| Date | Grid | Clue | Author | Editor |
| Wed Aug 21, 2024 | 24A | Assistant who's always being questioned | Stacey Yaruss McCullough | Fagliano |
| Wed Aug 14, 2024 | 25D | iPhone speaker? | Samuel A. Donaldson | Fagliano |
| Tue Aug 6, 2024 | 28D | Apple assistant (2) | Daniel Raymon | Fagliano |
| Sun Jul 7, 2024 | 67D | Assistant who handles more than 25 billion requests per month | David Karp | Fagliano |
| Sat Apr 27, 2024 | 44A | Popular assistant (2) | Rich Norris | Fagliano |
| Tue Mar 26, 2024 | 18D | Apple's digital assistant (2) | Laura Dershewitz and Katherine Baicker | Fagliano |
| Wed Mar 20, 2024 | 27D | Norwegian name that gained global prominence in 2010 | E. M. Capassakis | Fagliano |
| Sat Jan 13, 2024 | 27A | Who might mistakenly respond to a statement beginning "Seriously …" | Hoang-Kim Vu | Shortz |
| Mon Nov 20, 2023 | 37A | Apple device assistant | Sam Ezersky | Shortz |
| Fri Nov 3, 2023 | 36A | Who talks on the phone a lot | Robyn Weintraub | Shortz |
| Sat Jul 15, 2023 | 39D | Tech debut of 2011 | Jeff Chen | Shortz |
| Thu Jun 22, 2023 | 57D | Phony personality? | Michael Baker and Jeff Chen | Shortz |
| Sun Apr 23, 2023 | 83D | One who's always on the phone? | Katie Hale and Scott Hogan | Shortz |
| Wed Oct 5, 2022 | 2D | Assistant with many different voices | Jason Reich | Shortz |
| Sat Sep 3, 2022 | 24A | Who says "I don't have a family tree. But I have a pretty great file directory" | David Distenfeld | Shortz |
| Thu Jul 28, 2022 | 34D | Cortana : Microsoft :: ___ : Apple | Bill Pipal and Jeff Chen | Shortz |
| Mon Jun 20, 2022 | 11D | Apple's voice assistant | Christopher Youngs | Shortz |
| Sun Feb 6, 2022 | 77A | Voice heard by 500 million people | Stephen McCarthy | Shortz |
| Wed Dec 15, 2021 | 39A | One responsive to voice commands | Jessie Bullock and Ross Trudeau | Shortz |
| Sun Nov 28, 2021 | 65A | She can act as a D.J., nowadays | Jeff Kremer | Shortz |
| Sun Oct 24, 2021 | 96D | Who's talking on the phone? | Katie Hale | Shortz |
| Wed Sep 29, 2021 | 4D | Assistant with a goofy beatboxing routine (just ask) | Alex Eaton-Salners | Shortz |
| Tue Sep 21, 2021 | 60D | Rival of Alexa | Daniel Okulitch | Shortz |
| Sun Jun 13, 2021 | 87D | One with a phony personality? | Stephen McCarthy | Shortz |
| Mon May 31, 2021 | 6A | Apple's digital assistant (2) | Michael Lieberman | Shortz |
| Tue Mar 23, 2021 | 31D | Assistant who asks "What can I help you with?" | Dan Schoenholz | Shortz |
| Fri Feb 12, 2021 | 7D | Noted speaker of more than 20 languages | Grant Thackray | Shortz |
| Thu Dec 31, 2020 | 37A | Modern know-it-all (3) | David J. Kahn | Shortz |
| Fri Oct 23, 2020 | 45D | Who asks "What can I help you with?" | Robyn Weintraub | Shortz |
| Mon Oct 19, 2020 | 10D | In answer to the request "Talk dirty to me," she sometimes says "The carpet needs vacuuming" | Fred Piscop | Shortz |
| Tue Sep 1, 2020 | 44A | One always getting asked questions | David Steinberg | Shortz |
| Sat Feb 29, 2020 | 48D | Tech assistant | Andrew J. Ries | Shortz |
| Sun Oct 20, 2019 | 50A | One frequently saying "Sorry, I missed that" | Natan Last | Shortz |
| Mon Oct 7, 2019 | 40A | iPhone voice (2) | Keiran King | Shortz |
| Fri Jun 7, 2019 | 60A | Popular assistant (2) | Michael Hawkins | Shortz |
| Fri May 24, 2019 | 57D | Who often says "I found this on the web" | Stanley Newman | Shortz |
| Wed May 15, 2019 | 5D | Voice-activated assistant (2) | Zhouqin Burnikel | Shortz |
| Sat Apr 6, 2019 | 46D | Modern answer source | Ned White | Shortz |
| Tue Mar 26, 2019 | 23D | Voice of the Apple Watch | Zhouqin Burnikel | Shortz |
| Sat Mar 16, 2019 | 53D | Assistant to millions | Andrew J. Ries | Shortz |
| Sun Mar 10, 2019 | 79A | "Hey ___" | Adam Fromm | Shortz |
| Tue Oct 2, 2018 | 63A | Voice on a phone | Paul Coulter | Shortz |
| Sun Sep 16, 2018 | 95D | "Hey ___" (start of a phone voice command) | Joel Fagliano | Shortz |
| Thu Jun 28, 2018 | 48A | Real know-it-all? | Jeff Chen | Shortz |
| Wed Apr 18, 2018 | 32A | One who talks on the phone a lot? | Peter A. Collins and Bruce Haight | Shortz |
| Mon Feb 19, 2018 | 44A | Who asks "What can I help you with?" on an iPhone | Bruce Haight | Shortz |
| Wed Nov 15, 2017 | 4D | Familiar voice since 2011 | Steven E. Atwood | Shortz |
| Mon Aug 7, 2017 | 7D | iPhone assistant (2) | Kevin Christian | Shortz |
| Thu Jan 12, 2017 | 51D | Voice-activated assistant (2) | Joe Krozel | Shortz |
| Sun Oct 30, 2016 | 1A | One talking on the phone, nowadays? | Caleb Madison | Shortz |
| Sat Sep 24, 2016 | 52D | Modern know-it-all (3) | Mary Lou Guizzo | Shortz |
| Wed Sep 7, 2016 | 46A | iPhone assistant (2) | Kary Haddad | Shortz |
| Fri Jul 15, 2016 | 5D | When told "I'm sleepy," she sometimes says "I hope you're not driving" | Matt Ginsberg | Shortz |
| Sun Mar 27, 2016 | 72A | Voice from a phone | Patrick Blindauer | Shortz |
| Thu Dec 4, 2014 | 31A | One with all the answers? | Kacey Walker and David Quarfoot | Shortz |
| Mon Aug 11, 2014 | 63A | iPhone assistant who says that "42" is the meaning of life | David Steinberg and Bernice Gordon | Shortz |
| Sun Aug 10, 2014 | 89A | Modern know-it-all? (3) | Elizabeth C. Gorski | Shortz |
| Tue Apr 1, 2014 | 52D | Apple genius? | Andrew Reynolds | Shortz |
| Sat Jan 11, 2014 | 56D | iPhone talker | Martin Ashwood-Smith | Shortz |
| Sun Dec 15, 2013 | 95D | Her name is Norwegian for "beautiful woman who leads you to victory" | Jeff Chen | Shortz |
| Fri Dec 6, 2013 | 60A | In Australia her name is Karen | Elizabeth C. Gorski | Shortz |
| Thu Nov 21, 2013 | 68A | Her "birthday" is Oct. 4, 2011 | Jules P. Markey | Shortz |
| Sun Oct 20, 2013 | 109D | iPhone voice (2) | Elizabeth C. Gorski | Shortz |
| Fri Oct 4, 2013 | 55D | Apple assistant (2) | Bruce R. Sutphin | Shortz |
| Fri Aug 23, 2013 | 27D | Her voice was first heard in 2011 | Ian Livengood | Shortz |
| Thu May 10, 2012 | 12D | Phone voice? | Jules P. Markey | Shortz |