diff --git a/base/deprecated.jl b/base/deprecated.jl
index a2b7a78baa660..7d1201f00db2a 100644
--- a/base/deprecated.jl
+++ b/base/deprecated.jl
@@ -1719,6 +1719,14 @@ export hex2num
 # PR #23373
 @deprecate diagm(A::BitMatrix) diagm(vec(A))
 
+# PR #23271
+function IOContext(io::IO; kws...)
+    depwarn("IOContext(io, k=v, ...) is deprecated, use IOContext(io, :k => v, ...) instead.", :IOContext)
+    IOContext(io, (k=>v for (k, v) in kws)...)
+end
+
+@deprecate IOContext(io::IO, key, value) IOContext(io, key=>value)
+
 # END 0.7 deprecations
 
 # BEGIN 1.0 deprecations
diff --git a/base/interactiveutil.jl b/base/interactiveutil.jl
index 1e50a94bebbf5..aa0ad2e7ffa5b 100644
--- a/base/interactiveutil.jl
+++ b/base/interactiveutil.jl
@@ -384,8 +384,7 @@ function code_warntype(io::IO, f, @nospecialize(t))
         body.args = src.code
         body.typ = rettype
         # Fix slot names and types in function body
-        show_unquoted(IOContext(IOContext(emph_io, :SOURCEINFO => src),
-                                          :SOURCE_SLOTNAMES => slotnames),
+        show_unquoted(IOContext(emph_io, :SOURCEINFO => src, :SOURCE_SLOTNAMES => slotnames),
                       body, 2)
         print(emph_io, '\n')
     end
diff --git a/base/replutil.jl b/base/replutil.jl
index d5329602aacc0..5582c7a6b01fb 100644
--- a/base/replutil.jl
+++ b/base/replutil.jl
@@ -242,7 +242,8 @@ function showerror(io::IO, ex::DomainError, bt; backtrace=true)
     if isa(ex.val, AbstractArray)
         compact = get(io, :compact, true)
         limit = get(io, :limit, true)
-        print(IOContext(io, compact=compact, limit=limit), "DomainError with ", ex.val)
+        print(IOContext(io, :compact => compact, :limit => limit),
+              "DomainError with ", ex.val)
     else
         print(io, "DomainError with ", ex.val)
     end
@@ -360,7 +361,7 @@ function showerror(io::IO, ex::MethodError)
             print(io, "; ")
             for (i, (k, v)) in enumerate(kwargs)
                 print(io, k, "=")
-                show(IOContext(io, :limit=>true), v)
+                show(IOContext(io, :limit => true), v)
                 i == length(kwargs) || print(io, ", ")
             end
         end
diff --git a/base/show.jl b/base/show.jl
index 79678aab589a3..38a8343af2d6e 100644
--- a/base/show.jl
+++ b/base/show.jl
@@ -20,41 +20,32 @@ struct IOContext{IO_t <: IO} <: AbstractPipe
     end
 end
 
-"""
-    IOContext(io::IO; properties...)
+unwrapcontext(io::IO) = io, ImmutableDict{Symbol,Any}()
+unwrapcontext(io::IOContext) = io.io, io.dict
 
-The same as `IOContext(io::IO, KV::Pair)`, but accepting properties as keyword arguments.
-"""
-IOContext(io::IO; kws...) = IOContext(convert(IOContext, io); kws...)
-function IOContext(io::IOContext; kws...)
-    for (k, v) in kws
-        io = IOContext(io, k, v)
-    end
-    return io
+function IOContext(io::IO, dict::ImmutableDict)
+    io0 = unwrapcontext(io)[1]
+    IOContext{typeof(io0)}(io0, dict)
 end
 
-convert(::Type{IOContext}, io::IOContext) = io
-convert(::Type{IOContext}, io::IO) = IOContext(io, ImmutableDict{Symbol, Any}())
+convert(::Type{IOContext}, io::IO) = IOContext(unwrapcontext(io)...)
 
-IOContext(io::IOContext, dict::ImmutableDict) = typeof(io)(io.io, dict)
-IOContext(io::IO, dict::ImmutableDict) = IOContext{typeof(io)}(io, dict)
-
-IOContext(io::IOContext, key, value) = IOContext(io.io, ImmutableDict{Symbol, Any}(io.dict, key, value))
-IOContext(io::IO, key, value) = IOContext(io, ImmutableDict{Symbol, Any}(key, value))
-
-IOContext(io::IO, context::IO) = convert(IOContext, io)
+function IOContext(io::IO, KV::Pair)
+    io0, d = unwrapcontext(io)
+    IOContext(io0, ImmutableDict{Symbol,Any}(d, KV[1], KV[2]))
+end
 
 """
     IOContext(io::IO, context::IOContext)
 
 Create an `IOContext` that wraps an alternate `IO` but inherits the properties of `context`.
 """
-IOContext(io::IO, context::IOContext) = IOContext(io, context.dict)
+IOContext(io::IO, context::IO) = IOContext(unwrapcontext(io)[1], unwrapcontext(context)[2])
 
 """
-    IOContext(io::IO, KV::Pair)
+    IOContext(io::IO, KV::Pair...)
 
-Create an `IOContext` that wraps a given stream, adding the specified `key=>value` pair to
+Create an `IOContext` that wraps a given stream, adding the specified `key=>value` pairs to
 the properties of that stream (note that `io` can itself be an `IOContext`).
 
  - use `(key => value) in dict` to see if this particular combination is in the properties set
@@ -87,7 +78,7 @@ julia> f(IOContext(STDOUT, :short => true))
 short
 ```
 """
-IOContext(io::IO, KV::Pair) = IOContext(io, KV[1], KV[2])
+IOContext(io::IO, KV::Pair, KVs::Pair...) = IOContext(IOContext(io, KV), KVs...)
 
 show(io::IO, ctx::IOContext) = (print(io, "IOContext("); show(io, ctx.io); print(io, ")"))
 
@@ -1335,7 +1326,7 @@ function dumpsubtypes(io::IO, x::DataType, m::Module, n::Int, indent)
                     tp = t
                     while true
                         show(tvar_io, tp.var)
-                        tvar_io = IOContext(tvar_io, :unionall_env, tp.var)
+                        tvar_io = IOContext(tvar_io, :unionall_env => tp.var)
                         tp = tp.body
                         if isa(tp, UnionAll)
                             print(io, ", ")
diff --git a/test/dict.jl b/test/dict.jl
index 3954b342ed05f..dbd4771b2dfe1 100644
--- a/test/dict.jl
+++ b/test/dict.jl
@@ -268,7 +268,7 @@ for d in (Dict("\n" => "\n", "1" => "\n", "\n" => "2"),
     for cols in (12, 40, 80), rows in (2, 10, 24)
         # Ensure output is limited as requested
         s = IOBuffer()
-        io = Base.IOContext(Base.IOContext(s, :limit => true), :displaysize => (rows, cols))
+        io = Base.IOContext(s, :limit => true, :displaysize => (rows, cols))
         Base.show(io, MIME("text/plain"), d)
         out = split(String(take!(s)),'\n')
         for line in out[2:end]
@@ -278,7 +278,7 @@ for d in (Dict("\n" => "\n", "1" => "\n", "\n" => "2"),
 
         for f in (keys, values)
             s = IOBuffer()
-            io = Base.IOContext(Base.IOContext(s, :limit => true), :displaysize => (rows, cols))
+            io = Base.IOContext(s, :limit => true, :displaysize => (rows, cols))
             Base.show(io, MIME("text/plain"), f(d))
             out = split(String(take!(s)),'\n')
             for line in out[2:end]
@@ -311,7 +311,7 @@ end
 mutable struct Alpha end
 Base.show(io::IO, ::Alpha) = print(io,"α")
 let sbuff = IOBuffer(),
-    io = Base.IOContext(Base.IOContext(sbuff, :limit => true), :displaysize => (10, 20))
+    io = Base.IOContext(sbuff, :limit => true, :displaysize => (10, 20))
 
     Base.show(io, MIME("text/plain"), Dict(Alpha()=>1))
     local str = String(take!(sbuff))
diff --git a/test/offsetarray.jl b/test/offsetarray.jl
index 46ace5061822f..b2c642cdfced3 100644
--- a/test/offsetarray.jl
+++ b/test/offsetarray.jl
@@ -147,7 +147,7 @@ smry = summary(v)
 @test contains(smry, "OffsetArray{Float64,1")
 @test contains(smry, "with indices -1:1")
 function cmp_showf(printfunc, io, A)
-    ioc = IOContext(IOContext(io, :limit => true), :compact => true)
+    ioc = IOContext(io, :limit => true, :compact => true)
     printfunc(ioc, A)
     str1 = String(take!(io))
     printfunc(ioc, parent(A))
diff --git a/test/ranges.jl b/test/ranges.jl
index a953599223ad2..69fecf89d2630 100644
--- a/test/ranges.jl
+++ b/test/ranges.jl
@@ -850,7 +850,7 @@ end
 
 # stringmime/show should display the range or linspace nicely
 # to test print_range in range.jl
-replstrmime(x) = sprint((io,x) -> show(IOContext(io, limit=true, displaysize=(24, 80)), MIME("text/plain"), x), x)
+replstrmime(x) = sprint((io,x) -> show(IOContext(io, :limit => true, :displaysize => (24, 80)), MIME("text/plain"), x), x)
 @test replstrmime(1:4) == "1:4"
 @test stringmime("text/plain", 1:4) == "1:4"
 @test stringmime("text/plain", linspace(1,5,7)) == "1.0:0.6666666666666666:5.0"
diff --git a/test/replutil.jl b/test/replutil.jl
index 7049511f1ae52..4f91dd949ffdb 100644
--- a/test/replutil.jl
+++ b/test/replutil.jl
@@ -610,7 +610,7 @@ end
 
 @testset "Dict printing with limited rows" begin
     buf = IOBuffer()
-    io = IOContext(IOContext(buf, :displaysize => (4, 80)), :limit => true)
+    io = IOContext(buf, :displaysize => (4, 80), :limit => true)
     d = Base.ImmutableDict(1=>2)
     show(io, MIME"text/plain"(), d)
     @test String(take!(buf)) == "Base.ImmutableDict{$Int,$Int} with 1 entry: …"
diff --git a/test/show.jl b/test/show.jl
index 5d576dcd2920d..ebe4a6681f40f 100644
--- a/test/show.jl
+++ b/test/show.jl
@@ -3,7 +3,7 @@
 # For curmod_*
 include("testenv.jl")
 
-replstr(x) = sprint((io,x) -> show(IOContext(io, limit=true, displaysize=(24, 80)), MIME("text/plain"), x), x)
+replstr(x) = sprint((io,x) -> show(IOContext(io, :limit => true, :displaysize => (24, 80)), MIME("text/plain"), x), x)
 
 @test replstr(Array{Any}(2)) == "2-element Array{Any,1}:\n #undef\n #undef"
 @test replstr(Array{Any}(2,2)) == "2×2 Array{Any,2}:\n #undef  #undef\n #undef  #undef"
@@ -923,7 +923,7 @@ end
 @testset "Array printing with limited rows" begin
     arrstr = let buf = IOBuffer()
         function (A, rows)
-            Base.showarray(IOContext(buf, displaysize=(rows, 80), limit=true),
+            Base.showarray(IOContext(buf, :displaysize => (rows, 80), :limit => true),
                            A, false, header=true)
             String(take!(buf))
         end
diff --git a/test/sparse/sparse.jl b/test/sparse/sparse.jl
index 30e62f354afab..10719cce3c0c1 100644
--- a/test/sparse/sparse.jl
+++ b/test/sparse/sparse.jl
@@ -1794,14 +1794,14 @@ end
     show(io, MIME"text/plain"(), spzeros(Float32, Int64, 2, 2))
     @test String(take!(io)) == "2×2 SparseMatrixCSC{Float32,Int64} with 0 stored entries"
 
-    ioc = IOContext(io, displaysize = (5, 80), limit = true)
+    ioc = IOContext(io, :displaysize => (5, 80), :limit => true)
     show(ioc, MIME"text/plain"(), sparse(Int64[1], Int64[1], [1.0]))
     @test String(take!(io)) == "1×1 SparseMatrixCSC{Float64,Int64} with 1 stored entry:\n  [1, 1]  =  1.0"
     show(ioc, MIME"text/plain"(), sparse(Int64[1, 1], Int64[1, 2], [1.0, 2.0]))
     @test String(take!(io)) == "1×2 SparseMatrixCSC{Float64,Int64} with 2 stored entries:\n  ⋮"
 
     # even number of rows
-    ioc = IOContext(io, displaysize = (8, 80), limit = true)
+    ioc = IOContext(io, :displaysize => (8, 80), :limit => true)
     show(ioc, MIME"text/plain"(), sparse(Int64[1,2,3,4], Int64[1,1,2,2], [1.0,2.0,3.0,4.0]))
     @test String(take!(io)) == string("4×2 SparseMatrixCSC{Float64,Int64} with 4 stored entries:\n  [1, 1]",
                                       "  =  1.0\n  [2, 1]  =  2.0\n  [3, 2]  =  3.0\n  [4, 2]  =  4.0")
@@ -1815,7 +1815,7 @@ end
                                        "  =  1.0\n  ⋮\n  [5, 3]  =  1.0")
 
     # odd number of rows
-    ioc = IOContext(io, displaysize = (9, 80), limit = true)
+    ioc = IOContext(io, :displaysize => (9, 80), :limit => true)
     show(ioc, MIME"text/plain"(), sparse(Int64[1,2,3,4,5], Int64[1,1,2,2,3], [1.0,2.0,3.0,4.0,5.0]))
     @test String(take!(io)) == string("5×3 SparseMatrixCSC{Float64,Int64} with 5 stored entries:\n  [1, 1]",
                                       "  =  1.0\n  [2, 1]  =  2.0\n  [3, 2]  =  3.0\n  [4, 2]  =  4.0\n  [5, 3]  =  5.0")
@@ -1828,7 +1828,7 @@ end
     @test String(take!(io)) ==  string("6×3 SparseMatrixCSC{Float64,$Int} with 18 stored entries:\n  [1, 1]",
                                        "  =  1.0\n  [2, 1]  =  1.0\n  ⋮\n  [5, 3]  =  1.0\n  [6, 3]  =  1.0")
 
-    ioc = IOContext(io, displaysize = (9, 80))
+    ioc = IOContext(io, :displaysize => (9, 80))
     show(ioc, MIME"text/plain"(), sparse(Int64[1,2,3,4,5,6], Int64[1,1,2,2,3,3], [1.0,2.0,3.0,4.0,5.0,6.0]))
     @test String(take!(io)) ==  string("6×3 SparseMatrixCSC{Float64,Int64} with 6 stored entries:\n  [1, 1]  =  1.0\n",
         "  [2, 1]  =  2.0\n  [3, 2]  =  3.0\n  [4, 2]  =  4.0\n  [5, 3]  =  5.0\n  [6, 3]  =  6.0")