officer Greg Smitherman repriced several stock option grants on August 27, 2026. Existing options were cancelled in dispositions to the issuer and replaced with new options over the same numbers of shares at an exercise price of $4.97, retaining the original vesting schedules and expiration dates.
CLOUDASTRUCTURE, INC. (CSAI) reported that Chief Technology Officer Gregory Rayzman cancelled several batches of outstanding stock options with higher exercise prices and received new options for the same number of shares at an exercise price of $4.97 per share on August 27, 2026. The new options keep the original vesting schedules and expiration dates, covering both Class A and Class B common stock.
CLOUDASTRUCTURE, INC. (CSAI) director Ruba Qashu reported an option repricing on August 27, 2026. Previously granted stock options for an aggregate of 1,389 Class B shares at $64.80, 5,556 Class B shares at $81.00, and 3,334 Class A shares at $19.80 were disposed to the issuer and replaced with new options for the same share amounts at an exercise price of $4.97, equal to the closing stock price on August 26, 2026. The footnotes state the repriced options retain the original vesting schedules and expiration dates.
CLOUDASTRUCTURE, INC. (CSAI) reported that Chief Executive Officer and director James Patrick McCormick repriced several stock option grants on August 27, 2026. Existing options were first cancelled in dispositions to the issuer and then regranted for the same share amounts, vesting schedules, and expiration dates at a new exercise price of $4.97 per share, equal to the closing stock price on August 26, 2026.
The affected options cover both Class A and Class B common stock and had prior exercise prices as high as $81.00 per share. The company states that the repriced options retain the original vesting of 25% after one year followed by 36 substantially equal monthly installments, and no Rule 10b5-1 trading plan is reported for these transactions.
CLOUDASTRUCTURE, INC. (CSAI) reported that director Jeffrey E. Kirby exchanged previously granted stock options for new options at a lower exercise price in an option repricing on August 27, 2026. Older options for 10,001 shares were cancelled and replaced with new options for the same number of Class A common shares at an exercise price of $4.97, retaining their original expirations and vesting terms where stated.
CLOUDASTRUCTURE, INC. (CSAI) director Craig K. Johnson reported an option repricing on August 27, 2026. He cancelled and simultaneously received grants for matching stock options on 834 Class B and 10,001 Class A share equivalents, changing their exercise price to $4.97 while retaining the existing vesting and expiration terms.
The transactions are reported as dispositions to the issuer followed by grants, with no Rule 10b5-1 trading plan noted and no net change in the number of options held.
CLOUDASTRUCTURE, INC. (CSAI) reports that major shareholder Bentley Sheldon Richard cancelled several existing stock option awards and received new options on August 27, 2026 as part of an option repricing. The cancelled options had exercise prices of $55.80 and $81.00 per share, and were replaced with options exercisable at $4.97, equal to the reported closing stock price on August 26, 2026.
The repriced options cover Class A and Class B common stock and retain the same vesting schedule and expiration dates as the cancelled options, including awards expiring on January 26, 2032, June 5, 2034, and January 2, 2035. No Rule 10b5-1 trading plan is reported for these transactions.
CLOUDASTRUCTURE, INC. (CSAI) reported that Chief Financial Officer Greg Smitherman restructured several stock option awards on August 27, 2026. Existing options covering multiple tranches of Class A and Class B common stock were disposed of back to the issuer and replaced with new options for the same share amounts repriced to a $5.38 exercise price, while retaining the original vesting schedules and expiration dates.
CLOUDASTRUCTURE, INC. (CSAI) reported that Chief Technology Officer Gregory Rayzman adjusted several stock option awards on August 27, 2026. Existing options with higher exercise prices were cancelled and returned to the issuer and new options for the same share amounts were granted at an exercise price of $5.38, matching the August 26, 2026 closing stock price. The repriced options retain the same vesting schedules and expiration dates as the cancelled options.
CLOUDASTRUCTURE, INC. (CSAI) director Ruba Qashu reported an option repricing on August 27, 2026. Existing stock options on Class A and Class B common stock were cancelled and regranted in equal amounts, changing the exercise price to $5.38, the August 26, 2026 closing stock price, while retaining the original vesting and expiration dates.
Earlier grants vest either 25% after one year then monthly over 36 months or over 2 years, and the repriced options keep these schedules. The filing indicates the transactions were not made pursuant to a Rule 10b5-1 trading plan.
CLOUDASTRUCTURE, INC. (CSAI) reported that Chief Executive Officer and director James Patrick McCormick entered into a stock option repricing on August 27, 2026. Previously granted options with exercise prices of $55.80 and $81.00 on both Class A and Class B common stock were cancelled and the same number of options were regranted at an exercise price of $5.38 per share. According to the footnotes, the repriced options retain the same vesting schedules and expiration dates as the cancelled options.
CLOUDASTRUCTURE, INC. (CSAI) director Jeffrey E. Kirby reported option repricing transactions involving options to purchase Class A common stock. On 2026-08-27, he returned to the issuer options for 6,667 shares at a $135.00 exercise price and 3,334 shares at $19.80, and received replacement options for the same share amounts at a $5.38 exercise price, described as a repricing to the closing stock price on August 26, 2026. The repriced options retain the same vesting and expiration dates as the cancelled options, with one grant vesting over four years and another over two years.
CLOUDASTRUCTURE, INC. (CSAI) reported that director Craig K. Johnson adjusted several option awards on August 27, 2026 through an option repricing. Existing “Stock Options (Right to Buy)” were disposed of back to the issuer and an equal number of replacement options were granted.
The cancelled options included 834 options for Class B common stock with a $55.80 exercise price expiring January 26, 2032; 6,667 options for Class A common stock at $135.00 expiring May 1, 2035; and 3,334 options for Class A common stock at $19.80 expiring March 2, 2036. Footnotes state this Form 4 reports a repricing of those cancelled options to the closing stock price of $5.38 on August 26, 2026. Replacement options for the same share amounts and expiration dates were granted at the new $5.38 exercise price, retaining the same vesting schedules.
CLOUDASTRUCTURE, INC. (CSAI) reported that ten percent owner Bentley Sheldon Richard entered into a stock option repricing on August 27, 2026. Existing options with exercise prices of $55.80 and $81.00 per share covering both Class A and Class B common stock were cancelled and replaced with new options at an exercise price of $5.38 per share, equal in amount to the cancelled options. According to the footnotes, the repriced options retain the same vesting schedules and expiration dates, which range from January 26, 2032 to January 2, 2035.
Cloudastructure, Inc. founder and 10% owner Sheldon Richard Bentley reported selling a total of 50,000 shares of Class A Common Stock in pre-planned trades. On February 10, 2026, he executed an open-market sale of 25,000 shares at a weighted average price of $0.63, with individual trade prices ranging from $0.627 to $0.64.
On February 11, 2026, he sold an additional 25,000 shares at a weighted average price of $0.59, with trade prices between $0.578 and $0.607. All sales were made under a Rule 10b5-1 trading plan adopted on August 20, 2025, and following these transactions he reported beneficial ownership of 0 shares of Cloudastructure Class A Common Stock.
Cloudastructure, Inc. (CSAI) insider Sheldon Richard Bentley, a founder and more than 10% owner, reported planned stock sales under a Rule 10b5-1 trading plan adopted on August 20, 2025. He sold 25,000 shares of Class A Common Stock on February 3, 2026 at a weighted average price of $0.61, leaving 75,000 shares directly owned. On February 4, 2026 he sold another 25,000 shares at a weighted average price of $0.55, reducing his direct holdings to 50,000 shares.
Cloudastructure, Inc. 10% owner and founder Sheldon Richard Bentley sold a total of 50,000 shares of Class A Common Stock in late January 2026 under a pre-set Rule 10b5-1 trading plan.
He sold 25,000 shares on January 27 at a weighted average price of $0.86 and another 25,000 shares on January 28 at a weighted average price of $0.82, through multiple trades within the stated price ranges. Following these sales, he directly beneficially owns 100,000 shares of Cloudastructure Class A Common Stock.
Cloudastructure, Inc. insider activity: Founder and 10% owner Sheldon Richard Bentley reported selling a total of 50,000 shares of Class A Common Stock in two transactions. On January 20, 2026, he sold 25,000 shares at a weighted average price of $0.86, leaving 175,000 shares beneficially owned. On January 21, 2026, he sold another 25,000 shares at a weighted average price of $0.82, leaving 150,000 shares beneficially owned.
All of these sales were made under a pre-arranged Rule 10b5-1 trading plan adopted on August 20, 2025. The reported prices are weighted averages for multiple trades within disclosed price ranges on each day.
Cloudastructure founder and 10% owner Sheldon Richard Bentley reported two open-market sales of Class A Common Stock. He sold 25,000 shares on January 13, 2026 at a weighted average price of $0.88 and another 25,000 shares on January 14, 2026 at a weighted average price of $0.85. The filing notes that each reported price reflects a weighted average for multiple trades within price ranges of $0.871–$0.906 and $0.85–$0.86, respectively. All transactions were executed under a pre-arranged Rule 10b5-1 trading plan adopted on August 20, 2025. After these sales, Bentley directly owns 200,000 Class A shares of Cloudastructure.
Cloudastructure founder and 10% owner Sheldon Richard Bentley reported an insider transaction involving Class A and Class B shares. On January 12, 2026, Bentley exercised stock options to buy 200,000 shares of Class B Common Stock at a conversion price of $0.02 per share. According to the footnotes, each share of Class B Common Stock is convertible into one share of Class A Common Stock at any time, and the 200,000 Class B shares received from the option exercise were immediately converted into 200,000 shares of Class A Common Stock. Following the transaction, Bentley beneficially owned 250,000 shares of Class A Common Stock directly. The options were originally granted on February 20, 2020 and vested in full on April 15, 2023.
Cloudastructure, Inc. (CSAI) founder and 10% owner Sheldon Richard Bentley reported pre‑planned sales of Class A common stock. On January 6, 2026, he sold 25,000 shares at a weighted average price of $0.85, leaving 75,000 shares beneficially owned directly. On January 7, 2026, he sold another 25,000 shares at a weighted average price of $0.85, reducing his direct holdings to 50,000 shares.
All transactions were executed under a Rule 10b5-1 trading plan adopted on August 20, 2025, and the prices reflect multiple trades within disclosed ranges on each day.
Cloudastructure, Inc. director, founder and 10% owner Sheldon Richard Bentley reported selling Class A common stock in two transactions under a pre-arranged Rule 10b5-1 trading plan adopted on August 20, 2025. On 12/16/2025, he sold 25,000 shares at a weighted average price of $1.04, leaving 225,000 shares beneficially owned. On 12/17/2025, he sold another 25,000 shares at a weighted average price of $1.08, with 200,000 shares beneficially owned after the sale.
The filing notes that each reported price is a weighted average; the actual trades occurred in multiple lots in ranges of $1.025–$1.065 and $1.055–$1.09, and detailed breakdowns are available upon request.
Cloudastructure, Inc. (CSAI) reported insider share sales by a founder who is also a director, officer and 10% owner. The reporting person sold 25,000 shares of Class A common stock on 11/18/2025 at a weighted average price of $1.15 per share and another 25,000 shares on 11/19/2025 at a weighted average price of $1.05 per share. After these transactions, the insider beneficially owns 200,000 shares of Class A common stock directly.
All of the reported sales were effected under a pre-arranged Rule 10b5-1 trading plan adopted on August 20, 2025, which is designed to allow insiders to sell shares according to a set schedule. The prices disclosed are weighted averages, with the actual individual trade prices ranging from $1.08 to $1.205 for the first sale and from $1.025 to $1.09 for the second sale.
Cloudastructure (CSAI) reported insider activity by Sheldon Richard Bentley, an officer and founder. He sold a total of 50,000 shares of Class A Common Stock in two transactions under a Rule 10b5-1 trading plan adopted on August 20, 2025. On 11/11/2025, he sold 25,000 shares at a weighted average price of $1.37 with trades ranging from $1.35–$1.395. On 11/12/2025, he sold 25,000 shares at a weighted average price of $1.41 with trades ranging from $1.385–$1.445. Following these sales, he beneficially owned 50,000 shares, held directly.
Cloudastructure, Inc. (CSAI) reported insider share sales on a Form 4. The reporting person sold 25,000 Class A shares on 11/04/2025 at a weighted average price of $1.87 and 25,000 shares on 11/05/2025 at a weighted average price of $1.98, executed under a Rule 10b5-1 trading plan adopted on August 20, 2025.
Beneficial ownership was 125,000 shares after the first sale and 100,000 shares after the second, held directly. Price ranges were disclosed for each trading day as part of the weighted average methodology.
Cloudastructure (CSAI) insider Sheldon Richard Bentley reported open‑market sales of Class A Common Stock. On 10/28/2025, he sold 25,000 shares at a weighted average price of $1.38 (range $1.35–$1.42). On 10/29/2025, he sold 25,000 shares at a weighted average price of $1.39 (range $1.36–$1.47).
The transactions were effected under a Rule 10b5‑1 trading plan adopted on August 20, 2025. Following the reported sales, he beneficially owns 150,000 shares directly.
Cloudastructure (CSAI) insider activity: Sheldon Richard Bentley reported open‑market sales totaling 50,000 shares of Class A common stock over two days. On 10/21/2025, he sold 25,000 shares at a weighted average price of $1.45, with individual trades ranging from $1.41 to $1.52. On 10/22/2025, he sold another 25,000 shares at a weighted average price of $1.24, with trades ranging from $1.165 to $1.31.
Following these transactions, Bentley beneficially owned 200,000 shares directly. The filing notes all sales were made pursuant to a Rule 10b5-1 trading plan adopted on August 20, 2025.
Cloudastructure, Inc. (CSAI) insider Sheldon Richard Bentley reported open‑market sales of Class A common stock pursuant to a Rule 10b5‑1 trading plan. He sold 25,000 shares on 10/14/2025 at a weighted average price of $1.32 (individual trades ranged from $1.295 to $1.345) and 25,000 shares on 10/15/2025 at a weighted average price of $1.38 (range $1.32 to $1.44).
Following these transactions, Bentley beneficially owned 75,000 shares after the first sale and 50,000 shares after the second, held directly. The filing identifies him as a director and officer (founder).
Insider sales of Cloudastructure, Inc. class A common stock were reported by Director and Founder Sheldon Richard Bentley under a Rule 10b5-1 plan. The filing shows two dispositions: 25,000 shares sold on 10/07/2025 at a weighted-average price of $1.48, and 25,000 shares sold on 10/08/2025 at a weighted-average price of $1.44. After the first sale the reporting person beneficially owned 125,000 shares and after the second sale owned 100,000 shares. The sales were made pursuant to a Rule 10b5-1 trading plan adopted on 08/20/2025. The form is signed by an attorney-in-fact on 10/09/2025.
Insider sales reported by Sheldon Richard Bentley at Cloudastructure, Inc. (CSAI). Mr. Bentley, a founder, director and officer, sold a total of 50,000 shares of Class A common stock in two transactions on 09/30/2025 and 10/01/2025 under a Rule 10b5-1 trading plan adopted August 20, 2025. The first sale on 09/30/2025 disposed of 25,000 shares at a weighted-average price of $1.22, leaving 175,000 shares beneficially owned. The second sale on 10/01/2025 disposed of 25,000 shares at a weighted-average price of $1.29, leaving 150,000 shares beneficially owned. Footnotes disclose price ranges for the multiple trades and an undertaking to provide detailed per-price quantities upon request.