Pittman primarily uses Jarrell Guitars MPS Monte Pittman Signature Guitars, either with a Floyd Rose or stop tailpiece. His personal guitars use custom-wound Dimebucker, S7, and P-Rail pickups made by Maricela Juarez (MJ) at the Seymour Duncan Custom Shop. He uses the many available pickup configurations for both a variety of tones and output levels when he needs to be further back in the mix. His signature guitar also comes in "classic" with Jarrell pickups instead of Seymour Duncans. In addition to his signature guitars, Pittman uses a stock recent-issue Fender Jazzmaster for "Vogue," "Candy Shop," and "Human Nature," a Jerry Jones Electric Sitar for "I'm a Sinner," and a Gibson Melody Maker with a Bill Lawrence pickup and Swarovski crystals for "Like a Prayer." He uses Dunlop .88 picks and D'Addario .010s for strings.
His main acoustic is a Bourgeois OMS with Peruvian rosewood and Fishman electronics that's tuned down to C#. He also travels with a Bourgeois Ray LaMontagne model and an Alhambra nylon string that aren't used in the Madonna set but are used for solo shows Pittman does during the tour.
Madonna uses a 2002 Gibson Les Paul Standard with custom Seymour Duncan Alnico 2s overwound for Madonna's hands for more presence.
Pittman uses two Orange Rockerverb 100s with KT88s into two Orange 4x12s with Celestion Vintage 30s, run in stereo. He runs the Oranges' clean channel when using his Fractal Audio Axe-Fx II for amp tones, and the boost channel when he needs more gain or for feedback. He recreated his personal Marshall JCM800 sound in the Fractal, which he uses for his amp tone sometimes as well.
Madonna uses a Fractal Axe-FX II for her amps, triggered by her tech. She plays three songs, with three patches per song. "I Don't Give A" has a patch inspired by Meshuggah's Koloss album, "Turn Up the Radio" has a patch inspired by Allan Holdsworth based off a Dumble amp with volume swell chorus and doubled Mr. Mister sound, and "I'm a Sinner" has a raw, Patti Smith clean sound.
For effects, Pittman uses the Fractal Axe-Fx II with an MFC-101 controller for traditional effects as well as atmospheric tones and sound effects, and a variety of synth tones for doubling or complimenting keyboard parts. On the floor he uses an Ernie Ball Volume Pedal, Dunlop Jerry Cantrell Signature Wah, MXR Boost/Line Driver, MXR Dime Distortion, MXR Bass Octave Deluxe, MXR EQ (used for boost), MXR Carbon Copy, and a TC Electronic PolyTune. He explains that there's room for playing with different sounds during the set, so the pedals on the floor give him flexibility to do so. With his acoustic, he uses a Fishman Aura pedal that's stocked with models of his personal acoustics that he leaves at home.