The Internet, as we all know, will dispense advice on any topic, so it should come as no surprise that there’s a WikiHow page titled “How to Switch From Clarinet to Tenor-Saxophone.” Created a few years ago by an editor with the handle RockyRaccoon, whose other articles include “How to Apply Magnetic Nail Polish” and “How to Enjoy a Visit to Lambert’s Café,” it lays out a seven-step plan, complete with photos. I can’t vouch for the strategy on the whole, but Step One seems pretty unassailable: “Be sure that you really want to switch to tenor sax,” it reads, in boldface type.

What brought me to RockyRaccoon’s entry was a curiosity about the challenges faced by a certain breed of musician: those known primarily as jazz clarinetists who eke out a separate, fully developed voice on the tenor saxophone. I’m not talking about doublers, those smartly employable orchestral and studio aces who play an array of woodwinds, with more of a premium on versatility than individuality. More power to ’em, but what interests me here is the expressive and technical adjustment from one distinct instrument to the other, which can be fraught with a subtle peril.

The B-flat clarinet and the tenor saxophone share a resident key, many aspects of fingering and the same baseline properties of embouchure, which, of course, is the constriction of facial muscles that meet the reed and mouthpiece to produce sound. From a technical standpoint, the transition isn’t all that complicated-and, because jazz tends to offer more work for tenor players, not at all uncommon. Countless tenor saxophonists, I’m sure, began their musical journey with formative training on clarinet, though a lot of them later put the licorice stick behind them.

Meanwhile, most clarinetists will tell you that theirs is the more technically unforgiving instrument, and that moving from clarinet to tenor is far easier than the inverse. So wherein lies the problem? There’s an intangible aesthetic issue at play here, a matter of expressive potential. Tenor saxophonists who first forge a strong identity on clarinet can end up facing a sort of double bind: Their playing has to stand up not only against the tenor’s vaunted legacy, but also alongside their own firmly established voice.

Don Byron, who graced the cover of this magazine last month with a tenor resting on one shoulder, might be the most prominent recent example of this. In 2004, when he released his brilliant album Ivey-Divey, few would have predicted that the track heralding his near future would be “Goon Drag,” on which he drawls the theme on tenor saxophone. His following Blue Note release would be Do the Boomerang: The Music of Junior Walker, featuring his tenor extensively. Reviewing that album for Vibe, I observed that “his sleepy tone can’t compare to the raucous iridescence of Walker’s.” I have fewer reservations about Love, Peace, and Soul, his new gospel album on Savoy Jazz, but the tenor playing still doesn’t slay me.

I’ll admit to a similar prejudice regarding Anat Cohen, an endlessly engaging clarinetist who has rarely moved me comparably as a tenor saxophonist: There’s an effervescent surety that gets lost in translation somehow, even though her footing on tenor is sound. Evan Christopher plays some tenor too, but I haven’t heard it, and if I ever do he’ll have a high bar to clear, given that his clarinet work is so sublime.

Even in those clarinet-to-tenor players whose sound I favor, like Gregory Tardy and Chris Speed, I hear vestiges of tone and technique that betray their origins. I mentioned this to Speed some years ago, when he and Tardy were both working with trumpeter Dave Douglas, and he cringed. “I don’t like that you can hear that,” he said. “It makes me think of a pinched tone.” But in Speed’s case there’s a welcome vulnerability to his tenor playing that feels traceable to the clarinet; there are also some distinctive fingering patterns that he uses on both instruments, derived from his study of Balkan klezmer music. Because he works in a fairly non-idiomatic region of jazz, I don’t find myself comparing him to John Coltrane or Sonny Rollins or any of the other figures looming in this issue’s cover story. He has a style on tenor unlike any other I’ve heard.

And then there’s Ken Peplowski, whose bright and lyrical command as a clarinetist has long consigned him to a full retinue of Benny Goodman tribute concerts. “An inspiration when I was young was Jimmy Hamilton in Duke Ellington’s band, because he had this beautiful, very classical clarinet sound,” Peplowski said in a recent phone conversation. “He played tenor closer to Ben Webster, in a way: He was kind of rough, and had a growl in his sound. That always intrigued me, that that was the same guy.” To illustrate the point, he steered me toward “Jive Jam,” a bonus track from the reissue of Ella & Duke at the Cote D’Azur (Verve), on which Hamilton amiably spars with Webster and Paul Gonsalves, with enough coarseness in his tone to hold his ground.

Peplowski was quick to endorse some successful clarinet-to-tenor adaptors, including a few choices I heartily agree with: John Carter, Scott Robinson and Eddie Daniels. And he mentioned one of my favorite exceptions, Jimmy Giuffre, whose softly incantatory tenor, alongside Jim Hall’s guitar and Bob Brookmeyer’s valve trombone, forms the indelible overture to the film Jazz on a Summer’s Day. Peplowski also hipped me to something recorded earlier in 1958: “It’s You,” from an album of songs from The Music Man. On it Giuffre adopts a clear, placid tenor sound that’s worlds away from his clarinet style.

Similarly, I hear a different voice in Peplowski’s tenor than I do in his clarinet: hardier, drier, more behind the beat. His most recent album, In Search Of… (Capri), captures that point better than I could here, even if there are moments-certain altissimo phrases in the ballad “When Joanna Loved Me,” for instance-when I hear ghost traces of clarinet. In any case, it’s the example of an artist like Peplowski, rare as he is, who lends credibility to that instructive WikiHow page. The last step reads, hopefully: “Over time, you’ll be just as good at the saxophone as you are at the clarinet.”