diff --git a/crates/ruff_linter/resources/test/fixtures/flake8_bugbear/B033.py b/crates/ruff_linter/resources/test/fixtures/flake8_bugbear/B033.py
index c0e0ec6faf..4aa8e8d4b2 100644
--- a/crates/ruff_linter/resources/test/fixtures/flake8_bugbear/B033.py
+++ b/crates/ruff_linter/resources/test/fixtures/flake8_bugbear/B033.py
@@ -20,6 +20,12 @@ incorrect_set = {
     1,
 }
 incorrect_set = {False, 1, 0}
+incorrect_set_multiline_with_comment = {
+    "value1",
+    23,
+    # B033
+    "value1",
+}
 
 ###
 # Non-errors.
diff --git a/crates/ruff_linter/src/rules/flake8_bugbear/rules/duplicate_value.rs b/crates/ruff_linter/src/rules/flake8_bugbear/rules/duplicate_value.rs
index 0cb37df459..5d4c294903 100644
--- a/crates/ruff_linter/src/rules/flake8_bugbear/rules/duplicate_value.rs
+++ b/crates/ruff_linter/src/rules/flake8_bugbear/rules/duplicate_value.rs
@@ -1,4 +1,4 @@
-use ruff_diagnostics::Fix;
+use ruff_diagnostics::{Applicability, Fix};
 use rustc_hash::FxHashMap;
 
 use ruff_macros::{ViolationMetadata, derive_message_formats};
@@ -28,6 +28,20 @@ use crate::{FixAvailability, Violation};
 /// ```python
 /// {1, 2, 3}
 /// ```
+///
+/// ## Fix Safety
+/// This rule's fix is marked as unsafe if the replacement would remove comments attached to the
+/// original expression, potentially losing important context or documentation.
+///
+/// For example:
+/// ```python
+/// {
+///     1,
+///     2,
+///     # Comment
+///     1,
+/// }
+/// ```
 #[derive(ViolationMetadata)]
 #[violation_metadata(stable_since = "v0.0.271")]
 pub(crate) struct DuplicateValue {
@@ -68,10 +82,18 @@ pub(crate) fn duplicate_value(checker: &Checker, set: &ast::ExprSet) {
                     },
                     value.range(),
                 );
-
                 diagnostic.try_set_fix(|| {
-                    edits::remove_member(&set.elts, index, checker.locator().contents())
-                        .map(Fix::safe_edit)
+                    edits::remove_member(&set.elts, index, checker.locator().contents()).map(
+                        |edit| {
+                            let applicability = if checker.comment_ranges().intersects(edit.range())
+                            {
+                                Applicability::Unsafe
+                            } else {
+                                Applicability::Safe
+                            };
+                            Fix::applicable_edit(edit, applicability)
+                        },
+                    )
                 });
             }
         }
diff --git a/crates/ruff_linter/src/rules/flake8_bugbear/snapshots/ruff_linter__rules__flake8_bugbear__tests__B033_B033.py.snap b/crates/ruff_linter/src/rules/flake8_bugbear/snapshots/ruff_linter__rules__flake8_bugbear__tests__B033_B033.py.snap
index 817a97b1b3..339b89232e 100644
--- a/crates/ruff_linter/src/rules/flake8_bugbear/snapshots/ruff_linter__rules__flake8_bugbear__tests__B033_B033.py.snap
+++ b/crates/ruff_linter/src/rules/flake8_bugbear/snapshots/ruff_linter__rules__flake8_bugbear__tests__B033_B033.py.snap
@@ -157,7 +157,7 @@ help: Remove duplicate item
    -     1,
 20 | }
 21 | incorrect_set = {False, 1, 0}
-22 | 
+22 | incorrect_set_multiline_with_comment = {
 
 B033 [*] Sets should not contain duplicate items, but `False` and `0` has the same value
   --> B033.py:22:28
@@ -166,8 +166,8 @@ B033 [*] Sets should not contain duplicate items, but `False` and `0` has the sa
 21 | }
 22 | incorrect_set = {False, 1, 0}
    |                            ^
-23 |
-24 | ###
+23 | incorrect_set_multiline_with_comment = {
+24 |     "value1",
    |
 help: Remove duplicate item
 19 |     1,
@@ -175,6 +175,26 @@ help: Remove duplicate item
 21 | }
    - incorrect_set = {False, 1, 0}
 22 + incorrect_set = {False, 1}
-23 | 
-24 | ###
-25 | # Non-errors.
+23 | incorrect_set_multiline_with_comment = {
+24 |     "value1",
+25 |     23,
+
+B033 [*] Sets should not contain duplicate item `"value1"`
+  --> B033.py:27:5
+   |
+25 |     23,
+26 |     # B033
+27 |     "value1",
+   |     ^^^^^^^^
+28 | }
+   |
+help: Remove duplicate item
+23 | incorrect_set_multiline_with_comment = {
+24 |     "value1",
+25 |     23,
+   -     # B033
+   -     "value1",
+26 | }
+27 | 
+28 | ###
+note: This is an unsafe fix and may change runtime behavior