diff --git a/crates/ruff_linter/resources/test/fixtures/pyupgrade/UP040.pyi b/crates/ruff_linter/resources/test/fixtures/pyupgrade/UP040.pyi
index f97ba8887f..a721f4771a 100644
--- a/crates/ruff_linter/resources/test/fixtures/pyupgrade/UP040.pyi
+++ b/crates/ruff_linter/resources/test/fixtures/pyupgrade/UP040.pyi
@@ -12,3 +12,13 @@ x: TypeAlias = tuple[
     int,  # preserved
     float,
 ]
+
+T: TypeAlias = ( # comment0
+    # comment1
+    int  # comment2
+    # comment3
+    | # comment4
+    # comment5
+    str  # comment6
+    # comment7
+) # comment8
diff --git a/crates/ruff_linter/src/rules/pyupgrade/rules/pep695/non_pep695_type_alias.rs b/crates/ruff_linter/src/rules/pyupgrade/rules/pep695/non_pep695_type_alias.rs
index ff9215f962..e3a1cb96c1 100644
--- a/crates/ruff_linter/src/rules/pyupgrade/rules/pep695/non_pep695_type_alias.rs
+++ b/crates/ruff_linter/src/rules/pyupgrade/rules/pep695/non_pep695_type_alias.rs
@@ -170,25 +170,12 @@ pub(crate) fn non_pep695_type_alias_type(checker: &Checker, stmt: &StmtAssign) {
         return;
     };
 
-    // it would be easier to check for comments in the whole `stmt.range`, but because
-    // `create_diagnostic` uses the full source text of `value`, comments within `value` are
-    // actually preserved. thus, we have to check for comments in `stmt` but outside of `value`
-    let pre_value = TextRange::new(stmt.start(), value.start());
-    let post_value = TextRange::new(value.end(), stmt.end());
-    let comment_ranges = checker.comment_ranges();
-    let safety = if comment_ranges.intersects(pre_value) || comment_ranges.intersects(post_value) {
-        Applicability::Unsafe
-    } else {
-        Applicability::Safe
-    };
-
     checker.report_diagnostic(create_diagnostic(
         checker,
         stmt.into(),
         &target_name.id,
         value,
         &vars,
-        safety,
         TypeAliasKind::TypeAliasType,
     ));
 }
@@ -248,13 +235,6 @@ pub(crate) fn non_pep695_type_alias(checker: &Checker, stmt: &StmtAnnAssign) {
         name,
         value,
         &vars,
-        // The fix is only safe in a type stub because new-style aliases have different runtime behavior
-        // See https://github.com/astral-sh/ruff/issues/6434
-        if checker.source_type.is_stub() {
-            Applicability::Safe
-        } else {
-            Applicability::Unsafe
-        },
         TypeAliasKind::TypeAlias,
     ));
 }
@@ -266,19 +246,45 @@ fn create_diagnostic(
     name: &Name,
     value: &Expr,
     type_vars: &[TypeVar],
-    applicability: Applicability,
     type_alias_kind: TypeAliasKind,
 ) -> Diagnostic {
     let source = checker.source();
+    let comment_ranges = checker.comment_ranges();
+
     let range_with_parentheses =
-        parenthesized_range(value.into(), stmt.into(), checker.comment_ranges(), source)
+        parenthesized_range(value.into(), stmt.into(), comment_ranges, source)
             .unwrap_or(value.range());
+
     let content = format!(
         "type {name}{type_params} = {value}",
         type_params = DisplayTypeVars { type_vars, source },
         value = &source[range_with_parentheses]
     );
     let edit = Edit::range_replacement(content, stmt.range());
+
+    let applicability =
+        if type_alias_kind == TypeAliasKind::TypeAlias && !checker.source_type.is_stub() {
+            // The fix is always unsafe in non-stubs
+            // because new-style aliases have different runtime behavior.
+            // See https://github.com/astral-sh/ruff/issues/6434
+            Applicability::Unsafe
+        } else {
+            // In stub files, or in non-stub files for `TypeAliasType` assignments,
+            // the fix is only unsafe if it would delete comments.
+            //
+            // it would be easier to check for comments in the whole `stmt.range`, but because
+            // `create_diagnostic` uses the full source text of `value`, comments within `value` are
+            // actually preserved. thus, we have to check for comments in `stmt` but outside of `value`
+            let pre_value = TextRange::new(stmt.start(), range_with_parentheses.start());
+            let post_value = TextRange::new(range_with_parentheses.end(), stmt.end());
+
+            if comment_ranges.intersects(pre_value) || comment_ranges.intersects(post_value) {
+                Applicability::Unsafe
+            } else {
+                Applicability::Safe
+            }
+        };
+
     Diagnostic::new(
         NonPEP695TypeAlias {
             name: name.to_string(),
diff --git a/crates/ruff_linter/src/rules/pyupgrade/snapshots/ruff_linter__rules__pyupgrade__tests__UP040.pyi.snap b/crates/ruff_linter/src/rules/pyupgrade/snapshots/ruff_linter__rules__pyupgrade__tests__UP040.pyi.snap
index 30496127fa..7132708896 100644
--- a/crates/ruff_linter/src/rules/pyupgrade/snapshots/ruff_linter__rules__pyupgrade__tests__UP040.pyi.snap
+++ b/crates/ruff_linter/src/rules/pyupgrade/snapshots/ruff_linter__rules__pyupgrade__tests__UP040.pyi.snap
@@ -48,6 +48,8 @@ UP040.pyi:11:1: UP040 [*] Type alias `x` uses `TypeAlias` annotation instead of
 13 | |     float,
 14 | | ]
    | |_^ UP040
+15 |
+16 |   T: TypeAlias = ( # comment0
    |
    = help: Use the `type` keyword
 
@@ -60,3 +62,30 @@ UP040.pyi:11:1: UP040 [*] Type alias `x` uses `TypeAlias` annotation instead of
 12 12 |     int,  # preserved
 13 13 |     float,
 14 14 | ]
+
+UP040.pyi:16:1: UP040 [*] Type alias `T` uses `TypeAlias` annotation instead of the `type` keyword
+   |
+14 |   ]
+15 |
+16 | / T: TypeAlias = ( # comment0
+17 | |     # comment1
+18 | |     int  # comment2
+19 | |     # comment3
+20 | |     | # comment4
+21 | |     # comment5
+22 | |     str  # comment6
+23 | |     # comment7
+24 | | ) # comment8
+   | |_^ UP040
+   |
+   = help: Use the `type` keyword
+
+ℹ Safe fix
+13 13 |     float,
+14 14 | ]
+15 15 | 
+16    |-T: TypeAlias = ( # comment0
+   16 |+type T = ( # comment0
+17 17 |     # comment1
+18 18 |     int  # comment2
+19 19 |     # comment3