diff --git a/Cargo.lock b/Cargo.lock
index ffece1cb3..1a291035b 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -3283,6 +3283,10 @@ dependencies = [
  "pkcs8",
  "pymath",
  "rand_core 0.9.5",
+ "ruff_python_ast",
+ "ruff_python_parser",
+ "ruff_source_file",
+ "ruff_text_size",
  "rustix",
  "rustls",
  "rustls-native-certs",
diff --git a/crates/stdlib/Cargo.toml b/crates/stdlib/Cargo.toml
index a40a5bf24..7d230fcc0 100644
--- a/crates/stdlib/Cargo.toml
+++ b/crates/stdlib/Cargo.toml
@@ -31,6 +31,11 @@ rustpython-derive = { workspace = true }
 rustpython-vm = { workspace = true, default-features = false, features = ["compiler"]}
 rustpython-common = { workspace = true }
 
+ruff_python_parser = { workspace = true }
+ruff_python_ast = { workspace = true }
+ruff_text_size = { workspace = true }
+ruff_source_file = { workspace = true }
+
 ahash = { workspace = true }
 ascii = { workspace = true }
 cfg-if = { workspace = true }
diff --git a/crates/stdlib/src/lib.rs b/crates/stdlib/src/lib.rs
index 8c234c22f..04aa623d1 100644
--- a/crates/stdlib/src/lib.rs
+++ b/crates/stdlib/src/lib.rs
@@ -49,6 +49,7 @@ mod pystruct;
 mod random;
 mod statistics;
 mod suggestions;
+mod tokenize;
 // TODO: maybe make this an extension module, if we ever get those
 // mod re;
 #[cfg(all(feature = "host_env", not(target_arch = "wasm32")))]
@@ -225,6 +226,7 @@ pub fn stdlib_module_defs(ctx: &Context) -> Vec<&'static builtins::PyModuleDef>
         ssl::module_def(ctx),
         statistics::module_def(ctx),
         suggestions::module_def(ctx),
+        tokenize::module_def(ctx),
         #[cfg(all(feature = "host_env", unix, not(target_os = "redox")))]
         syslog::module_def(ctx),
         #[cfg(all(
diff --git a/crates/stdlib/src/tokenize.rs b/crates/stdlib/src/tokenize.rs
new file mode 100644
index 000000000..33667a203
--- /dev/null
+++ b/crates/stdlib/src/tokenize.rs
@@ -0,0 +1,391 @@
+pub(crate) use _tokenize::module_def;
+
+#[pymodule]
+mod _tokenize {
+    use crate::{
+        common::lock::PyRwLock,
+        vm::{
+            AsObject, Py, PyPayload, PyResult, VirtualMachine,
+            builtins::{PyBytes, PyStr, PyType},
+            convert::ToPyObject,
+            function::ArgCallable,
+            protocol::PyIterReturn,
+            types::{Constructor, IterNext, Iterable, SelfIter},
+        },
+    };
+    use ruff_python_ast::PySourceType;
+    use ruff_python_ast::token::{Token, TokenKind, Tokens};
+    use ruff_python_parser::{ParseError, parse_unchecked_source};
+    use ruff_source_file::{LineIndex, LineRanges};
+    use ruff_text_size::{Ranged, TextRange};
+    use std::{cmp::Ordering, fmt};
+
+    /// `__import__("token").OP`
+    const TOKEN_OP: u8 = 55;
+
+    #[pyattr]
+    #[pyclass(name = "TokenizerIter")]
+    #[derive(PyPayload)]
+    pub struct PyTokenizerIter {
+        readline: ArgCallable, // TODO: This should be PyObject
+        extra_tokens: bool,
+        encoding: Option<String>,
+        state: PyRwLock<PyTokenizerIterState>,
+    }
+
+    impl PyTokenizerIter {
+        fn readline(&self, vm: &VirtualMachine) -> PyResult<String> {
+            // TODO: When `readline` is PyObject,
+            // we need to check if it's callable and raise a type error if it's not.
+            let raw_line = match self.readline.invoke((), vm) {
+                Ok(v) => v,
+                Err(err) => {
+                    if err.fast_isinstance(vm.ctx.exceptions.stop_iteration) {
+                        return Ok(String::new());
+                    }
+                    return Err(err);
+                }
+            };
+            Ok(match &self.encoding {
+                Some(encoding) => {
+                    let bytes = raw_line
+                        .downcast::<PyBytes>()
+                        .map_err(|_| vm.new_type_error("readline() returned a non-bytes object"))?;
+                    vm.state
+                        .codec_registry
+                        .decode_text(bytes.into(), encoding, None, vm)
+                        .map(|s| s.to_string())?
+                }
+                None => raw_line
+                    .downcast::<PyStr>()
+                    .map(|s| s.to_string())
+                    .map_err(|_| vm.new_type_error("readline() returned a non-string object"))?,
+            })
+        }
+    }
+
+    impl fmt::Debug for PyTokenizerIter {
+        fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
+            f.debug_struct("PyTokenizerIter")
+                .field("readline", &self.readline)
+                .field("encoding", &self.encoding)
+                .field("extra_tokens", &self.extra_tokens)
+                .finish()
+        }
+    }
+
+    #[pyclass(with(Constructor, Iterable, IterNext))]
+    impl PyTokenizerIter {}
+
+    impl Constructor for PyTokenizerIter {
+        type Args = PyTokenizerIterArgs;
+
+        fn py_new(_cls: &Py<PyType>, args: Self::Args, _vm: &VirtualMachine) -> PyResult<Self> {
+            let Self::Args {
+                readline,
+                extra_tokens,
+                encoding,
+            } = args;
+
+            Ok(Self {
+                readline,
+                extra_tokens,
+                encoding: encoding.map(|s| s.to_string()),
+                state: PyRwLock::new(PyTokenizerIterState::default()),
+            })
+        }
+    }
+
+    impl SelfIter for PyTokenizerIter {}
+
+    impl IterNext for PyTokenizerIter {
+        fn next(zelf: &Py<Self>, vm: &VirtualMachine) -> PyResult<PyIterReturn> {
+            let mut state = {
+                let guard = zelf.state.read();
+                guard.clone()
+            };
+
+            if state.eof {
+                return Ok(PyIterReturn::StopIteration(None));
+            }
+
+            let token = loop {
+                // TODO: Check here for errors. Raise SyntaxError if needed
+
+                if let Some(tok) = state.next_token() {
+                    break tok;
+                }
+
+                let nline = zelf.readline(vm)?;
+                if nline.is_empty() {
+                    state.eof = true;
+                    *zelf.state.write() = state.clone();
+
+                    let line_num = &state.start().0;
+                    let out = vm
+                        .ctx
+                        .new_tuple(vec![
+                            token_kind_value(TokenKind::EndOfFile).to_pyobject(vm),
+                            vm.ctx.new_str("").into(),
+                            vm.ctx
+                                .new_tuple(vec![line_num.to_pyobject(vm), (-1).to_pyobject(vm)])
+                                .into(),
+                            vm.ctx
+                                .new_tuple(vec![line_num.to_pyobject(vm), (-1).to_pyobject(vm)])
+                                .into(),
+                            vm.ctx.new_str(state.current_line()).into(),
+                        ])
+                        .into();
+                    return Ok(PyIterReturn::Return(out));
+                }
+                state.push_line(&nline);
+            };
+
+            *zelf.state.write() = state.clone();
+
+            let token_kind = token.kind();
+            let token_value = if zelf.extra_tokens && token_kind.is_operator() {
+                TOKEN_OP
+            } else {
+                token_kind_value(token_kind)
+            };
+            let (start_x, start_y) = &state.start();
+            let (end_x, end_y) = &state.end();
+
+            let mut token_repr = &state.source[state.range()];
+            if !zelf.extra_tokens {
+                token_repr = token_repr.trim();
+            }
+
+            let out = vm
+                .ctx
+                .new_tuple(vec![
+                    token_value.to_pyobject(vm),
+                    vm.ctx.new_str(token_repr).into(),
+                    vm.ctx
+                        .new_tuple(vec![start_x.to_pyobject(vm), start_y.to_pyobject(vm)])
+                        .into(),
+                    vm.ctx
+                        .new_tuple(vec![end_x.to_pyobject(vm), end_y.to_pyobject(vm)])
+                        .into(),
+                    vm.ctx.new_str(state.current_line()).into(),
+                ])
+                .into();
+            Ok(PyIterReturn::Return(out))
+        }
+    }
+
+    #[derive(FromArgs)]
+    pub struct PyTokenizerIterArgs {
+        #[pyarg(positional)]
+        readline: ArgCallable,
+        #[pyarg(named)]
+        extra_tokens: bool,
+        #[pyarg(named, optional)]
+        encoding: Option<rustpython_vm::PyRef<PyStr>>,
+    }
+
+    #[derive(Clone, Debug)]
+    struct PyTokenizerIterState {
+        /// Source code.
+        source: String,
+        prev_token: Option<Token>,
+        /// Tokens of `source`.
+        tokens: Tokens,
+        /// Errors of `source`
+        errors: Vec<ParseError>,
+        /// LineIndex of `source`.
+        line_index: LineIndex,
+        /// Marker that says we already emitted EOF, and needs to stop iterating.
+        eof: bool,
+    }
+
+    impl PyTokenizerIterState {
+        fn push_line(&mut self, line: &str) {
+            self.source.push_str(line);
+
+            let parsed = parse_unchecked_source(&self.source, PySourceType::Python);
+            self.tokens = parsed.tokens().clone();
+            self.errors = parsed.errors().to_vec();
+            self.line_index = LineIndex::from_source_text(&self.source);
+        }
+
+        #[must_use]
+        fn current_line(&self) -> &str {
+            let (kind, range): (TokenKind, TextRange) = match self.prev_token {
+                Some(token) => token.as_tuple(),
+                None => (TokenKind::Unknown, TextRange::default()),
+            };
+
+            match kind {
+                TokenKind::Newline => self.source.full_line_str(range.start()),
+                _ => self.source.full_lines_str(range),
+            }
+        }
+
+        #[must_use]
+        fn next_token(&mut self) -> Option<Token> {
+            for token in self.tokens.iter() {
+                let (kind, range): (TokenKind, TextRange) = token.as_tuple();
+
+                if matches!(kind, TokenKind::NonLogicalNewline) {
+                    continue;
+                }
+
+                if matches!(range.ordering(self.range()), Ordering::Greater) {
+                    self.prev_token = Some(*token);
+                    return self.prev_token;
+                }
+            }
+
+            None
+        }
+
+        #[must_use]
+        fn range(&self) -> TextRange {
+            match self.prev_token {
+                Some(token) => token.range(),
+                None => TextRange::default(),
+            }
+        }
+
+        #[must_use]
+        fn start(&self) -> (usize, usize) {
+            let lc = self
+                .line_index
+                .line_column(self.range().start(), &self.source);
+            (lc.line.get(), lc.column.to_zero_indexed())
+        }
+
+        #[must_use]
+        fn end(&self) -> (usize, usize) {
+            let lc = self
+                .line_index
+                .line_column(self.range().end(), &self.source);
+            (lc.line.get(), lc.column.to_zero_indexed())
+        }
+    }
+
+    impl Default for PyTokenizerIterState {
+        fn default() -> Self {
+            const SOURCE: &str = "";
+            let parsed = parse_unchecked_source(SOURCE, PySourceType::Python);
+
+            Self {
+                source: SOURCE.to_owned(),
+                prev_token: None,
+                tokens: parsed.tokens().clone(),
+                errors: parsed.errors().to_vec(),
+                line_index: LineIndex::from_source_text(SOURCE),
+                eof: false,
+            }
+        }
+    }
+
+    const fn token_kind_value(kind: TokenKind) -> u8 {
+        match kind {
+            TokenKind::EndOfFile => 0,
+            TokenKind::Name
+            | TokenKind::For
+            | TokenKind::In
+            | TokenKind::Pass
+            | TokenKind::Class
+            | TokenKind::And
+            | TokenKind::Is
+            | TokenKind::Raise
+            | TokenKind::True
+            | TokenKind::False
+            | TokenKind::Assert
+            | TokenKind::Try
+            | TokenKind::While
+            | TokenKind::Yield
+            | TokenKind::Lambda
+            | TokenKind::None
+            | TokenKind::Not
+            | TokenKind::Or
+            | TokenKind::Break
+            | TokenKind::Continue
+            | TokenKind::Global
+            | TokenKind::Nonlocal
+            | TokenKind::Return
+            | TokenKind::Except
+            | TokenKind::Import
+            | TokenKind::Case
+            | TokenKind::Match
+            | TokenKind::Type
+            | TokenKind::Await
+            | TokenKind::With
+            | TokenKind::Del
+            | TokenKind::Finally
+            | TokenKind::From
+            | TokenKind::Def
+            | TokenKind::If
+            | TokenKind::Else
+            | TokenKind::Elif
+            | TokenKind::As
+            | TokenKind::Async => 1,
+            TokenKind::Int | TokenKind::Complex | TokenKind::Float => 2,
+            TokenKind::String => 3,
+            TokenKind::Newline | TokenKind::NonLogicalNewline => 4,
+            TokenKind::Indent => 5,
+            TokenKind::Dedent => 6,
+            TokenKind::Lpar => 7,
+            TokenKind::Rpar => 8,
+            TokenKind::Lsqb => 9,
+            TokenKind::Rsqb => 10,
+            TokenKind::Colon => 11,
+            TokenKind::Comma => 12,
+            TokenKind::Semi => 13,
+            TokenKind::Plus => 14,
+            TokenKind::Minus => 15,
+            TokenKind::Star => 16,
+            TokenKind::Slash => 17,
+            TokenKind::Vbar => 18,
+            TokenKind::Amper => 19,
+            TokenKind::Less => 20,
+            TokenKind::Greater => 21,
+            TokenKind::Equal => 22,
+            TokenKind::Dot => 23,
+            TokenKind::Percent => 24,
+            TokenKind::Lbrace => 25,
+            TokenKind::Rbrace => 26,
+            TokenKind::EqEqual => 27,
+            TokenKind::NotEqual => 28,
+            TokenKind::LessEqual => 29,
+            TokenKind::GreaterEqual => 30,
+            TokenKind::Tilde => 31,
+            TokenKind::CircumFlex => 32,
+            TokenKind::LeftShift => 33,
+            TokenKind::RightShift => 34,
+            TokenKind::DoubleStar => 35,
+            TokenKind::PlusEqual => 36,
+            TokenKind::MinusEqual => 37,
+            TokenKind::StarEqual => 38,
+            TokenKind::SlashEqual => 39,
+            TokenKind::PercentEqual => 40,
+            TokenKind::AmperEqual => 41,
+            TokenKind::VbarEqual => 42,
+            TokenKind::CircumflexEqual => 43,
+            TokenKind::LeftShiftEqual => 44,
+            TokenKind::RightShiftEqual => 45,
+            TokenKind::DoubleStarEqual => 46,
+            TokenKind::DoubleSlash => 47,
+            TokenKind::DoubleSlashEqual => 48,
+            TokenKind::At => 49,
+            TokenKind::AtEqual => 50,
+            TokenKind::Rarrow => 51,
+            TokenKind::Ellipsis => 52,
+            TokenKind::ColonEqual => 53,
+            TokenKind::Exclamation => 54,
+            TokenKind::FStringStart => 59,
+            TokenKind::FStringMiddle => 60,
+            TokenKind::FStringEnd => 61,
+            TokenKind::Comment => 62,
+            TokenKind::TStringStart => 62,  // 3.14 compatible
+            TokenKind::TStringMiddle => 63, // 3.14 compatible
+            TokenKind::TStringEnd => 64,    // 3.14 compatible
+            TokenKind::IpyEscapeCommand | TokenKind::Question => 0, // Ruff's specific
+            TokenKind::Unknown => 0,
+        }
+    }
+}