We present deep Hubble Space Telescope (HST) photometry of the ultra-faint dwarf (UFD) galaxies Pegasus III (Peg III) and Pisces II (Psc II), two of the most distant satellites in the halo of the Milky Way (MW). We measure the structure of both galaxies, derive mass-to-light ratios with newly determined absolute magnitudes, and compare our findings to expectations from UFD-mass simulations. For Peg III, we find an elliptical half-light radius of
a
h
=
1
.′
88
−
0.33
+
0.42
(
118
−
30
+
31
pc) and
M
V
=
−
4.17
−
0.22
+
0.19
;
for Psc II, we measure
a
h
=
1
.′
31
−
0.09
+
0.10
(69 ± 8 pc) and
M
V
=
−
4.28
−
0.16
+
0.19
. We do not find any morphological features that indicate a significant interaction between the two has occurred, despite their close separation of only ∼40 kpc. Using proper motions (PMs) from Gaia early Data Release 3, we investigate the possibility of any past association by integrating orbits for the two UFDs in an MW-only and a combined MW and Large Magellanic Cloud (LMC) potential. We find that including the gravitational influence of the LMC is crucial, even for these outer-halo satellites, and that a possible orbital history exists where Peg III and Psc II experienced a close (∼10–20 kpc) passage about each other just over ∼1 Gyr ago, followed by a collective passage around the LMC (∼30–60 kpc) just under ∼1 Gyr ago. Considering the large uncertainties on the PMs and the restrictive priors imposed to derive them, improved PM measurements for Peg III and Psc II will be necessary to clarify their relationship. This would add to the rare findings of confirmed pairs of satellites within the Local Group.