diff --git a/deps/checksums/StyledStrings-ac472083359dde956aed8c61d43b8158ac84d9ce.tar.gz/md5 b/deps/checksums/StyledStrings-ac472083359dde956aed8c61d43b8158ac84d9ce.tar.gz/md5
deleted file mode 100644
index 758a74bce9dae..0000000000000
--- a/deps/checksums/StyledStrings-ac472083359dde956aed8c61d43b8158ac84d9ce.tar.gz/md5
+++ /dev/null
@@ -1 +0,0 @@
-6969fb6d2e8585d26beef865910ec8ef
diff --git a/deps/checksums/StyledStrings-ac472083359dde956aed8c61d43b8158ac84d9ce.tar.gz/sha512 b/deps/checksums/StyledStrings-ac472083359dde956aed8c61d43b8158ac84d9ce.tar.gz/sha512
deleted file mode 100644
index 3d1ac8791e14d..0000000000000
--- a/deps/checksums/StyledStrings-ac472083359dde956aed8c61d43b8158ac84d9ce.tar.gz/sha512
+++ /dev/null
@@ -1 +0,0 @@
-281292e8478d72ab66b84cbd4f42e5dc2dd5054e8c54a79de8f0c0537d28962b460e67fe71230ead6b02386b87d0423879d51ce53a2b2427ce55866d62d6ebde
diff --git a/deps/checksums/StyledStrings-d7496d24d3f05536bce6a7eb4cd8ca05a75c02aa.tar.gz/md5 b/deps/checksums/StyledStrings-d7496d24d3f05536bce6a7eb4cd8ca05a75c02aa.tar.gz/md5
new file mode 100644
index 0000000000000..3a5fccdec0fba
--- /dev/null
+++ b/deps/checksums/StyledStrings-d7496d24d3f05536bce6a7eb4cd8ca05a75c02aa.tar.gz/md5
@@ -0,0 +1 @@
+a02cd2c8bedd83b74917cf3821c89f46
diff --git a/deps/checksums/StyledStrings-d7496d24d3f05536bce6a7eb4cd8ca05a75c02aa.tar.gz/sha512 b/deps/checksums/StyledStrings-d7496d24d3f05536bce6a7eb4cd8ca05a75c02aa.tar.gz/sha512
new file mode 100644
index 0000000000000..a042e4f306275
--- /dev/null
+++ b/deps/checksums/StyledStrings-d7496d24d3f05536bce6a7eb4cd8ca05a75c02aa.tar.gz/sha512
@@ -0,0 +1 @@
+2e86daa832533f0369e66e359d7d8f47002f93525f83233c809007a13dfd05a201bcd273b3cb4f3eba2586e98cc9afa43c242f67dc18b91fc898d98a0bd8fde9
diff --git a/doc/Manifest.toml b/doc/Manifest.toml
index 254becb59a0c7..cb9d42561be5f 100644
--- a/doc/Manifest.toml
+++ b/doc/Manifest.toml
@@ -114,6 +114,10 @@ deps = ["Artifacts", "LibSSH2_jll", "Libdl", "MbedTLS_jll", "Zlib_jll", "nghttp2
 uuid = "deac9b47-8bc7-5906-a0fe-35ac56dc84c0"
 version = "8.6.0+0"
 
+[[deps.JuliaSyntaxHighlighting]]
+deps = ["StyledStrings"]
+uuid = "dc6e5ff7-fb65-4e79-a425-ec3bc9c03011"
+
 [[deps.LibGit2]]
 deps = ["LibGit2_jll", "NetworkOptions", "Printf", "SHA"]
 uuid = "76f85450-5226-5b5a-8eaa-529ad045b433"
@@ -145,7 +149,7 @@ uuid = "56ddb016-857b-54e1-b83d-db4d58db5568"
 version = "1.11.0"
 
 [[deps.Markdown]]
-deps = ["Base64"]
+deps = ["Base64", "JuliaSyntaxHighlighting", "StyledStrings"]
 uuid = "d6f4376e-aef5-505a-96c1-9c027394607a"
 version = "1.11.0"
 
diff --git a/stdlib/Manifest.toml b/stdlib/Manifest.toml
index 4e4f48b4e6af4..8d59f63c4733c 100644
--- a/stdlib/Manifest.toml
+++ b/stdlib/Manifest.toml
@@ -140,7 +140,7 @@ uuid = "3a97d323-0669-5f0c-9066-3539efd106a3"
 version = "4.2.1+0"
 
 [[deps.Markdown]]
-deps = ["Base64"]
+deps = ["Base64", "JuliaSyntaxHighlighting", "StyledStrings"]
 uuid = "d6f4376e-aef5-505a-96c1-9c027394607a"
 version = "1.11.0"
 
diff --git a/stdlib/Markdown/Project.toml b/stdlib/Markdown/Project.toml
index b40de17b9422d..e2edcdefea537 100644
--- a/stdlib/Markdown/Project.toml
+++ b/stdlib/Markdown/Project.toml
@@ -4,6 +4,8 @@ version = "1.11.0"
 
 [deps]
 Base64 = "2a0f44e3-6c83-55bd-87e4-b1978d98bd5f"
+StyledStrings = "f489334b-da3d-4c2e-b8f0-e476e12c162b"
+JuliaSyntaxHighlighting = "dc6e5ff7-fb65-4e79-a425-ec3bc9c03011"
 
 [extras]
 Test = "8dfed614-e22c-5e08-85e1-65c5234f0b40"
diff --git a/stdlib/Markdown/src/Common/Common.jl b/stdlib/Markdown/src/Common/Common.jl
index 3036f2b4b730b..4bd3e5b4af8d6 100644
--- a/stdlib/Markdown/src/Common/Common.jl
+++ b/stdlib/Markdown/src/Common/Common.jl
@@ -1,5 +1,7 @@
 # This file is a part of Julia. License is MIT: https://julialang.org/license
 
+abstract type MarkdownElement end
+
 include("block.jl")
 include("inline.jl")
 
diff --git a/stdlib/Markdown/src/Common/block.jl b/stdlib/Markdown/src/Common/block.jl
index bd184b60c40fa..1b5cc1a752bcb 100644
--- a/stdlib/Markdown/src/Common/block.jl
+++ b/stdlib/Markdown/src/Common/block.jl
@@ -4,7 +4,7 @@
 # Paragraphs
 # ––––––––––
 
-mutable struct Paragraph
+mutable struct Paragraph <: MarkdownElement
     content
 end
 
@@ -39,7 +39,7 @@ end
 # Headers
 # –––––––
 
-mutable struct Header{level}
+mutable struct Header{level} <: MarkdownElement
     text
 end
 
@@ -95,7 +95,7 @@ end
 # Code
 # ––––
 
-mutable struct Code
+mutable struct Code <: MarkdownElement
     language::String
     code::String
 end
@@ -124,7 +124,7 @@ end
 # Footnote
 # --------
 
-mutable struct Footnote
+mutable struct Footnote <: MarkdownElement
     id::String
     text
 end
@@ -159,7 +159,7 @@ end
 # Quotes
 # ––––––
 
-mutable struct BlockQuote
+mutable struct BlockQuote <: MarkdownElement
     content
 end
 
@@ -188,7 +188,7 @@ end
 # Admonitions
 # -----------
 
-mutable struct Admonition
+mutable struct Admonition <: MarkdownElement
     category::String
     title::String
     content::Vector
@@ -246,7 +246,7 @@ end
 # Lists
 # –––––
 
-mutable struct List
+mutable struct List <: MarkdownElement
     items::Vector{Any}
     ordered::Int # `-1` is unordered, `>= 0` is ordered.
     loose::Bool # TODO: Renderers should use this field
@@ -332,7 +332,7 @@ pushitem!(list, buffer) = push!(list.items, parse(String(take!(buffer))).content
 # HorizontalRule
 # ––––––––––––––
 
-mutable struct HorizontalRule
+mutable struct HorizontalRule <: MarkdownElement
 end
 
 function horizontalrule(stream::IO, block::MD)
diff --git a/stdlib/Markdown/src/Common/inline.jl b/stdlib/Markdown/src/Common/inline.jl
index fda716a10fae7..a2a4140f80050 100644
--- a/stdlib/Markdown/src/Common/inline.jl
+++ b/stdlib/Markdown/src/Common/inline.jl
@@ -4,7 +4,7 @@
 # Emphasis
 # ––––––––
 
-mutable struct Italic
+mutable struct Italic <: MarkdownElement
     text
 end
 
@@ -20,7 +20,7 @@ function underscore_italic(stream::IO, md::MD)
     return result === nothing ? nothing : Italic(parseinline(result, md))
 end
 
-mutable struct Bold
+mutable struct Bold <: MarkdownElement
     text
 end
 
@@ -66,7 +66,7 @@ end
 # Images & Links
 # ––––––––––––––
 
-mutable struct Image
+mutable struct Image <: MarkdownElement
     url::String
     alt::String
 end
@@ -85,7 +85,7 @@ function image(stream::IO, md::MD)
     end
 end
 
-mutable struct Link
+mutable struct Link <: MarkdownElement
     text
     url::String
 end
@@ -156,7 +156,7 @@ end
 # Punctuation
 # –––––––––––
 
-mutable struct LineBreak end
+mutable struct LineBreak <: MarkdownElement end
 
 @trigger '\\' ->
 function linebreak(stream::IO, md::MD)
diff --git a/stdlib/Markdown/src/GitHub/table.jl b/stdlib/Markdown/src/GitHub/table.jl
index 29f956e9a0710..7c174007a75ba 100644
--- a/stdlib/Markdown/src/GitHub/table.jl
+++ b/stdlib/Markdown/src/GitHub/table.jl
@@ -140,15 +140,15 @@ end
 
 function term(io::IO, md::Table, columns)
     margin_str = " "^margin
-    cells = mapmap(x -> terminline_string(io, x), md.rows)
-    padcells!(cells, md.align, len = ansi_length)
+    cells = mapmap(x -> annotprint(terminline, x), md.rows)
+    padcells!(cells, md.align, len = textwidth)
     for i = 1:length(cells)
         print(io, margin_str)
         join(io, cells[i], " ")
         if i == 1
             println(io)
             print(io, margin_str)
-            join(io, ["–"^ansi_length(cells[i][j]) for j = 1:length(cells[1])], " ")
+            join(io, ["–"^textwidth(cells[i][j]) for j = 1:length(cells[1])], " ")
         end
         i < length(cells) && println(io)
     end
diff --git a/stdlib/Markdown/src/Markdown.jl b/stdlib/Markdown/src/Markdown.jl
index 93d8dbc39fc59..935b5d981d6f9 100644
--- a/stdlib/Markdown/src/Markdown.jl
+++ b/stdlib/Markdown/src/Markdown.jl
@@ -9,9 +9,12 @@ literals `md"..."` and `doc"..."`.
 """
 module Markdown
 
-import Base: show, ==, with_output_color, mapany
+import Base: AnnotatedString, AnnotatedIOBuffer, show, ==, with_output_color, mapany
 using Base64: stringmime
 
+using StyledStrings: StyledStrings, Face, addface!, @styled_str, styled
+using JuliaSyntaxHighlighting: highlight, highlight!
+
 # Margin for printing in terminal.
 const margin = 2
 
@@ -32,6 +35,26 @@ include("render/terminal/render.jl")
 
 export @md_str, @doc_str
 
+const MARKDOWN_FACES = [
+    :markdown_header => Face(weight=:bold),
+    :markdown_h1 => Face(height=1.25, inherit=:markdown_header),
+    :markdown_h2 => Face(height=1.20, inherit=:markdown_header),
+    :markdown_h3 => Face(height=1.15, inherit=:markdown_header),
+    :markdown_h4 => Face(height=1.12, inherit=:markdown_header),
+    :markdown_h5 => Face(height=1.08, inherit=:markdown_header),
+    :markdown_h6 => Face(height=1.05, inherit=:markdown_header),
+    :markdown_admonition => Face(weight=:bold),
+    :markdown_code => Face(inherit=:code),
+    :markdown_footnote => Face(inherit=:bright_yellow),
+    :markdown_hrule => Face(inherit=:shadow),
+    :markdown_inlinecode => Face(inherit=:markdown_code),
+    :markdown_latex => Face(inherit=:magenta),
+    :markdown_link => Face(underline=:bright_blue),
+    :markdown_list => Face(foreground=:blue),
+]
+
+__init__() = foreach(addface!, MARKDOWN_FACES)
+
 parse(markdown::AbstractString; flavor = julia) = parse(IOBuffer(markdown), flavor = flavor)
 parse_file(file::AbstractString; flavor = julia) = parse(read(file, String), flavor = flavor)
 
diff --git a/stdlib/Markdown/src/render/html.jl b/stdlib/Markdown/src/render/html.jl
index e7d436f2ccbda..829fa6c7bf986 100644
--- a/stdlib/Markdown/src/render/html.jl
+++ b/stdlib/Markdown/src/render/html.jl
@@ -67,6 +67,9 @@ end
 
 function html(io::IO, code::Code)
     withtag(io, :pre) do
+        if code.language == "styled"
+            code = Code("", String(styled(code.code)))
+        end
         maybe_lang = !isempty(code.language) ? Any[:class=>"language-$(code.language)"] : []
         withtag(io, :code, maybe_lang...) do
             htmlesc(io, code.code)
@@ -134,6 +137,9 @@ function htmlinline(io::IO, content::Vector)
 end
 
 function htmlinline(io::IO, code::Code)
+    if code.language == "styled"
+        code = Code("", String(styled(code.code)))
+    end
     withtag(io, :code) do
         htmlesc(io, code.code)
     end
diff --git a/stdlib/Markdown/src/render/latex.jl b/stdlib/Markdown/src/render/latex.jl
index df52b2849f2b0..fad0508ce0e59 100644
--- a/stdlib/Markdown/src/render/latex.jl
+++ b/stdlib/Markdown/src/render/latex.jl
@@ -33,6 +33,9 @@ function latex(io::IO, header::Header{l}) where l
 end
 
 function latex(io::IO, code::Code)
+    if code.language == "styled"
+        code = Code("", String(styled(code.code)))
+    end
     occursin("\\end{verbatim}", code.code) && error("Cannot include \"\\end{verbatim}\" in a latex code block")
     wrapblock(io, "verbatim") do
         println(io, code.code)
diff --git a/stdlib/Markdown/src/render/rst.jl b/stdlib/Markdown/src/render/rst.jl
index 752916c581a07..e441ee0495da0 100644
--- a/stdlib/Markdown/src/render/rst.jl
+++ b/stdlib/Markdown/src/render/rst.jl
@@ -23,10 +23,16 @@ end
 function rst(io::IO, code::Code)
     if code.language == "jldoctest"
         println(io, ".. doctest::\n")
-    elseif code.language != "rst"
+    elseif code.language in ("", "julia", "julia-repl")
         println(io, ".. code-block:: julia\n")
+    elseif code.language == "rst"
+    elseif code.language == "styled"
+        code = Code("", String(styled(code.code)))
+        println(io, "::\n")
+    else
+        println(io, "::\n")
     end
-    for l in lines(code.code)
+    for l in eachsplit(code.code, '\n')
         println(io, "    ", l)
     end
 end
@@ -90,7 +96,7 @@ end
 
 function rst(io::IO, l::LaTeX)
     println(io, ".. math::\n")
-    for line in lines(l.formula)
+    for line in eachsplit(l.formula, '\n')
         println(io, "    ", line)
     end
 end
diff --git a/stdlib/Markdown/src/render/terminal/formatting.jl b/stdlib/Markdown/src/render/terminal/formatting.jl
index a031de4d9ad82..009fd2eb3af18 100644
--- a/stdlib/Markdown/src/render/terminal/formatting.jl
+++ b/stdlib/Markdown/src/render/terminal/formatting.jl
@@ -1,68 +1,68 @@
 # This file is a part of Julia. License is MIT: https://julialang.org/license
 
-# Wrapping
+const AnnotIO = Union{AnnotatedIOBuffer, IOContext{AnnotatedIOBuffer}}
 
-function ansi_length(s)
-    replace(s, r"\e\[[0-9]+m" => "") |> textwidth
+function annotprint(f::Function, args...)
+    buf = AnnotatedIOBuffer()
+    f(buf, args...)
+    read(seekstart(buf), AnnotatedString)
 end
 
-words(s) = split(s, " ")
-lines(s) = split(s, "\n")
+"""
+    with_output_annotations(f::Function, io::AnnotIO, annots::Pair{Symbol, <:Any}...)
 
-function wrapped_line(io::IO, s::AbstractString, width, i)
-    ws = words(s)
-    lines = String[]
-    for word in ws
-        word_length = ansi_length(word)
-        word_length == 0 && continue
-        if isempty(lines) || i + word_length + 1 > width
-            i = word_length
-            if length(lines) > 0
-                last_line = lines[end]
-                maybe_underline = findlast(Base.text_colors[:underline], last_line)
-                if !isnothing(maybe_underline)
-                    # disable underline style at end of line if not already disabled.
-                    maybe_disable_underline = max(
-                        last(something(findlast(Base.disable_text_style[:underline], last_line), -1)),
-                        last(something(findlast(Base.text_colors[:normal], last_line), -1)),
-                    )
+Call `f(io)`, and apply `annots` to the output created by doing so.
+"""
+function with_output_annotations(f::Function, io::AnnotIO, annots::Pair{Symbol, <:Any}...)
+    @nospecialize annots
+    aio = if io isa AnnotatedIOBuffer io else io.io end
+    start = position(aio) + 1
+    f(io)
+    stop = position(aio)
+    sortedindex = searchsortedlast(aio.annotations, (start:stop,), by=first)
+    for (i, annot) in enumerate(annots)
+        insert!(aio.annotations, sortedindex + i, (start:stop, annot))
+    end
+end
 
-                    if maybe_disable_underline < 0 || maybe_disable_underline < last(maybe_underline)
+"""
+    wraplines(content::AnnotatedString, width::Integer = 80, column::Integer = 0)
 
-                        lines[end] = last_line * Base.disable_text_style[:underline]
-                        word = Base.text_colors[:underline] * word
-                    end
+Wrap `content` into a vector of lines of at most `width` (according to
+`textwidth`), with the first line starting at `column`.
+"""
+function wraplines(content::Union{Annot, SubString{<:Annot}}, width::Integer = 80, column::Integer = 0) where { Annot <: AnnotatedString}
+    s, lines = String(content), SubString{Annot}[]
+    i, lastwrap, slen = firstindex(s), 0, ncodeunits(s)
+    most_recent_break_opportunity = 1
+    while i < slen
+        if isspace(s[i]) && s[i] != '\n'
+            most_recent_break_opportunity = i
+        elseif s[i] == '\n'
+            push!(lines, content[nextind(s, lastwrap):prevind(s, i)])
+            lastwrap = i
+            column = 0
+        elseif column >= width && most_recent_break_opportunity > 1
+            if lastwrap == most_recent_break_opportunity
+                nextbreak = findfirst(isspace, @view s[nextind(s, lastwrap):end])
+                if isnothing(nextbreak)
+                    break
+                else
+                    most_recent_break_opportunity = lastwrap + nextbreak
                 end
+                i = most_recent_break_opportunity
+            else
+                i = nextind(s, most_recent_break_opportunity)
             end
-            push!(lines, word)
-        else
-            i += word_length + 1
-            lines[end] *= " " * word   # this could be more efficient
+            push!(lines, content[nextind(s, lastwrap):prevind(s, most_recent_break_opportunity)])
+            lastwrap = most_recent_break_opportunity
+            column = 0
         end
+        column += textwidth(s[i])
+        i = nextind(s, i)
     end
-    return i, lines
-end
-
-function wrapped_lines(io::IO, s::AbstractString; width = 80, i = 0)
-    ls = String[]
-    for ss in lines(s)
-        i, line = wrapped_line(io, ss, width, i)
-        append!(ls, line)
+    if lastwrap < slen
+        push!(lines, content[nextind(s, lastwrap):end])
     end
-    return ls
+    lines
 end
-
-wrapped_lines(io::IO, f::Function, args...; width = 80, i = 0) =
-    wrapped_lines(io, sprint(f, args...; context=io), width = width, i = 0)
-
-function print_wrapped(io::IO, s...; width = 80, pre = "", i = 0)
-    lines = wrapped_lines(io, s..., width = width, i = i)
-    isempty(lines) && return 0, 0
-    print(io, lines[1])
-    for line in lines[2:end]
-        print(io, '\n', pre, line)
-    end
-    length(lines), length(pre) + ansi_length(lines[end])
-end
-
-print_wrapped(f::Function, io::IO, args...; kws...) = print_wrapped(io, f, args...; kws...)
diff --git a/stdlib/Markdown/src/render/terminal/render.jl b/stdlib/Markdown/src/render/terminal/render.jl
index 20b1ef6d041fc..2afd0bd99ff9f 100644
--- a/stdlib/Markdown/src/render/terminal/render.jl
+++ b/stdlib/Markdown/src/render/terminal/render.jl
@@ -16,118 +16,135 @@ end
 term(io::IO, md::MD, columns = cols(io)) = term(io, md.content, columns)
 
 function term(io::IO, md::Paragraph, columns)
-    print(io, ' '^margin)
-    print_wrapped(io, width = columns-2margin, pre = ' '^margin) do io
-        terminline(io, md.content)
+    lines = wraplines(annotprint(terminline, md.content), columns-2margin)
+    for (i, line) in enumerate(lines)
+        print(io, ' '^margin, line)
+        i < length(lines) && println(io)
     end
 end
 
 function term(io::IO, md::BlockQuote, columns)
-    s = sprint(term, md.content, columns - 10; context=io)
-    lines = split(rstrip(s), '\n')
-    print(io, ' '^margin, '│', lines[1])
-    for i = 2:length(lines)
-        print(io, '\n', ' '^margin, '│', lines[i])
+    content = annotprint(term, md.content, columns - 10)
+    lines = wraplines(rstrip(content), columns - 10)
+    for (i, line) in enumerate(lines)
+        print(io, ' '^margin, '│', line)
+        i < length(lines) && println(io)
     end
 end
 
 function term(io::IO, md::Admonition, columns)
-    col = :default
-    # If the types below are modified, the page manual/documentation.md must be updated accordingly.
-    if md.category == "danger"
-        col = Base.error_color()
-    elseif md.category == "warning"
-        col = Base.warn_color()
-    elseif md.category in ("info", "note")
-        col = Base.info_color()
-    elseif md.category == "tip"
-        col = :green
+    accent = if md.category == "danger"
+        :error
+    elseif md.category in ("warning", "info", "note", "tip")
+        Symbol(md.category)
+    elseif md.category == "compat"
+        :bright_cyan
+    else
+        :default
     end
-    printstyled(io, ' '^margin, "│ "; color=col, bold=true)
-    printstyled(io, isempty(md.title) ? md.category : md.title; color=col, bold=true)
-    printstyled(io, '\n', ' '^margin, '│', '\n'; color=col, bold=true)
-    s = sprint(term, md.content, columns - 10; context=io)
-    lines = split(rstrip(s), '\n')
-    for i in eachindex(lines)
-        printstyled(io, ' '^margin, '│'; color=col, bold=true)
-        print(io, lines[i])
-        i < lastindex(lines) && println(io)
+    title = if isempty(md.title) md.category else md.title end
+    print(io, ' '^margin, styled"{$accent,markdown_admonition:│ $title}",
+          '\n', ' '^margin, styled"{$accent,markdown_admonition:│}", '\n')
+    content = annotprint(term, md.content, columns - 10)
+    lines = split(rstrip(content), '\n')
+    for (i, line) in enumerate(lines)
+        print(io, ' '^margin, styled"{$accent,markdown_admonition:│}", line)
+        i < length(lines) && println(io)
     end
 end
 
 function term(io::IO, f::Footnote, columns)
     print(io, ' '^margin, "│ ")
-    printstyled(io, "[^$(f.id)]", bold=true)
+    print(io, styled"{markdown_footnote:[^$(f.id)]}")
     println(io, '\n', ' '^margin, '│')
-    s = sprint(term, f.text, columns - 10; context=io)
-    lines = split(rstrip(s), '\n')
-    for i in eachindex(lines)
-        print(io, ' '^margin, '│', lines[i])
-        i < lastindex(lines) && println(io)
+    content = annotprint(term, f.text, columns - 10)
+    lines = split(rstrip(content), '\n')
+    for (i, line) in enumerate(lines)
+        print(io, ' '^margin, '│', line)
+        i < length(lines) && println(io)
     end
 end
 
 function term(io::IO, md::List, columns)
     for (i, point) in enumerate(md.items)
-        print(io, ' '^2margin, isordered(md) ? "$(i + md.ordered - 1). " : "•  ")
-        print_wrapped(io, width = columns-(4margin+2), pre = ' '^(2margin+3),
-                          i = 2margin+2) do io
-            term(io, point, columns - 10)
+        bullet = isordered(md) ? "$(i + md.ordered - 1)." : "• "
+        print(io, ' '^2margin, styled"{markdown_list:$bullet} ")
+        content = annotprint(term, point, columns - 10)
+        lines = split(rstrip(content), '\n')
+        for (l, line) in enumerate(lines)
+            l > 1 && print(io, ' '^(2margin+3))
+            print(io, lstrip(line))
+            l < length(lines) && println(io)
         end
-        i < lastindex(md.items) && print(io, '\n', '\n')
-    end
-end
-
-function _term_header(io::IO, md, char, columns)
-    text = terminline_string(io, md.text)
-    with_output_color(:bold, io) do io
-        pre = ' '^margin
-        print(io, pre)
-        line_no, lastline_width = print_wrapped(io, text,
-                                                width=columns - 4margin; pre)
-        line_width = min(lastline_width, columns)
-        if line_no > 1
-            line_width = max(line_width, div(columns, 3)+length(pre))
-        end
-        header_width = max(0, line_width-length(pre))
-        char != ' ' && header_width > 0 && print(io, '\n', ' '^(margin), char^header_width)
+        i < length(md.items) && print(io, '\n'^(1 + md.loose))
     end
 end
 
 const _header_underlines = collect("≡=–-⋅ ")
 # TODO settle on another option with unicode e.g. "≡=≃–∼⋅" ?
 
-function term(io::IO, md::Header{l}, columns) where l
+function term(io::AnnotIO, md::Header{l}, columns) where l
+    face = Symbol("markdown_h$l")
     underline = _header_underlines[l]
-    _term_header(io, md, underline, columns)
+    pre = ' '^margin
+    local line_width
+    with_output_annotations(io, :face => face) do io
+        headline = annotprint(terminline, md.text)
+        lines = wraplines(headline, columns - 4margin)
+        for (i, line) in enumerate(lines)
+            print(io, pre, line)
+            i < length(lines) && println(io)
+        end
+        line_width = if length(lines) == 1
+            min(textwidth(lines[end]), columns)
+        elseif length(lines) > 1
+            max(textwidth(lines[end]), div(columns, 3)+length(pre))
+        else
+            0
+        end
+    end
+    header_width = max(0, line_width)
+    if underline != ' ' && header_width > 0
+        print(io, '\n', ' '^(margin))
+        with_output_annotations(io -> print(io, underline^header_width), io, :face => face)
+    end
 end
 
 function term(io::IO, md::Code, columns)
-    with_output_color(:cyan, io) do io
-        L = lines(md.code)
-        for i in eachindex(L)
-            print(io, ' '^margin, L[i])
-            i < lastindex(L) && println(io)
-        end
+    code = if md.language ∈ ("", "julia", "julia-repl", "jldoctest")
+        highlight(md.code)
+    elseif md.language == "styled"
+        styled(md.code)
+    else
+        styled"{markdown_code:$(md.code)}"
+    end
+    lines = split(code, '\n')
+    for (i, line) in enumerate(lines)
+        print(io, ' '^margin, line)
+        i < length(lines) && println(io)
     end
 end
 
 function term(io::IO, tex::LaTeX, columns)
-    printstyled(io, ' '^margin, tex.formula, color=:magenta)
+    print(io, ' '^margin, styled"{markdown_latex:$(tex.formula)}")
 end
 
 term(io::IO, br::LineBreak, columns) = nothing # line breaks already printed between subsequent elements
 
 function term(io::IO, br::HorizontalRule, columns)
-   print(io, ' '^margin, '─'^(columns - 2margin))
+    print(io, ' '^margin, styled"{markdown_hrule:$('─'^(columns - 2margin))}")
+end
+
+function term(io::IO, md::MarkdownElement, columns)
+    a = IOContext(AnnotatedIOBuffer(), io)
+    term(a, md, columns)
+    print(io, read(seekstart(a.io), AnnotatedString))
 end
 
 term(io::IO, x, _) = show(io, MIME"text/plain"(), x)
 
 # Inline Content
 
-terminline_string(io::IO, md) = sprint(terminline, md; context=io)
-
 terminline(io::IO, content...) = terminline(io, collect(content))
 
 function terminline(io::IO, content::Vector)
@@ -140,12 +157,12 @@ function terminline(io::IO, md::AbstractString)
     print(io, replace(md, r"[\s\t\n]+" => ' '))
 end
 
-function terminline(io::IO, md::Bold)
-    with_output_color(terminline, :bold, io, md.text)
+function terminline(io::AnnotIO, md::Bold)
+    with_output_annotations(io -> terminline(io, md.text), io, :face => :bold)
 end
 
-function terminline(io::IO, md::Italic)
-    with_output_color(terminline, :underline, io, md.text)
+function terminline(io::AnnotIO, md::Italic)
+    with_output_annotations(io -> terminline(io, md.text), io, :face => :italic)
 end
 
 function terminline(io::IO, md::LineBreak)
@@ -156,20 +173,36 @@ function terminline(io::IO, md::Image)
     terminline(io, "(Image: $(md.alt))")
 end
 
-terminline(io::IO, f::Footnote) = with_output_color(terminline, :bold, io, "[^$(f.id)]")
+function terminline(io::IO, f::Footnote)
+    print(io, styled"{markdown_footnote:[^$(f.id)]}")
+end
 
-function terminline(io::IO, md::Link)
-    url = !Base.startswith(md.url, "@ref") ? " ($(md.url))" : ""
-    text = terminline_string(io, md.text)
-    terminline(io, text, url)
+function terminline(io::AnnotIO, md::Link)
+    annots = if occursin(r"^(https?|file)://", md.url)
+        (:face => :markdown_link, :link => md.url)
+    else
+        (:face => :markdown_link,)
+    end
+    with_output_annotations(io -> terminline(io, md.text), io, annots...)
 end
 
 function terminline(io::IO, code::Code)
-    printstyled(io, code.code, color=:cyan)
+    body = if code.language == "styled"
+        styled(code.code)
+    else
+        code.code
+    end
+    print(io, styled"{markdown_inlinecode:$body}")
 end
 
 function terminline(io::IO, tex::LaTeX)
-    printstyled(io, tex.formula, color=:magenta)
+    print(io, styled"{markdown_latex:$(tex.formula)}")
+end
+
+function terminline(io::IO, md::MarkdownElement)
+    a = IOContext(AnnotatedIOBuffer(), io)
+    terminline(a, md)
+    print(io, read(seekstart(a.io), AnnotatedString))
 end
 
 terminline(io::IO, x) = show(io, MIME"text/plain"(), x)
diff --git a/stdlib/Markdown/test/runtests.jl b/stdlib/Markdown/test/runtests.jl
index 116282a0bea3b..a3026683ad1e7 100644
--- a/stdlib/Markdown/test/runtests.jl
+++ b/stdlib/Markdown/test/runtests.jl
@@ -1,6 +1,6 @@
 # This file is a part of Julia. License is MIT: https://julialang.org/license
 
-using Test, Markdown
+using Test, Markdown, StyledStrings
 import Markdown: MD, Paragraph, Header, Italic, Bold, LineBreak, plain, term, html, rst, Table, Code, LaTeX, Footnote
 import Base: show
 
@@ -233,7 +233,7 @@ World""" |> plain == "Hello\n\n---\n\nWorld\n"
 
 # multiple whitespace is ignored
 @test sprint(term, md"a  b") == "  a b"
-@test sprint(term, md"[x](https://julialang.org)") == "  x (https://julialang.org)"
+@test sprint(term, md"[x](https://julialang.org)") == "  x"
 @test sprint(term, md"[x](@ref)") == "  x"
 @test sprint(term, md"[x](@ref something)") == "  x"
 @test sprint(term, md"![x](https://julialang.org)") == "  (Image: x)"
@@ -298,6 +298,7 @@ end
 let doc =
     md"""
     1. a bc def ghij a bc def ghij a bc def ghij a bc def ghij a bc def ghij a bc def ghij a bc def ghij a bc def ghij a bc def ghij
+
     2. a bc def ghij a bc def ghij a bc def ghij a bc def ghij a bc def ghij a bc def ghij a bc def ghij a bc def ghij a bc def ghij
     """
     str = sprint(term, doc, 50)
@@ -376,8 +377,8 @@ table = md"""
 # mime output
 let out =
     @test sprint(show, "text/plain", book) ==
-        "  Title\n  ≡≡≡≡≡\n\n  Some discussion\n\n  │  A quote\n\n  Section important\n  =================\n\n  Some bolded\n\n    •  list1\n\n    •  list2"
-    @test sprint(show, "text/plain", md"#") == "  " # edge case of empty header
+        "  Title\n  ≡≡≡≡≡\n\n  Some discussion\n\n  │  A quote\n\n  Section important\n  =================\n\n  Some bolded\n\n    •  list1\n    •  list2"
+    @test sprint(show, "text/plain", md"#") == "" # edge case of empty header
     @test sprint(show, "text/markdown", book) ==
         """
         # Title
@@ -1157,7 +1158,7 @@ let buf = IOBuffer()
     show(buf, "text/markdown", md"*emph*")
     @test String(take!(buf)) == "*emph*\n"
     show(IOContext(buf, :color=>true), "text/plain", md"*emph*")
-    @test String(take!(buf)) == "  \e[4memph\e[24m"
+    @test String(take!(buf)) in ("  \e[3memph\e[23m", "  \e[4memph\e[24m")
 end
 
 let word = "Markdown" # disable underline when wrapping lines
@@ -1166,8 +1167,8 @@ let word = "Markdown" # disable underline when wrapping lines
     long_italic_text = Markdown.parse('_' * join(fill(word, 10), ' ') * '_')
     show(ctx, MIME("text/plain"), long_italic_text)
     lines = split(String(take!(buf)), '\n')
-    @test endswith(lines[begin], Base.disable_text_style[:underline])
-    @test startswith(lines[begin+1], ' '^Markdown.margin * Base.text_colors[:underline])
+    @test endswith(lines[begin], r"\e\[2[34]m")
+    @test startswith(lines[begin+1], Regex(' '^Markdown.margin * "\e\\[[34]m"))
 end
 
 let word = "Markdown" # pre is of size Markdown.margin when wrapping title
@@ -1176,7 +1177,9 @@ let word = "Markdown" # pre is of size Markdown.margin when wrapping title
     long_title = Markdown.parse("# " * join(fill(word, 3)))
     show(ctx, MIME("text/plain"), long_title)
     lines = split(String(take!(buf)), '\n')
-    @test all(startswith(Base.text_colors[:bold] * ' '^Markdown.margin), lines)
+    @test all(l -> startswith(l, ' '^Markdown.margin * StyledStrings.ANSI_STYLE_CODES.bold_weight) ||
+                   startswith(l, StyledStrings.ANSI_STYLE_CODES.bold_weight * ' '^Markdown.margin),
+              lines)
 end
 
 struct Struct49454 end
@@ -1259,8 +1262,9 @@ end
     s = @md_str """
        Misc:\\
        - line\\
+         break
        """
-    @test sprint(show, MIME("text/plain"), s) == "  Misc:\n  - line"
+    @test sprint(show, MIME("text/plain"), s) == "  Misc:\n  - line\n   break"
 end
 
 @testset "pullrequest #41552: a code block has \\end{verbatim}" begin
diff --git a/stdlib/StyledStrings.version b/stdlib/StyledStrings.version
index 81a599f125406..2067083aec74b 100644
--- a/stdlib/StyledStrings.version
+++ b/stdlib/StyledStrings.version
@@ -1,4 +1,4 @@
 STYLEDSTRINGS_BRANCH = main
-STYLEDSTRINGS_SHA1 = ac472083359dde956aed8c61d43b8158ac84d9ce
+STYLEDSTRINGS_SHA1 = d7496d24d3f05536bce6a7eb4cd8ca05a75c02aa
 STYLEDSTRINGS_GIT_URL := https://github.com/JuliaLang/StyledStrings.jl.git
 STYLEDSTRINGS_TAR_URL = https://api.github.com/repos/JuliaLang/StyledStrings.jl/tarball/$1
diff --git a/test/precompile.jl b/test/precompile.jl
index ffd6e24789aba..ea99653fe89be 100644
--- a/test/precompile.jl
+++ b/test/precompile.jl
@@ -445,6 +445,7 @@ precompile_test_harness(false) do dir
             # and their dependencies
             Dict(Base.PkgId(Base.root_module(Base, :SHA)) => Base.module_build_id(Base.root_module(Base, :SHA))),
             Dict(Base.PkgId(Base.root_module(Base, :Markdown)) => Base.module_build_id(Base.root_module(Base, :Markdown))),
+            Dict(Base.PkgId(Base.root_module(Base, :JuliaSyntaxHighlighting)) => Base.module_build_id(Base.root_module(Base, :JuliaSyntaxHighlighting))),
             Dict(Base.PkgId(Base.root_module(Base, :StyledStrings)) => Base.module_build_id(Base.root_module(Base, :StyledStrings))),
             # and their dependencies
             Dict(Base.PkgId(Base.root_module(Base, :Base64)) => Base.module_build_id(Base.root_module(Base, :Base64))),