diff --git a/crates/ruff_linter/resources/test/fixtures/flake8_type_checking/quote.py b/crates/ruff_linter/resources/test/fixtures/flake8_type_checking/quote.py
index d13e8cd970f8c..547cd30117672 100644
--- a/crates/ruff_linter/resources/test/fixtures/flake8_type_checking/quote.py
+++ b/crates/ruff_linter/resources/test/fixtures/flake8_type_checking/quote.py
@@ -12,13 +12,6 @@ def baz() -> DataFrame[int]:
         ...
 
 
-def f():
-    from pandas import DataFrame
-
-    def baz() -> DataFrame["int"]:
-        ...
-
-
 def f():
     import pandas as pd
 
diff --git a/crates/ruff_linter/resources/test/fixtures/flake8_type_checking/quote2.py b/crates/ruff_linter/resources/test/fixtures/flake8_type_checking/quote2.py
new file mode 100644
index 0000000000000..4433416da5087
--- /dev/null
+++ b/crates/ruff_linter/resources/test/fixtures/flake8_type_checking/quote2.py
@@ -0,0 +1,87 @@
+def f():
+    from django.contrib.auth.models import AbstractBaseUser
+
+    def test_remove_inner_quotes_double(self, user: AbstractBaseUser["int"]):
+        pass
+
+
+def f():
+    from django.contrib.auth.models import AbstractBaseUser
+
+    def test_remove_inner_quotes_single(self, user: AbstractBaseUser['int']):
+        pass
+
+
+def f():
+    from django.contrib.auth.models import AbstractBaseUser
+
+    def test_remove_inner_quotes_mixed(self, user: AbstractBaseUser['int', "str"]):
+        pass
+
+
+def f():
+    from typing import Annotated, Literal
+
+    from django.contrib.auth.models import AbstractBaseUser
+
+    def test_literal_annotation_args_contain_quotes(self, type1: AbstractBaseUser[Literal["user", "admin"], Annotated["int", "1", 2]]):
+        pass
+
+
+def f():
+    from typing import Literal
+
+    from django.contrib.auth.models import AbstractBaseUser
+
+    def test_union_contain_inner_quotes(self, type1: AbstractBaseUser["int" | Literal["int"]]):
+        pass
+
+
+def f():
+    from typing import Literal
+
+    from django.contrib.auth.models import AbstractBaseUser
+
+    def test_inner_literal_mixed_quotes(user: AbstractBaseUser[Literal['user', "admin"]]):
+        pass
+
+
+def f():
+    from typing import Literal
+
+    from django.contrib.auth.models import AbstractBaseUser
+
+    def test_inner_literal_single_quote(user: AbstractBaseUser[Literal['int'], str]):
+        pass
+
+
+def f():
+    from typing import Literal
+
+    from django.contrib.auth.models import AbstractBaseUser
+
+    def test_mixed_quotes_literal(user: AbstractBaseUser[Literal['user'], "int"]):
+        pass
+
+
+def f():
+    from typing import Annotated, Literal
+
+    from django.contrib.auth.models import AbstractBaseUser
+
+    def test_annotated_literal_mixed_quotes(user: AbstractBaseUser[Annotated[str, "max_length=20", Literal['user', "admin"]]]):
+        pass
+
+
+def f():
+    from typing import Literal, Union
+
+    def test_union_literal_no_removal(arg: Union[Literal["true", "false"], None]):
+        pass
+
+
+def f():
+    from typing import Literal, Optional
+
+    def test_optional_literal_no_removal(arg: Optional[Literal["red", "blue"]]):
+        pass
diff --git a/crates/ruff_linter/resources/test/fixtures/flake8_type_checking/quote3.py b/crates/ruff_linter/resources/test/fixtures/flake8_type_checking/quote3.py
new file mode 100644
index 0000000000000..b360230b4e6e1
--- /dev/null
+++ b/crates/ruff_linter/resources/test/fixtures/flake8_type_checking/quote3.py
@@ -0,0 +1,44 @@
+def f():
+    from typing import Literal, Union
+
+    from django.contrib.auth.models import AbstractBaseUser
+
+    def test_union_literal_mixed_quotes(user: AbstractBaseUser[Union[Literal['active', "inactive"], str]]):
+        pass
+
+
+def f():
+    from typing import Callable, Literal
+
+    from django.contrib.auth.models import AbstractBaseUser
+
+    def test_callable_literal_mixed_quotes(callable_fn: AbstractBaseUser[Callable[["int", Literal['admin', "user"]], 'bool']]):
+        pass
+
+
+def f():
+    from typing import Annotated, Callable, Literal
+
+    from django.contrib.auth.models import AbstractBaseUser
+
+    def test_callable_annotated_literal(callable_fn: AbstractBaseUser[Callable[[int, Annotated[str, Literal['active', "inactive"]]], bool]]):
+        pass
+
+
+def f():
+    from typing import literal
+
+    from django.contrib.auth import models
+
+    def test_attribute(arg: models.AbstractBaseUser["int"]):
+        pass
+
+
+def f():
+    from typing import Literal
+
+    from django.contrib.auth import models
+
+    def test_attribute_typing_literal(arg: models.AbstractBaseUser[Literal["admin"]]):
+        pass
+
diff --git a/crates/ruff_linter/src/rules/flake8_type_checking/helpers.rs b/crates/ruff_linter/src/rules/flake8_type_checking/helpers.rs
index 09973b7ff3637..346665411081a 100644
--- a/crates/ruff_linter/src/rules/flake8_type_checking/helpers.rs
+++ b/crates/ruff_linter/src/rules/flake8_type_checking/helpers.rs
@@ -1,4 +1,6 @@
 use anyhow::Result;
+use ast::visitor::source_order;
+use ruff_python_ast::visitor::source_order::SourceOrderVisitor;
 use std::cmp::Reverse;
 
 use ruff_diagnostics::Edit;
@@ -9,7 +11,6 @@ use ruff_python_codegen::{Generator, Stylist};
 use ruff_python_semantic::{
     analyze, Binding, BindingKind, Modules, NodeId, ResolvedReference, ScopeKind, SemanticModel,
 };
-use ruff_source_file::Locator;
 use ruff_text_size::Ranged;
 
 use crate::rules::flake8_type_checking::settings::Settings;
@@ -223,9 +224,7 @@ pub(crate) fn is_singledispatch_implementation(
 pub(crate) fn quote_annotation(
     node_id: NodeId,
     semantic: &SemanticModel,
-    locator: &Locator,
     stylist: &Stylist,
-    generator: Generator,
 ) -> Result<Edit> {
     let expr = semantic.expression(node_id).expect("Expression not found");
     if let Some(parent_id) = semantic.parent_expression_id(node_id) {
@@ -235,7 +234,7 @@ pub(crate) fn quote_annotation(
                     // If we're quoting the value of a subscript, we need to quote the entire
                     // expression. For example, when quoting `DataFrame` in `DataFrame[int]`, we
                     // should generate `"DataFrame[int]"`.
-                    return quote_annotation(parent_id, semantic, locator, stylist, generator);
+                    return quote_annotation(parent_id, semantic, stylist);
                 }
             }
             Some(Expr::Attribute(parent)) => {
@@ -243,7 +242,7 @@ pub(crate) fn quote_annotation(
                     // If we're quoting the value of an attribute, we need to quote the entire
                     // expression. For example, when quoting `DataFrame` in `pd.DataFrame`, we
                     // should generate `"pd.DataFrame"`.
-                    return quote_annotation(parent_id, semantic, locator, stylist, generator);
+                    return quote_annotation(parent_id, semantic, stylist);
                 }
             }
             Some(Expr::Call(parent)) => {
@@ -251,7 +250,7 @@ pub(crate) fn quote_annotation(
                     // If we're quoting the function of a call, we need to quote the entire
                     // expression. For example, when quoting `DataFrame` in `DataFrame()`, we
                     // should generate `"DataFrame()"`.
-                    return quote_annotation(parent_id, semantic, locator, stylist, generator);
+                    return quote_annotation(parent_id, semantic, stylist);
                 }
             }
             Some(Expr::BinOp(parent)) => {
@@ -259,27 +258,17 @@ pub(crate) fn quote_annotation(
                     // If we're quoting the left or right side of a binary operation, we need to
                     // quote the entire expression. For example, when quoting `DataFrame` in
                     // `DataFrame | Series`, we should generate `"DataFrame | Series"`.
-                    return quote_annotation(parent_id, semantic, locator, stylist, generator);
+                    return quote_annotation(parent_id, semantic, stylist);
                 }
             }
             _ => {}
         }
     }
 
-    // If the annotation already contains a quote, avoid attempting to re-quote it. For example:
-    // ```python
-    // from typing import Literal
-    //
-    // Set[Literal["Foo"]]
-    // ```
-    let text = locator.slice(expr);
-    if text.contains('\'') || text.contains('"') {
-        return Err(anyhow::anyhow!("Annotation already contains a quote"));
-    }
-
-    // Quote the entire expression.
     let quote = stylist.quote();
-    let annotation = generator.expr(expr);
+    let mut quote_annotator = QuoteAnnotator::new(semantic, stylist);
+    quote_annotator.visit_expr(expr);
+    let annotation = quote_annotator.into_annotation();
 
     Ok(Edit::range_replacement(
         format!("{quote}{annotation}{quote}"),
@@ -306,3 +295,111 @@ pub(crate) fn filter_contained(edits: Vec<Edit>) -> Vec<Edit> {
     }
     filtered
 }
+
+#[derive(Copy, PartialEq, Clone)]
+enum QuoteAnnotatorState {
+    Literal,
+    AnnotatedFirst,
+    AnnotatedRest,
+    Other,
+}
+
+pub(crate) struct QuoteAnnotator<'a> {
+    stylist: &'a Stylist<'a>,
+    semantic: &'a SemanticModel<'a>,
+    state: Vec<QuoteAnnotatorState>,
+    annotation: String,
+}
+
+impl<'a> QuoteAnnotator<'a> {
+    fn new(semantic: &'a SemanticModel<'a>, stylist: &'a Stylist<'a>) -> Self {
+        Self {
+            stylist,
+            semantic,
+            state: Vec::new(),
+            annotation: String::new(),
+        }
+    }
+
+    fn into_annotation(self) -> String {
+        self.annotation
+    }
+}
+
+impl<'a> source_order::SourceOrderVisitor<'a> for QuoteAnnotator<'a> {
+    fn visit_expr(&mut self, expr: &'a Expr) {
+        let generator = Generator::from(self.stylist);
+
+        match expr {
+            Expr::Subscript(ast::ExprSubscript { value, slice, .. }) => {
+                let value_expr = generator.expr(value);
+                self.annotation.push_str(&value_expr);
+                self.annotation.push('[');
+
+                if let Some(qualified_name) = self.semantic.resolve_qualified_name(value) {
+                    if self
+                        .semantic
+                        .match_typing_qualified_name(&qualified_name, "Literal")
+                    {
+                        self.state.push(QuoteAnnotatorState::Literal);
+                    } else if self
+                        .semantic
+                        .match_typing_qualified_name(&qualified_name, "Annotated")
+                    {
+                        self.state.push(QuoteAnnotatorState::AnnotatedFirst);
+                    } else {
+                        self.state.push(QuoteAnnotatorState::Other);
+                    }
+                }
+
+                self.visit_expr(slice);
+                self.state.pop();
+                self.annotation.push(']');
+            }
+            Expr::Tuple(ast::ExprTuple { elts, .. }) => {
+                let Some((first, remaining)) = elts.split_first() else {
+                    return;
+                };
+                self.visit_expr(first);
+                if let Some(last) = self.state.last_mut() {
+                    if *last == QuoteAnnotatorState::AnnotatedFirst {
+                        *last = QuoteAnnotatorState::AnnotatedRest;
+                    }
+                }
+                for expr in remaining {
+                    self.annotation.push_str(", ");
+                    self.visit_expr(expr);
+                }
+                self.state.pop();
+            }
+            Expr::BinOp(ast::ExprBinOp {
+                left, op, right, ..
+            }) => {
+                debug_assert_eq!(*op, ast::Operator::BitOr);
+                self.visit_expr(left);
+                self.annotation.push_str(" | ");
+                self.visit_expr(right);
+            }
+            _ => {
+                let source = match self.state.last().copied() {
+                    Some(QuoteAnnotatorState::Literal | QuoteAnnotatorState::AnnotatedRest) => {
+                        let mut source = generator.expr(expr);
+                        source = source.replace(
+                            self.stylist.quote().as_char(),
+                            &self.stylist.quote().opposite().as_char().to_string(),
+                        );
+                        source
+                    }
+                    None
+                    | Some(QuoteAnnotatorState::AnnotatedFirst | QuoteAnnotatorState::Other) => {
+                        let mut source = generator.expr(expr);
+                        source = source.replace(self.stylist.quote().as_char(), "");
+                        source = source.replace(self.stylist.quote().opposite().as_char(), "");
+                        source
+                    }
+                };
+                self.annotation.push_str(&source);
+            }
+        }
+    }
+}
diff --git a/crates/ruff_linter/src/rules/flake8_type_checking/mod.rs b/crates/ruff_linter/src/rules/flake8_type_checking/mod.rs
index 30fc9c5aa7d8b..f8abd210b3bfd 100644
--- a/crates/ruff_linter/src/rules/flake8_type_checking/mod.rs
+++ b/crates/ruff_linter/src/rules/flake8_type_checking/mod.rs
@@ -60,6 +60,10 @@ mod tests {
 
     #[test_case(Rule::RuntimeImportInTypeCheckingBlock, Path::new("quote.py"))]
     #[test_case(Rule::TypingOnlyThirdPartyImport, Path::new("quote.py"))]
+    #[test_case(Rule::RuntimeImportInTypeCheckingBlock, Path::new("quote2.py"))]
+    #[test_case(Rule::TypingOnlyThirdPartyImport, Path::new("quote2.py"))]
+    #[test_case(Rule::RuntimeImportInTypeCheckingBlock, Path::new("quote3.py"))]
+    #[test_case(Rule::TypingOnlyThirdPartyImport, Path::new("quote3.py"))]
     fn quote(rule_code: Rule, path: &Path) -> Result<()> {
         let snapshot = format!("quote_{}_{}", rule_code.as_ref(), path.to_string_lossy());
         let diagnostics = test_path(
diff --git a/crates/ruff_linter/src/rules/flake8_type_checking/rules/runtime_import_in_type_checking_block.rs b/crates/ruff_linter/src/rules/flake8_type_checking/rules/runtime_import_in_type_checking_block.rs
index d9d7b45e2e5c6..fda7243224fd5 100644
--- a/crates/ruff_linter/src/rules/flake8_type_checking/rules/runtime_import_in_type_checking_block.rs
+++ b/crates/ruff_linter/src/rules/flake8_type_checking/rules/runtime_import_in_type_checking_block.rs
@@ -270,9 +270,7 @@ fn quote_imports(checker: &Checker, node_id: NodeId, imports: &[ImportBinding])
                         Some(quote_annotation(
                             reference.expression_id()?,
                             checker.semantic(),
-                            checker.locator(),
                             checker.stylist(),
-                            checker.generator(),
                         ))
                     } else {
                         None
diff --git a/crates/ruff_linter/src/rules/flake8_type_checking/rules/typing_only_runtime_import.rs b/crates/ruff_linter/src/rules/flake8_type_checking/rules/typing_only_runtime_import.rs
index 32bdb7046f7a3..c51b515d03c6a 100644
--- a/crates/ruff_linter/src/rules/flake8_type_checking/rules/typing_only_runtime_import.rs
+++ b/crates/ruff_linter/src/rules/flake8_type_checking/rules/typing_only_runtime_import.rs
@@ -505,9 +505,7 @@ fn fix_imports(checker: &Checker, node_id: NodeId, imports: &[ImportBinding]) ->
                         Some(quote_annotation(
                             reference.expression_id()?,
                             checker.semantic(),
-                            checker.locator(),
                             checker.stylist(),
-                            checker.generator(),
                         ))
                     } else {
                         None
diff --git a/crates/ruff_linter/src/rules/flake8_type_checking/snapshots/ruff_linter__rules__flake8_type_checking__tests__quote_runtime-import-in-type-checking-block_quote.py.snap b/crates/ruff_linter/src/rules/flake8_type_checking/snapshots/ruff_linter__rules__flake8_type_checking__tests__quote_runtime-import-in-type-checking-block_quote.py.snap
index ae71c56c8195a..de91616ce86fa 100644
--- a/crates/ruff_linter/src/rules/flake8_type_checking/snapshots/ruff_linter__rules__flake8_type_checking__tests__quote_runtime-import-in-type-checking-block_quote.py.snap
+++ b/crates/ruff_linter/src/rules/flake8_type_checking/snapshots/ruff_linter__rules__flake8_type_checking__tests__quote_runtime-import-in-type-checking-block_quote.py.snap
@@ -1,24 +1,22 @@
 ---
 source: crates/ruff_linter/src/rules/flake8_type_checking/mod.rs
 ---
-quote.py:64:28: TCH004 [*] Quote references to `pandas.DataFrame`. Import is in a type-checking block.
+quote.py:57:28: TCH004 [*] Quote references to `pandas.DataFrame`. Import is in a type-checking block.
    |
-63 |     if TYPE_CHECKING:
-64 |         from pandas import DataFrame
+56 |     if TYPE_CHECKING:
+57 |         from pandas import DataFrame
    |                            ^^^^^^^^^ TCH004
-65 | 
-66 |     def func(value: DataFrame):
+58 | 
+59 |     def func(value: DataFrame):
    |
    = help: Quote references
 
 ℹ Unsafe fix
-63 63 |     if TYPE_CHECKING:
-64 64 |         from pandas import DataFrame
-65 65 | 
-66    |-    def func(value: DataFrame):
-   66 |+    def func(value: "DataFrame"):
-67 67 |         ...
-68 68 | 
-69 69 | 
-
-
+56 56 |     if TYPE_CHECKING:
+57 57 |         from pandas import DataFrame
+58 58 | 
+59    |-    def func(value: DataFrame):
+   59 |+    def func(value: "DataFrame"):
+60 60 |         ...
+61 61 | 
+62 62 |
diff --git a/crates/ruff_linter/src/rules/flake8_type_checking/snapshots/ruff_linter__rules__flake8_type_checking__tests__quote_runtime-import-in-type-checking-block_quote2.py.snap b/crates/ruff_linter/src/rules/flake8_type_checking/snapshots/ruff_linter__rules__flake8_type_checking__tests__quote_runtime-import-in-type-checking-block_quote2.py.snap
new file mode 100644
index 0000000000000..6c5ead27428ce
--- /dev/null
+++ b/crates/ruff_linter/src/rules/flake8_type_checking/snapshots/ruff_linter__rules__flake8_type_checking__tests__quote_runtime-import-in-type-checking-block_quote2.py.snap
@@ -0,0 +1,4 @@
+---
+source: crates/ruff_linter/src/rules/flake8_type_checking/mod.rs
+---
+
diff --git a/crates/ruff_linter/src/rules/flake8_type_checking/snapshots/ruff_linter__rules__flake8_type_checking__tests__quote_runtime-import-in-type-checking-block_quote3.py.snap b/crates/ruff_linter/src/rules/flake8_type_checking/snapshots/ruff_linter__rules__flake8_type_checking__tests__quote_runtime-import-in-type-checking-block_quote3.py.snap
new file mode 100644
index 0000000000000..6c5ead27428ce
--- /dev/null
+++ b/crates/ruff_linter/src/rules/flake8_type_checking/snapshots/ruff_linter__rules__flake8_type_checking__tests__quote_runtime-import-in-type-checking-block_quote3.py.snap
@@ -0,0 +1,4 @@
+---
+source: crates/ruff_linter/src/rules/flake8_type_checking/mod.rs
+---
+
diff --git a/crates/ruff_linter/src/rules/flake8_type_checking/snapshots/ruff_linter__rules__flake8_type_checking__tests__quote_runtime-import-in-type-checking-block_quote_annotations.py.snap b/crates/ruff_linter/src/rules/flake8_type_checking/snapshots/ruff_linter__rules__flake8_type_checking__tests__quote_runtime-import-in-type-checking-block_quote_annotations.py.snap
new file mode 100644
index 0000000000000..6c5ead27428ce
--- /dev/null
+++ b/crates/ruff_linter/src/rules/flake8_type_checking/snapshots/ruff_linter__rules__flake8_type_checking__tests__quote_runtime-import-in-type-checking-block_quote_annotations.py.snap
@@ -0,0 +1,4 @@
+---
+source: crates/ruff_linter/src/rules/flake8_type_checking/mod.rs
+---
+
diff --git a/crates/ruff_linter/src/rules/flake8_type_checking/snapshots/ruff_linter__rules__flake8_type_checking__tests__quote_typing-only-third-party-import_quote.py.snap b/crates/ruff_linter/src/rules/flake8_type_checking/snapshots/ruff_linter__rules__flake8_type_checking__tests__quote_typing-only-third-party-import_quote.py.snap
index d9bb6a9824812..cc72734ecf5e9 100644
--- a/crates/ruff_linter/src/rules/flake8_type_checking/snapshots/ruff_linter__rules__flake8_type_checking__tests__quote_typing-only-third-party-import_quote.py.snap
+++ b/crates/ruff_linter/src/rules/flake8_type_checking/snapshots/ruff_linter__rules__flake8_type_checking__tests__quote_typing-only-third-party-import_quote.py.snap
@@ -55,23 +55,43 @@ quote.py:9:24: TCH002 [*] Move third-party import `pandas.DataFrame` into a type
 13 16 | 
 14 17 | 
 
-quote.py:16:24: TCH002 Move third-party import `pandas.DataFrame` into a type-checking block
+quote.py:16:22: TCH002 [*] Move third-party import `pandas` into a type-checking block
    |
 15 | def f():
-16 |     from pandas import DataFrame
-   |                        ^^^^^^^^^ TCH002
+16 |     import pandas as pd
+   |                      ^^ TCH002
 17 | 
-18 |     def baz() -> DataFrame["int"]:
+18 |     def baz() -> pd.DataFrame:
    |
    = help: Move into type-checking block
 
+ℹ Unsafe fix
+   1  |+from typing import TYPE_CHECKING
+   2  |+
+   3  |+if TYPE_CHECKING:
+   4  |+    import pandas as pd
+1  5  | def f():
+2  6  |     from pandas import DataFrame
+3  7  | 
+--------------------------------------------------------------------------------
+13 17 | 
+14 18 | 
+15 19 | def f():
+16    |-    import pandas as pd
+17 20 | 
+18    |-    def baz() -> pd.DataFrame:
+   21 |+    def baz() -> "pd.DataFrame":
+19 22 |         ...
+20 23 | 
+21 24 | 
+
 quote.py:23:22: TCH002 [*] Move third-party import `pandas` into a type-checking block
    |
 22 | def f():
 23 |     import pandas as pd
    |                      ^^ TCH002
 24 | 
-25 |     def baz() -> pd.DataFrame:
+25 |     def baz() -> pd.DataFrame.Extra:
    |
    = help: Move into type-checking block
 
@@ -89,8 +109,8 @@ quote.py:23:22: TCH002 [*] Move third-party import `pandas` into a type-checking
 22 26 | def f():
 23    |-    import pandas as pd
 24 27 | 
-25    |-    def baz() -> pd.DataFrame:
-   28 |+    def baz() -> "pd.DataFrame":
+25    |-    def baz() -> pd.DataFrame.Extra:
+   28 |+    def baz() -> "pd.DataFrame.Extra":
 26 29 |         ...
 27 30 | 
 28 31 | 
@@ -101,7 +121,7 @@ quote.py:30:22: TCH002 [*] Move third-party import `pandas` into a type-checking
 30 |     import pandas as pd
    |                      ^^ TCH002
 31 | 
-32 |     def baz() -> pd.DataFrame.Extra:
+32 |     def baz() -> pd.DataFrame | int:
    |
    = help: Move into type-checking block
 
@@ -119,19 +139,19 @@ quote.py:30:22: TCH002 [*] Move third-party import `pandas` into a type-checking
 29 33 | def f():
 30    |-    import pandas as pd
 31 34 | 
-32    |-    def baz() -> pd.DataFrame.Extra:
-   35 |+    def baz() -> "pd.DataFrame.Extra":
+32    |-    def baz() -> pd.DataFrame | int:
+   35 |+    def baz() -> "pd.DataFrame | int":
 33 36 |         ...
 34 37 | 
 35 38 | 
 
-quote.py:37:22: TCH002 [*] Move third-party import `pandas` into a type-checking block
+quote.py:38:24: TCH002 [*] Move third-party import `pandas.DataFrame` into a type-checking block
    |
-36 | def f():
-37 |     import pandas as pd
-   |                      ^^ TCH002
-38 | 
-39 |     def baz() -> pd.DataFrame | int:
+37 | def f():
+38 |     from pandas import DataFrame
+   |                        ^^^^^^^^^ TCH002
+39 | 
+40 |     def baz() -> DataFrame():
    |
    = help: Move into type-checking block
 
@@ -139,29 +159,30 @@ quote.py:37:22: TCH002 [*] Move third-party import `pandas` into a type-checking
    1  |+from typing import TYPE_CHECKING
    2  |+
    3  |+if TYPE_CHECKING:
-   4  |+    import pandas as pd
+   4  |+    from pandas import DataFrame
 1  5  | def f():
 2  6  |     from pandas import DataFrame
 3  7  | 
 --------------------------------------------------------------------------------
-34 38 | 
 35 39 | 
-36 40 | def f():
-37    |-    import pandas as pd
-38 41 | 
-39    |-    def baz() -> pd.DataFrame | int:
-   42 |+    def baz() -> "pd.DataFrame | int":
-40 43 |         ...
-41 44 | 
+36 40 | 
+37 41 | def f():
+38    |-    from pandas import DataFrame
+39 42 | 
+40    |-    def baz() -> DataFrame():
+   43 |+    def baz() -> "DataFrame()":
+41 44 |         ...
 42 45 | 
+43 46 | 
 
-quote.py:45:24: TCH002 [*] Move third-party import `pandas.DataFrame` into a type-checking block
+quote.py:47:24: TCH002 [*] Move third-party import `pandas.DataFrame` into a type-checking block
    |
-44 | def f():
-45 |     from pandas import DataFrame
-   |                        ^^^^^^^^^ TCH002
+45 |     from typing import Literal
 46 | 
-47 |     def baz() -> DataFrame():
+47 |     from pandas import DataFrame
+   |                        ^^^^^^^^^ TCH002
+48 | 
+49 |     def baz() -> DataFrame[Literal["int"]]:
    |
    = help: Move into type-checking block
 
@@ -174,35 +195,84 @@ quote.py:45:24: TCH002 [*] Move third-party import `pandas.DataFrame` into a typ
 2  6  |     from pandas import DataFrame
 3  7  | 
 --------------------------------------------------------------------------------
-42 46 | 
-43 47 | 
 44 48 | def f():
-45    |-    from pandas import DataFrame
-46 49 | 
-47    |-    def baz() -> DataFrame():
-   50 |+    def baz() -> "DataFrame()":
-48 51 |         ...
-49 52 | 
-50 53 | 
+45 49 |     from typing import Literal
+46 50 | 
+47    |-    from pandas import DataFrame
+48 51 | 
+49    |-    def baz() -> DataFrame[Literal["int"]]:
+   52 |+    def baz() -> "DataFrame[Literal['int']]":
+50 53 |         ...
+51 54 | 
+52 55 | 
 
-quote.py:54:24: TCH002 Move third-party import `pandas.DataFrame` into a type-checking block
+quote.py:64:24: TCH002 [*] Move third-party import `pandas.DataFrame` into a type-checking block
    |
-52 |     from typing import Literal
-53 | 
-54 |     from pandas import DataFrame
+63 | def f():
+64 |     from pandas import DataFrame, Series
    |                        ^^^^^^^^^ TCH002
-55 | 
-56 |     def baz() -> DataFrame[Literal["int"]]:
+65 | 
+66 |     def baz() -> DataFrame | Series:
    |
    = help: Move into type-checking block
 
+ℹ Unsafe fix
+   1  |+from typing import TYPE_CHECKING
+   2  |+
+   3  |+if TYPE_CHECKING:
+   4  |+    from pandas import DataFrame, Series
+1  5  | def f():
+2  6  |     from pandas import DataFrame
+3  7  | 
+--------------------------------------------------------------------------------
+61 65 | 
+62 66 | 
+63 67 | def f():
+64    |-    from pandas import DataFrame, Series
+65 68 | 
+66    |-    def baz() -> DataFrame | Series:
+   69 |+    def baz() -> "DataFrame | Series":
+67 70 |         ...
+68 71 | 
+69 72 | 
+
+quote.py:64:35: TCH002 [*] Move third-party import `pandas.Series` into a type-checking block
+   |
+63 | def f():
+64 |     from pandas import DataFrame, Series
+   |                                   ^^^^^^ TCH002
+65 | 
+66 |     def baz() -> DataFrame | Series:
+   |
+   = help: Move into type-checking block
+
+ℹ Unsafe fix
+   1  |+from typing import TYPE_CHECKING
+   2  |+
+   3  |+if TYPE_CHECKING:
+   4  |+    from pandas import DataFrame, Series
+1  5  | def f():
+2  6  |     from pandas import DataFrame
+3  7  | 
+--------------------------------------------------------------------------------
+61 65 | 
+62 66 | 
+63 67 | def f():
+64    |-    from pandas import DataFrame, Series
+65 68 | 
+66    |-    def baz() -> DataFrame | Series:
+   69 |+    def baz() -> "DataFrame | Series":
+67 70 |         ...
+68 71 | 
+69 72 | 
+
 quote.py:71:24: TCH002 [*] Move third-party import `pandas.DataFrame` into a type-checking block
    |
 70 | def f():
 71 |     from pandas import DataFrame, Series
    |                        ^^^^^^^^^ TCH002
 72 | 
-73 |     def baz() -> DataFrame | Series:
+73 |     def baz() -> (
    |
    = help: Move into type-checking block
 
@@ -220,11 +290,24 @@ quote.py:71:24: TCH002 [*] Move third-party import `pandas.DataFrame` into a typ
 70 74 | def f():
 71    |-    from pandas import DataFrame, Series
 72 75 | 
-73    |-    def baz() -> DataFrame | Series:
-   76 |+    def baz() -> "DataFrame | Series":
-74 77 |         ...
-75 78 | 
-76 79 | 
+73 76 |     def baz() -> (
+74    |-        DataFrame |
+75    |-        Series
+   77 |+        "DataFrame | Series"
+76 78 |     ):
+77 79 |         ...
+78 80 | 
+79 81 |     class C:
+80    |-        x: DataFrame[
+81    |-            int
+82    |-        ] = 1
+   82 |+        x: "DataFrame[int]" = 1
+83 83 | 
+84    |-    def func() -> DataFrame[[DataFrame[_P, _R]], DataFrame[_P, _R]]:
+   84 |+    def func() -> "DataFrame[[DataFrame[_P, _R]], DataFrame[_P, _R]]":
+85 85 |         ...
+86 86 | 
+87 87 | 
 
 quote.py:71:35: TCH002 [*] Move third-party import `pandas.Series` into a type-checking block
    |
@@ -232,7 +315,7 @@ quote.py:71:35: TCH002 [*] Move third-party import `pandas.Series` into a type-c
 71 |     from pandas import DataFrame, Series
    |                                   ^^^^^^ TCH002
 72 | 
-73 |     def baz() -> DataFrame | Series:
+73 |     def baz() -> (
    |
    = help: Move into type-checking block
 
@@ -250,19 +333,32 @@ quote.py:71:35: TCH002 [*] Move third-party import `pandas.Series` into a type-c
 70 74 | def f():
 71    |-    from pandas import DataFrame, Series
 72 75 | 
-73    |-    def baz() -> DataFrame | Series:
-   76 |+    def baz() -> "DataFrame | Series":
-74 77 |         ...
-75 78 | 
-76 79 | 
+73 76 |     def baz() -> (
+74    |-        DataFrame |
+75    |-        Series
+   77 |+        "DataFrame | Series"
+76 78 |     ):
+77 79 |         ...
+78 80 | 
+79 81 |     class C:
+80    |-        x: DataFrame[
+81    |-            int
+82    |-        ] = 1
+   82 |+        x: "DataFrame[int]" = 1
+83 83 | 
+84    |-    def func() -> DataFrame[[DataFrame[_P, _R]], DataFrame[_P, _R]]:
+   84 |+    def func() -> "DataFrame[[DataFrame[_P, _R]], DataFrame[_P, _R]]":
+85 85 |         ...
+86 86 | 
+87 87 | 
 
-quote.py:78:24: TCH002 [*] Move third-party import `pandas.DataFrame` into a type-checking block
+quote.py:89:24: TCH002 [*] Move third-party import `pandas.DataFrame` into a type-checking block
    |
-77 | def f():
-78 |     from pandas import DataFrame, Series
+88 | def f():
+89 |     from pandas import DataFrame, Series
    |                        ^^^^^^^^^ TCH002
-79 | 
-80 |     def baz() -> (
+90 | 
+91 |     def func(self) -> DataFrame | list[Series]:
    |
    = help: Move into type-checking block
 
@@ -275,37 +371,22 @@ quote.py:78:24: TCH002 [*] Move third-party import `pandas.DataFrame` into a typ
 2  6  |     from pandas import DataFrame
 3  7  | 
 --------------------------------------------------------------------------------
-75 79 | 
-76 80 | 
-77 81 | def f():
-78    |-    from pandas import DataFrame, Series
-79 82 | 
-80 83 |     def baz() -> (
-81    |-        DataFrame |
-82    |-        Series
-   84 |+        "DataFrame | Series"
-83 85 |     ):
-84 86 |         ...
-85 87 | 
-86 88 |     class C:
-87    |-        x: DataFrame[
-88    |-            int
-89    |-        ] = 1
-   89 |+        x: "DataFrame[int]" = 1
-90 90 | 
-91    |-    def func() -> DataFrame[[DataFrame[_P, _R]], DataFrame[_P, _R]]:
-   91 |+    def func() -> "DataFrame[[DataFrame[_P, _R]], DataFrame[_P, _R]]":
-92 92 |         ...
-93 93 | 
-94 94 | 
+86 90 | 
+87 91 | 
+88 92 | def f():
+89    |-    from pandas import DataFrame, Series
+90 93 | 
+91    |-    def func(self) -> DataFrame | list[Series]:
+   94 |+    def func(self) -> "DataFrame | list[Series]":
+92 95 |         pass
 
-quote.py:78:35: TCH002 [*] Move third-party import `pandas.Series` into a type-checking block
+quote.py:89:35: TCH002 [*] Move third-party import `pandas.Series` into a type-checking block
    |
-77 | def f():
-78 |     from pandas import DataFrame, Series
+88 | def f():
+89 |     from pandas import DataFrame, Series
    |                                   ^^^^^^ TCH002
-79 | 
-80 |     def baz() -> (
+90 | 
+91 |     def func(self) -> DataFrame | list[Series]:
    |
    = help: Move into type-checking block
 
@@ -318,82 +399,11 @@ quote.py:78:35: TCH002 [*] Move third-party import `pandas.Series` into a type-c
 2  6  |     from pandas import DataFrame
 3  7  | 
 --------------------------------------------------------------------------------
-75 79 | 
-76 80 | 
-77 81 | def f():
-78    |-    from pandas import DataFrame, Series
-79 82 | 
-80 83 |     def baz() -> (
-81    |-        DataFrame |
-82    |-        Series
-   84 |+        "DataFrame | Series"
-83 85 |     ):
-84 86 |         ...
-85 87 | 
-86 88 |     class C:
-87    |-        x: DataFrame[
-88    |-            int
-89    |-        ] = 1
-   89 |+        x: "DataFrame[int]" = 1
-90 90 | 
-91    |-    def func() -> DataFrame[[DataFrame[_P, _R]], DataFrame[_P, _R]]:
-   91 |+    def func() -> "DataFrame[[DataFrame[_P, _R]], DataFrame[_P, _R]]":
-92 92 |         ...
-93 93 | 
-94 94 | 
-
-quote.py:96:24: TCH002 [*] Move third-party import `pandas.DataFrame` into a type-checking block
-   |
-95 | def f():
-96 |     from pandas import DataFrame, Series
-   |                        ^^^^^^^^^ TCH002
-97 | 
-98 |     def func(self) -> DataFrame | list[Series]:
-   |
-   = help: Move into type-checking block
-
-ℹ Unsafe fix
-    1   |+from typing import TYPE_CHECKING
-    2   |+
-    3   |+if TYPE_CHECKING:
-    4   |+    from pandas import DataFrame, Series
-1   5   | def f():
-2   6   |     from pandas import DataFrame
-3   7   | 
---------------------------------------------------------------------------------
-93  97  | 
-94  98  | 
-95  99  | def f():
-96      |-    from pandas import DataFrame, Series
-97  100 | 
-98      |-    def func(self) -> DataFrame | list[Series]:
-    101 |+    def func(self) -> "DataFrame | list[Series]":
-99  102 |         pass
-
-quote.py:96:35: TCH002 [*] Move third-party import `pandas.Series` into a type-checking block
-   |
-95 | def f():
-96 |     from pandas import DataFrame, Series
-   |                                   ^^^^^^ TCH002
-97 | 
-98 |     def func(self) -> DataFrame | list[Series]:
-   |
-   = help: Move into type-checking block
-
-ℹ Unsafe fix
-    1   |+from typing import TYPE_CHECKING
-    2   |+
-    3   |+if TYPE_CHECKING:
-    4   |+    from pandas import DataFrame, Series
-1   5   | def f():
-2   6   |     from pandas import DataFrame
-3   7   | 
---------------------------------------------------------------------------------
-93  97  | 
-94  98  | 
-95  99  | def f():
-96      |-    from pandas import DataFrame, Series
-97  100 | 
-98      |-    def func(self) -> DataFrame | list[Series]:
-    101 |+    def func(self) -> "DataFrame | list[Series]":
-99  102 |         pass
+86 90 | 
+87 91 | 
+88 92 | def f():
+89    |-    from pandas import DataFrame, Series
+90 93 | 
+91    |-    def func(self) -> DataFrame | list[Series]:
+   94 |+    def func(self) -> "DataFrame | list[Series]":
+92 95 |         pass
diff --git a/crates/ruff_linter/src/rules/flake8_type_checking/snapshots/ruff_linter__rules__flake8_type_checking__tests__quote_typing-only-third-party-import_quote2.py.snap b/crates/ruff_linter/src/rules/flake8_type_checking/snapshots/ruff_linter__rules__flake8_type_checking__tests__quote_typing-only-third-party-import_quote2.py.snap
new file mode 100644
index 0000000000000..dc87bebfccda0
--- /dev/null
+++ b/crates/ruff_linter/src/rules/flake8_type_checking/snapshots/ruff_linter__rules__flake8_type_checking__tests__quote_typing-only-third-party-import_quote2.py.snap
@@ -0,0 +1,272 @@
+---
+source: crates/ruff_linter/src/rules/flake8_type_checking/mod.rs
+---
+quote2.py:2:44: TCH002 [*] Move third-party import `django.contrib.auth.models.AbstractBaseUser` into a type-checking block
+  |
+1 | def f():
+2 |     from django.contrib.auth.models import AbstractBaseUser
+  |                                            ^^^^^^^^^^^^^^^^ TCH002
+3 | 
+4 |     def test_remove_inner_quotes_double(self, user: AbstractBaseUser["int"]):
+  |
+  = help: Move into type-checking block
+
+ℹ Unsafe fix
+1   |-def f():
+  1 |+from typing import TYPE_CHECKING
+  2 |+
+  3 |+if TYPE_CHECKING:
+2 4 |     from django.contrib.auth.models import AbstractBaseUser
+  5 |+def f():
+3 6 | 
+4   |-    def test_remove_inner_quotes_double(self, user: AbstractBaseUser["int"]):
+  7 |+    def test_remove_inner_quotes_double(self, user: "AbstractBaseUser[int]"):
+5 8 |         pass
+6 9 | 
+7 10 | 
+
+quote2.py:9:44: TCH002 [*] Move third-party import `django.contrib.auth.models.AbstractBaseUser` into a type-checking block
+   |
+ 8 | def f():
+ 9 |     from django.contrib.auth.models import AbstractBaseUser
+   |                                            ^^^^^^^^^^^^^^^^ TCH002
+10 | 
+11 |     def test_remove_inner_quotes_single(self, user: AbstractBaseUser['int']):
+   |
+   = help: Move into type-checking block
+
+ℹ Unsafe fix
+   1  |+from typing import TYPE_CHECKING
+   2  |+
+   3  |+if TYPE_CHECKING:
+   4  |+    from django.contrib.auth.models import AbstractBaseUser
+1  5  | def f():
+2  6  |     from django.contrib.auth.models import AbstractBaseUser
+3  7  | 
+--------------------------------------------------------------------------------
+6  10 | 
+7  11 | 
+8  12 | def f():
+9     |-    from django.contrib.auth.models import AbstractBaseUser
+10 13 | 
+11    |-    def test_remove_inner_quotes_single(self, user: AbstractBaseUser['int']):
+   14 |+    def test_remove_inner_quotes_single(self, user: "AbstractBaseUser[int]"):
+12 15 |         pass
+13 16 | 
+14 17 | 
+
+quote2.py:16:44: TCH002 [*] Move third-party import `django.contrib.auth.models.AbstractBaseUser` into a type-checking block
+   |
+15 | def f():
+16 |     from django.contrib.auth.models import AbstractBaseUser
+   |                                            ^^^^^^^^^^^^^^^^ TCH002
+17 | 
+18 |     def test_remove_inner_quotes_mixed(self, user: AbstractBaseUser['int', "str"]):
+   |
+   = help: Move into type-checking block
+
+ℹ Unsafe fix
+   1  |+from typing import TYPE_CHECKING
+   2  |+
+   3  |+if TYPE_CHECKING:
+   4  |+    from django.contrib.auth.models import AbstractBaseUser
+1  5  | def f():
+2  6  |     from django.contrib.auth.models import AbstractBaseUser
+3  7  | 
+--------------------------------------------------------------------------------
+13 17 | 
+14 18 | 
+15 19 | def f():
+16    |-    from django.contrib.auth.models import AbstractBaseUser
+17 20 | 
+18    |-    def test_remove_inner_quotes_mixed(self, user: AbstractBaseUser['int', "str"]):
+   21 |+    def test_remove_inner_quotes_mixed(self, user: "AbstractBaseUser[int, str]"):
+19 22 |         pass
+20 23 | 
+21 24 | 
+
+quote2.py:25:44: TCH002 [*] Move third-party import `django.contrib.auth.models.AbstractBaseUser` into a type-checking block
+   |
+23 |     from typing import Annotated, Literal
+24 | 
+25 |     from django.contrib.auth.models import AbstractBaseUser
+   |                                            ^^^^^^^^^^^^^^^^ TCH002
+26 | 
+27 |     def test_literal_annotation_args_contain_quotes(self, type1: AbstractBaseUser[Literal["user", "admin"], Annotated["int", "1", 2]]):
+   |
+   = help: Move into type-checking block
+
+ℹ Unsafe fix
+   1  |+from typing import TYPE_CHECKING
+   2  |+
+   3  |+if TYPE_CHECKING:
+   4  |+    from django.contrib.auth.models import AbstractBaseUser
+1  5  | def f():
+2  6  |     from django.contrib.auth.models import AbstractBaseUser
+3  7  | 
+--------------------------------------------------------------------------------
+22 26 | def f():
+23 27 |     from typing import Annotated, Literal
+24 28 | 
+25    |-    from django.contrib.auth.models import AbstractBaseUser
+26 29 | 
+27    |-    def test_literal_annotation_args_contain_quotes(self, type1: AbstractBaseUser[Literal["user", "admin"], Annotated["int", "1", 2]]):
+   30 |+    def test_literal_annotation_args_contain_quotes(self, type1: "AbstractBaseUser[Literal['user', 'admin'], Annotated[int, '1', 2]]"):
+28 31 |         pass
+29 32 | 
+30 33 | 
+
+quote2.py:34:44: TCH002 [*] Move third-party import `django.contrib.auth.models.AbstractBaseUser` into a type-checking block
+   |
+32 |     from typing import Literal
+33 | 
+34 |     from django.contrib.auth.models import AbstractBaseUser
+   |                                            ^^^^^^^^^^^^^^^^ TCH002
+35 | 
+36 |     def test_union_contain_inner_quotes(self, type1: AbstractBaseUser["int" | Literal["int"]]):
+   |
+   = help: Move into type-checking block
+
+ℹ Unsafe fix
+   1  |+from typing import TYPE_CHECKING
+   2  |+
+   3  |+if TYPE_CHECKING:
+   4  |+    from django.contrib.auth.models import AbstractBaseUser
+1  5  | def f():
+2  6  |     from django.contrib.auth.models import AbstractBaseUser
+3  7  | 
+--------------------------------------------------------------------------------
+31 35 | def f():
+32 36 |     from typing import Literal
+33 37 | 
+34    |-    from django.contrib.auth.models import AbstractBaseUser
+35 38 | 
+36    |-    def test_union_contain_inner_quotes(self, type1: AbstractBaseUser["int" | Literal["int"]]):
+   39 |+    def test_union_contain_inner_quotes(self, type1: "AbstractBaseUser[int | Literal['int']]"):
+37 40 |         pass
+38 41 | 
+39 42 | 
+
+quote2.py:43:44: TCH002 [*] Move third-party import `django.contrib.auth.models.AbstractBaseUser` into a type-checking block
+   |
+41 |     from typing import Literal
+42 | 
+43 |     from django.contrib.auth.models import AbstractBaseUser
+   |                                            ^^^^^^^^^^^^^^^^ TCH002
+44 | 
+45 |     def test_inner_literal_mixed_quotes(user: AbstractBaseUser[Literal['user', "admin"]]):
+   |
+   = help: Move into type-checking block
+
+ℹ Unsafe fix
+   1  |+from typing import TYPE_CHECKING
+   2  |+
+   3  |+if TYPE_CHECKING:
+   4  |+    from django.contrib.auth.models import AbstractBaseUser
+1  5  | def f():
+2  6  |     from django.contrib.auth.models import AbstractBaseUser
+3  7  | 
+--------------------------------------------------------------------------------
+40 44 | def f():
+41 45 |     from typing import Literal
+42 46 | 
+43    |-    from django.contrib.auth.models import AbstractBaseUser
+44 47 | 
+45    |-    def test_inner_literal_mixed_quotes(user: AbstractBaseUser[Literal['user', "admin"]]):
+   48 |+    def test_inner_literal_mixed_quotes(user: "AbstractBaseUser[Literal['user', 'admin']]"):
+46 49 |         pass
+47 50 | 
+48 51 | 
+
+quote2.py:52:44: TCH002 [*] Move third-party import `django.contrib.auth.models.AbstractBaseUser` into a type-checking block
+   |
+50 |     from typing import Literal
+51 | 
+52 |     from django.contrib.auth.models import AbstractBaseUser
+   |                                            ^^^^^^^^^^^^^^^^ TCH002
+53 | 
+54 |     def test_inner_literal_single_quote(user: AbstractBaseUser[Literal['int'], str]):
+   |
+   = help: Move into type-checking block
+
+ℹ Unsafe fix
+   1  |+from typing import TYPE_CHECKING
+   2  |+
+   3  |+if TYPE_CHECKING:
+   4  |+    from django.contrib.auth.models import AbstractBaseUser
+1  5  | def f():
+2  6  |     from django.contrib.auth.models import AbstractBaseUser
+3  7  | 
+--------------------------------------------------------------------------------
+49 53 | def f():
+50 54 |     from typing import Literal
+51 55 | 
+52    |-    from django.contrib.auth.models import AbstractBaseUser
+53 56 | 
+54    |-    def test_inner_literal_single_quote(user: AbstractBaseUser[Literal['int'], str]):
+   57 |+    def test_inner_literal_single_quote(user: "AbstractBaseUser[Literal['int'], str]"):
+55 58 |         pass
+56 59 | 
+57 60 | 
+
+quote2.py:61:44: TCH002 [*] Move third-party import `django.contrib.auth.models.AbstractBaseUser` into a type-checking block
+   |
+59 |     from typing import Literal
+60 | 
+61 |     from django.contrib.auth.models import AbstractBaseUser
+   |                                            ^^^^^^^^^^^^^^^^ TCH002
+62 | 
+63 |     def test_mixed_quotes_literal(user: AbstractBaseUser[Literal['user'], "int"]):
+   |
+   = help: Move into type-checking block
+
+ℹ Unsafe fix
+   1  |+from typing import TYPE_CHECKING
+   2  |+
+   3  |+if TYPE_CHECKING:
+   4  |+    from django.contrib.auth.models import AbstractBaseUser
+1  5  | def f():
+2  6  |     from django.contrib.auth.models import AbstractBaseUser
+3  7  | 
+--------------------------------------------------------------------------------
+58 62 | def f():
+59 63 |     from typing import Literal
+60 64 | 
+61    |-    from django.contrib.auth.models import AbstractBaseUser
+62 65 | 
+63    |-    def test_mixed_quotes_literal(user: AbstractBaseUser[Literal['user'], "int"]):
+   66 |+    def test_mixed_quotes_literal(user: "AbstractBaseUser[Literal['user'], int]"):
+64 67 |         pass
+65 68 | 
+66 69 | 
+
+quote2.py:70:44: TCH002 [*] Move third-party import `django.contrib.auth.models.AbstractBaseUser` into a type-checking block
+   |
+68 |     from typing import Annotated, Literal
+69 | 
+70 |     from django.contrib.auth.models import AbstractBaseUser
+   |                                            ^^^^^^^^^^^^^^^^ TCH002
+71 | 
+72 |     def test_annotated_literal_mixed_quotes(user: AbstractBaseUser[Annotated[str, "max_length=20", Literal['user', "admin"]]]):
+   |
+   = help: Move into type-checking block
+
+ℹ Unsafe fix
+   1  |+from typing import TYPE_CHECKING
+   2  |+
+   3  |+if TYPE_CHECKING:
+   4  |+    from django.contrib.auth.models import AbstractBaseUser
+1  5  | def f():
+2  6  |     from django.contrib.auth.models import AbstractBaseUser
+3  7  | 
+--------------------------------------------------------------------------------
+67 71 | def f():
+68 72 |     from typing import Annotated, Literal
+69 73 | 
+70    |-    from django.contrib.auth.models import AbstractBaseUser
+71 74 | 
+72    |-    def test_annotated_literal_mixed_quotes(user: AbstractBaseUser[Annotated[str, "max_length=20", Literal['user', "admin"]]]):
+   75 |+    def test_annotated_literal_mixed_quotes(user: "AbstractBaseUser[Annotated[str, 'max_length=20', Literal['user', 'admin']]]"):
+73 76 |         pass
+74 77 | 
+75 78 |
diff --git a/crates/ruff_linter/src/rules/flake8_type_checking/snapshots/ruff_linter__rules__flake8_type_checking__tests__quote_typing-only-third-party-import_quote3.py.snap b/crates/ruff_linter/src/rules/flake8_type_checking/snapshots/ruff_linter__rules__flake8_type_checking__tests__quote_typing-only-third-party-import_quote3.py.snap
new file mode 100644
index 0000000000000..579cc74973b14
--- /dev/null
+++ b/crates/ruff_linter/src/rules/flake8_type_checking/snapshots/ruff_linter__rules__flake8_type_checking__tests__quote_typing-only-third-party-import_quote3.py.snap
@@ -0,0 +1,152 @@
+---
+source: crates/ruff_linter/src/rules/flake8_type_checking/mod.rs
+---
+quote3.py:4:44: TCH002 [*] Move third-party import `django.contrib.auth.models.AbstractBaseUser` into a type-checking block
+  |
+2 |     from typing import Literal, Union
+3 | 
+4 |     from django.contrib.auth.models import AbstractBaseUser
+  |                                            ^^^^^^^^^^^^^^^^ TCH002
+5 | 
+6 |     def test_union_literal_mixed_quotes(user: AbstractBaseUser[Union[Literal['active', "inactive"], str]]):
+  |
+  = help: Move into type-checking block
+
+ℹ Unsafe fix
+   1  |+from typing import TYPE_CHECKING
+   2  |+
+   3  |+if TYPE_CHECKING:
+   4  |+    from django.contrib.auth.models import AbstractBaseUser
+1  5  | def f():
+2  6  |     from typing import Literal, Union
+3  7  | 
+4     |-    from django.contrib.auth.models import AbstractBaseUser
+5  8  | 
+6     |-    def test_union_literal_mixed_quotes(user: AbstractBaseUser[Union[Literal['active', "inactive"], str]]):
+   9  |+    def test_union_literal_mixed_quotes(user: 'AbstractBaseUser[Union[Literal["active", "inactive"], str]]'):
+7  10 |         pass
+8  11 | 
+9  12 | 
+
+quote3.py:13:44: TCH002 [*] Move third-party import `django.contrib.auth.models.AbstractBaseUser` into a type-checking block
+   |
+11 |     from typing import Callable, Literal
+12 | 
+13 |     from django.contrib.auth.models import AbstractBaseUser
+   |                                            ^^^^^^^^^^^^^^^^ TCH002
+14 | 
+15 |     def test_callable_literal_mixed_quotes(callable_fn: AbstractBaseUser[Callable[["int", Literal['admin', "user"]], 'bool']]):
+   |
+   = help: Move into type-checking block
+
+ℹ Unsafe fix
+   1  |+from typing import TYPE_CHECKING
+   2  |+
+   3  |+if TYPE_CHECKING:
+   4  |+    from django.contrib.auth.models import AbstractBaseUser
+1  5  | def f():
+2  6  |     from typing import Literal, Union
+3  7  | 
+--------------------------------------------------------------------------------
+10 14 | def f():
+11 15 |     from typing import Callable, Literal
+12 16 | 
+13    |-    from django.contrib.auth.models import AbstractBaseUser
+14 17 | 
+15    |-    def test_callable_literal_mixed_quotes(callable_fn: AbstractBaseUser[Callable[["int", Literal['admin', "user"]], 'bool']]):
+   18 |+    def test_callable_literal_mixed_quotes(callable_fn: 'AbstractBaseUser[Callable[[int, Literal[admin, user]], bool]]'):
+16 19 |         pass
+17 20 | 
+18 21 | 
+
+quote3.py:22:44: TCH002 [*] Move third-party import `django.contrib.auth.models.AbstractBaseUser` into a type-checking block
+   |
+20 |     from typing import Annotated, Callable, Literal
+21 | 
+22 |     from django.contrib.auth.models import AbstractBaseUser
+   |                                            ^^^^^^^^^^^^^^^^ TCH002
+23 | 
+24 |     def test_callable_annotated_literal(callable_fn: AbstractBaseUser[Callable[[int, Annotated[str, Literal['active', "inactive"]]], bool]]):
+   |
+   = help: Move into type-checking block
+
+ℹ Unsafe fix
+   1  |+from typing import TYPE_CHECKING
+   2  |+
+   3  |+if TYPE_CHECKING:
+   4  |+    from django.contrib.auth.models import AbstractBaseUser
+1  5  | def f():
+2  6  |     from typing import Literal, Union
+3  7  | 
+--------------------------------------------------------------------------------
+19 23 | def f():
+20 24 |     from typing import Annotated, Callable, Literal
+21 25 | 
+22    |-    from django.contrib.auth.models import AbstractBaseUser
+23 26 | 
+24    |-    def test_callable_annotated_literal(callable_fn: AbstractBaseUser[Callable[[int, Annotated[str, Literal['active', "inactive"]]], bool]]):
+   27 |+    def test_callable_annotated_literal(callable_fn: 'AbstractBaseUser[Callable[[int, Annotated[str, Literal[active, inactive]]], bool]]'):
+25 28 |         pass
+26 29 | 
+27 30 | 
+
+quote3.py:31:37: TCH002 [*] Move third-party import `django.contrib.auth.models` into a type-checking block
+   |
+29 |     from typing import literal
+30 | 
+31 |     from django.contrib.auth import models
+   |                                     ^^^^^^ TCH002
+32 | 
+33 |     def test_attribute(arg: models.AbstractBaseUser["int"]):
+   |
+   = help: Move into type-checking block
+
+ℹ Unsafe fix
+   1  |+from typing import TYPE_CHECKING
+   2  |+
+   3  |+if TYPE_CHECKING:
+   4  |+    from django.contrib.auth import models
+1  5  | def f():
+2  6  |     from typing import Literal, Union
+3  7  | 
+--------------------------------------------------------------------------------
+28 32 | def f():
+29 33 |     from typing import literal
+30 34 | 
+31    |-    from django.contrib.auth import models
+32 35 | 
+33    |-    def test_attribute(arg: models.AbstractBaseUser["int"]):
+   36 |+    def test_attribute(arg: 'models.AbstractBaseUser[int]'):
+34 37 |         pass
+35 38 | 
+36 39 | 
+
+quote3.py:40:37: TCH002 [*] Move third-party import `django.contrib.auth.models` into a type-checking block
+   |
+38 |     from typing import Literal
+39 | 
+40 |     from django.contrib.auth import models
+   |                                     ^^^^^^ TCH002
+41 | 
+42 |     def test_attribute_typing_literal(arg: models.AbstractBaseUser[Literal["admin"]]):
+   |
+   = help: Move into type-checking block
+
+ℹ Unsafe fix
+   1  |+from typing import TYPE_CHECKING
+   2  |+
+   3  |+if TYPE_CHECKING:
+   4  |+    from django.contrib.auth import models
+1  5  | def f():
+2  6  |     from typing import Literal, Union
+3  7  | 
+--------------------------------------------------------------------------------
+37 41 | def f():
+38 42 |     from typing import Literal
+39 43 | 
+40    |-    from django.contrib.auth import models
+41 44 | 
+42    |-    def test_attribute_typing_literal(arg: models.AbstractBaseUser[Literal["admin"]]):
+   45 |+    def test_attribute_typing_literal(arg: 'models.AbstractBaseUser[Literal["admin"]]'):
+43 46 |         pass
+44 47 |
diff --git a/crates/ruff_linter/src/rules/flake8_type_checking/snapshots/ruff_linter__rules__flake8_type_checking__tests__quote_typing-only-third-party-import_quote_annotations.py.snap b/crates/ruff_linter/src/rules/flake8_type_checking/snapshots/ruff_linter__rules__flake8_type_checking__tests__quote_typing-only-third-party-import_quote_annotations.py.snap
new file mode 100644
index 0000000000000..a8907800043a6
--- /dev/null
+++ b/crates/ruff_linter/src/rules/flake8_type_checking/snapshots/ruff_linter__rules__flake8_type_checking__tests__quote_typing-only-third-party-import_quote_annotations.py.snap
@@ -0,0 +1,425 @@
+---
+source: crates/ruff_linter/src/rules/flake8_type_checking/mod.rs
+---
+quote_annotations.py:2:44: TCH002 [*] Move third-party import `django.contrib.auth.models.AbstractBaseUser` into a type-checking block
+  |
+1 | def f():
+2 |     from django.contrib.auth.models import AbstractBaseUser
+  |                                            ^^^^^^^^^^^^^^^^ TCH002
+3 | 
+4 |     def test_remove_inner_quotes_double(self, user: AbstractBaseUser["int"], view: "type[CondorBaseViewSet]"):
+  |
+  = help: Move into type-checking block
+
+ℹ Unsafe fix
+1   |-def f():
+  1 |+from typing import TYPE_CHECKING
+  2 |+
+  3 |+if TYPE_CHECKING:
+2 4 |     from django.contrib.auth.models import AbstractBaseUser
+  5 |+def f():
+3 6 | 
+4   |-    def test_remove_inner_quotes_double(self, user: AbstractBaseUser["int"], view: "type[CondorBaseViewSet]"):
+  7 |+    def test_remove_inner_quotes_double(self, user: "AbstractBaseUser[int]", view: "type[CondorBaseViewSet]"):
+5 8 |         pass
+6 9 | 
+7 10 | 
+
+quote_annotations.py:9:44: TCH002 [*] Move third-party import `django.contrib.auth.models.AbstractBaseUser` into a type-checking block
+   |
+ 8 | def f():
+ 9 |     from django.contrib.auth.models import AbstractBaseUser
+   |                                            ^^^^^^^^^^^^^^^^ TCH002
+10 | 
+11 |     def test_remove_inner_quotes_single(self, user: AbstractBaseUser['int']):
+   |
+   = help: Move into type-checking block
+
+ℹ Unsafe fix
+   1  |+from typing import TYPE_CHECKING
+   2  |+
+   3  |+if TYPE_CHECKING:
+   4  |+    from django.contrib.auth.models import AbstractBaseUser
+1  5  | def f():
+2  6  |     from django.contrib.auth.models import AbstractBaseUser
+3  7  | 
+--------------------------------------------------------------------------------
+6  10 | 
+7  11 | 
+8  12 | def f():
+9     |-    from django.contrib.auth.models import AbstractBaseUser
+10 13 | 
+11    |-    def test_remove_inner_quotes_single(self, user: AbstractBaseUser['int']):
+   14 |+    def test_remove_inner_quotes_single(self, user: "AbstractBaseUser[int]"):
+12 15 |         pass
+13 16 | 
+14 17 | 
+
+quote_annotations.py:16:44: TCH002 [*] Move third-party import `django.contrib.auth.models.AbstractBaseUser` into a type-checking block
+   |
+15 | def f():
+16 |     from django.contrib.auth.models import AbstractBaseUser
+   |                                            ^^^^^^^^^^^^^^^^ TCH002
+17 | 
+18 |     def test_remove_inner_quotes_mixed(self, user: AbstractBaseUser['int', "str"]):
+   |
+   = help: Move into type-checking block
+
+ℹ Unsafe fix
+   1  |+from typing import TYPE_CHECKING
+   2  |+
+   3  |+if TYPE_CHECKING:
+   4  |+    from django.contrib.auth.models import AbstractBaseUser
+1  5  | def f():
+2  6  |     from django.contrib.auth.models import AbstractBaseUser
+3  7  | 
+--------------------------------------------------------------------------------
+13 17 | 
+14 18 | 
+15 19 | def f():
+16    |-    from django.contrib.auth.models import AbstractBaseUser
+17 20 | 
+18    |-    def test_remove_inner_quotes_mixed(self, user: AbstractBaseUser['int', "str"]):
+   21 |+    def test_remove_inner_quotes_mixed(self, user: "AbstractBaseUser[int, str]"):
+19 22 |         pass
+20 23 | 
+21 24 | 
+
+quote_annotations.py:25:44: TCH002 [*] Move third-party import `django.contrib.auth.models.AbstractBaseUser` into a type-checking block
+   |
+23 |     from typing import Annotated, Literal
+24 | 
+25 |     from django.contrib.auth.models import AbstractBaseUser
+   |                                            ^^^^^^^^^^^^^^^^ TCH002
+26 | 
+27 |     def test_literal_annotation_args_contain_quotes(self, type1: AbstractBaseUser[Literal["user", "admin"], Annotated["int", "1", 2]]):
+   |
+   = help: Move into type-checking block
+
+ℹ Unsafe fix
+   1  |+from typing import TYPE_CHECKING
+   2  |+
+   3  |+if TYPE_CHECKING:
+   4  |+    from django.contrib.auth.models import AbstractBaseUser
+1  5  | def f():
+2  6  |     from django.contrib.auth.models import AbstractBaseUser
+3  7  | 
+--------------------------------------------------------------------------------
+22 26 | def f():
+23 27 |     from typing import Annotated, Literal
+24 28 | 
+25    |-    from django.contrib.auth.models import AbstractBaseUser
+26 29 | 
+27    |-    def test_literal_annotation_args_contain_quotes(self, type1: AbstractBaseUser[Literal["user", "admin"], Annotated["int", "1", 2]]):
+   30 |+    def test_literal_annotation_args_contain_quotes(self, type1: "AbstractBaseUser[Literal['user', 'admin'], Annotated[int, '1', 2]]"):
+28 31 |         pass
+29 32 | 
+30 33 | 
+
+quote_annotations.py:34:44: TCH002 [*] Move third-party import `django.contrib.auth.models.AbstractBaseUser` into a type-checking block
+   |
+32 |     from typing import Literal
+33 | 
+34 |     from django.contrib.auth.models import AbstractBaseUser
+   |                                            ^^^^^^^^^^^^^^^^ TCH002
+35 | 
+36 |     def test_union_contain_inner_quotes(self, type1: AbstractBaseUser["int" | Literal["int"]]):
+   |
+   = help: Move into type-checking block
+
+ℹ Unsafe fix
+   1  |+from typing import TYPE_CHECKING
+   2  |+
+   3  |+if TYPE_CHECKING:
+   4  |+    from django.contrib.auth.models import AbstractBaseUser
+1  5  | def f():
+2  6  |     from django.contrib.auth.models import AbstractBaseUser
+3  7  | 
+--------------------------------------------------------------------------------
+31 35 | def f():
+32 36 |     from typing import Literal
+33 37 | 
+34    |-    from django.contrib.auth.models import AbstractBaseUser
+35 38 | 
+36    |-    def test_union_contain_inner_quotes(self, type1: AbstractBaseUser["int" | Literal["int"]]):
+   39 |+    def test_union_contain_inner_quotes(self, type1: "AbstractBaseUser[int | Literal['int']]"):
+37 40 |         pass
+38 41 | 
+39 42 | 
+
+quote_annotations.py:43:44: TCH002 [*] Move third-party import `django.contrib.auth.models.AbstractBaseUser` into a type-checking block
+   |
+41 |     from typing import Literal
+42 | 
+43 |     from django.contrib.auth.models import AbstractBaseUser
+   |                                            ^^^^^^^^^^^^^^^^ TCH002
+44 | 
+45 |     def test_inner_literal_mixed_quotes(user: AbstractBaseUser[Literal['user', "admin"]]):
+   |
+   = help: Move into type-checking block
+
+ℹ Unsafe fix
+   1  |+from typing import TYPE_CHECKING
+   2  |+
+   3  |+if TYPE_CHECKING:
+   4  |+    from django.contrib.auth.models import AbstractBaseUser
+1  5  | def f():
+2  6  |     from django.contrib.auth.models import AbstractBaseUser
+3  7  | 
+--------------------------------------------------------------------------------
+40 44 | def f():
+41 45 |     from typing import Literal
+42 46 | 
+43    |-    from django.contrib.auth.models import AbstractBaseUser
+44 47 | 
+45    |-    def test_inner_literal_mixed_quotes(user: AbstractBaseUser[Literal['user', "admin"]]):
+   48 |+    def test_inner_literal_mixed_quotes(user: "AbstractBaseUser[Literal['user', 'admin']]"):
+46 49 |         pass
+47 50 | 
+48 51 | 
+
+quote_annotations.py:52:44: TCH002 [*] Move third-party import `django.contrib.auth.models.AbstractBaseUser` into a type-checking block
+   |
+50 |     from typing import Literal
+51 | 
+52 |     from django.contrib.auth.models import AbstractBaseUser
+   |                                            ^^^^^^^^^^^^^^^^ TCH002
+53 | 
+54 |     def test_inner_literal_single_quote(user: AbstractBaseUser[Literal['int'], str]):
+   |
+   = help: Move into type-checking block
+
+ℹ Unsafe fix
+   1  |+from typing import TYPE_CHECKING
+   2  |+
+   3  |+if TYPE_CHECKING:
+   4  |+    from django.contrib.auth.models import AbstractBaseUser
+1  5  | def f():
+2  6  |     from django.contrib.auth.models import AbstractBaseUser
+3  7  | 
+--------------------------------------------------------------------------------
+49 53 | def f():
+50 54 |     from typing import Literal
+51 55 | 
+52    |-    from django.contrib.auth.models import AbstractBaseUser
+53 56 | 
+54    |-    def test_inner_literal_single_quote(user: AbstractBaseUser[Literal['int'], str]):
+   57 |+    def test_inner_literal_single_quote(user: "AbstractBaseUser[Literal['int'], str]"):
+55 58 |         pass
+56 59 | 
+57 60 | 
+
+quote_annotations.py:61:44: TCH002 [*] Move third-party import `django.contrib.auth.models.AbstractBaseUser` into a type-checking block
+   |
+59 |     from typing import Literal
+60 | 
+61 |     from django.contrib.auth.models import AbstractBaseUser
+   |                                            ^^^^^^^^^^^^^^^^ TCH002
+62 | 
+63 |     def test_mixed_quotes_literal(user: AbstractBaseUser[Literal['user'], "int"]):
+   |
+   = help: Move into type-checking block
+
+ℹ Unsafe fix
+   1  |+from typing import TYPE_CHECKING
+   2  |+
+   3  |+if TYPE_CHECKING:
+   4  |+    from django.contrib.auth.models import AbstractBaseUser
+1  5  | def f():
+2  6  |     from django.contrib.auth.models import AbstractBaseUser
+3  7  | 
+--------------------------------------------------------------------------------
+58 62 | def f():
+59 63 |     from typing import Literal
+60 64 | 
+61    |-    from django.contrib.auth.models import AbstractBaseUser
+62 65 | 
+63    |-    def test_mixed_quotes_literal(user: AbstractBaseUser[Literal['user'], "int"]):
+   66 |+    def test_mixed_quotes_literal(user: "AbstractBaseUser[Literal['user'], int]"):
+64 67 |         pass
+65 68 | 
+66 69 | 
+
+quote_annotations.py:70:44: TCH002 [*] Move third-party import `django.contrib.auth.models.AbstractBaseUser` into a type-checking block
+   |
+68 |     from typing import Annotated, Literal
+69 | 
+70 |     from django.contrib.auth.models import AbstractBaseUser
+   |                                            ^^^^^^^^^^^^^^^^ TCH002
+71 | 
+72 |     def test_annotated_literal_mixed_quotes(user: AbstractBaseUser[Annotated[str, "max_length=20", Literal['user', "admin"]]]):
+   |
+   = help: Move into type-checking block
+
+ℹ Unsafe fix
+   1  |+from typing import TYPE_CHECKING
+   2  |+
+   3  |+if TYPE_CHECKING:
+   4  |+    from django.contrib.auth.models import AbstractBaseUser
+1  5  | def f():
+2  6  |     from django.contrib.auth.models import AbstractBaseUser
+3  7  | 
+--------------------------------------------------------------------------------
+67 71 | def f():
+68 72 |     from typing import Annotated, Literal
+69 73 | 
+70    |-    from django.contrib.auth.models import AbstractBaseUser
+71 74 | 
+72    |-    def test_annotated_literal_mixed_quotes(user: AbstractBaseUser[Annotated[str, "max_length=20", Literal['user', "admin"]]]):
+   75 |+    def test_annotated_literal_mixed_quotes(user: "AbstractBaseUser[Annotated[str, 'max_length=20', Literal['user', 'admin']]]"):
+73 76 |         pass
+74 77 | 
+75 78 | 
+
+quote_annotations.py:79:44: TCH002 [*] Move third-party import `django.contrib.auth.models.AbstractBaseUser` into a type-checking block
+   |
+77 |     from typing import Literal, Union
+78 | 
+79 |     from django.contrib.auth.models import AbstractBaseUser
+   |                                            ^^^^^^^^^^^^^^^^ TCH002
+80 | 
+81 |     def test_union_literal_mixed_quotes(user: AbstractBaseUser[Union[Literal['active', "inactive"], str]]):
+   |
+   = help: Move into type-checking block
+
+ℹ Unsafe fix
+   1  |+from typing import TYPE_CHECKING
+   2  |+
+   3  |+if TYPE_CHECKING:
+   4  |+    from django.contrib.auth.models import AbstractBaseUser
+1  5  | def f():
+2  6  |     from django.contrib.auth.models import AbstractBaseUser
+3  7  | 
+--------------------------------------------------------------------------------
+76 80 | def f():
+77 81 |     from typing import Literal, Union
+78 82 | 
+79    |-    from django.contrib.auth.models import AbstractBaseUser
+80 83 | 
+81    |-    def test_union_literal_mixed_quotes(user: AbstractBaseUser[Union[Literal['active', "inactive"], str]]):
+   84 |+    def test_union_literal_mixed_quotes(user: "AbstractBaseUser[Union[Literal['active', 'inactive'], str]]"):
+82 85 |         pass
+83 86 | 
+84 87 | 
+
+quote_annotations.py:88:44: TCH002 [*] Move third-party import `django.contrib.auth.models.AbstractBaseUser` into a type-checking block
+   |
+86 |     from typing import Callable, Literal
+87 | 
+88 |     from django.contrib.auth.models import AbstractBaseUser
+   |                                            ^^^^^^^^^^^^^^^^ TCH002
+89 | 
+90 |     def test_callable_literal_mixed_quotes(callable_fn: AbstractBaseUser[Callable[["int", Literal['admin', "user"]], 'bool']]):
+   |
+   = help: Move into type-checking block
+
+ℹ Unsafe fix
+   1  |+from typing import TYPE_CHECKING
+   2  |+
+   3  |+if TYPE_CHECKING:
+   4  |+    from django.contrib.auth.models import AbstractBaseUser
+1  5  | def f():
+2  6  |     from django.contrib.auth.models import AbstractBaseUser
+3  7  | 
+--------------------------------------------------------------------------------
+85 89 | def f():
+86 90 |     from typing import Callable, Literal
+87 91 | 
+88    |-    from django.contrib.auth.models import AbstractBaseUser
+89 92 | 
+90    |-    def test_callable_literal_mixed_quotes(callable_fn: AbstractBaseUser[Callable[["int", Literal['admin', "user"]], 'bool']]):
+   93 |+    def test_callable_literal_mixed_quotes(callable_fn: "AbstractBaseUser[Callable[[int, Literal[admin, user]], bool]]"):
+91 94 |         pass
+92 95 | 
+93 96 | 
+
+quote_annotations.py:97:44: TCH002 [*] Move third-party import `django.contrib.auth.models.AbstractBaseUser` into a type-checking block
+   |
+95 |     from typing import Annotated, Callable, Literal
+96 | 
+97 |     from django.contrib.auth.models import AbstractBaseUser
+   |                                            ^^^^^^^^^^^^^^^^ TCH002
+98 | 
+99 |     def test_callable_annotated_literal(callable_fn: AbstractBaseUser[Callable[[int, Annotated[str, Literal['active', "inactive"]]], bool]]):
+   |
+   = help: Move into type-checking block
+
+ℹ Unsafe fix
+    1   |+from typing import TYPE_CHECKING
+    2   |+
+    3   |+if TYPE_CHECKING:
+    4   |+    from django.contrib.auth.models import AbstractBaseUser
+1   5   | def f():
+2   6   |     from django.contrib.auth.models import AbstractBaseUser
+3   7   | 
+--------------------------------------------------------------------------------
+94  98  | def f():
+95  99  |     from typing import Annotated, Callable, Literal
+96  100 | 
+97      |-    from django.contrib.auth.models import AbstractBaseUser
+98  101 | 
+99      |-    def test_callable_annotated_literal(callable_fn: AbstractBaseUser[Callable[[int, Annotated[str, Literal['active', "inactive"]]], bool]]):
+    102 |+    def test_callable_annotated_literal(callable_fn: "AbstractBaseUser[Callable[[int, Annotated[str, Literal[active, inactive]]], bool]]"):
+100 103 |         pass
+101 104 | 
+102 105 | 
+
+quote_annotations.py:120:37: TCH002 [*] Move third-party import `django.contrib.auth.models` into a type-checking block
+    |
+118 |     from typing import literal
+119 | 
+120 |     from django.contrib.auth import models
+    |                                     ^^^^^^ TCH002
+121 | 
+122 |     def test_attribute(arg: models.AbstractBaseUser["int"]):
+    |
+    = help: Move into type-checking block
+
+ℹ Unsafe fix
+    1   |+from typing import TYPE_CHECKING
+    2   |+
+    3   |+if TYPE_CHECKING:
+    4   |+    from django.contrib.auth import models
+1   5   | def f():
+2   6   |     from django.contrib.auth.models import AbstractBaseUser
+3   7   | 
+--------------------------------------------------------------------------------
+117 121 | def f():
+118 122 |     from typing import literal
+119 123 | 
+120     |-    from django.contrib.auth import models
+121 124 | 
+122     |-    def test_attribute(arg: models.AbstractBaseUser["int"]):
+    125 |+    def test_attribute(arg: "models.AbstractBaseUser[int]"):
+123 126 |         pass
+124 127 | 
+125 128 | 
+
+quote_annotations.py:129:37: TCH002 [*] Move third-party import `django.contrib.auth.models` into a type-checking block
+    |
+127 |     from typing import Literal
+128 | 
+129 |     from django.contrib.auth import models
+    |                                     ^^^^^^ TCH002
+130 | 
+131 |     def test_attribute_typing_literal(arg: models.AbstractBaseUser[Literal["admin"]]):
+    |
+    = help: Move into type-checking block
+
+ℹ Unsafe fix
+    1   |+from typing import TYPE_CHECKING
+    2   |+
+    3   |+if TYPE_CHECKING:
+    4   |+    from django.contrib.auth import models
+1   5   | def f():
+2   6   |     from django.contrib.auth.models import AbstractBaseUser
+3   7   | 
+--------------------------------------------------------------------------------
+126 130 | def f():
+127 131 |     from typing import Literal
+128 132 | 
+129     |-    from django.contrib.auth import models
+130 133 | 
+131     |-    def test_attribute_typing_literal(arg: models.AbstractBaseUser[Literal["admin"]]):
+    134 |+    def test_attribute_typing_literal(arg: "models.AbstractBaseUser[Literal['admin']]"):
+132 135 |         pass
diff --git a/crates/ruff_linter/src/rules/flake8_type_checking/snapshots/ruff_linter__rules__flake8_type_checking__tests__runtime-import-in-type-checking-block_quote.py.snap b/crates/ruff_linter/src/rules/flake8_type_checking/snapshots/ruff_linter__rules__flake8_type_checking__tests__runtime-import-in-type-checking-block_quote.py.snap
index c09777853b97a..cc6b8d74f43b5 100644
--- a/crates/ruff_linter/src/rules/flake8_type_checking/snapshots/ruff_linter__rules__flake8_type_checking__tests__runtime-import-in-type-checking-block_quote.py.snap
+++ b/crates/ruff_linter/src/rules/flake8_type_checking/snapshots/ruff_linter__rules__flake8_type_checking__tests__runtime-import-in-type-checking-block_quote.py.snap
@@ -1,13 +1,13 @@
 ---
 source: crates/ruff_linter/src/rules/flake8_type_checking/mod.rs
 ---
-quote.py:64:28: TCH004 [*] Move import `pandas.DataFrame` out of type-checking block. Import is used for more than type hinting.
+quote.py:57:28: TCH004 [*] Move import `pandas.DataFrame` out of type-checking block. Import is used for more than type hinting.
    |
-63 |     if TYPE_CHECKING:
-64 |         from pandas import DataFrame
+56 |     if TYPE_CHECKING:
+57 |         from pandas import DataFrame
    |                            ^^^^^^^^^ TCH004
-65 | 
-66 |     def func(value: DataFrame):
+58 | 
+59 |     def func(value: DataFrame):
    |
    = help: Move out of type-checking block
 
@@ -17,13 +17,11 @@ quote.py:64:28: TCH004 [*] Move import `pandas.DataFrame` out of type-checking b
 2  3  |     from pandas import DataFrame
 3  4  | 
 --------------------------------------------------------------------------------
-61 62 |     from typing import TYPE_CHECKING
-62 63 | 
-63 64 |     if TYPE_CHECKING:
-64    |-        from pandas import DataFrame
-   65 |+        pass
-65 66 | 
-66 67 |     def func(value: DataFrame):
-67 68 |         ...
-
-
+54 55 |     from typing import TYPE_CHECKING
+55 56 | 
+56 57 |     if TYPE_CHECKING:
+57    |-        from pandas import DataFrame
+   58 |+        pass
+58 59 | 
+59 60 |     def func(value: DataFrame):
+60 61 |         ...