diff --git a/base/rational.jl b/base/rational.jl
index 5288492e72e71..1b060384d95b2 100644
--- a/base/rational.jl
+++ b/base/rational.jl
@@ -95,7 +95,7 @@ end
 function show(io::IO, x::Rational)
     show(io, numerator(x))
 
-    if isone(denominator(x)) && get(io, :typeinfo, Any) <: Rational
+    if isone(denominator(x)) && nonnothing_nonmissing_typeinfo(io) <: Rational
         return
     end
 
diff --git a/base/ryu/Ryu.jl b/base/ryu/Ryu.jl
index 9b236caeb6ff1..89589aa4ab668 100644
--- a/base/ryu/Ryu.jl
+++ b/base/ryu/Ryu.jl
@@ -112,7 +112,7 @@ end
 function Base.show(io::IO, x::T, forceuntyped::Bool=false, fromprint::Bool=false) where {T <: Base.IEEEFloat}
     compact = get(io, :compact, false)::Bool
     buf = Base.StringVector(neededdigits(T))
-    typed = !forceuntyped && !compact && get(io, :typeinfo, Any) != typeof(x)
+    typed = !forceuntyped && !compact && Base.nonnothing_nonmissing_typeinfo(io) != typeof(x)
     pos = writeshortest(buf, 1, x, false, false, true, -1,
         (x isa Float32 && !fromprint) ? UInt8('f') : UInt8('e'), false, UInt8('.'), typed, compact)
     write(io, resize!(buf, pos - 1))
diff --git a/base/show.jl b/base/show.jl
index eb9f7bcece49d..db0b429f3386f 100644
--- a/base/show.jl
+++ b/base/show.jl
@@ -1231,8 +1231,9 @@ function show(io::IO, tn::Core.TypeName)
     print(io, ")")
 end
 
+nonnothing_nonmissing_typeinfo(io::IO) = nonmissingtype(nonnothingtype(get(io, :typeinfo, Any)))
+show(io::IO, b::Bool) = print(io, nonnothing_nonmissing_typeinfo(io) === Bool ? (b ? "1" : "0") : (b ? "true" : "false"))
 show(io::IO, ::Nothing) = print(io, "nothing")
-show(io::IO, b::Bool) = print(io, get(io, :typeinfo, Any) === Bool ? (b ? "1" : "0") : (b ? "true" : "false"))
 show(io::IO, n::Signed) = (write(io, string(n)); nothing)
 show(io::IO, n::Unsigned) = print(io, "0x", string(n, pad = sizeof(n)<<1, base = 16))
 print(io::IO, n::Unsigned) = print(io, string(n))
diff --git a/test/show.jl b/test/show.jl
index 08a29612b245c..b6106c710931c 100644
--- a/test/show.jl
+++ b/test/show.jl
@@ -2170,6 +2170,20 @@ replstrcolor(x) = sprint((io, x) -> show(IOContext(io, :limit => true, :color =>
     @test_repr "Bool[1, 0]"
 end
 
+@testset "Unions with Bool (#39590)" begin
+    @test repr([missing, false]) == "Union{Missing, Bool}[missing, 0]"
+    @test_repr "Union{Bool, Nothing}[1, 0, nothing]"
+end
+
+# issue #26847
+@test_repr "Union{Missing, Float32}[1.0]"
+
+# intersection of #45396 and #48822
+@test_repr "Union{Missing, Rational{Int64}}[missing, 1//2, 2]"
+
+# Don't go too far with #48822
+@test_repr "Union{String, Bool}[true]"
+
 # issue #30505
 @test repr(Union{Tuple{Char}, Tuple{Char, Char}}[('a','b')]) == "Union{Tuple{Char}, Tuple{Char, Char}}[('a', 'b')]"
 
diff --git a/test/sorting.jl b/test/sorting.jl
index 35635d8588f93..ad821e38efe55 100644
--- a/test/sorting.jl
+++ b/test/sorting.jl
@@ -1036,40 +1036,30 @@ end
     @test issorted(sort!(rand(100), Base.Sort.InitialOptimizations(DispatchLoopTestAlg()), Base.Order.Forward))
 end
 
-@testset "partialsort tests added for BracketedSort #52006" begin
-    x = rand(Int, 1000)
-    @test partialsort(x, 1) == minimum(x)
-    @test partialsort(x, 1000) == maximum(x)
-    sx = sort(x)
-    for i in [1, 2, 4, 10, 11, 425, 500, 845, 991, 997, 999, 1000]
-        @test partialsort(x, i) == sx[i]
-    end
-    for i in [1:1, 1:2, 1:5, 1:8, 1:9, 1:11, 1:108, 135:812, 220:586, 363:368, 450:574, 458:597, 469:638, 487:488, 500:501, 584:594, 1000:1000]
-        @test partialsort(x, i) == sx[i]
+# Pathologize 0 is a noop, pathologize 3 is fully pathological
+function pathologize!(x, level)
+    Base.require_one_based_indexing(x)
+    k2 = Int(cbrt(length(x))^2)
+    seed = hash(length(x), Int === Int64 ? 0x85eb830e0216012d : 0xae6c4e15)
+    for a in 1:level
+        seed = hash(a, seed)
+        x[mod.(hash.(1:k2, seed), range.(1:k2,lastindex(x)))] .= a
     end
+    x
+end
 
-    # Semi-pathological input
-    seed = hash(1000, Int === Int64 ? 0x85eb830e0216012d : 0xae6c4e15)
-    seed = hash(1, seed)
-    for i in 1:100
-        j = mod(hash(i, seed), i:1000)
-        x[j] = typemax(Int)
+@testset "partialsort tests added for BracketedSort #52006" begin
+    for x in [pathologize!.(Ref(rand(Int, 1000)), 0:3); pathologize!.(Ref(rand(1000)), 0:3); [pathologize!(rand(Int, 1_000_000), 3)]]
+        @test partialsort(x, 1) == minimum(x)
+        @test partialsort(x, lastindex(x)) == maximum(x)
+        sx = sort(x)
+        for i in [1, 2, 4, 10, 11, 425, 500, 845, 991, 997, 999, 1000]
+            @test partialsort(x, i) == sx[i]
+        end
+        for i in [1:1, 1:2, 1:5, 1:8, 1:9, 1:11, 1:108, 135:812, 220:586, 363:368, 450:574, 458:597, 469:638, 487:488, 500:501, 584:594, 1000:1000]
+            @test partialsort(x, i) == sx[i]
+        end
     end
-    @test partialsort(x, 500) == sort(x)[500]
-
-    # Fully pathological input
-    # it would be too much trouble to actually construct a valid pathological input, so we
-    # construct an invalid pathological input.
-    # This test is kind of sketchy because it passes invalid inputs to the function
-    # Temporarily removed due to flakey test failures. See #52642 for details.
-    # for i in [1:6, 1:483, 1:957, 77:86, 118:478, 223:227, 231:970, 317:958, 500:501, 500:501, 500:501, 614:620, 632:635, 658:665, 933:940, 937:942, 997:1000, 999:1000]
-    #     x = rand(1:5, 1000)
-    #     @test partialsort(x, i, lt=(<=)) == sort(x)[i]
-    # end
-    # for i in [1, 7, 8, 490, 495, 852, 993, 996, 1000]
-    #     x = rand(1:5, 1000)
-    #     @test partialsort(x, i, lt=(<=)) == sort(x)[i]
-    # end
 end
 
 # This testset is at the end of the file because it is slow.