diff --git a/base/show.jl b/base/show.jl
index 650a697316b9d..93026fa7e2fe7 100644
--- a/base/show.jl
+++ b/base/show.jl
@@ -532,8 +532,9 @@ function makeproper(io::IO, x::Type)
                 push!(y, typ)
             end
         end
-        normal || (x = Union{y...})
-        properx = rewrap_unionall(x, properx)
+        if !normal
+            properx = rewrap_unionall(Union{y...}, properx)
+        end
     end
     has_free_typevars(properx) && return Any
     return properx
@@ -554,7 +555,7 @@ function make_typealias(@nospecialize(x::Type))
         for name in names(mod)
             if isdefined(mod, name) && !isdeprecated(mod, name) && isconst(mod, name)
                 alias = getfield(mod, name)
-                if alias isa Type && !has_free_typevars(alias) && !isvarargtype(alias) && !print_without_params(alias) && x <: alias
+                if alias isa Type && !has_free_typevars(alias) && !print_without_params(alias) && x <: alias
                     if alias isa UnionAll
                         (ti, env) = ccall(:jl_type_intersection_with_env, Any, (Any, Any), x, alias)::SimpleVector
                         # ti === Union{} && continue # impossible, since we already checked that x <: alias
@@ -580,8 +581,8 @@ function make_typealias(@nospecialize(x::Type))
                             applied = rewrap_unionall(applied, p)
                         end
                         has_free_typevars(applied) && continue
-                        applied == x || continue # it couldn't figure out the parameter matching
-                    elseif alias <: x
+                        applied === x || continue # it couldn't figure out the parameter matching
+                    elseif alias === x
                         env = Core.svec()
                     else
                         continue # not a complete match
@@ -596,7 +597,7 @@ function make_typealias(@nospecialize(x::Type))
     end
 end
 
-function show_typealias(io::IO, name::GlobalRef, x::Type, env::SimpleVector)
+function show_typealias(io::IO, name::GlobalRef, x::Type, env::SimpleVector, wheres::Vector)
     if !(get(io, :compact, false)::Bool)
         # Print module prefix unless alias is visible from module passed to
         # IOContext. If :module is not set, default to Main. nothing can be used
@@ -612,34 +613,70 @@ function show_typealias(io::IO, name::GlobalRef, x::Type, env::SimpleVector)
     n == 0 && return
 
     print(io, "{")
-    let io = IOContext(io)
-        for i = n:-1:1
-            p = env[i]
-            if p isa TypeVar
-                io = IOContext(io, :unionall_env => p)
+    param_io = IOContext(io)
+    for i = 1:length(wheres)
+        p = wheres[i]::TypeVar
+        param_io = IOContext(param_io, :unionall_env => p)
+    end
+    for i = 1:n
+        p = env[i]
+        show(param_io, p)
+        i < n && print(io, ", ")
+    end
+    print(io, "}")
+end
+
+function make_wheres(io::IO, env::SimpleVector, @nospecialize(x::Type))
+    seen = IdSet()
+    wheres = TypeVar[]
+    # record things printed by the context
+    if io isa IOContext
+        for (key, val) in io.dict
+            if key === :unionall_env && val isa TypeVar && has_typevar(x, val)
+                push!(seen, val)
             end
         end
-        for i = 1:n
-            p = env[i]
-            show(io, p)
-            i < n && print(io, ", ")
+    end
+    # record things in x to print outermost
+    while x isa UnionAll
+        if !(x.var in seen)
+            push!(seen, x.var)
+            push!(wheres, x.var)
         end
+        x = x.body
     end
-    print(io, "}")
-    for i = n:-1:1
+    # record remaining things in env to print innermost
+    for i = length(env):-1:1
         p = env[i]
-        if p isa TypeVar && !io_has_tvar_name(io, p.name, x)
-            print(io, " where ")
-            show(io, p)
+        if p isa TypeVar && !(p in seen)
+            push!(seen, p)
+            pushfirst!(wheres, p)
         end
     end
+    return wheres
+end
+
+function show_wheres(io::IO, env::Vector)
+    isempty(env) && return
+    io = IOContext(io)
+    n = length(env)
+    for i = 1:n
+        p = env[i]::TypeVar
+        print(io, n == 1 ? " where " : i == 1 ? " where {" : ", ")
+        show(io, p)
+        io = IOContext(io, :unionall_env => p)
+    end
+    n > 1 && print(io, "}")
+    nothing
 end
 
 function show_typealias(io::IO, x::Type)
     properx = makeproper(io, x)
     alias = make_typealias(properx)
     alias === nothing && return false
-    show_typealias(io, alias[1], x, alias[2])
+    wheres = make_wheres(io, alias[2], x)
+    show_typealias(io, alias[1], x, alias[2], wheres)
+    show_wheres(io, wheres)
     return true
 end
 
@@ -661,7 +698,7 @@ function make_typealiases(@nospecialize(x::Type))
         for name in names(mod)
             if isdefined(mod, name) && !isdeprecated(mod, name) && isconst(mod, name)
                 alias = getfield(mod, name)
-                if alias isa Type && !has_free_typevars(alias) && !isvarargtype(alias) && !print_without_params(alias) && !(alias <: Tuple)
+                if alias isa Type && !has_free_typevars(alias) && !print_without_params(alias) && !(alias <: Tuple)
                     (ti, env) = ccall(:jl_type_intersection_with_env, Any, (Any, Any), x, alias)::SimpleVector
                     ti === Union{} && continue
                     mod in modulesof!(Set{Module}(), alias) || continue # make sure this alias wasn't from an unrelated part of the Union
@@ -735,13 +772,17 @@ function show_unionaliases(io::IO, x::Union)
     end
     if first && length(aliases) == 1
         alias = aliases[1]
-        show_typealias(io, alias[1], x, alias[2])
+        wheres = make_wheres(io, alias[2], x)
+        show_typealias(io, alias[1], x, alias[2], wheres)
+        show_wheres(io, wheres)
     else
         for alias in aliases
             print(io, first ? "Union{" : ", ")
             first = false
             env = alias[2]
-            show_typealias(io, alias[1], x, alias[2])
+            wheres = make_wheres(io, alias[2], x)
+            show_typealias(io, alias[1], x, alias[2], wheres)
+            show_wheres(io, wheres)
         end
         print(io, "}")
     end
@@ -751,7 +792,7 @@ function show(io::IO, ::MIME"text/plain", @nospecialize(x::Type))
     show(io, x)
     if !print_without_params(x) && get(io, :compact, true)
         properx = makeproper(io, x)
-        if make_typealias(properx) !== nothing || x <: make_typealiases(properx)[2]
+        if make_typealias(properx) !== nothing || (unwrap_unionall(x) isa Union && x <: make_typealiases(properx)[2])
             print(io, " (alias for ")
             show(IOContext(io, :compact => false), x)
             print(io, ")")
@@ -786,22 +827,30 @@ function show(io::IO, @nospecialize(x::Type))
     end
 
     x = x::UnionAll
-    if x.var.name === :_ || io_has_tvar_name(io, x.var.name, x)
-        counter = 1
-        while true
-            newname = Symbol(x.var.name, counter)
-            if !io_has_tvar_name(io, newname, x)
-                newtv = TypeVar(newname, x.var.lb, x.var.ub)
-                x = UnionAll(newtv, x{newtv})
-                break
+    wheres = TypeVar[]
+    let io = IOContext(io)
+        while x isa UnionAll
+            var = x.var
+            if var.name === :_ || io_has_tvar_name(io, var.name, x)
+                counter = 1
+                while true
+                    newname = Symbol(var.name, counter)
+                    if !io_has_tvar_name(io, newname, x)
+                        var = TypeVar(newname, var.lb, var.ub)
+                        x = x{var}
+                        break
+                    end
+                    counter += 1
+                end
+            else
+                x = x.body
             end
-            counter += 1
+            push!(wheres, var)
+            io = IOContext(io, :unionall_env => var)
         end
+        show(io, x)
     end
-
-    show(IOContext(io, :unionall_env => x.var), x.body)
-    print(io, " where ")
-    show(io, x.var)
+    show_wheres(io, wheres)
 end
 
 # Check whether 'sym' (defined in module 'parent') is visible from module 'from'
diff --git a/test/show.jl b/test/show.jl
index 3b918c064fcb0..65fd558cf9280 100644
--- a/test/show.jl
+++ b/test/show.jl
@@ -634,7 +634,7 @@ end
 # `where` syntax
 @test_repr "A where T<:B"
 @test_repr "A where T<:(Array{T} where T<:Real)"
-@test_repr "Array{T} where T<:Array{S} where S<:Real"
+@test_repr "Array{T} where {S<:Real, T<:Array{S}}"
 @test_repr "x::Array{T} where T"
 @test_repr "(a::b) where T"
 @test_repr "a::b where T"
@@ -1568,12 +1568,12 @@ end
 end
 
 let x = TypeVar(:_), y = TypeVar(:_)
-    @test repr(UnionAll(x, UnionAll(y, Pair{x,y}))) == "Pair{_1, _2} where _2 where _1"
+    @test repr(UnionAll(x, UnionAll(y, Pair{x,y}))) == "Pair{_1, _2} where {_1, _2}"
     @test repr(UnionAll(x, UnionAll(y, Pair{UnionAll(x,Ref{x}),y}))) == "Pair{Ref{_1} where _1, _1} where _1"
     x = TypeVar(:a)
     y = TypeVar(:a)
     z = TypeVar(:a)
-    @test repr(UnionAll(z, UnionAll(x, UnionAll(y, Tuple{x,y,z})))) == "Tuple{a1, a2, a} where a2 where a1 where a"
+    @test repr(UnionAll(z, UnionAll(x, UnionAll(y, Tuple{x,y,z})))) == "Tuple{a1, a2, a} where {a, a1, a2}"
 end
 
 @testset "showarg" begin
@@ -2070,15 +2070,21 @@ end
 end
 
 module M37012
+export AValue, B2
 struct AnInteger{S<:Integer} end
 struct AStruct{N} end
 const AValue{S} = Union{AStruct{S}, AnInteger{S}}
+struct BStruct{T,S} end
+const B2{S,T} = BStruct{T,S}
 end
 @test Base.make_typealias(M37012.AStruct{1}) === nothing
 @test isempty(Base.make_typealiases(M37012.AStruct{1})[1])
 @test string(M37012.AStruct{1}) == "$(curmod_prefix)M37012.AStruct{1}"
 @test string(Union{Nothing, Number, Vector}) == "Union{Nothing, Number, Vector{T} where T}"
 @test string(Union{Nothing, AbstractVecOrMat}) == "Union{Nothing, AbstractVecOrMat{T} where T}"
+@test string(M37012.BStruct{T, T} where T) == "$(curmod_prefix)M37012.B2{T, T} where T"
+@test string(M37012.BStruct{T, S} where {T<:Unsigned, S<:Signed}) == "$(curmod_prefix)M37012.B2{S, T} where {T<:Unsigned, S<:Signed}"
+@test string(M37012.BStruct{T, S} where {T<:Signed, S<:T}) == "$(curmod_prefix)M37012.B2{S, T} where {T<:Signed, S<:T}"
 
 @test sprint(show, :(./)) == ":((./))"
 @test sprint(show, :((.|).(.&, b))) == ":((.|).((.&), b))"