diff --git a/Cargo.toml b/Cargo.toml
index b2afea8f85..2c4cc88edb 100644
--- a/Cargo.toml
+++ b/Cargo.toml
@@ -77,7 +77,7 @@ wasm-bindgen = { version = "0.2.83" }
 is_executable = "1.0.1"
 
 [dev-dependencies]
-insta = { version = "1.19.1", features = ["yaml", "redactions"] }
+insta = { version = "1.19.0", features = ["yaml", "redactions"] }
 test-case = { version = "2.2.2" }
 wasm-bindgen-test = { version = "0.3.33" }
 
diff --git a/README.md b/README.md
index 29c348b609..7e94906b0c 100644
--- a/README.md
+++ b/README.md
@@ -850,6 +850,7 @@ For more, see [pyupgrade](https://pypi.org/project/pyupgrade/) on PyPI.
 | UP033 | functools-cache | Use `@functools.cache` instead of `@functools.lru_cache(maxsize=None)` | 🛠 |
 | UP034 | extraneous-parentheses | Avoid extraneous parentheses | 🛠 |
 | UP035 | import-replacements | Import from `{module}` instead: {names} | 🛠 |
+| UP036 | outdated-version-block | Version block is outdated for minimum Python version | 🛠 |
 
 ### flake8-2020 (YTT)
 
diff --git a/foo.py b/foo.py
new file mode 100644
index 0000000000..a4c70ac96d
--- /dev/null
+++ b/foo.py
@@ -0,0 +1,4 @@
+import sys
+
+expected_error = \
+    []
diff --git a/resources/test/fixtures/pyupgrade/UP036_0.py b/resources/test/fixtures/pyupgrade/UP036_0.py
new file mode 100644
index 0000000000..d223d58c68
--- /dev/null
+++ b/resources/test/fixtures/pyupgrade/UP036_0.py
@@ -0,0 +1,180 @@
+import sys
+
+if sys.version_info < (3,0):
+    print("py2")
+else:
+    print("py3")
+
+if sys.version_info < (3,0):
+    if True:
+        print("py2!")
+    else:
+        print("???")
+else:
+    print("py3")
+
+if sys.version_info < (3,0): print("PY2!")
+else: print("PY3!")
+
+if True:
+    if sys.version_info < (3,0):
+        print("PY2")
+    else:
+        print("PY3")
+
+if sys.version_info < (3,0): print(1 if True else 3)
+else:
+    print("py3")
+
+if sys.version_info < (3,0):
+    def f():
+        print("py2")
+else:
+    def f():
+        print("py3")
+        print("This the next")
+
+if sys.version_info > (3,0):
+    print("py3")
+else:
+    print("py2")
+
+
+x = 1
+
+if sys.version_info > (3,0):
+    print("py3")
+else:
+    print("py2")
+    # ohai
+
+x = 1
+
+if sys.version_info > (3,0): print("py3")
+else: print("py2")
+
+if sys.version_info > (3,):
+    print("py3")
+else:
+    print("py2")
+
+if True:
+    if sys.version_info > (3,):
+        print("py3")
+    else:
+        print("py2")
+
+if sys.version_info < (3,):
+    print("py2")
+else:
+    print("py3")
+
+def f():
+    if sys.version_info < (3,0):
+        try:
+            yield
+        finally:
+            pass
+    else:
+        yield
+
+
+class C:
+    def g():
+        pass
+
+    if sys.version_info < (3,0):
+        def f(py2):
+            pass
+    else:
+        def f(py3):
+            pass
+
+    def h():
+        pass
+
+if True:
+    if sys.version_info < (3,0):
+        2
+    else:
+        3
+
+    # comment
+
+if sys.version_info < (3,0):
+    def f():
+        print("py2")
+    def g():
+        print("py2")
+else:
+    def f():
+        print("py3")
+    def g():
+        print("py3")
+
+if True:
+    if sys.version_info > (3,):
+        print(3)
+    # comment
+    print(2+3)
+
+if True:
+    if sys.version_info > (3,): print(3)
+
+if True:
+    if sys.version_info > (3,):
+        print(3)
+
+
+if True:
+    if sys.version_info <= (3, 0):
+        expected_error = []
+    else:
+        expected_error = [
+"<stdin>:1:5: Generator expression must be parenthesized",
+"max(1 for i in range(10), key=lambda x: x+1)",
+"    ^",
+        ]
+
+
+if sys.version_info <= (3, 0):
+    expected_error = []
+else:
+    expected_error = [
+"<stdin>:1:5: Generator expression must be parenthesized",
+"max(1 for i in range(10), key=lambda x: x+1)",
+"    ^",
+    ]
+
+
+if sys.version_info > (3,0):
+    """this
+is valid"""
+
+    """the indentation on
+    this line is significant"""
+
+    "this is" \
+    "allowed too"
+
+    ("so is"
+     "this for some reason")
+
+if sys.version_info > (3, 0): expected_error = \
+    []
+
+if sys.version_info > (3, 0): expected_error = []
+
+if sys.version_info > (3, 0): \
+    expected_error = []
+
+if True:
+    if sys.version_info > (3, 0): expected_error = \
+    []
+
+if True:
+    if sys.version_info > (3, 0): expected_error = []
+
+if True:
+    if sys.version_info > (3, 0): \
+    expected_error = []
diff --git a/resources/test/fixtures/pyupgrade/UP036_1.py b/resources/test/fixtures/pyupgrade/UP036_1.py
new file mode 100644
index 0000000000..108ea43c19
--- /dev/null
+++ b/resources/test/fixtures/pyupgrade/UP036_1.py
@@ -0,0 +1,76 @@
+import sys
+
+if sys.version_info == 2:
+    2
+else:
+    3
+
+if sys.version_info < (3,):
+    2
+else:
+    3
+
+if sys.version_info < (3,0):
+    2
+else:
+    3
+
+if sys.version_info == 3:
+    3
+else:
+    2
+
+if sys.version_info > (3,):
+    3
+else:
+    2
+
+if sys.version_info >= (3,):
+    3
+else:
+    2
+
+from sys import version_info
+
+if version_info > (3,):
+    3
+else:
+    2
+
+if True:
+    print(1)
+elif sys.version_info < (3,0):
+    print(2)
+else:
+    print(3)
+
+if True:
+    print(1)
+elif sys.version_info > (3,):
+    print(3)
+else:
+    print(2)
+
+if True:
+    print(1)
+elif sys.version_info > (3,):
+    print(3)
+
+def f():
+    if True:
+        print(1)
+    elif sys.version_info > (3,):
+        print(3)
+
+if True:
+    print(1)
+elif sys.version_info < (3,0):
+    print(2)
+else:
+    print(3)
+
+def f():
+    if True:
+        print(1)
+    elif sys.version_info > (3,):
+        print(3)
diff --git a/resources/test/fixtures/pyupgrade/UP036_2.py b/resources/test/fixtures/pyupgrade/UP036_2.py
new file mode 100644
index 0000000000..9c588d790e
--- /dev/null
+++ b/resources/test/fixtures/pyupgrade/UP036_2.py
@@ -0,0 +1,62 @@
+import sys
+from sys import version_info
+
+if sys.version_info > (3, 5):
+    3+6
+else:
+    3-5
+
+if version_info > (3, 5):
+    3+6
+else:
+    3-5
+
+if sys.version_info >= (3,6):
+    3+6
+else:
+    3-5
+
+if version_info >= (3,6):
+    3+6
+else:
+    3-5
+
+if sys.version_info < (3,6):
+    3-5
+else:
+    3+6
+
+if sys.version_info <= (3,5):
+    3-5
+else:
+    3+6
+
+if sys.version_info <= (3, 5):
+    3-5
+else:
+    3+6
+
+if sys.version_info >= (3, 5):
+    pass
+
+if sys.version_info < (3,0):
+    pass
+
+if True:
+    if sys.version_info < (3,0):
+        pass
+
+if sys.version_info < (3,0):
+    pass
+elif False:
+    pass
+
+if sys.version_info > (3,):
+    pass
+elif False:
+    pass
+
+if sys.version_info[0] > "2":
+    3
+else:
+    2
diff --git a/resources/test/fixtures/pyupgrade/UP036_3.py b/resources/test/fixtures/pyupgrade/UP036_3.py
new file mode 100644
index 0000000000..287d6ad3b4
--- /dev/null
+++ b/resources/test/fixtures/pyupgrade/UP036_3.py
@@ -0,0 +1,24 @@
+import sys
+
+if            sys.version_info < (3,0):
+    print("py2")
+    for item in range(10):
+        print(f"PY2-{item}")
+else                                :
+    print("py3")
+    for item in range(10):
+        print(f"PY3-{item}")
+
+if False:
+    if            sys.version_info < (3,0):
+        print("py2")
+        for item in range(10):
+            print(f"PY2-{item}")
+    else                                :
+        print("py3")
+        for item in range(10):
+            print(f"PY3-{item}")
+
+
+if            sys.version_info < (3,0): print("PY2!")
+else                               : print("PY3!")
diff --git a/resources/test/fixtures/pyupgrade/UP036_4.py b/resources/test/fixtures/pyupgrade/UP036_4.py
new file mode 100644
index 0000000000..e3eead1251
--- /dev/null
+++ b/resources/test/fixtures/pyupgrade/UP036_4.py
@@ -0,0 +1,45 @@
+import sys
+
+if True:
+    if sys.version_info < (3, 3):
+        cmd = [sys.executable, "-m", "test.regrtest"]
+
+
+if True:
+    if foo:
+        pass
+    elif sys.version_info < (3, 3):
+        cmd = [sys.executable, "-m", "test.regrtest"]
+
+if True:
+    if foo:
+        pass
+    elif sys.version_info < (3, 3):
+        cmd = [sys.executable, "-m", "test.regrtest"]
+    elif foo:
+        cmd = [sys.executable, "-m", "test", "-j0"]
+
+    if foo:
+        pass
+    elif sys.version_info < (3, 3):
+        cmd = [sys.executable, "-m", "test.regrtest"]
+
+    if sys.version_info < (3, 3):
+        cmd = [sys.executable, "-m", "test.regrtest"]
+
+    if foo:
+        pass
+    elif sys.version_info < (3, 3):
+        cmd = [sys.executable, "-m", "test.regrtest"]
+    else:
+        cmd = [sys.executable, "-m", "test", "-j0"]
+
+    if sys.version_info < (3, 3):
+        cmd = [sys.executable, "-m", "test.regrtest"]
+    else:
+        cmd = [sys.executable, "-m", "test", "-j0"]
+
+    if sys.version_info < (3, 3):
+        cmd = [sys.executable, "-m", "test.regrtest"]
+    elif foo:
+        cmd = [sys.executable, "-m", "test", "-j0"]
diff --git a/ruff.schema.json b/ruff.schema.json
index 11755b354b..ed9569277c 100644
--- a/ruff.schema.json
+++ b/ruff.schema.json
@@ -1905,6 +1905,7 @@
         "UP033",
         "UP034",
         "UP035",
+        "UP036",
         "W",
         "W2",
         "W29",
diff --git a/setup.py b/setup.py
index aeef6f2ca3..a8d82c4a0a 100644
--- a/setup.py
+++ b/setup.py
@@ -22,3 +22,5 @@ sys.exit(1)
 # To be removed once GitHub catches up.
 
 setup(name="ruff", install_requires=[])
+if True: a = 1; \
+  b = 2
diff --git a/src/checkers/ast.rs b/src/checkers/ast.rs
index d112e85676..a80f8790e2 100644
--- a/src/checkers/ast.rs
+++ b/src/checkers/ast.rs
@@ -1500,6 +1500,9 @@ where
                         self.current_stmt_parent().map(Into::into),
                     );
                 }
+                if self.settings.rules.enabled(&Rule::OutdatedVersionBlock) {
+                    pyupgrade::rules::outdated_version_block(self, stmt, test, body, orelse);
+                }
             }
             StmtKind::Assert { test, msg } => {
                 if self.settings.rules.enabled(&Rule::AssertTuple) {
diff --git a/src/registry.rs b/src/registry.rs
index 3f656eec12..3fdf74c4dd 100644
--- a/src/registry.rs
+++ b/src/registry.rs
@@ -256,6 +256,7 @@ ruff_macros::define_rule_mapping!(
     UP033 => violations::FunctoolsCache,
     UP034 => violations::ExtraneousParentheses,
     UP035 => rules::pyupgrade::rules::ImportReplacements,
+    UP036 => rules::pyupgrade::rules::OutdatedVersionBlock,
     // pydocstyle
     D100 => violations::PublicModule,
     D101 => violations::PublicClass,
diff --git a/src/rules/pyupgrade/fixes.rs b/src/rules/pyupgrade/fixes.rs
index 4546efdbd6..90a1bc444d 100644
--- a/src/rules/pyupgrade/fixes.rs
+++ b/src/rules/pyupgrade/fixes.rs
@@ -1,5 +1,7 @@
+use anyhow::{bail, Result};
 use libcst_native::{
-    Codegen, CodegenState, Expression, ParenthesizableWhitespace, SmallStatement, Statement,
+    Codegen, CodegenState, CompoundStatement, Expression, ParenthesizableWhitespace,
+    SmallStatement, Statement, Suite,
 };
 use rustpython_ast::{Expr, Keyword, Location};
 use rustpython_parser::lexer;
@@ -7,9 +9,47 @@ use rustpython_parser::lexer::Tok;
 
 use crate::ast::types::Range;
 use crate::autofix::helpers::remove_argument;
+use crate::cst::matchers::match_module;
 use crate::fix::Fix;
 use crate::source_code::{Locator, Stylist};
 
+/// Safely adjust the indentation of the indented block at [`Range`].
+pub fn adjust_indentation(
+    range: Range,
+    indentation: &str,
+    locator: &Locator,
+    stylist: &Stylist,
+) -> Result<String> {
+    let contents = locator.slice_source_code_range(&range);
+
+    let module_text = format!("def f():{}{contents}", stylist.line_ending().as_str());
+
+    let mut tree = match_module(&module_text)?;
+
+    let [Statement::Compound(CompoundStatement::FunctionDef(embedding))] = &mut *tree.body else {
+        bail!("Expected statement to be embedded in a function definition")
+    };
+
+    let Suite::IndentedBlock(indented_block) = &mut embedding.body else {
+        bail!("Expected indented block")
+    };
+    indented_block.indent = Some(indentation);
+
+    let mut state = CodegenState {
+        default_newline: stylist.line_ending(),
+        default_indent: stylist.indentation(),
+        ..Default::default()
+    };
+    indented_block.codegen(&mut state);
+
+    let module_text = state.to_string();
+    let module_text = module_text
+        .strip_prefix(stylist.line_ending().as_str())
+        .unwrap()
+        .to_string();
+    Ok(module_text)
+}
+
 /// Generate a fix to remove a base from a `ClassDef` statement.
 pub fn remove_class_def_base(
     locator: &Locator,
diff --git a/src/rules/pyupgrade/mod.rs b/src/rules/pyupgrade/mod.rs
index 33de7d5eb3..db906786cb 100644
--- a/src/rules/pyupgrade/mod.rs
+++ b/src/rules/pyupgrade/mod.rs
@@ -58,6 +58,11 @@ mod tests {
     #[test_case(Rule::FunctoolsCache, Path::new("UP033.py"); "UP033")]
     #[test_case(Rule::ExtraneousParentheses, Path::new("UP034.py"); "UP034")]
     #[test_case(Rule::ImportReplacements, Path::new("UP035.py"); "UP035")]
+    #[test_case(Rule::OutdatedVersionBlock, Path::new("UP036_0.py"); "UP036_0")]
+    #[test_case(Rule::OutdatedVersionBlock, Path::new("UP036_1.py"); "UP036_1")]
+    #[test_case(Rule::OutdatedVersionBlock, Path::new("UP036_2.py"); "UP036_2")]
+    #[test_case(Rule::OutdatedVersionBlock, Path::new("UP036_3.py"); "UP036_3")]
+    #[test_case(Rule::OutdatedVersionBlock, Path::new("UP036_4.py"); "UP036_4")]
     fn rules(rule_code: Rule, path: &Path) -> Result<()> {
         let snapshot = format!("{}_{}", rule_code.code(), path.to_string_lossy());
         let diagnostics = test_path(
diff --git a/src/rules/pyupgrade/rules/mod.rs b/src/rules/pyupgrade/rules/mod.rs
index a49cd9c975..c58ec44a3d 100644
--- a/src/rules/pyupgrade/rules/mod.rs
+++ b/src/rules/pyupgrade/rules/mod.rs
@@ -11,6 +11,7 @@ pub(crate) use lru_cache_without_parameters::lru_cache_without_parameters;
 pub(crate) use native_literals::native_literals;
 pub(crate) use open_alias::open_alias;
 pub(crate) use os_error_alias::os_error_alias;
+pub(crate) use outdated_version_block::{outdated_version_block, OutdatedVersionBlock};
 pub(crate) use printf_string_formatting::printf_string_formatting;
 pub(crate) use redundant_open_modes::redundant_open_modes;
 pub(crate) use replace_stdout_stderr::replace_stdout_stderr;
@@ -46,6 +47,7 @@ mod lru_cache_without_parameters;
 mod native_literals;
 mod open_alias;
 mod os_error_alias;
+mod outdated_version_block;
 mod printf_string_formatting;
 mod redundant_open_modes;
 mod replace_stdout_stderr;
diff --git a/src/rules/pyupgrade/rules/outdated_version_block.rs b/src/rules/pyupgrade/rules/outdated_version_block.rs
new file mode 100644
index 0000000000..e9bac98a4e
--- /dev/null
+++ b/src/rules/pyupgrade/rules/outdated_version_block.rs
@@ -0,0 +1,442 @@
+use std::cmp::Ordering;
+
+use log::error;
+use num_bigint::{BigInt, Sign};
+use rustpython_ast::Location;
+use rustpython_parser::ast::{Cmpop, Constant, Expr, ExprKind, Located, Stmt};
+use rustpython_parser::lexer;
+use rustpython_parser::lexer::Tok;
+
+use ruff_macros::derive_message_formats;
+
+use crate::ast::types::{Range, RefEquality};
+use crate::ast::whitespace::indentation;
+use crate::autofix::helpers::delete_stmt;
+use crate::checkers::ast::Checker;
+use crate::define_violation;
+use crate::fix::Fix;
+use crate::registry::Diagnostic;
+use crate::rules::pyupgrade::fixes::adjust_indentation;
+use crate::settings::types::PythonVersion;
+use crate::source_code::Locator;
+use crate::violation::AlwaysAutofixableViolation;
+
+define_violation!(
+    pub struct OutdatedVersionBlock;
+);
+impl AlwaysAutofixableViolation for OutdatedVersionBlock {
+    #[derive_message_formats]
+    fn message(&self) -> String {
+        format!("Version block is outdated for minimum Python version")
+    }
+
+    fn autofix_title(&self) -> String {
+        "Remove outdated version block".to_string()
+    }
+}
+
+#[derive(Debug)]
+struct BlockMetadata {
+    /// The first non-whitespace token in the block.
+    starter: Tok,
+    /// The location of the first `elif` token, if any.
+    elif: Option<Location>,
+    /// The location of the `else` token, if any.
+    else_: Option<Location>,
+}
+
+impl BlockMetadata {
+    fn new(starter: Tok, elif: Option<Location>, else_: Option<Location>) -> Self {
+        Self {
+            starter,
+            elif,
+            else_,
+        }
+    }
+}
+
+fn metadata<T>(locator: &Locator, located: &Located<T>) -> Option<BlockMetadata> {
+    indentation(locator, located)?;
+
+    // Start the selection at the start-of-line. This ensures consistent indentation in the
+    // token stream, in the event that the entire block is indented.
+    let text = locator.slice_source_code_range(&Range::new(
+        Location::new(located.location.row(), 0),
+        located.end_location.unwrap(),
+    ));
+
+    let mut starter: Option<Tok> = None;
+    let mut elif = None;
+    let mut else_ = None;
+
+    for (start, tok, _) in
+        lexer::make_tokenizer_located(text, Location::new(located.location.row(), 0))
+            .flatten()
+            .filter(|(_, tok, _)| {
+                !matches!(
+                    tok,
+                    Tok::Indent
+                        | Tok::Dedent
+                        | Tok::NonLogicalNewline
+                        | Tok::Newline
+                        | Tok::Comment(..)
+                )
+            })
+    {
+        if starter.is_none() {
+            starter = Some(tok.clone());
+        } else {
+            if matches!(tok, Tok::Elif) && elif.is_none() {
+                elif = Some(start);
+            }
+            if matches!(tok, Tok::Else) && else_.is_none() {
+                else_ = Some(start);
+            }
+        }
+        if starter.is_some() && elif.is_some() && else_.is_some() {
+            break;
+        }
+    }
+    Some(BlockMetadata::new(starter.unwrap(), elif, else_))
+}
+
+/// Converts a `BigInt` to a `u32`, if the number is negative, it will return 0
+fn bigint_to_u32(number: &BigInt) -> u32 {
+    let the_number = number.to_u32_digits();
+    match the_number.0 {
+        Sign::Minus | Sign::NoSign => 0,
+        Sign::Plus => *the_number.1.first().unwrap(),
+    }
+}
+
+/// Gets the version from the tuple
+fn extract_version(elts: &[Expr]) -> Vec<u32> {
+    let mut version: Vec<u32> = vec![];
+    for elt in elts {
+        if let ExprKind::Constant {
+            value: Constant::Int(item),
+            ..
+        } = &elt.node
+        {
+            let number = bigint_to_u32(item);
+            version.push(number);
+        } else {
+            return version;
+        }
+    }
+    version
+}
+
+/// Returns true if the `if_version` is less than the `PythonVersion`
+fn compare_version(if_version: &[u32], py_version: PythonVersion, or_equal: bool) -> bool {
+    let mut if_version_iter = if_version.iter();
+    if let Some(if_major) = if_version_iter.next() {
+        let (py_major, py_minor) = py_version.as_tuple();
+        match if_major.cmp(&py_major) {
+            Ordering::Less => true,
+            Ordering::Equal => {
+                if let Some(if_minor) = if_version_iter.next() {
+                    // Check the if_minor number (the minor version).
+                    if or_equal {
+                        *if_minor <= py_minor
+                    } else {
+                        *if_minor < py_minor
+                    }
+                } else {
+                    // Assume Python 3.0.
+                    true
+                }
+            }
+            Ordering::Greater => false,
+        }
+    } else {
+        false
+    }
+}
+
+/// Convert a [`StmtKind::If`], retaining the `else`.
+fn fix_py2_block(
+    checker: &mut Checker,
+    stmt: &Stmt,
+    body: &[Stmt],
+    orelse: &[Stmt],
+    block: &BlockMetadata,
+) -> Option<Fix> {
+    if orelse.is_empty() {
+        // Delete the entire statement. If this is an `elif`, know it's the only child of its
+        // parent, so avoid passing in the parent at all. Otherwise, `delete_stmt` will erroneously
+        // include a `pass`.
+        let deleted: Vec<&Stmt> = checker
+            .deletions
+            .iter()
+            .map(std::convert::Into::into)
+            .collect();
+        let defined_by = checker.current_stmt();
+        let defined_in = checker.current_stmt_parent();
+        return match delete_stmt(
+            defined_by.into(),
+            if block.starter == Tok::If {
+                defined_in.map(std::convert::Into::into)
+            } else {
+                None
+            },
+            &deleted,
+            checker.locator,
+            checker.indexer,
+            checker.stylist,
+        ) {
+            Ok(fix) => {
+                checker.deletions.insert(RefEquality(defined_by.into()));
+                Some(fix)
+            }
+            Err(err) => {
+                error!("Failed to remove block: {}", err);
+                None
+            }
+        };
+    }
+
+    // If we only have an `if` and an `else`, dedent the `else` block.
+    if block.starter == Tok::If && block.elif.is_none() {
+        let start = orelse.first().unwrap();
+        let end = orelse.last().unwrap();
+
+        if indentation(checker.locator, start).is_none() {
+            // Inline `else` block (e.g., `else: x = 1`).
+            Some(Fix::replacement(
+                checker
+                    .locator
+                    .slice_source_code_range(&Range::new(start.location, end.end_location.unwrap()))
+                    .to_string(),
+                stmt.location,
+                stmt.end_location.unwrap(),
+            ))
+        } else {
+            indentation(checker.locator, stmt)
+                .and_then(|indentation| {
+                    adjust_indentation(
+                        Range::new(
+                            Location::new(start.location.row(), 0),
+                            end.end_location.unwrap(),
+                        ),
+                        indentation,
+                        checker.locator,
+                        checker.stylist,
+                    )
+                    .ok()
+                })
+                .map(|contents| {
+                    Fix::replacement(
+                        contents,
+                        Location::new(stmt.location.row(), 0),
+                        stmt.end_location.unwrap(),
+                    )
+                })
+        }
+    } else {
+        let mut end_location = orelse.last().unwrap().location;
+        if block.starter == Tok::If && block.elif.is_some() {
+            // Turn the `elif` into an `if`.
+            end_location = block.elif.unwrap();
+            end_location.go_right();
+            end_location.go_right();
+        } else if block.starter == Tok::Elif {
+            if let Some(elif) = block.elif {
+                end_location = elif;
+            } else if let Some(else_) = block.else_ {
+                end_location = else_;
+            } else {
+                end_location = body.last().unwrap().end_location.unwrap();
+            }
+        }
+        Some(Fix::deletion(stmt.location, end_location))
+    }
+}
+
+/// Convert a [`StmtKind::If`], removing the `else` block.
+fn fix_py3_block(
+    checker: &mut Checker,
+    stmt: &Stmt,
+    test: &Expr,
+    body: &[Stmt],
+    block: &BlockMetadata,
+) -> Option<Fix> {
+    match block.starter {
+        Tok::If => {
+            // If the first statement is an if, use the body of this statement, and ignore the rest.
+            let start = body.first().unwrap();
+            let end = body.last().unwrap();
+
+            if indentation(checker.locator, start).is_none() {
+                // Inline `if` block (e.g., `if ...: x = 1`).
+                Some(Fix::replacement(
+                    checker
+                        .locator
+                        .slice_source_code_range(&Range::new(
+                            start.location,
+                            end.end_location.unwrap(),
+                        ))
+                        .to_string(),
+                    stmt.location,
+                    stmt.end_location.unwrap(),
+                ))
+            } else {
+                indentation(checker.locator, stmt)
+                    .and_then(|indentation| {
+                        adjust_indentation(
+                            Range::new(
+                                Location::new(start.location.row(), 0),
+                                end.end_location.unwrap(),
+                            ),
+                            indentation,
+                            checker.locator,
+                            checker.stylist,
+                        )
+                        .ok()
+                    })
+                    .map(|contents| {
+                        Fix::replacement(
+                            contents,
+                            Location::new(stmt.location.row(), 0),
+                            stmt.end_location.unwrap(),
+                        )
+                    })
+            }
+        }
+        Tok::Elif => {
+            // Replace the `elif` with an `else, preserve the body of the elif, and remove the rest.
+            let end = body.last().unwrap();
+            let text = checker.locator.slice_source_code_range(&Range::new(
+                test.end_location.unwrap(),
+                end.end_location.unwrap(),
+            ));
+            Some(Fix::replacement(
+                format!("else{text}"),
+                stmt.location,
+                stmt.end_location.unwrap(),
+            ))
+        }
+        _ => None,
+    }
+}
+
+/// UP036
+pub fn outdated_version_block(
+    checker: &mut Checker,
+    stmt: &Stmt,
+    test: &Expr,
+    body: &[Stmt],
+    orelse: &[Stmt],
+) {
+    let ExprKind::Compare {
+        left,
+        ops,
+        comparators,
+    } = &test.node else {
+        return;
+    };
+
+    if !checker.resolve_call_path(left).map_or(false, |call_path| {
+        call_path.as_slice() == ["sys", "version_info"]
+    }) {
+        return;
+    }
+
+    if ops.len() == 1 && comparators.len() == 1 {
+        let comparison = &comparators[0].node;
+        let op = &ops[0];
+        match comparison {
+            ExprKind::Tuple { elts, .. } => {
+                let version = extract_version(elts);
+                let target = checker.settings.target_version;
+                if op == &Cmpop::Lt || op == &Cmpop::LtE {
+                    if compare_version(&version, target, op == &Cmpop::LtE) {
+                        let mut diagnostic =
+                            Diagnostic::new(OutdatedVersionBlock, Range::from_located(stmt));
+                        if checker.patch(diagnostic.kind.rule()) {
+                            if let Some(block) = metadata(checker.locator, stmt) {
+                                if let Some(fix) =
+                                    fix_py2_block(checker, stmt, body, orelse, &block)
+                                {
+                                    diagnostic.amend(fix);
+                                }
+                            }
+                        }
+                        checker.diagnostics.push(diagnostic);
+                    }
+                } else if op == &Cmpop::Gt || op == &Cmpop::GtE {
+                    if compare_version(&version, target, op == &Cmpop::GtE) {
+                        let mut diagnostic =
+                            Diagnostic::new(OutdatedVersionBlock, Range::from_located(stmt));
+                        if checker.patch(diagnostic.kind.rule()) {
+                            if let Some(block) = metadata(checker.locator, stmt) {
+                                if let Some(fix) = fix_py3_block(checker, stmt, test, body, &block)
+                                {
+                                    diagnostic.amend(fix);
+                                }
+                            }
+                        }
+                        checker.diagnostics.push(diagnostic);
+                    }
+                }
+            }
+            ExprKind::Constant {
+                value: Constant::Int(number),
+                ..
+            } => {
+                let version_number = bigint_to_u32(number);
+                if version_number == 2 && op == &Cmpop::Eq {
+                    let mut diagnostic =
+                        Diagnostic::new(OutdatedVersionBlock, Range::from_located(stmt));
+                    if checker.patch(diagnostic.kind.rule()) {
+                        if let Some(block) = metadata(checker.locator, stmt) {
+                            if let Some(fix) = fix_py2_block(checker, stmt, body, orelse, &block) {
+                                diagnostic.amend(fix);
+                            }
+                        }
+                    }
+                    checker.diagnostics.push(diagnostic);
+                } else if version_number == 3 && op == &Cmpop::Eq {
+                    let mut diagnostic =
+                        Diagnostic::new(OutdatedVersionBlock, Range::from_located(stmt));
+                    if checker.patch(diagnostic.kind.rule()) {
+                        if let Some(block) = metadata(checker.locator, stmt) {
+                            if let Some(fix) = fix_py3_block(checker, stmt, test, body, &block) {
+                                diagnostic.amend(fix);
+                            }
+                        }
+                    }
+                    checker.diagnostics.push(diagnostic);
+                }
+            }
+            _ => (),
+        }
+    }
+}
+
+#[cfg(test)]
+mod tests {
+    use test_case::test_case;
+
+    use super::*;
+
+    #[test_case(PythonVersion::Py37, &[2], true, true; "compare-2.0")]
+    #[test_case(PythonVersion::Py37, &[2, 0], true, true; "compare-2.0-whole")]
+    #[test_case(PythonVersion::Py37, &[3], true, true; "compare-3.0")]
+    #[test_case(PythonVersion::Py37, &[3, 0], true, true; "compare-3.0-whole")]
+    #[test_case(PythonVersion::Py37, &[3, 1], true, true; "compare-3.1")]
+    #[test_case(PythonVersion::Py37, &[3, 5], true, true; "compare-3.5")]
+    #[test_case(PythonVersion::Py37, &[3, 7], true, true; "compare-3.7")]
+    #[test_case(PythonVersion::Py37, &[3, 7], false, false; "compare-3.7-not-equal")]
+    #[test_case(PythonVersion::Py37, &[3, 8], false , false; "compare-3.8")]
+    #[test_case(PythonVersion::Py310, &[3,9], true, true; "compare-3.9")]
+    #[test_case(PythonVersion::Py310, &[3, 11], true, false; "compare-3.11")]
+    fn test_compare_version(
+        version: PythonVersion,
+        version_vec: &[u32],
+        or_equal: bool,
+        expected: bool,
+    ) {
+        assert_eq!(compare_version(version_vec, version, or_equal), expected);
+    }
+}
diff --git a/src/rules/pyupgrade/snapshots/ruff__rules__pyupgrade__tests__UP036_UP036_0.py.snap b/src/rules/pyupgrade/snapshots/ruff__rules__pyupgrade__tests__UP036_UP036_0.py.snap
new file mode 100644
index 0000000000..0eae75df5a
--- /dev/null
+++ b/src/rules/pyupgrade/snapshots/ruff__rules__pyupgrade__tests__UP036_UP036_0.py.snap
@@ -0,0 +1,535 @@
+---
+source: src/rules/pyupgrade/mod.rs
+expression: diagnostics
+---
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 3
+    column: 0
+  end_location:
+    row: 6
+    column: 16
+  fix:
+    content:
+      - "print(\"py3\")"
+    location:
+      row: 3
+      column: 0
+    end_location:
+      row: 6
+      column: 16
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 8
+    column: 0
+  end_location:
+    row: 14
+    column: 16
+  fix:
+    content:
+      - "print(\"py3\")"
+    location:
+      row: 8
+      column: 0
+    end_location:
+      row: 14
+      column: 16
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 16
+    column: 0
+  end_location:
+    row: 17
+    column: 19
+  fix:
+    content:
+      - "print(\"PY3!\")"
+    location:
+      row: 16
+      column: 0
+    end_location:
+      row: 17
+      column: 19
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 20
+    column: 4
+  end_location:
+    row: 23
+    column: 20
+  fix:
+    content:
+      - "    print(\"PY3\")"
+    location:
+      row: 20
+      column: 0
+    end_location:
+      row: 23
+      column: 20
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 25
+    column: 0
+  end_location:
+    row: 27
+    column: 16
+  fix:
+    content:
+      - "print(\"py3\")"
+    location:
+      row: 25
+      column: 0
+    end_location:
+      row: 27
+      column: 16
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 29
+    column: 0
+  end_location:
+    row: 35
+    column: 30
+  fix:
+    content:
+      - "def f():"
+      - "    print(\"py3\")"
+      - "    print(\"This the next\")"
+    location:
+      row: 29
+      column: 0
+    end_location:
+      row: 35
+      column: 30
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 37
+    column: 0
+  end_location:
+    row: 40
+    column: 16
+  fix:
+    content:
+      - "print(\"py3\")"
+    location:
+      row: 37
+      column: 0
+    end_location:
+      row: 40
+      column: 16
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 45
+    column: 0
+  end_location:
+    row: 48
+    column: 16
+  fix:
+    content:
+      - "print(\"py3\")"
+    location:
+      row: 45
+      column: 0
+    end_location:
+      row: 48
+      column: 16
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 53
+    column: 0
+  end_location:
+    row: 54
+    column: 18
+  fix:
+    content:
+      - "print(\"py3\")"
+    location:
+      row: 53
+      column: 0
+    end_location:
+      row: 54
+      column: 18
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 56
+    column: 0
+  end_location:
+    row: 59
+    column: 16
+  fix:
+    content:
+      - "print(\"py3\")"
+    location:
+      row: 56
+      column: 0
+    end_location:
+      row: 59
+      column: 16
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 62
+    column: 4
+  end_location:
+    row: 65
+    column: 20
+  fix:
+    content:
+      - "    print(\"py3\")"
+    location:
+      row: 62
+      column: 0
+    end_location:
+      row: 65
+      column: 20
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 67
+    column: 0
+  end_location:
+    row: 70
+    column: 16
+  fix:
+    content:
+      - "print(\"py3\")"
+    location:
+      row: 67
+      column: 0
+    end_location:
+      row: 70
+      column: 16
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 73
+    column: 4
+  end_location:
+    row: 79
+    column: 13
+  fix:
+    content:
+      - "    yield"
+    location:
+      row: 73
+      column: 0
+    end_location:
+      row: 79
+      column: 13
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 86
+    column: 4
+  end_location:
+    row: 91
+    column: 16
+  fix:
+    content:
+      - "    def f(py3):"
+      - "        pass"
+    location:
+      row: 86
+      column: 0
+    end_location:
+      row: 91
+      column: 16
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 97
+    column: 4
+  end_location:
+    row: 100
+    column: 9
+  fix:
+    content:
+      - "    3"
+    location:
+      row: 97
+      column: 0
+    end_location:
+      row: 100
+      column: 9
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 104
+    column: 0
+  end_location:
+    row: 113
+    column: 20
+  fix:
+    content:
+      - "def f():"
+      - "    print(\"py3\")"
+      - "def g():"
+      - "    print(\"py3\")"
+    location:
+      row: 104
+      column: 0
+    end_location:
+      row: 113
+      column: 20
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 116
+    column: 4
+  end_location:
+    row: 117
+    column: 16
+  fix:
+    content:
+      - "    print(3)"
+    location:
+      row: 116
+      column: 0
+    end_location:
+      row: 117
+      column: 16
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 122
+    column: 4
+  end_location:
+    row: 122
+    column: 40
+  fix:
+    content:
+      - print(3)
+    location:
+      row: 122
+      column: 4
+    end_location:
+      row: 122
+      column: 40
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 125
+    column: 4
+  end_location:
+    row: 126
+    column: 16
+  fix:
+    content:
+      - "    print(3)"
+    location:
+      row: 125
+      column: 0
+    end_location:
+      row: 126
+      column: 16
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 130
+    column: 4
+  end_location:
+    row: 137
+    column: 9
+  fix:
+    content:
+      - "    expected_error = ["
+      - "\"<stdin>:1:5: Generator expression must be parenthesized\","
+      - "\"max(1 for i in range(10), key=lambda x: x+1)\","
+      - "\"    ^\","
+      - "    ]"
+    location:
+      row: 130
+      column: 0
+    end_location:
+      row: 137
+      column: 9
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 140
+    column: 0
+  end_location:
+    row: 147
+    column: 5
+  fix:
+    content:
+      - "expected_error = ["
+      - "\"<stdin>:1:5: Generator expression must be parenthesized\","
+      - "\"max(1 for i in range(10), key=lambda x: x+1)\","
+      - "\"    ^\","
+      - "]"
+    location:
+      row: 140
+      column: 0
+    end_location:
+      row: 147
+      column: 5
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 150
+    column: 0
+  end_location:
+    row: 161
+    column: 28
+  fix:
+    content:
+      - "\"\"\"this"
+      - "is valid\"\"\""
+      - ""
+      - "\"\"\"the indentation on"
+      - "    this line is significant\"\"\""
+      - ""
+      - "\"this is\" \\"
+      - "    \"allowed too\""
+      - ""
+      - "(\"so is\""
+      - " \"this for some reason\")"
+    location:
+      row: 150
+      column: 0
+    end_location:
+      row: 161
+      column: 28
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 163
+    column: 0
+  end_location:
+    row: 164
+    column: 6
+  fix:
+    content:
+      - "expected_error = \\"
+      - "    []"
+    location:
+      row: 163
+      column: 0
+    end_location:
+      row: 164
+      column: 6
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 166
+    column: 0
+  end_location:
+    row: 166
+    column: 49
+  fix:
+    content:
+      - "expected_error = []"
+    location:
+      row: 166
+      column: 0
+    end_location:
+      row: 166
+      column: 49
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 168
+    column: 0
+  end_location:
+    row: 169
+    column: 23
+  fix:
+    content:
+      - "expected_error = []"
+    location:
+      row: 168
+      column: 0
+    end_location:
+      row: 169
+      column: 23
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 172
+    column: 4
+  end_location:
+    row: 173
+    column: 6
+  fix:
+    content:
+      - "expected_error = \\"
+      - "    []"
+    location:
+      row: 172
+      column: 4
+    end_location:
+      row: 173
+      column: 6
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 176
+    column: 4
+  end_location:
+    row: 176
+    column: 53
+  fix:
+    content:
+      - "expected_error = []"
+    location:
+      row: 176
+      column: 4
+    end_location:
+      row: 176
+      column: 53
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 179
+    column: 4
+  end_location:
+    row: 180
+    column: 23
+  fix:
+    content:
+      - "    expected_error = []"
+    location:
+      row: 179
+      column: 0
+    end_location:
+      row: 180
+      column: 23
+  parent: ~
+
diff --git a/src/rules/pyupgrade/snapshots/ruff__rules__pyupgrade__tests__UP036_UP036_1.py.snap b/src/rules/pyupgrade/snapshots/ruff__rules__pyupgrade__tests__UP036_UP036_1.py.snap
new file mode 100644
index 0000000000..a3476a6186
--- /dev/null
+++ b/src/rules/pyupgrade/snapshots/ruff__rules__pyupgrade__tests__UP036_UP036_1.py.snap
@@ -0,0 +1,243 @@
+---
+source: src/rules/pyupgrade/mod.rs
+expression: diagnostics
+---
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 3
+    column: 0
+  end_location:
+    row: 6
+    column: 5
+  fix:
+    content:
+      - "3"
+    location:
+      row: 3
+      column: 0
+    end_location:
+      row: 6
+      column: 5
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 8
+    column: 0
+  end_location:
+    row: 11
+    column: 5
+  fix:
+    content:
+      - "3"
+    location:
+      row: 8
+      column: 0
+    end_location:
+      row: 11
+      column: 5
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 13
+    column: 0
+  end_location:
+    row: 16
+    column: 5
+  fix:
+    content:
+      - "3"
+    location:
+      row: 13
+      column: 0
+    end_location:
+      row: 16
+      column: 5
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 18
+    column: 0
+  end_location:
+    row: 21
+    column: 5
+  fix:
+    content:
+      - "3"
+    location:
+      row: 18
+      column: 0
+    end_location:
+      row: 21
+      column: 5
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 23
+    column: 0
+  end_location:
+    row: 26
+    column: 5
+  fix:
+    content:
+      - "3"
+    location:
+      row: 23
+      column: 0
+    end_location:
+      row: 26
+      column: 5
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 28
+    column: 0
+  end_location:
+    row: 31
+    column: 5
+  fix:
+    content:
+      - "3"
+    location:
+      row: 28
+      column: 0
+    end_location:
+      row: 31
+      column: 5
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 35
+    column: 0
+  end_location:
+    row: 38
+    column: 5
+  fix:
+    content:
+      - "3"
+    location:
+      row: 35
+      column: 0
+    end_location:
+      row: 38
+      column: 5
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 42
+    column: 0
+  end_location:
+    row: 45
+    column: 12
+  fix:
+    content:
+      - ""
+    location:
+      row: 42
+      column: 0
+    end_location:
+      row: 44
+      column: 0
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 49
+    column: 0
+  end_location:
+    row: 52
+    column: 12
+  fix:
+    content:
+      - "else:"
+      - "    print(3)"
+    location:
+      row: 49
+      column: 0
+    end_location:
+      row: 52
+      column: 12
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 56
+    column: 0
+  end_location:
+    row: 57
+    column: 12
+  fix:
+    content:
+      - "else:"
+      - "    print(3)"
+    location:
+      row: 56
+      column: 0
+    end_location:
+      row: 57
+      column: 12
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 62
+    column: 4
+  end_location:
+    row: 63
+    column: 16
+  fix:
+    content:
+      - "else:"
+      - "        print(3)"
+    location:
+      row: 62
+      column: 4
+    end_location:
+      row: 63
+      column: 16
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 67
+    column: 0
+  end_location:
+    row: 70
+    column: 12
+  fix:
+    content:
+      - ""
+    location:
+      row: 67
+      column: 0
+    end_location:
+      row: 69
+      column: 0
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 75
+    column: 4
+  end_location:
+    row: 76
+    column: 16
+  fix:
+    content:
+      - "else:"
+      - "        print(3)"
+    location:
+      row: 75
+      column: 4
+    end_location:
+      row: 76
+      column: 16
+  parent: ~
+
diff --git a/src/rules/pyupgrade/snapshots/ruff__rules__pyupgrade__tests__UP036_UP036_2.py.snap b/src/rules/pyupgrade/snapshots/ruff__rules__pyupgrade__tests__UP036_UP036_2.py.snap
new file mode 100644
index 0000000000..a492598723
--- /dev/null
+++ b/src/rules/pyupgrade/snapshots/ruff__rules__pyupgrade__tests__UP036_UP036_2.py.snap
@@ -0,0 +1,221 @@
+---
+source: src/rules/pyupgrade/mod.rs
+expression: diagnostics
+---
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 4
+    column: 0
+  end_location:
+    row: 7
+    column: 7
+  fix:
+    content:
+      - 3+6
+    location:
+      row: 4
+      column: 0
+    end_location:
+      row: 7
+      column: 7
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 9
+    column: 0
+  end_location:
+    row: 12
+    column: 7
+  fix:
+    content:
+      - 3+6
+    location:
+      row: 9
+      column: 0
+    end_location:
+      row: 12
+      column: 7
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 14
+    column: 0
+  end_location:
+    row: 17
+    column: 7
+  fix:
+    content:
+      - 3+6
+    location:
+      row: 14
+      column: 0
+    end_location:
+      row: 17
+      column: 7
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 19
+    column: 0
+  end_location:
+    row: 22
+    column: 7
+  fix:
+    content:
+      - 3+6
+    location:
+      row: 19
+      column: 0
+    end_location:
+      row: 22
+      column: 7
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 24
+    column: 0
+  end_location:
+    row: 27
+    column: 7
+  fix:
+    content:
+      - 3+6
+    location:
+      row: 24
+      column: 0
+    end_location:
+      row: 27
+      column: 7
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 29
+    column: 0
+  end_location:
+    row: 32
+    column: 7
+  fix:
+    content:
+      - 3+6
+    location:
+      row: 29
+      column: 0
+    end_location:
+      row: 32
+      column: 7
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 34
+    column: 0
+  end_location:
+    row: 37
+    column: 7
+  fix:
+    content:
+      - 3+6
+    location:
+      row: 34
+      column: 0
+    end_location:
+      row: 37
+      column: 7
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 39
+    column: 0
+  end_location:
+    row: 40
+    column: 8
+  fix:
+    content:
+      - pass
+    location:
+      row: 39
+      column: 0
+    end_location:
+      row: 40
+      column: 8
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 42
+    column: 0
+  end_location:
+    row: 43
+    column: 8
+  fix:
+    content:
+      - ""
+    location:
+      row: 42
+      column: 0
+    end_location:
+      row: 44
+      column: 0
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 46
+    column: 4
+  end_location:
+    row: 47
+    column: 12
+  fix:
+    content:
+      - pass
+    location:
+      row: 46
+      column: 4
+    end_location:
+      row: 47
+      column: 12
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 49
+    column: 0
+  end_location:
+    row: 52
+    column: 8
+  fix:
+    content:
+      - ""
+    location:
+      row: 49
+      column: 0
+    end_location:
+      row: 51
+      column: 2
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 54
+    column: 0
+  end_location:
+    row: 57
+    column: 8
+  fix:
+    content:
+      - pass
+    location:
+      row: 54
+      column: 0
+    end_location:
+      row: 57
+      column: 8
+  parent: ~
+
diff --git a/src/rules/pyupgrade/snapshots/ruff__rules__pyupgrade__tests__UP036_UP036_3.py.snap b/src/rules/pyupgrade/snapshots/ruff__rules__pyupgrade__tests__UP036_UP036_3.py.snap
new file mode 100644
index 0000000000..82a0607c0b
--- /dev/null
+++ b/src/rules/pyupgrade/snapshots/ruff__rules__pyupgrade__tests__UP036_UP036_3.py.snap
@@ -0,0 +1,63 @@
+---
+source: src/rules/pyupgrade/mod.rs
+expression: diagnostics
+---
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 3
+    column: 0
+  end_location:
+    row: 10
+    column: 28
+  fix:
+    content:
+      - "print(\"py3\")"
+      - "for item in range(10):"
+      - "    print(f\"PY3-{item}\")"
+    location:
+      row: 3
+      column: 0
+    end_location:
+      row: 10
+      column: 28
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 13
+    column: 4
+  end_location:
+    row: 20
+    column: 32
+  fix:
+    content:
+      - "    print(\"py3\")"
+      - "    for item in range(10):"
+      - "        print(f\"PY3-{item}\")"
+    location:
+      row: 13
+      column: 0
+    end_location:
+      row: 20
+      column: 32
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 23
+    column: 0
+  end_location:
+    row: 24
+    column: 50
+  fix:
+    content:
+      - "print(\"PY3!\")"
+    location:
+      row: 23
+      column: 0
+    end_location:
+      row: 24
+      column: 50
+  parent: ~
+
diff --git a/src/rules/pyupgrade/snapshots/ruff__rules__pyupgrade__tests__UP036_UP036_4.py.snap b/src/rules/pyupgrade/snapshots/ruff__rules__pyupgrade__tests__UP036_UP036_4.py.snap
new file mode 100644
index 0000000000..bcdf8a5bed
--- /dev/null
+++ b/src/rules/pyupgrade/snapshots/ruff__rules__pyupgrade__tests__UP036_UP036_4.py.snap
@@ -0,0 +1,149 @@
+---
+source: src/rules/pyupgrade/mod.rs
+expression: diagnostics
+---
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 4
+    column: 4
+  end_location:
+    row: 5
+    column: 53
+  fix:
+    content:
+      - pass
+    location:
+      row: 4
+      column: 4
+    end_location:
+      row: 5
+      column: 53
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 11
+    column: 4
+  end_location:
+    row: 12
+    column: 53
+  fix:
+    content:
+      - ""
+    location:
+      row: 11
+      column: 0
+    end_location:
+      row: 13
+      column: 0
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 17
+    column: 4
+  end_location:
+    row: 20
+    column: 51
+  fix:
+    content:
+      - ""
+    location:
+      row: 17
+      column: 4
+    end_location:
+      row: 19
+      column: 4
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 24
+    column: 4
+  end_location:
+    row: 25
+    column: 53
+  fix:
+    content:
+      - ""
+    location:
+      row: 24
+      column: 0
+    end_location:
+      row: 26
+      column: 0
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 27
+    column: 4
+  end_location:
+    row: 28
+    column: 53
+  fix:
+    content:
+      - ""
+    location:
+      row: 27
+      column: 0
+    end_location:
+      row: 29
+      column: 0
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 32
+    column: 4
+  end_location:
+    row: 35
+    column: 51
+  fix:
+    content:
+      - ""
+    location:
+      row: 32
+      column: 4
+    end_location:
+      row: 34
+      column: 4
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 37
+    column: 4
+  end_location:
+    row: 40
+    column: 51
+  fix:
+    content:
+      - "    cmd = [sys.executable, \"-m\", \"test\", \"-j0\"]"
+    location:
+      row: 37
+      column: 0
+    end_location:
+      row: 40
+      column: 51
+  parent: ~
+- kind:
+    OutdatedVersionBlock: ~
+  location:
+    row: 42
+    column: 4
+  end_location:
+    row: 45
+    column: 51
+  fix:
+    content:
+      - ""
+    location:
+      row: 42
+      column: 4
+    end_location:
+      row: 44
+      column: 6
+  parent: ~
+
diff --git a/src/settings/types.rs b/src/settings/types.rs
index ab4682d2c6..324adf3450 100644
--- a/src/settings/types.rs
+++ b/src/settings/types.rs
@@ -49,6 +49,18 @@ impl FromStr for PythonVersion {
     }
 }
 
+impl PythonVersion {
+    pub fn as_tuple(&self) -> (u32, u32) {
+        match self {
+            PythonVersion::Py37 => (3, 7),
+            PythonVersion::Py38 => (3, 8),
+            PythonVersion::Py39 => (3, 9),
+            PythonVersion::Py310 => (3, 10),
+            PythonVersion::Py311 => (3, 11),
+        }
+    }
+}
+
 #[derive(Debug, Clone, Hash, PartialEq, PartialOrd, Eq, Ord)]
 pub enum FilePattern {
     Builtin(&'static str),