I have time for this. 😀 Here are the pertinent dates for transactions having bearing on his 40-man status from his MLB.com page.
August 8, 2019 Minnesota Twins selected the contract of Randy Dobnak from Rochester Red Wings.
August 15, 2019 Minnesota Twins optioned RHP Randy Dobnak to Rochester Red Wings.
September 16, 2020 Minnesota Twins optioned RHP Randy Dobnak to Twins Alternate Training Site
May 3, 2021 Minnesota Twins optioned RHP Randy Dobnak to St. Paul Saints.
September 16, 2022 Minnesota Twins sent RHP Randy Dobnak outright to St. Paul Saints
July 30, 2024 Minnesota Twins selected the contract of RHP Randy Dobnak from St. Paul Saints.
September 18, 2024 Minnesota Twins sent RHP Randy Dobnak outright to St. Paul Saints.
September 29, 2024 Minnesota Twins selected the contract of RHP Randy Dobnak from St. Paul Saints.
November 5, 2024 Minnesota Twins sent RHP Randy Dobnak outright to St. Paul Saints.
To summarize, he was optioned during each of three years 2019-21, so after that, by league rules, he had to pass through waivers in order to be outrighted to the minors again. He didn't pitch in the majors in 2023. And I believe that waivers are good for the remainder of a given season. So by my count, he's cleared waivers twice. Which, of course, is kind of a lot, if other teams coveted him.