diff --git a/crates/ruff_python_parser/src/snapshots/ruff_python_parser__string__tests__raw_byte_literal_1.snap b/crates/ruff_python_parser/src/snapshots/ruff_python_parser__string__tests__raw_byte_literal_1.snap
index a69618db66..aca165c1ee 100644
--- a/crates/ruff_python_parser/src/snapshots/ruff_python_parser__string__tests__raw_byte_literal_1.snap
+++ b/crates/ruff_python_parser/src/snapshots/ruff_python_parser__string__tests__raw_byte_literal_1.snap
@@ -22,7 +22,7 @@ expression: parse_ast
                                 flags: BytesLiteralFlags {
                                     quote_style: Single,
                                     prefix: Raw {
-                                        uppercase_r: true,
+                                        uppercase_r: false,
                                     },
                                     triple_quoted: false,
                                 },
diff --git a/crates/ruff_python_parser/src/snapshots/ruff_python_parser__string__tests__raw_byte_literal_2.snap b/crates/ruff_python_parser/src/snapshots/ruff_python_parser__string__tests__raw_byte_literal_2.snap
index 09e09ac8bb..283c38784b 100644
--- a/crates/ruff_python_parser/src/snapshots/ruff_python_parser__string__tests__raw_byte_literal_2.snap
+++ b/crates/ruff_python_parser/src/snapshots/ruff_python_parser__string__tests__raw_byte_literal_2.snap
@@ -20,7 +20,7 @@ expression: parse_ast
                                 flags: BytesLiteralFlags {
                                     quote_style: Single,
                                     prefix: Raw {
-                                        uppercase_r: true,
+                                        uppercase_r: false,
                                     },
                                     triple_quoted: false,
                                 },
diff --git a/crates/ruff_python_parser/src/string_token_flags.rs b/crates/ruff_python_parser/src/string_token_flags.rs
index faf2f675d4..a03352906d 100644
--- a/crates/ruff_python_parser/src/string_token_flags.rs
+++ b/crates/ruff_python_parser/src/string_token_flags.rs
@@ -167,12 +167,12 @@ impl StringPrefix {
 
         // bytestrings
         if flags.contains(StringFlags::B_PREFIX) {
-            if flags.contains(StringFlags::R_PREFIX_LOWER) {
-                return Self::Bytes(ByteStringPrefix::Raw { uppercase_r: true });
-            }
             if flags.contains(StringFlags::R_PREFIX_LOWER) {
                 return Self::Bytes(ByteStringPrefix::Raw { uppercase_r: false });
             }
+            if flags.contains(StringFlags::R_PREFIX_UPPER) {
+                return Self::Bytes(ByteStringPrefix::Raw { uppercase_r: true });
+            }
             return Self::Bytes(ByteStringPrefix::Regular);
         }