The most basal lepidosauriforms and lepidosaurs to scale

Lepidosauriform fossils are extremely rare in the Mesozoic and Paleozoic.
In the Earliest Permian we find Tridentinosaurus (Fig. 1; Dal Piaz 1931,1932; Leonardi 1959), a taxon ancestral to the pseudo-rib-gliders of the Late Permian (Coelurosauravus) through the Early Cretaceous (Xianlong) and close to the origin of all other lepidosauriforms, including living snakes, lizards and the tuatara (genus: Sphenodon).

Sometime during the Early Permian
the Lepidosauria split between the Sphenodontia + Drepanosauria and the Tritosauria + Protosquamata in the large reptile tree (LRT, 1381 taxa).

Short-legged
Jesairosaurus, in the Early Triassic, nests basal to the clade of slow-moving, arboreal drepanosaurs. On another branch, Megachirella (Middle Triassic) and Gephyrosaurus (Early Jurassic) are basal members of the Sphenodontia.

Long-legged
and probably arboreal Saurosternon and Palaegama, (both Late Permian) are the earliest known Lepidosauria, but they are basal to the Tritosauria + Protosquamata clades.

Late-surviving, long-legged basal Tritosauria
include tiny Tijubina and Huehuecuetzpalli (both Early Cretaceous). This clade gave rise to giant Tanystropheus, exotic Longisquama and volant Pteranodon.

Tiny and long-legged Late Permian
Lacertulus is the basal taxon in the previously unrecognized clade Protosquamata, the parent clade to the extant Squamata. This taxon documents the antiquity of this clade.

Going back to the Early Permian
we have a long-torso, short-legged specimen, MNC TA-1045, that nests in the LRT just outside the extant Squamata (Iguana). MNC TA-1045 was found alongside the genus Ascendonanus (MNC-TA0924), a basal archosauromorph diapsid with a shorter torso you can see here. The MNC TA-1045 specimen pushes the genesis of the lepidosaurs back to the Early Permian, nearly coeval with the basalmost lepidosauriform shown in figure 1, Tridentinosaurus.

The Lepidosauromorph-Archosauromorph dichotomy
was already present in the Viséan (Early Carboniferous, 330 mya), so the new Lepidosauromorpha had 30 million years to diverge into captorhinomorphs, diadectomorphs, millerettids and lepidosauriforms by the time Tridentinosaurus first appears in the Earliest Permian (300 mya).

Late surviving,
but basalmost lepidosauromorphs include Sophineta , Paliguana and Coletta (all Early Triassic). These taxa have an upper temporal fenestra not seen in outgroup taxa.

Proximal outgroups for the Lepidosauriforms
include the late-surviving owenettids: Barasaurus (Late Permian) and kin, Owenetta (Late Permian) and kin, and the late-surviving macroleterids (Middle Permian) and nycteroleterids (Middle Permian) before them.

At least that’s what the data says so far.
With every new taxon the tree grows stronger and more precise, so the odds of changing the tree topology with additional taxa continue to drop. Looking forward to seeing more Paleozoic arboreal lepidosauromorph discoveries as they arrive.

References
Dal Piaz Gb. 1932 (1931). Scoperta degli avanzi di un rettile (lacertide) nei tufi compresi entro i porfidi quarziferi permiani del Trentino. Atti Soc. Ital. Progr. Scienze, XX Riunione, v. 2, pp. 280-281. [The discovery of the remains of a reptile (lacertide) in tuffs including within the Permian quartz porphyry of Trentino.]
Leonardi P 1959. Tridentinosaurus antiquus Gb. Dal Piaz, rettile protorosauro permiano del Trentino orientale. Memorie di Scienze Geologiche 21: 3–15.

www.reptileevolution.com/reptile-tree.htm