Voyager 1 & 2 have (2012 and 2018, respectively). One can argue that Pioneer 10 & 11 have as well, but contact with them has been lost.
I recall some striking plots showing a dramatic decrease in the flux of particles in one instrument or another at the boundary.
Here's a table of all the probes in the get-outta-the-solar-system sweepstakes:
https://en.wikipedia.org/wiki/List_of_artificial_objects_leaving_the_Solar_System
And here's the NASA announcement about Voyager 2 passing outside the solar system:
https://www.nasa.gov/news-release/nasas-voyager-2-probe-enters-interstellar-space/
Happy Christmas to you, too! And upcoming Hogmanay, since I seem to recall you're in Scotland now.