gh-131507: Add support for syntax highlighting in PyREPL (GH-133247)

Co-authored-by: Victorien <65306057+Viicos@users.noreply.github.com>
Co-authored-by: Hugo van Kemenade <1324225+hugovk@users.noreply.github.com>

21 files changed, 654 insertions, 99 deletions

diff --git a/Doc/whatsnew/3.14.rst b/Doc/whatsnew/3.14.rst
index 8e8578f6a99..2f8b652d47e 100644
--- a/Doc/whatsnew/3.14.rst
+++ b/Doc/whatsnew/3.14.rst
@@ -560,6 +560,23 @@ For further information on how to build Python, see
 (Contributed by Ken Jin in :gh:`128563`, with ideas on how to implement this
 in CPython by Mark Shannon, Garrett Gu, Haoran Xu, and Josh Haberman.)
 
+Syntax highlighting in PyREPL
+-----------------------------
+
+The default :term:`interactive` shell now highlights Python syntax as you
+type.  The feature is enabled by default unless the
+:envvar:`PYTHON_BASIC_REPL` environment is set or any color-disabling
+environment variables are used. See :ref:`using-on-controlling-color` for
+details.
+
+The default color theme for syntax highlighting strives for good contrast
+and uses exclusively the 4-bit VGA standard ANSI color codes for maximum
+compatibility. The theme can be customized using an experimental API
+``_colorize.set_theme()``.  This can be called interactively, as well as
+in the :envvar:`PYTHONSTARTUP` script.
+
+(Contributed by Łukasz Langa in :gh:`131507`.)
+
 
 Other language changes
 ======================
diff --git a/Lib/_colorize.py b/Lib/_colorize.py
index a39ff2ce5c1..54895488e74 100644
--- a/Lib/_colorize.py
+++ b/Lib/_colorize.py
@@ -7,7 +7,22 @@ COLORIZE = True
 
 # types
 if False:
-    from typing import IO
+    from typing import IO, Literal
+
+    type ColorTag = Literal[
+        "PROMPT",
+        "KEYWORD",
+        "BUILTIN",
+        "COMMENT",
+        "STRING",
+        "NUMBER",
+        "OP",
+        "DEFINITION",
+        "SOFT_KEYWORD",
+        "RESET",
+    ]
+
+    theme: dict[ColorTag, str]
 
 
 class ANSIColors:
@@ -23,6 +38,7 @@ class ANSIColors:
     WHITE = "\x1b[37m"  # more like LIGHT GRAY
     YELLOW = "\x1b[33m"
 
+    BOLD = "\x1b[1m"
     BOLD_BLACK = "\x1b[1;30m"  # DARK GRAY
     BOLD_BLUE = "\x1b[1;34m"
     BOLD_CYAN = "\x1b[1;36m"
@@ -120,3 +136,28 @@ def can_colorize(*, file: IO[str] | IO[bytes] | None = None) -> bool:
         return os.isatty(file.fileno())
     except io.UnsupportedOperation:
         return hasattr(file, "isatty") and file.isatty()
+
+
+def set_theme(t: dict[ColorTag, str] | None = None) -> None:
+    global theme
+
+    if t:
+        theme = t
+        return
+
+    colors = get_colors()
+    theme = {
+        "PROMPT": colors.BOLD_MAGENTA,
+        "KEYWORD": colors.BOLD_BLUE,
+        "BUILTIN": colors.CYAN,
+        "COMMENT": colors.RED,
+        "STRING": colors.GREEN,
+        "NUMBER": colors.YELLOW,
+        "OP": colors.RESET,
+        "DEFINITION": colors.BOLD,
+        "SOFT_KEYWORD": colors.BOLD_BLUE,
+        "RESET": colors.RESET,
+    }
+
+
+set_theme()
diff --git a/Lib/_pyrepl/_module_completer.py b/Lib/_pyrepl/_module_completer.py
index 1fb043e0b70..347f05607c7 100644
--- a/Lib/_pyrepl/_module_completer.py
+++ b/Lib/_pyrepl/_module_completer.py
@@ -2,6 +2,7 @@ from __future__ import annotations
 
 import pkgutil
 import sys
+import token
 import tokenize
 from io import StringIO
 from contextlib import contextmanager
@@ -180,8 +181,8 @@ class ImportParser:
     when parsing multiple statements.
     """
     _ignored_tokens = {
-        tokenize.INDENT, tokenize.DEDENT, tokenize.COMMENT,
-        tokenize.NL, tokenize.NEWLINE, tokenize.ENDMARKER
+        token.INDENT, token.DEDENT, token.COMMENT,
+        token.NL, token.NEWLINE, token.ENDMARKER
     }
     _keywords = {'import', 'from', 'as'}
 
@@ -350,11 +351,11 @@ class TokenQueue:
     def peek_name(self) -> bool:
         if not (tok := self.peek()):
             return False
-        return tok.type == tokenize.NAME
+        return tok.type == token.NAME
 
     def pop_name(self) -> str:
         tok = self.pop()
-        if tok.type != tokenize.NAME:
+        if tok.type != token.NAME:
             raise ParseError('pop_name')
         return tok.string
 
diff --git a/Lib/_pyrepl/commands.py b/Lib/_pyrepl/commands.py
index cbb6d85f683..2054a8e400f 100644
--- a/Lib/_pyrepl/commands.py
+++ b/Lib/_pyrepl/commands.py
@@ -21,6 +21,7 @@
 
 from __future__ import annotations
 import os
+import time
 
 # Categories of actions:
 #  killing
@@ -31,6 +32,7 @@ import os
 #  finishing
 # [completion]
 
+from .trace import trace
 
 # types
 if False:
@@ -471,19 +473,24 @@ class show_history(Command):
 
 
 class paste_mode(Command):
-
     def do(self) -> None:
         self.reader.paste_mode = not self.reader.paste_mode
         self.reader.dirty = True
 
 
-class enable_bracketed_paste(Command):
-    def do(self) -> None:
-        self.reader.paste_mode = True
-        self.reader.in_bracketed_paste = True
-
-class disable_bracketed_paste(Command):
-    def do(self) -> None:
-        self.reader.paste_mode = False
-        self.reader.in_bracketed_paste = False
-        self.reader.dirty = True
+class perform_bracketed_paste(Command):
+    def do(self) -> None:
+        done = "\x1b[201~"
+        data = ""
+        start = time.time()
+        while done not in data:
+            self.reader.console.wait(100)
+            ev = self.reader.console.getpending()
+            data += ev.data
+        trace(
+            "bracketed pasting of {l} chars done in {s:.2f}s",
+            l=len(data),
+            s=time.time() - start,
+        )
+        self.reader.insert(data.replace(done, ""))
+        self.reader.last_refresh_cache.invalidated = True
diff --git a/Lib/_pyrepl/mypy.ini b/Lib/_pyrepl/mypy.ini
index eabd0e9b440..9375a55b53c 100644
--- a/Lib/_pyrepl/mypy.ini
+++ b/Lib/_pyrepl/mypy.ini
@@ -23,7 +23,3 @@ check_untyped_defs = False
 # Various internal modules that typeshed deliberately doesn't have stubs for:
 [mypy-_abc.*,_opcode.*,_overlapped.*,_testcapi.*,_testinternalcapi.*,test.*]
 ignore_missing_imports = True
-
-# Other untyped parts of the stdlib
-[mypy-idlelib.*]
-ignore_missing_imports = True
diff --git a/Lib/_pyrepl/reader.py b/Lib/_pyrepl/reader.py
index 7fc2422dac9..65c2230dfd6 100644
--- a/Lib/_pyrepl/reader.py
+++ b/Lib/_pyrepl/reader.py
@@ -22,14 +22,13 @@
 from __future__ import annotations
 
 import sys
+import _colorize
 
 from contextlib import contextmanager
 from dataclasses import dataclass, field, fields
-from _colorize import can_colorize, ANSIColors
-
 
 from . import commands, console, input
-from .utils import wlen, unbracket, disp_str
+from .utils import wlen, unbracket, disp_str, gen_colors
 from .trace import trace
 
 
@@ -38,8 +37,7 @@ Command = commands.Command
 from .types import Callback, SimpleContextManager, KeySpec, CommandName
 
 
-# syntax classes:
-
+# syntax classes
 SYNTAX_WHITESPACE, SYNTAX_WORD, SYNTAX_SYMBOL = range(3)
 
 
@@ -105,8 +103,7 @@ default_keymap: tuple[tuple[KeySpec, CommandName], ...] = tuple(
         (r"\M-9", "digit-arg"),
         (r"\M-\n", "accept"),
         ("\\\\", "self-insert"),
-        (r"\x1b[200~", "enable_bracketed_paste"),
-        (r"\x1b[201~", "disable_bracketed_paste"),
+        (r"\x1b[200~", "perform-bracketed-paste"),
         (r"\x03", "ctrl-c"),
     ]
     + [(c, "self-insert") for c in map(chr, range(32, 127)) if c != "\\"]
@@ -144,16 +141,17 @@ class Reader:
     Instance variables of note include:
 
       * buffer:
-        A *list* (*not* a string at the moment :-) containing all the
-        characters that have been entered.
+        A per-character list containing all the characters that have been
+        entered. Does not include color information.
       * console:
         Hopefully encapsulates the OS dependent stuff.
       * pos:
         A 0-based index into 'buffer' for where the insertion point
         is.
       * screeninfo:
-        Ahem.  This list contains some info needed to move the
-        insertion point around reasonably efficiently.
+        A list of screen position tuples. Each list element is a tuple
+        representing information on visible line length for a given line.
+        Allows for efficient skipping of color escape sequences.
       * cxy, lxy:
         the position of the insertion point in screen ...
       * syntax_table:
@@ -203,7 +201,6 @@ class Reader:
     dirty: bool = False
     finished: bool = False
     paste_mode: bool = False
-    in_bracketed_paste: bool = False
     commands: dict[str, type[Command]] = field(default_factory=make_default_commands)
     last_command: type[Command] | None = None
     syntax_table: dict[str, int] = field(default_factory=make_default_syntax_table)
@@ -221,7 +218,6 @@ class Reader:
     ## cached metadata to speed up screen refreshes
     @dataclass
     class RefreshCache:
-        in_bracketed_paste: bool = False
         screen: list[str] = field(default_factory=list)
         screeninfo: list[tuple[int, list[int]]] = field(init=False)
         line_end_offsets: list[int] = field(default_factory=list)
@@ -235,7 +231,6 @@ class Reader:
                          screen: list[str],
                          screeninfo: list[tuple[int, list[int]]],
             ) -> None:
-            self.in_bracketed_paste = reader.in_bracketed_paste
             self.screen = screen.copy()
             self.screeninfo = screeninfo.copy()
             self.pos = reader.pos
@@ -248,8 +243,7 @@ class Reader:
                 return False
             dimensions = reader.console.width, reader.console.height
             dimensions_changed = dimensions != self.dimensions
-            paste_changed = reader.in_bracketed_paste != self.in_bracketed_paste
-            return not (dimensions_changed or paste_changed)
+            return not dimensions_changed
 
         def get_cached_location(self, reader: Reader) -> tuple[int, int]:
             if self.invalidated:
@@ -279,7 +273,7 @@ class Reader:
         self.screeninfo = [(0, [])]
         self.cxy = self.pos2xy()
         self.lxy = (self.pos, 0)
-        self.can_colorize = can_colorize()
+        self.can_colorize = _colorize.can_colorize()
 
         self.last_refresh_cache.screeninfo = self.screeninfo
         self.last_refresh_cache.pos = self.pos
@@ -316,6 +310,12 @@ class Reader:
         pos -= offset
 
         prompt_from_cache = (offset and self.buffer[offset - 1] != "\n")
+
+        if self.can_colorize:
+            colors = list(gen_colors(self.get_unicode()))
+        else:
+            colors = None
+        trace("colors = {colors}", colors=colors)
         lines = "".join(self.buffer[offset:]).split("\n")
         cursor_found = False
         lines_beyond_cursor = 0
@@ -343,9 +343,8 @@ class Reader:
                 screeninfo.append((0, []))
             pos -= line_len + 1
             prompt, prompt_len = self.process_prompt(prompt)
-            chars, char_widths = disp_str(line)
+            chars, char_widths = disp_str(line, colors, offset)
             wrapcount = (sum(char_widths) + prompt_len) // self.console.width
-            trace("wrapcount = {wrapcount}", wrapcount=wrapcount)
             if wrapcount == 0 or not char_widths:
                 offset += line_len + 1  # Takes all of the line plus the newline
                 last_refresh_line_end_offsets.append(offset)
@@ -479,7 +478,7 @@ class Reader:
         'lineno'."""
         if self.arg is not None and cursor_on_line:
             prompt = f"(arg: {self.arg}) "
-        elif self.paste_mode and not self.in_bracketed_paste:
+        elif self.paste_mode:
             prompt = "(paste) "
         elif "\n" in self.buffer:
             if lineno == 0:
@@ -492,7 +491,11 @@ class Reader:
             prompt = self.ps1
 
         if self.can_colorize:
-            prompt = f"{ANSIColors.BOLD_MAGENTA}{prompt}{ANSIColors.RESET}"
+            prompt = (
+                f"{_colorize.theme["PROMPT"]}"
+                f"{prompt}"
+                f"{_colorize.theme["RESET"]}"
+            )
         return prompt
 
     def push_input_trans(self, itrans: input.KeymapTranslator) -> None:
@@ -567,6 +570,7 @@ class Reader:
     def update_cursor(self) -> None:
         """Move the cursor to reflect changes in self.pos"""
         self.cxy = self.pos2xy()
+        trace("update_cursor({pos}) = {cxy}", pos=self.pos, cxy=self.cxy)
         self.console.move_cursor(*self.cxy)
 
     def after_command(self, cmd: Command) -> None:
@@ -633,9 +637,6 @@ class Reader:
 
     def refresh(self) -> None:
         """Recalculate and refresh the screen."""
-        if self.in_bracketed_paste and self.buffer and not self.buffer[-1] == "\n":
-            return
-
         # this call sets up self.cxy, so call it first.
         self.screen = self.calc_screen()
         self.console.refresh(self.screen, self.cxy)
diff --git a/Lib/_pyrepl/readline.py b/Lib/_pyrepl/readline.py
index 9d58829faf1..560a9db1921 100644
--- a/Lib/_pyrepl/readline.py
+++ b/Lib/_pyrepl/readline.py
@@ -276,10 +276,6 @@ class maybe_accept(commands.Command):
         r = self.reader  # type: ignore[assignment]
         r.dirty = True  # this is needed to hide the completion menu, if visible
 
-        if self.reader.in_bracketed_paste:
-            r.insert("\n")
-            return
-
         # if there are already several lines and the cursor
         # is not on the last one, always insert a new \n.
         text = r.get_unicode()
diff --git a/Lib/_pyrepl/simple_interact.py b/Lib/_pyrepl/simple_interact.py
index 4c74466118b..e2274629b65 100644
--- a/Lib/_pyrepl/simple_interact.py
+++ b/Lib/_pyrepl/simple_interact.py
@@ -157,7 +157,6 @@ def run_multiline_interactive_console(
             r.pos = len(r.get_unicode())
             r.dirty = True
             r.refresh()
-            r.in_bracketed_paste = False
             console.write("\nKeyboardInterrupt\n")
             console.resetbuffer()
         except MemoryError:
diff --git a/Lib/_pyrepl/unix_console.py b/Lib/_pyrepl/unix_console.py
index 96379bc20f3..07b160d2324 100644
--- a/Lib/_pyrepl/unix_console.py
+++ b/Lib/_pyrepl/unix_console.py
@@ -150,8 +150,6 @@ class UnixConsole(Console):
 
         self.pollob = poll()
         self.pollob.register(self.input_fd, select.POLLIN)
-        self.input_buffer = b""
-        self.input_buffer_pos = 0
         curses.setupterm(term or None, self.output_fd)
         self.term = term
 
@@ -199,22 +197,8 @@ class UnixConsole(Console):
         self.event_queue = EventQueue(self.input_fd, self.encoding)
         self.cursor_visible = 1
 
-    def more_in_buffer(self) -> bool:
-        return bool(
-            self.input_buffer
-            and self.input_buffer_pos < len(self.input_buffer)
-        )
-
     def __read(self, n: int) -> bytes:
-        if not self.more_in_buffer():
-            self.input_buffer = os.read(self.input_fd, 10000)
-
-        ret = self.input_buffer[self.input_buffer_pos : self.input_buffer_pos + n]
-        self.input_buffer_pos += len(ret)
-        if self.input_buffer_pos >= len(self.input_buffer):
-            self.input_buffer = b""
-            self.input_buffer_pos = 0
-        return ret
+        return os.read(self.input_fd, n)
 
 
     def change_encoding(self, encoding: str) -> None:
@@ -422,7 +406,6 @@ class UnixConsole(Console):
         """
         return (
             not self.event_queue.empty()
-            or self.more_in_buffer()
             or bool(self.pollob.poll(timeout))
         )
 
@@ -525,6 +508,7 @@ class UnixConsole(Console):
                 e.raw += e.raw
 
             amount = struct.unpack("i", ioctl(self.input_fd, FIONREAD, b"\0\0\0\0"))[0]
+            trace("getpending({a})", a=amount)
             raw = self.__read(amount)
             data = str(raw, self.encoding, "replace")
             e.data += data
diff --git a/Lib/_pyrepl/utils.py b/Lib/_pyrepl/utils.py
index 7437fbe1ab9..fe154aa59a0 100644
--- a/Lib/_pyrepl/utils.py
+++ b/Lib/_pyrepl/utils.py
@@ -1,6 +1,17 @@
+from __future__ import annotations
+import builtins
+import functools
+import keyword
 import re
+import token as T
+import tokenize
 import unicodedata
-import functools
+import _colorize
+
+from collections import deque
+from io import StringIO
+from tokenize import TokenInfo as TI
+from typing import Iterable, Iterator, Match, NamedTuple, Self
 
 from .types import CharBuffer, CharWidths
 from .trace import trace
@@ -8,6 +19,32 @@ from .trace import trace
 ANSI_ESCAPE_SEQUENCE = re.compile(r"\x1b\[[ -@]*[A-~]")
 ZERO_WIDTH_BRACKET = re.compile(r"\x01.*?\x02")
 ZERO_WIDTH_TRANS = str.maketrans({"\x01": "", "\x02": ""})
+IDENTIFIERS_AFTER = {"def", "class"}
+BUILTINS = {str(name) for name in dir(builtins) if not name.startswith('_')}
+
+
+class Span(NamedTuple):
+    """Span indexing that's inclusive on both ends."""
+
+    start: int
+    end: int
+
+    @classmethod
+    def from_re(cls, m: Match[str], group: int | str) -> Self:
+        re_span = m.span(group)
+        return cls(re_span[0], re_span[1] - 1)
+
+    @classmethod
+    def from_token(cls, token: TI, line_len: list[int]) -> Self:
+        return cls(
+            line_len[token.start[0] - 1] + token.start[1],
+            line_len[token.end[0] - 1] + token.end[1] - 1,
+        )
+
+
+class ColorSpan(NamedTuple):
+    span: Span
+    tag: _colorize.ColorTag
 
 
 @functools.cache
@@ -41,17 +78,207 @@ def unbracket(s: str, including_content: bool = False) -> str:
     return s.translate(ZERO_WIDTH_TRANS)
 
 
-def disp_str(buffer: str) -> tuple[CharBuffer, CharWidths]:
-    r"""Decompose the input buffer into a printable variant.
+def gen_colors(buffer: str) -> Iterator[ColorSpan]:
+    """Returns a list of index spans to color using the given color tag.
+
+    The input `buffer` should be a valid start of a Python code block, i.e.
+    it cannot be a block starting in the middle of a multiline string.
+    """
+    sio = StringIO(buffer)
+    line_lengths = [0] + [len(line) for line in sio.readlines()]
+    # make line_lengths cumulative
+    for i in range(1, len(line_lengths)):
+        line_lengths[i] += line_lengths[i-1]
+
+    sio.seek(0)
+    gen = tokenize.generate_tokens(sio.readline)
+    last_emitted: ColorSpan | None = None
+    try:
+        for color in gen_colors_from_token_stream(gen, line_lengths):
+            yield color
+            last_emitted = color
+    except tokenize.TokenError as te:
+        yield from recover_unterminated_string(
+            te, line_lengths, last_emitted, buffer
+        )
+
+
+def recover_unterminated_string(
+    exc: tokenize.TokenError,
+    line_lengths: list[int],
+    last_emitted: ColorSpan | None,
+    buffer: str,
+) -> Iterator[ColorSpan]:
+    msg, loc = exc.args
+    if loc is None:
+        return
+
+    line_no, column = loc
+
+    if msg.startswith(
+        (
+            "unterminated string literal",
+            "unterminated f-string literal",
+            "unterminated t-string literal",
+            "EOF in multi-line string",
+            "unterminated triple-quoted f-string literal",
+            "unterminated triple-quoted t-string literal",
+        )
+    ):
+        start = line_lengths[line_no - 1] + column - 1
+        end = line_lengths[-1] - 1
+
+        # in case FSTRING_START was already emitted
+        if last_emitted and start <= last_emitted.span.start:
+            trace("before last emitted = {s}", s=start)
+            start = last_emitted.span.end + 1
+
+        span = Span(start, end)
+        trace("yielding span {a} -> {b}", a=span.start, b=span.end)
+        yield ColorSpan(span, "STRING")
+    else:
+        trace(
+            "unhandled token error({buffer}) = {te}",
+            buffer=repr(buffer),
+            te=str(exc),
+        )
+
+
+def gen_colors_from_token_stream(
+    token_generator: Iterator[TI],
+    line_lengths: list[int],
+) -> Iterator[ColorSpan]:
+    token_window = prev_next_window(token_generator)
+
+    is_def_name = False
+    bracket_level = 0
+    for prev_token, token, next_token in token_window:
+        assert token is not None
+        if token.start == token.end:
+            continue
+
+        match token.type:
+            case (
+                T.STRING
+                | T.FSTRING_START | T.FSTRING_MIDDLE | T.FSTRING_END
+                | T.TSTRING_START | T.TSTRING_MIDDLE | T.TSTRING_END
+            ):
+                span = Span.from_token(token, line_lengths)
+                yield ColorSpan(span, "STRING")
+            case T.COMMENT:
+                span = Span.from_token(token, line_lengths)
+                yield ColorSpan(span, "COMMENT")
+            case T.NUMBER:
+                span = Span.from_token(token, line_lengths)
+                yield ColorSpan(span, "NUMBER")
+            case T.OP:
+                if token.string in "([{":
+                    bracket_level += 1
+                elif token.string in ")]}":
+                    bracket_level -= 1
+                span = Span.from_token(token, line_lengths)
+                yield ColorSpan(span, "OP")
+            case T.NAME:
+                if is_def_name:
+                    is_def_name = False
+                    span = Span.from_token(token, line_lengths)
+                    yield ColorSpan(span, "DEFINITION")
+                elif keyword.iskeyword(token.string):
+                    span = Span.from_token(token, line_lengths)
+                    yield ColorSpan(span, "KEYWORD")
+                    if token.string in IDENTIFIERS_AFTER:
+                        is_def_name = True
+                elif (
+                    keyword.issoftkeyword(token.string)
+                    and bracket_level == 0
+                    and is_soft_keyword_used(prev_token, token, next_token)
+                ):
+                    span = Span.from_token(token, line_lengths)
+                    yield ColorSpan(span, "SOFT_KEYWORD")
+                elif token.string in BUILTINS:
+                    span = Span.from_token(token, line_lengths)
+                    yield ColorSpan(span, "BUILTIN")
+
+
+keyword_first_sets_match = {"False", "None", "True", "await", "lambda", "not"}
+keyword_first_sets_case = {"False", "None", "True"}
+
+
+def is_soft_keyword_used(*tokens: TI | None) -> bool:
+    """Returns True if the current token is a keyword in this context.
+
+    For the `*tokens` to match anything, they have to be a three-tuple of
+    (previous, current, next).
+    """
+    trace("is_soft_keyword_used{t}", t=tokens)
+    match tokens:
+        case (
+            None | TI(T.NEWLINE) | TI(T.INDENT) | TI(string=":"),
+            TI(string="match"),
+            TI(T.NUMBER | T.STRING | T.FSTRING_START | T.TSTRING_START)
+            | TI(T.OP, string="(" | "*" | "[" | "{" | "~" | "...")
+        ):
+            return True
+        case (
+            None | TI(T.NEWLINE) | TI(T.INDENT) | TI(string=":"),
+            TI(string="match"),
+            TI(T.NAME, string=s)
+        ):
+            if keyword.iskeyword(s):
+                return s in keyword_first_sets_match
+            return True
+        case (
+            None | TI(T.NEWLINE) | TI(T.INDENT) | TI(string=":"),
+            TI(string="case"),
+            TI(T.NUMBER | T.STRING | T.FSTRING_START | T.TSTRING_START)
+            | TI(T.OP, string="(" | "*" | "-" | "[" | "{")
+        ):
+            return True
+        case (
+            None | TI(T.NEWLINE) | TI(T.INDENT) | TI(string=":"),
+            TI(string="case"),
+            TI(T.NAME, string=s)
+        ):
+            if keyword.iskeyword(s):
+                return s in keyword_first_sets_case
+            return True
+        case (TI(string="case"), TI(string="_"), TI(string=":")):
+            return True
+        case _:
+            return False
+
+
+def disp_str(
+    buffer: str, colors: list[ColorSpan] | None = None, start_index: int = 0
+) -> tuple[CharBuffer, CharWidths]:
+    r"""Decompose the input buffer into a printable variant with applied colors.
 
     Returns a tuple of two lists:
-    - the first list is the input buffer, character by character;
+    - the first list is the input buffer, character by character, with color
+      escape codes added (while those codes contain multiple ASCII characters,
+      each code is considered atomic *and is attached for the corresponding
+      visible character*);
     - the second list is the visible width of each character in the input
       buffer.
 
+    Note on colors:
+    - The `colors` list, if provided, is partially consumed within. We're using
+      a list and not a generator since we need to hold onto the current
+      unfinished span between calls to disp_str in case of multiline strings.
+    - The `colors` list is computed from the start of the input block. `buffer`
+      is only a subset of that input block, a single line within. This is why
+      we need `start_index` to inform us which position is the start of `buffer`
+      actually within user input. This allows us to match color spans correctly.
+
     Examples:
     >>> utils.disp_str("a = 9")
     (['a', ' ', '=', ' ', '9'], [1, 1, 1, 1, 1])
+
+    >>> line = "while 1:"
+    >>> colors = list(utils.gen_colors(line))
+    >>> utils.disp_str(line, colors=colors)
+    (['\x1b[1;34mw', 'h', 'i', 'l', 'e\x1b[0m', ' ', '1', ':'], [1, 1, 1, 1, 1, 1, 1, 1])
+
     """
     chars: CharBuffer = []
     char_widths: CharWidths = []
@@ -59,7 +286,20 @@ def disp_str(buffer: str) -> tuple[CharBuffer, CharWidths]:
     if not buffer:
         return chars, char_widths
 
-    for c in buffer:
+    while colors and colors[0].span.end < start_index:
+        # move past irrelevant spans
+        colors.pop(0)
+
+    pre_color = ""
+    post_color = ""
+    if colors and colors[0].span.start < start_index:
+        # looks like we're continuing a previous color (e.g. a multiline str)
+        pre_color = _colorize.theme[colors[0].tag]
+
+    for i, c in enumerate(buffer, start_index):
+        if colors and colors[0].span.start == i:  # new color starts now
+            pre_color = _colorize.theme[colors[0].tag]
+
         if c == "\x1a":  # CTRL-Z on Windows
             chars.append(c)
             char_widths.append(2)
@@ -73,5 +313,43 @@ def disp_str(buffer: str) -> tuple[CharBuffer, CharWidths]:
         else:
             chars.append(c)
             char_widths.append(str_width(c))
-    trace("disp_str({buffer}) = {s}, {b}", buffer=repr(buffer), s=chars, b=char_widths)
+
+        if colors and colors[0].span.end == i:  # current color ends now
+            post_color = _colorize.theme["RESET"]
+            colors.pop(0)
+
+        chars[-1] = pre_color + chars[-1] + post_color
+        pre_color = ""
+        post_color = ""
+
+    if colors and colors[0].span.start < i and colors[0].span.end > i:
+        # even though the current color should be continued, reset it for now.
+        # the next call to `disp_str()` will revive it.
+        chars[-1] += _colorize.theme["RESET"]
+
     return chars, char_widths
+
+
+def prev_next_window[T](
+    iterable: Iterable[T]
+) -> Iterator[tuple[T | None, ...]]:
+    """Generates three-tuples of (previous, current, next) items.
+
+    On the first iteration previous is None. On the last iteration next
+    is None. In case of exception next is None and the exception is re-raised
+    on a subsequent next() call.
+
+    Inspired by `sliding_window` from `itertools` recipes.
+    """
+
+    iterator = iter(iterable)
+    window = deque((None, next(iterator)), maxlen=3)
+    try:
+        for x in iterator:
+            window.append(x)
+            yield tuple(window)
+    except Exception:
+        raise
+    finally:
+        window.append(None)
+        yield tuple(window)
diff --git a/Lib/_pyrepl/windows_console.py b/Lib/_pyrepl/windows_console.py
index 17942c8df07..77985e59a93 100644
--- a/Lib/_pyrepl/windows_console.py
+++ b/Lib/_pyrepl/windows_console.py
@@ -426,6 +426,20 @@ class WindowsConsole(Console):
 
         return rec
 
+    def _read_input_bulk(
+        self, block: bool, n: int
+    ) -> tuple[ctypes.Array[INPUT_RECORD], int]:
+        rec = (n * INPUT_RECORD)()
+        read = DWORD()
+
+        if not block and not self.wait(timeout=0):
+            return rec, 0
+
+        if not ReadConsoleInput(InHandle, rec, n, read):
+            raise WinError(GetLastError())
+
+        return rec, read.value
+
     def get_event(self, block: bool = True) -> Event | None:
         """Return an Event instance.  Returns None if |block| is false
         and there is no event pending, otherwise waits for the
@@ -521,7 +535,23 @@ class WindowsConsole(Console):
     def getpending(self) -> Event:
         """Return the characters that have been typed but not yet
         processed."""
-        return Event("key", "", b"")
+        e = Event("key", "", b"")
+
+        while not self.event_queue.empty():
+            e2 = self.event_queue.get()
+            if e2:
+                e.data += e2.data
+
+        recs, rec_count = self._read_input_bulk(False, 1024)
+        for i in range(rec_count):
+            rec = recs[i]
+            if rec and rec.EventType == KEY_EVENT:
+                key_event = rec.Event.KeyEvent
+                ch = key_event.uChar.UnicodeChar
+                if ch == "\r":
+                    ch += "\n"
+                e.data += ch
+        return e
 
     def wait(self, timeout: float | None) -> bool:
         """Wait for an event."""
diff --git a/Lib/test/test_pyrepl/test_pyrepl.py b/Lib/test/test_pyrepl/test_pyrepl.py
index 75a5afad562..93029ab6e08 100644
--- a/Lib/test/test_pyrepl/test_pyrepl.py
+++ b/Lib/test/test_pyrepl/test_pyrepl.py
@@ -45,6 +45,7 @@ class ReplTestCase(TestCase):
         cmdline_args: list[str] | None = None,
         cwd: str | None = None,
         skip: bool = False,
+        timeout: float = SHORT_TIMEOUT,
     ) -> tuple[str, int]:
         temp_dir = None
         if cwd is None:
@@ -52,7 +53,12 @@ class ReplTestCase(TestCase):
             cwd = temp_dir.name
         try:
             return self._run_repl(
-                repl_input, env=env, cmdline_args=cmdline_args, cwd=cwd, skip=skip,
+                repl_input,
+                env=env,
+                cmdline_args=cmdline_args,
+                cwd=cwd,
+                skip=skip,
+                timeout=timeout,
             )
         finally:
             if temp_dir is not None:
@@ -66,6 +72,7 @@ class ReplTestCase(TestCase):
         cmdline_args: list[str] | None,
         cwd: str,
         skip: bool,
+        timeout: float,
     ) -> tuple[str, int]:
         assert pty
         master_fd, slave_fd = pty.openpty()
@@ -103,7 +110,7 @@ class ReplTestCase(TestCase):
         os.write(master_fd, repl_input.encode("utf-8"))
 
         output = []
-        while select.select([master_fd], [], [], SHORT_TIMEOUT)[0]:
+        while select.select([master_fd], [], [], timeout)[0]:
             try:
                 data = os.read(master_fd, 1024).decode("utf-8")
                 if not data:
@@ -114,12 +121,12 @@ class ReplTestCase(TestCase):
         else:
             os.close(master_fd)
             process.kill()
-            process.wait(timeout=SHORT_TIMEOUT)
+            process.wait(timeout=timeout)
             self.fail(f"Timeout while waiting for output, got: {''.join(output)}")
 
         os.close(master_fd)
         try:
-            exit_code = process.wait(timeout=SHORT_TIMEOUT)
+            exit_code = process.wait(timeout=timeout)
         except subprocess.TimeoutExpired:
             process.kill()
             exit_code = process.wait()
@@ -1561,25 +1568,29 @@ class TestMain(ReplTestCase):
 
     def test_history_survive_crash(self):
         env = os.environ.copy()
-        commands = "1\nexit()\n"
-        output, exit_code = self.run_repl(commands, env=env, skip=True)
 
         with tempfile.NamedTemporaryFile() as hfile:
             env["PYTHON_HISTORY"] = hfile.name
-            commands = "spam\nimport time\ntime.sleep(1000)\npreved\n"
+
+            commands = "1\n2\n3\nexit()\n"
+            output, exit_code = self.run_repl(commands, env=env, skip=True)
+
+            commands = "spam\nimport time\ntime.sleep(1000)\nquit\n"
             try:
-                self.run_repl(commands, env=env)
+                self.run_repl(commands, env=env, timeout=3)
             except AssertionError:
                 pass
 
             history = pathlib.Path(hfile.name).read_text()
+            self.assertIn("2", history)
+            self.assertIn("exit()", history)
             self.assertIn("spam", history)
-            self.assertIn("time", history)
+            self.assertIn("import time", history)
             self.assertNotIn("sleep", history)
-            self.assertNotIn("preved", history)
+            self.assertNotIn("quit", history)
 
     def test_keyboard_interrupt_after_isearch(self):
-        output, exit_code = self.run_repl(["\x12", "\x03", "exit"])
+        output, exit_code = self.run_repl("\x12\x03exit\n")
         self.assertEqual(exit_code, 0)
 
     def test_prompt_after_help(self):
diff --git a/Lib/test/test_pyrepl/test_reader.py b/Lib/test/test_pyrepl/test_reader.py
index 109cb603ae8..8d7fcf538d2 100644
--- a/Lib/test/test_pyrepl/test_reader.py
+++ b/Lib/test/test_pyrepl/test_reader.py
@@ -1,14 +1,21 @@
 import itertools
 import functools
 import rlcompleter
+from textwrap import dedent
 from unittest import TestCase
 from unittest.mock import MagicMock
 
 from .support import handle_all_events, handle_events_narrow_console
 from .support import ScreenEqualMixin, code_to_events
-from .support import prepare_reader, prepare_console
+from .support import prepare_console, reader_force_colors
+from .support import reader_no_colors as prepare_reader
 from _pyrepl.console import Event
 from _pyrepl.reader import Reader
+from _colorize import theme
+
+
+overrides = {"RESET": "z", "SOFT_KEYWORD": "K"}
+colors = {overrides.get(k, k[0].lower()): v for k, v in theme.items()}
 
 
 class TestReader(ScreenEqualMixin, TestCase):
@@ -123,8 +130,9 @@ class TestReader(ScreenEqualMixin, TestCase):
     def test_control_characters(self):
         code = 'flag = "🏳️‍🌈"'
         events = code_to_events(code)
-        reader, _ = handle_all_events(events)
+        reader, _ = handle_all_events(events, prepare_reader=reader_force_colors)
         self.assert_screen_equal(reader, 'flag = "🏳️\\u200d🌈"', clean=True)
+        self.assert_screen_equal(reader, 'flag {o}={z} {s}"🏳️\\u200d🌈"{z}'.format(**colors))
 
     def test_setpos_from_xy_multiple_lines(self):
         # fmt: off
@@ -355,3 +363,140 @@ class TestReader(ScreenEqualMixin, TestCase):
         reader, _ = handle_all_events(events)
         reader.setpos_from_xy(8, 0)
         self.assertEqual(reader.pos, 7)
+
+    def test_syntax_highlighting_basic(self):
+        code = dedent(
+            """\
+            import re, sys
+            def funct(case: str = sys.platform) -> None:
+                match = re.search(
+                    "(me)",
+                    '''
+                    Come on
+                      Come on now
+                        You know that it's time to emerge
+                    ''',
+                )
+                match case:
+                    case "emscripten": print("on the web")
+                    case "ios" | "android": print("on the phone")
+                    case _: print('arms around', match.group(1))
+            """
+        )
+        expected = dedent(
+            """\
+            {k}import{z} re{o},{z} sys
+            {a}{k}def{z} {d}funct{z}{o}({z}case{o}:{z} {b}str{z} {o}={z} sys{o}.{z}platform{o}){z} {o}->{z} {k}None{z}{o}:{z}
+                match {o}={z} re{o}.{z}search{o}({z}
+                    {s}"(me)"{z}{o},{z}
+                    {s}'''{z}
+            {s}        Come on{z}
+            {s}          Come on now{z}
+            {s}            You know that it's time to emerge{z}
+            {s}        '''{z}{o},{z}
+                {o}){z}
+                {K}match{z} case{o}:{z}
+                    {K}case{z} {s}"emscripten"{z}{o}:{z} {b}print{z}{o}({z}{s}"on the web"{z}{o}){z}
+                    {K}case{z} {s}"ios"{z} {o}|{z} {s}"android"{z}{o}:{z} {b}print{z}{o}({z}{s}"on the phone"{z}{o}){z}
+                    {K}case{z} {K}_{z}{o}:{z} {b}print{z}{o}({z}{s}'arms around'{z}{o},{z} match{o}.{z}group{o}({z}{n}1{z}{o}){z}{o}){z}
+            """
+        )
+        expected_sync = expected.format(a="", **colors)
+        events = code_to_events(code)
+        reader, _ = handle_all_events(events, prepare_reader=reader_force_colors)
+        self.assert_screen_equal(reader, code, clean=True)
+        self.assert_screen_equal(reader, expected_sync)
+        self.assertEqual(reader.pos, 2**7 + 2**8)
+        self.assertEqual(reader.cxy, (0, 14))
+
+        async_msg = "{k}async{z} ".format(**colors)
+        expected_async = expected.format(a=async_msg, **colors)
+        more_events = itertools.chain(
+            code_to_events(code),
+            [Event(evt="key", data="up", raw=bytearray(b"\x1bOA"))] * 13,
+            code_to_events("async "),
+        )
+        reader, _ = handle_all_events(more_events, prepare_reader=reader_force_colors)
+        self.assert_screen_equal(reader, expected_async)
+        self.assertEqual(reader.pos, 21)
+        self.assertEqual(reader.cxy, (6, 1))
+
+    def test_syntax_highlighting_incomplete_string_first_line(self):
+        code = dedent(
+            """\
+            def unfinished_function(arg: str = "still typing
+            """
+        )
+        expected = dedent(
+            """\
+            {k}def{z} {d}unfinished_function{z}{o}({z}arg{o}:{z} {b}str{z} {o}={z} {s}"still typing{z}
+            """
+        ).format(**colors)
+        events = code_to_events(code)
+        reader, _ = handle_all_events(events, prepare_reader=reader_force_colors)
+        self.assert_screen_equal(reader, code, clean=True)
+        self.assert_screen_equal(reader, expected)
+
+    def test_syntax_highlighting_incomplete_string_another_line(self):
+        code = dedent(
+            """\
+            def unfinished_function(
+                arg: str = "still typing
+            """
+        )
+        expected = dedent(
+            """\
+            {k}def{z} {d}unfinished_function{z}{o}({z}
+                arg{o}:{z} {b}str{z} {o}={z} {s}"still typing{z}
+            """
+        ).format(**colors)
+        events = code_to_events(code)
+        reader, _ = handle_all_events(events, prepare_reader=reader_force_colors)
+        self.assert_screen_equal(reader, code, clean=True)
+        self.assert_screen_equal(reader, expected)
+
+    def test_syntax_highlighting_incomplete_multiline_string(self):
+        code = dedent(
+            """\
+            def unfinished_function():
+                '''Still writing
+                the docstring
+            """
+        )
+        expected = dedent(
+            """\
+            {k}def{z} {d}unfinished_function{z}{o}({z}{o}){z}{o}:{z}
+                {s}'''Still writing{z}
+            {s}    the docstring{z}
+            """
+        ).format(**colors)
+        events = code_to_events(code)
+        reader, _ = handle_all_events(events, prepare_reader=reader_force_colors)
+        self.assert_screen_equal(reader, code, clean=True)
+        self.assert_screen_equal(reader, expected)
+
+    def test_syntax_highlighting_incomplete_fstring(self):
+        code = dedent(
+            """\
+            def unfinished_function():
+                var = f"Single-quote but {
+                1
+                +
+                1
+                } multi-line!
+            """
+        )
+        expected = dedent(
+            """\
+            {k}def{z} {d}unfinished_function{z}{o}({z}{o}){z}{o}:{z}
+                var {o}={z} {s}f"{z}{s}Single-quote but {z}{o}{OB}{z}
+                {n}1{z}
+                {o}+{z}
+                {n}1{z}
+                {o}{CB}{z}{s} multi-line!{z}
+            """
+        ).format(OB="{", CB="}", **colors)
+        events = code_to_events(code)
+        reader, _ = handle_all_events(events, prepare_reader=reader_force_colors)
+        self.assert_screen_equal(reader, code, clean=True)
+        self.assert_screen_equal(reader, expected)
diff --git a/Lib/test/test_pyrepl/test_unix_console.py b/Lib/test/test_pyrepl/test_unix_console.py
index 2f5c150402b..7acb84a94f7 100644
--- a/Lib/test/test_pyrepl/test_unix_console.py
+++ b/Lib/test/test_pyrepl/test_unix_console.py
@@ -33,10 +33,12 @@ def unix_console(events, **kwargs):
 
 handle_events_unix_console = partial(
     handle_all_events,
-    prepare_console=partial(unix_console),
+    prepare_reader=reader_no_colors,
+    prepare_console=unix_console,
 )
 handle_events_narrow_unix_console = partial(
     handle_all_events,
+    prepare_reader=reader_no_colors,
     prepare_console=partial(unix_console, width=5),
 )
 handle_events_short_unix_console = partial(
diff --git a/Lib/test/test_pyrepl/test_utils.py b/Lib/test/test_pyrepl/test_utils.py
index 0d59968206a..8ce1e537138 100644
--- a/Lib/test/test_pyrepl/test_utils.py
+++ b/Lib/test/test_pyrepl/test_utils.py
@@ -1,6 +1,6 @@
 from unittest import TestCase
 
-from _pyrepl.utils import str_width, wlen
+from _pyrepl.utils import str_width, wlen, prev_next_window
 
 
 class TestUtils(TestCase):
@@ -25,3 +25,38 @@ class TestUtils(TestCase):
 
         self.assertEqual(wlen('hello'), 5)
         self.assertEqual(wlen('hello' + '\x1a'), 7)
+
+    def test_prev_next_window(self):
+        def gen_normal():
+            yield 1
+            yield 2
+            yield 3
+            yield 4
+
+        pnw = prev_next_window(gen_normal())
+        self.assertEqual(next(pnw), (None, 1, 2))
+        self.assertEqual(next(pnw), (1, 2, 3))
+        self.assertEqual(next(pnw), (2, 3, 4))
+        self.assertEqual(next(pnw), (3, 4, None))
+        with self.assertRaises(StopIteration):
+            next(pnw)
+
+        def gen_short():
+            yield 1
+
+        pnw = prev_next_window(gen_short())
+        self.assertEqual(next(pnw), (None, 1, None))
+        with self.assertRaises(StopIteration):
+            next(pnw)
+
+        def gen_raise():
+            yield from gen_normal()
+            1/0
+
+        pnw = prev_next_window(gen_raise())
+        self.assertEqual(next(pnw), (None, 1, 2))
+        self.assertEqual(next(pnw), (1, 2, 3))
+        self.assertEqual(next(pnw), (2, 3, 4))
+        self.assertEqual(next(pnw), (3, 4, None))
+        with self.assertRaises(ZeroDivisionError):
+            next(pnw)
diff --git a/Lib/test/test_pyrepl/test_windows_console.py b/Lib/test/test_pyrepl/test_windows_console.py
index 69f2d5af2a4..e95fec46a85 100644
--- a/Lib/test/test_pyrepl/test_windows_console.py
+++ b/Lib/test/test_pyrepl/test_windows_console.py
@@ -12,6 +12,7 @@ from unittest import TestCase
 from unittest.mock import MagicMock, call
 
 from .support import handle_all_events, code_to_events
+from .support import reader_no_colors as default_prepare_reader
 
 try:
     from _pyrepl.console import Event, Console
@@ -47,14 +48,22 @@ class WindowsConsoleTests(TestCase):
             setattr(console, key, val)
         return console
 
-    def handle_events(self, events: Iterable[Event], **kwargs):
-        return handle_all_events(events, partial(self.console, **kwargs))
+    def handle_events(
+        self,
+        events: Iterable[Event],
+        prepare_console=None,
+        prepare_reader=None,
+        **kwargs,
+    ):
+        prepare_console = prepare_console or partial(self.console, **kwargs)
+        prepare_reader = prepare_reader or default_prepare_reader
+        return handle_all_events(events, prepare_console, prepare_reader)
 
     def handle_events_narrow(self, events):
         return self.handle_events(events, width=5)
 
-    def handle_events_short(self, events):
-        return self.handle_events(events, height=1)
+    def handle_events_short(self, events, **kwargs):
+        return self.handle_events(events, height=1, **kwargs)
 
     def handle_events_height_3(self, events):
         return self.handle_events(events, height=3)
diff --git a/Lib/token.py b/Lib/token.py
index a1fde61cd8a..f61723cc09d 100644
--- a/Lib/token.py
+++ b/Lib/token.py
@@ -134,11 +134,11 @@ EXACT_TOKEN_TYPES = {
     '~': TILDE,
 }
 
-def ISTERMINAL(x):
+def ISTERMINAL(x: int) -> bool:
     return x < NT_OFFSET
 
-def ISNONTERMINAL(x):
+def ISNONTERMINAL(x: int) -> bool:
     return x >= NT_OFFSET
 
-def ISEOF(x):
+def ISEOF(x: int) -> bool:
     return x == ENDMARKER
diff --git a/Misc/NEWS.d/next/Core_and_Builtins/2025-03-21-19-03-42.gh-issue-131507.q9fvyM.rst b/Misc/NEWS.d/next/Core_and_Builtins/2025-03-21-19-03-42.gh-issue-131507.q9fvyM.rst
new file mode 100644
index 00000000000..354a116c533
--- /dev/null
+++ b/Misc/NEWS.d/next/Core_and_Builtins/2025-03-21-19-03-42.gh-issue-131507.q9fvyM.rst
@@ -0,0 +1 @@
+PyREPL now supports syntax highlighing. Contributed by Łukasz Langa.
diff --git a/Misc/mypy/token.py b/Misc/mypy/token.py
new file mode 120000
index 00000000000..0a39f726dda
--- /dev/null
+++ b/Misc/mypy/token.py
@@ -0,0 +1 @@
+../../Lib/token.py
\ No newline at end of file
diff --git a/Misc/mypy/typed-stdlib.txt b/Misc/mypy/typed-stdlib.txt
index 9b27ee0d2de..07b88ba7445 100644
--- a/Misc/mypy/typed-stdlib.txt
+++ b/Misc/mypy/typed-stdlib.txt
@@ -2,4 +2,5 @@
 
 _colorize.py
 _pyrepl
+token.py
 tomllib
\ No newline at end of file
diff --git a/Tools/build/generate_token.py b/Tools/build/generate_token.py
index a64806763f3..9ee5ec86e75 100755
--- a/Tools/build/generate_token.py
+++ b/Tools/build/generate_token.py
@@ -278,13 +278,13 @@ EXACT_TOKEN_TYPES = {
 %s
 }
 
-def ISTERMINAL(x):
+def ISTERMINAL(x: int) -> bool:
     return x < NT_OFFSET
 
-def ISNONTERMINAL(x):
+def ISNONTERMINAL(x: int) -> bool:
     return x >= NT_OFFSET
 
-def ISEOF(x):
+def ISEOF(x: int) -> bool:
     return x == ENDMARKER
 '''